Taylor-Hana-Maui1

A woman enjoying a vacation on the Hawaiian Islands of Oahu and Maui

There is nothing like a trip to Hawaii! From an early age, visiting the Hawaiian Islands had been a dream and I was so excited to have had the opportunity to finally visit in March 2021. After incredible experiences at two Hawaiian Islands, I am excited to finally share my 10 Day Oahu and Maui itinerary!

Some fun facts about Hawaii are that there are a total of 137 islands, but only eight of them are recognized and seven are inhabited. The eight islands based on popularity are Oahu, Maui, the island of Hawaii (also known as The Big Island), Kauai, Molokai, Lanai, Niihau and Kahoolawe. The capital of Hawaii is Honolulu, which is located on the island of Oahu, it became the 50th state on August 21, 1959.

A woman enjoying her 10 day Oahu and Maui itinerary

During my 10-day trip to Hawaii, I adventured with fellow travel blogger Alex of East Coast Contessa. We spent the first half of our trip on the island of Oahu and the second half on the island of Maui, discovering West Maui and Hana. Both islands were beautiful and offered a lot of wonderful gems, but they both differed as well.

If you are planning a Hawaiian Islands trip, I recommend following along this wonderful 10 day Oahu and Maui itinerary.

**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like.


Pin the Below Image to Keep Handy

10-day Oahu and Maui Itinerary

Traveling to Hawaii in 2021:

A woman at the botanical gardens on Oahu, which was part of her 10 day Oahu and Maui itinerary

Even though Hawaii is part of the United States, there was a quarantine mandate when I traveled there in March 2021. Everyone traveling to Hawaii from mainland USA can test out of the 10-day quarantine for Oahu, Maui, Molokai, Lanai and the Big Island by following the state’s Safe Travels program. (Kauai joined the Hawaii Safe Travels Program on April 5, 2021.)

For those traveling to Hawaii and want to avoid the 10-day quarantine, you can take an NAAT PCR test from a Hawaii Trusted Traveler testing site within 72 hours from the last leg of your trip. Since I flew from Newark Airport in New Jersey to Honolulu with a layover in Los Angeles, I needed to take my test within 72 hours from when I departed LAX. (Please be mindful of the time differences.) You can see which testing sites are part of Hawaii’s Safe Travels Program. I took my test at American Family Care+ Urgent Care.

A beach in Maui, Hawaii

After getting my negative test results back, stating that I took it at a Trusted Traveler’s site, I had to enroll in Hawaii’s Safe Travels Program where I uploaded a PDF file of my negative test results and filled out a health questionnaire within 24 hours prior to the last leg of my trip. I then received a QR code that allowed me to hop on my flight to Hawaii. (Please make sure you follow all directions because you will only get one QR code!) Alex had to do the same thing, but she traveled from Evansville Regional Airport in Indiana to Honolulu with a layover in Dallas/Fort Worth.

Please note that when you fly United Airlines, you could save time when you arrive in Hawaii by getting “Cleared” ahead of time. All you must do is show your QR code from the Safe Travels site and your ID to the customer service desk during the last leg of your trip (so I did mine at LAX) and they will issue you a wrist band that you quickly show upon arrival in Hawaii.

A woman admiring a waterfall on the Road to Hana, part of a 10 day Oahu and Maui itinerary

In addition, since both Alex and I traveled from Oahu to Maui, we needed to take a second rt-PCR test in Oahu within 72 hours before we departed to Maui because there are inter island restrictions. Since we were only in Oahu for four days, we had to take our tests on our second day. (As of April 9, 2021, all travelers to Maui will need to take an additional test when they land in Maui to avoid a 10-day quarantine.)

We took our PCR test at The National Kidney Foundation of Hawaii at The Monarch Hotel in Honolulu. They take walk ups and it was a self-swab test. (It was super easy to do and there is someone instructing you through the entire process.)

We got our negative results via email within six hours after we took our test. Once we got our results, we uploaded them onto the Hawaii Safe Travels site again, filled out another health questionnaire within 24 hours prior to our departure to Maui and got another QR code that we needed to present upon arrival on the island.

Getting to Oahu and then Maui:

A beautiful Hawaiian sunset

Getting to Hawaii is easy. I flew from Newark Liberty International Airport in New Jersey to Honolulu International Airport in Hawaii on the island of Oahu with a short layover in Los Angeles International Airport in California. After spending 4 days on Oahu, we flew from Honolulu International Airport to Maui’s Kahului Airport where we spent the remaining 6 days on Maui. I found super affordable flights through Skyscanner!

No matter which island you visit in Hawaii, I HIGHLY recommend renting a car so that you can explore and not miss out on anything. Oahu’s TheBus is known as Hawaii’s best public transportation method and you can take it to different areas around the island. In Maui, there is also a public bus transit system that includes 13 different routes, including one that goes to and from the airport. Please note that there are no bus routes to Hana.

Both Oahu and Maui have Uber and Lyft services!

10 Day Oahu and Maui Itinerary

A woman enjoying a 10 day Oahu and Maui itinerary vacation

Oahu Itinerary:

Discover the top 10 best things to do on Oahu!

Day 1: Arrive in Honolulu

A woman horseback riding on the North Shore of Oahu, which was part of a 10 day Oahu and Maui itinerary

Arrive in: Honolulu International Airport

Where to Stay: Honolulu/Waikiki

Hotel Recommendation: The Equus Hotel

Where to Eat in Honolulu/Waikiki:

A woman at The Equus Hotel in Honolulu

Both Alex and I arrived in Honolulu later in the evening, so the only things we did on that day was check into The Equus, grab dinner at Chiba-Ken, which is a Japanese restaurant in the city, and enjoy Paniolo Bar at the hotel.

Overall, The Equus Hotel is known as Hawaii’s Best Lifestyle Hotel and it offers comfortable rooms, a welcoming bar that is open for everyone to enjoy delicious food and beverages and there is also a refreshing dipping pool to cool off in.

Day 2: Enjoy Waikiki Beach, Hike Diamond Head and Admire the Views at Nu’Uanu Pali

A woman enjoying Waikiki beach during her time on Oahu

One of the most popular beaches in the world and a popular thing to include during your 10 day Oahu and Maui itinerary is spend time at Waikiki Beach.

This beautiful beach features two miles of white sand beaches, comforting aqua blue waters and high-rise beachfront hotels. Other great things to do at Waikiki Beach is to take a surfing lesson, watch professional surfers, enjoy an event and walk around Ala Moana Regional Park that surrounds the beach area.

Not too far from Waikiki is Diamond Head. This beautiful mountain is a volcanic cone, located in the most popular State Park of Hawaii. Hiking Diamond Head will take you to the edge of the 300,000-year-old crater. This hike includes a 1.8-mile, easy to moderate trail and it costs $1 USD per walk-in visitor and $5 USD per vehicle to enter Diamond Head State Monument. It is also heavily trafficked.

A woman enjoying the views at Nu'Uanu Pali, which was part of a 10 day Oahu and Maui itinerary

Another epic thing to do on the second day (or first full day) of your 10 day Oahu and Maui itinerary is enjoy the panoramic views at Nu’Uanu Pali Lookout. It is free to get into this area and it costs $3 USD to park your vehicle. It’s an amazing spot for sunrise!

For dinner, head over to one of the best Thai restaurants in Honolulu called Maile’s Thai at Ward. Both the food and drinks are unbelievable!

Day 3: Tour Pearl Harbor, Adventure around the North Shore, Attend a Hawaiian Luau

Pearl Harbor on Oahu

A 10 day Oahu and Maui itinerary would not be complete without paying a visit to Pearl Harbor. Visiting Pearl Harbor on Oahu is both a somber and educational experience.

During a tour through Pearl Harbor, stories will be told of those who were there on December 7, 1949, when the bombing took place. A tour through Pearl Harbor will also take you on a boat ride to the Peace Memorial. While you’re on the boat, you will see plaques sticking out of the water, indicating where ships sank on December 7, 1949.  The actual Peace Memorial stands above the USS Arizona, which is the only ship that sank that wasn’t taken out of the water.

Fumi's Shrimp Truck on the North Shore of Oahu

After exploring Pearl Harbor, head to the North Shore that features beautiful beaches, breathtaking waterfalls, awesome food trucks and more!

Check out Waimea Falls on the North Shore before having lunch at Fumi’s Shrimp Truck; it is beautiful! Even though there are a plethora of food trucks ranging from traditional Hawaiian to poke and fresh seafood to shaved iced, Fumi’s Shrimp Truck is one of the best along the North Shore! (The coconut shrimp and buttered garlic shrimp are bomb.)

A woman horseback riding at Hawaii Polo Club on the North Shore

When you’re finished with lunch, head over to Hawai’i Polo Club to enjoy a lovely horseback ride along the beach in Waialua. You can admire all of the stunning views of the aqua blue ocean and nearby mountains. On certain days, you can even see sea turtles, whales and even Hawaiian monk seals.

Later in the day, it is fun to attend a traditional Hawaiian luau such as Ka Moana Luau at Sea Life Park. At a luau you can enjoy and dance to live music, watch cultural performances and savor traditional hula cuisine such as poi, pulled pork, poke, coconut pudding and more.

Day 4: Visit Ho’omaluhia Botanical Garden and Byodo-In Temple and Relax at Lanikai Beach

Exploring Ho'omaluhia Botanical Garden on Oahu, which is part of a 10 day Oahu and Maui itinerary

A stunning gem and place that takes your breath away on Oahu is Ho’omaluhia Botanical Garden. Located on 400 acres, these gorgeous gardens represent botanical collections from the Philippines, Malaysia, Tropical America, Polynesia, India, Sri Lanka and Africa.

Overall, Ho’omaluhia Botanical Gardens is one of the most beautiful spots on Oahu and it should most definitely be on your 10 day itinerary for Oahu and Maui. You can also go fishing, set up a campsite, enjoy a picnic, walk around and do so much more at this spot!

A woman admiring the peacefulness at Byodo-In Temple on Oahu, which is part of a 10 day Oahu and Maui itinerary

Another amazing spot to visit on Oahu is Byodo-In Temple. Hawaii has a lot of Japanese influence and there is a Buddhist temple, located at the bottom of Ko’olau Mountain in the Valley of the Temples Memorial Park, to walk around and admire.

Byodo-In Temple was made in memory of the first Japanese immigrants to Hawaii. This temple on Oahu is a smaller replica of the Byodo-In Temple in Uji, Kyoto, Japan. There is a lush garden, a koi pond, meditation area and so much more.

Charcoal pancakes from Basalt in Waikiki

After checking out the gardens and temple, head back to Waikiki to enjoy brunch at Basalt. This award-winning restaurant features an incredible brunch and dinner menu along with a great happy hour and wine list. For brunch, their signature charcoal buttermilk pancakes and French toast with coco-macnut crunch are two popular staples to try! The French pressed coffee and guava mimosa did not disappoint as well.

Once you’re finished with brunch, get ready to head to the beach! Known as Oahu’s “most beautiful” beach, Lanikai in Kailua is a favorite amongst many.

A woman enjoying a beach day at Lanikai Beach in Kailua

At Lanikai Beach, you can relax on the warm sand, swim in the stunning blue waters, go on a hike, have fun on a rowboat and/or kayak plus, grab food in town and shop! No matter what, you MUST put Lanikai Beach on your 10 Day itinerary for Oahu and Maui. (If you’re looking for great ice cream in Kailua, head to Banan in town. They have delicious ice cream and you can even enjoy a sundae in a pineapple!)

For dinner, make reservations for Duke’s Waikiki. It is a great Hawaiian restaurant that is known for its wonderful dishes and amazing hula pie for dessert!

Maui Itinerary:

A woman enjoying her 10 day Oahu and Maui itinerary

Discover more about West Maui and the best spots on Road to Hana in detail.

Arrive in: Kahului Airport

Where to Stay: Days 5-7, stay at Napili Kai Beach Resort in Lahaina and Days 8-10, stay at Hana Maui Resort in Hana

Where to Eat in West Maui:

Where to Eat in Hana:

Day 5: Fly to Maui

A woman enjoying her stay at Napili Kai Beach Resort in West Maui

After enjoying one last breakfast on Oahu, head over to the airport to fly to Maui, the next island to explore on your 10 day itinerary!

After landing in Maui, we rented another vehicle and drove around an hour to Napili Kai Beach Resort in West Maui. This beautiful beach resort is located in Lahaina and it is perfect for those on a family vacation, honeymoon/couples’ getaway, girls’ trip and more.

A woman sitting on a rock in Lahaina

When you first arrive and check into the hotel, I recommend enjoying the resort and relaxing. Napili Kai has its own beach on Napili Bay where you can relax and sunbathe on the beach as well as stand up paddle board, swim, surf and boogie board in the ocean. There are also four pools and two hot tubs to enjoy, a spa, various events and more at this great resort!

For dinner on your first night in West Maui, I recommend eating next door to Napili Kai at Merriman’s, which is located at Kapalua Resort. 90% of everything served at Merriman’s are locally grown or caught, using sustainable methods. When you go out to dinner at Merriman’s, you can enjoy a 4-course prix-fixe dinner or choose a meal from the amazing bar menu.

Day 6: Soak Up the Sun at Lahaina Beach and Explore Dragon’s Teeth

A woman enjoying the waves at Dragon's Teeth, which is part of a 10 day Oahu and Maui itinerary

On your second day in West Maui, enjoy breakfast at Napili Kai’s Sea House Restaurant. You can savor everything from an all-American breakfast to cinnamon rolls and Korean fried rice to frittatas. After breakfast, relax at the beach! The beaches in Lahaina are so beautiful.

A cool spot to enjoy in Maui and a bucket list item on a 10 day Oahu and Maui itinerary is Dragon’s Teeth at Makaluapuna Point. This epic spot features cool rock formations and is a great place to watch giant Pacific waves crash along the cliffs. The unique rock formations at Dragon’s Teeth were formed when the lava from the West Maui volcano went into the ocean. Heavy winds and waves forced it back and it cooled into black teeth-looking rocks. There is also a labyrinth at Dragon’s Teeth!

An Hawaiian shaved ice from Coconut Caboose in Maui

For an afternoon snack, I recommend checking out Coconut Caboose, which is a fun food truck that sells Hawaiian shaved ice, located off of Honoapiilani Highway that overlooks Honokahua Bay.

Everything that Coconut Caboose offers is vegan and organic and all of their shaved ice is made out of frozen coconut water from coconuts hand-picked earlier in the morning. In addition to Hawaiian shaved ice, Coconut Caboose also has raw coconut gelato, fresh coconuts, popsicles, juices and more!

After watching the sunset at Napili Kai, enjoy a lovely seafood dinner at the resort’s Sea House Restaurant. They also have great tropical drinks as well.

Day 7: Day Trip to Wailea and Sunset Dinner at Whaler’s Village

A woman enjoying a beach day in Wailea, which is part of a 10 day Oahu and Maui itinerary

Another great spot to add to your 10 day Oahu and Maui itinerary is Wailea, which features stunning beaches!

On day 7, drive a little over an hour to Maluaka Beach, which is also known as Turtle Town in Wailea-Makena. This specific beach is free to relax at, swim and even spot sea turtles if you’re lucky! The sand is soft, the water is a clear aqua blue and there are breathtaking views all around.

In addition to the beach, there are also great restaurants, shops, golf courses and hiking trails to enjoy in Wailea! Check it all out if you have time.

Hula pie from Hula Grill in Maui

Later in the day, head back to West Maui and enjoy a sunset while watching the surfers at Black Rock Beach, located at the north end of Ka’anapali Beach. Overall, Black Rock Beach is great for sunbathers, surfers, boogie boarders and snorkelers.

During your time at Black Rock Beach, also grab dinner at Hula Grill in Whaler’s Village. Both Duke’s, which I talk about above in Oahu, and Hula Grill are owned by the same parent company and feature delicious Hawaiian cuisine. An evening at Hula Grill would not be complete without enjoying a Hula pie for dessert. (I recommend sharing it because it is huge!) It is made with macadamia nut ice cream, hot fudge, toasted macadamia nuts and whipped cream and it includes an Oreo cookie crust! It’s delicious!

Day 8: Snorkel at Molokini Crater

On your last morning in West Maui, I recommend grabbing breakfast in the town of Lahaina at Cruzin’ Café. This quaint breakfast spot and coffee shop offers locally roasted Hawaiian coffee, Italian sodas, breakfast sandwiches, hoagies, shaka dogs (which are hog dogs in a Hawaiian sweet roll) and Hawaiian shaved ice.

Molokini Crater in Maui

One of the most memorable day excursions in Hawaii that you must include on your 10 day itinerary for Oahu and Maui is to go snorkeling at Molokini Crater with GetYourGuide. During this three-hour snorkeling excursion with Maui Snorkeling, you will take a boat from Maalaea Harbor to Molokini Crater.

During the sail to Molokini Crater, you will enjoy breathtaking views and even see a few whales. Overall, Molokini Crater is a crescent-shaped atoll and it was formed from a volcanic eruption that happened around 230,000 years ago. You can enjoy snorkeling and diving at this wonderful location and during your adventure, you can even spot different fish, coral, nurse sharks and more!

A woman snorkeling at Molokini Crater, which is part of a 10 day Oahu and Maui itinerary

The overall experience visiting Molokini Crater with GetYourGuide was a lot of fun. There was also a packed lunch available for us and they even set up an inflatable water slide that you could take from the top deck of the boat into the ocean. It was loads of fun!

After your epic day of snorkeling, head over to Hana Maui Resort. I recommend driving over to the resort as soon as your tour ends because it takes around two hours to get there and you will need to drive the Road to Hana since that is where Hana Maui is situated.

Hana Maui Resort in Hana, Hawaii

One of the most important things to bring on a journey around the Road to Hana is a map/GPS. Please make sure to download directions on your phone when you have service because there is barely any cell phone reception on the Road to Hana. I also recommend bringing proper hiking clothing, an optional change of clothes (I brought a dress for pictures), cash, comfortable hiking shoes or sneakers, bug spray, sunscreen, motion sickness medication (if you get car sick easily), an umbrella or poncho, a water bottle, a swimsuit for the beaches, sunglasses, a hat and hand sanitizer (since some of the restrooms along the road don’t have soap containers).

Once you arrive at Hana Maui and check in, I recommend grabbing dinner at Hana Ranch Restaurant, which features farm-to-table Hawaiian cuisine and great drinks.

Day 9: Drive the Road to Hana

A woman enjoying a drive along Road to Hana in Maui, which is part of a 10 day Oahu and Maui itinerary

A MUST do during a 10 day Oahu and Maui itinerary is drive the Road to Hana. I recommend waking up early to start your adventure because there is so much to see and do along this amazing road! I also don’t recommend driving Road to Hana at night since there are no streetlights and everything closes at a certain time. You definitely don’t want to miss out on anything and you don’t want to put yourself in danger!

Our day exploring Road to Hana in Maui was a self-guided driving tour with our own vehicle. There are numerous guided tours that you can take around Road to Hana and you can download the Shaka Guide, which is a Road to Hana app that guides you on a tour for a small price.

Hana Lava Tube on Road to Hana

For breakfast, I recommend savoring fruit bread and a freshly brewed cup of coffee at Nahiku Café. After you fuel up, explore the Hana Lava Tube! At $12 USD per person (cash only), you will be given a flashlight and can head into the caves to explore. Before you enter the cave itself, there are beautiful gardens with stunning plant life for you to admire.

The cave at Hana Lava Tube was formed a little less than a thousand years ago because of molten lava coming up from underground and flowing towards the ocean. As the lava was draining out, that was when the tunnel was formed. It will take you around 40 minutes to walk through and explore Hana Lava Tube. It is a cool experience!

Coconut Glen's vegan ice cream on Road to Hana in Maui

After exploring Hava Lava Tube, cool off to some vegan ice cream at Coconut Glens. This colorful food truck offers organic and vegan ice cream in a variety of different flavors and it’s delicious!

As you continue on, explore the beautiful Hanawai Falls, the waterfalls at Pua’a Ka’a State Wayside Park, Makapipi Falls and admire the stunning views at all of the overlooks. When you drive along the Road to Hana, you will come across numerous areas where you can pull over.

A woman enjoying Road to Hana on a 10 day Oahu and Maui itinerary

In the afternoon, visit Ka’enae Peninsula, which is a traditional Hawaiian village that suffered devastation after a tsunami that happened in 1946 without warning. Overall, there are beautiful viewpoints along Ka’enae Peninsula for you to enjoy! If you’re hungry, head over to Aunty Sandy’s Banana Bread for delicious banana bread, a smoothie, sandwich or coconut candy.

The last spot to stop at along the Road to Hana before turning around to make your way back to Hana Maui Resort is Bamboo Forest at Haleakala National Park. It will cost you $30 USD to get into the National Park and they also accept the America the Beautiful pass.

Before you go, make sure there is no flash flooding because that is when this specific hike can be dangerous. Overall, the hike isn’t too hard and you will see stunning waterfalls, bayan trees, natural pools and more!

A woman walking on a black sand beach on Road to Hana

On your way back to the resort, your last stop along the Road to Hana should be the Black Sand Beach in Wai’anapanapa State Park. Known as the closest spot to Hana Maui Resort, Wai’anapanapa State Park costs $5 USD to enter and $10 USD to park your vehicle.

The scenery at Wai’anapanapa State Park is beautiful. You can sit and relax at the black sand beach or do an easy hike to see the ocean caves, sea arches, blow hole and more.

Day 10: Taste Pineapple Wine at Maui Wine

A woman enjoying Maui Wine, which is part of a 10 day Oahu and Maui itinerary

On your last day in Maui, I recommend grabbing breakfast at Hana Ranch Restaurant before hitting the road for your next adventure.

Located near the start/end of Road to Hana is Maui Wine, which is a renowned winery on the island. Overall, Maui Wine produces wines made from estate grown grapes, pineapples and raspberries. (It will take you around two hours to drive from Hana Maui Resort to Maui Wine and please be mindful that you will be going in the opposite direction from when you drove on your Road to Hana adventure the day before. The opposite side of Road to Hana is definitely rougher and will require more patience and awareness.)

Pineapple wine tasting at Maui Wine

During a visit to Maui Wine, you have to do the pineapple wine tasting and also try the pineapple champagne, especially if you love pineapple! The food is also tasty.

When you arrive back to Hana, check out the food truck park located next to Hana Maui Resort. This food truck park includes a Thai restaurant, a BBQ joint, places to get tropical fruit bowls and coffee, plus more.

Day 11: Fly Home

A woman enjoying her 10 day Oahu and Maui itinerary

On day 11, wake up at a decent time to head back to Kahului Airport to fly home or to your next destination. It will take you around two hours to drive from the resort to the airport and you will need to take the Road to Hana to get there!


A woman enjoying sunrise at Hana Maui Resort

I hope you all enjoyed discovering the best 10 day itinerary for Oahu and Maui. If you have any questions, please email me at [email protected]

(Alex’s mom made us beautiful, homemade flower crowns and seashell headbands for our Hawaii adventure. Click here to get one for your Polynesian trip!)

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., HI State Capital: Honolulu, Time Zone: Hawaiian-Aleutian Standard Time

Click here to join my private blog sharing Facebook group.

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

Shop my Hawaii Look:

Related posts

Best Cabin Weekend in Broken Bow, Oklahoma

During late April 2021, I was excited to have scratched off another U.S. state off my bucket list – Oklahoma!...

What to do with One Day in Dallas

Dallas, Texas is a thriving city located in Northeastern Texas. It is the 9th largest city in the United States...

Top Peninsula Papagayo Exclusive Resort

Peninsula Papagayo is located on Costa Rica’s Pacific Coast and it is known as Latin America’s ultimate and exclusive coastal...

30 Comments

  1. Kim Deer on May 28, 2021 at 6:53 pm

    What an awesome Itinerary for Oahu and Maui ~ You really provided awesome options for touring and eating! So many fabulous things to do there and so many great authentic restaurants to eat at! Your photos are amazing and brings everything to life ~ felt like I went there with you. Dad and I will get back there soon again! And I will definitely use this guide ~ Great blog and beautiful photos of those two breathtaking islands.
    Love you,
    Mom xoxo <3

    • Taylor Deer on May 28, 2021 at 6:58 pm

      Thank you mom! It sure was an incredible trip. I want to go back. <3 love you too!

  2. Sarah Blevins on May 28, 2021 at 7:16 pm

    This has so much great information! Thank you! We have been wanting to get to Hawaii – especially Maui for a long time and I am inspired to really start planning a visit.

    • Taylor Deer on May 29, 2021 at 1:21 am

      Thank you so much Sarah! You would love Hawaii. It is so beautiful! Maui was amazing. 🙂

  3. Erin on May 28, 2021 at 7:58 pm

    The temple looks so beautiful, and I’m really craving a shaved ice from the Coconut Caboose. (If only I could hop on over to Hawaii to satisfy my craving! lol) I love that you lived up to your flower child title with all of the flower crowns in this post. 🙂 Looks like a fantastic trip!

    • Taylor Deer on May 29, 2021 at 1:22 am

      Thank you so much Erin! It really was a great trip. I honestly didn’t want to leave lol. Coconut Caboose truly did have the best shaved ice! 🙂

  4. Sharyn on May 29, 2021 at 4:50 am

    This is such a great itinerary. I love visiting Hawaii but mostly stay in Oahu. Next trip I will head to Maui.

    • Taylor Deer on May 29, 2021 at 10:22 pm

      Thank you Sharyn! Hawaii is so beautiful and I hope to visit Kauai and the Big Island next time. 🙂

  5. Ha on May 29, 2021 at 5:45 am

    Your trip to Oahu and Maui looks amazing! The beaches are so clean and I’m in love with the sunset scene too. I’d love to try charcoal pancake as well. Yummy!

    • Taylor Deer on May 29, 2021 at 10:23 pm

      It really was an incredible place! I loved the beaches as well and the pancakes at Basalt were amazing! 🙂

  6. Jennifer Connarn on May 29, 2021 at 11:58 am

    This looks like the trip of my dreams! What an incredible experience, it sounds like you girls stayed busy and eat/saw so much! I’ve never been to Hawaii but if I ever plan a trip there, I will refer back to some of your tips in this post. So fun!

    • Taylor Deer on May 29, 2021 at 10:27 pm

      It was definitely the trip of my dreams! We had such a great time. You would love Hawaii once you have the opportunity to go. 🙂

  7. Brittany on May 29, 2021 at 3:37 pm

    This is such an awesome guide for Oahu and Maui, Taylor! I’m dying to visit Maui now after my trip to Oahu. Snorkeling at Molokini Crater sounds like an incredible experience. I’d also love to try the pineapple wine. It sounds delicious!

    • Taylor Deer on May 29, 2021 at 10:28 pm

      Thank you so much Brittany! You would absolutely love Maui! I hope to get back as well as see more islands. 🙂

  8. Anna on May 29, 2021 at 4:19 pm

    Looks like such an amazing trip! I would love to get out to Hawaii maybe next year so I’ll be sure to use this and help plan my trip. 🙂

    • Taylor Deer on May 29, 2021 at 10:29 pm

      It really was Anna! I never wanted to leave. 🙂 You would totally love Hawaii!

  9. Rachel H Beland on May 29, 2021 at 4:53 pm

    Pineapple wine!?? Um yes please! The only time I went to Hawaii I was a kid, I need to go back…. just for the wine 😉 Amazing post and a great initerary.

    • Taylor Deer on May 29, 2021 at 10:30 pm

      Yes, the pineapple wine was absolutely delicious! Thank you Rachel, you would love Hawaii as an adult. 🙂

  10. Chirasree Banerjee on May 29, 2021 at 9:36 pm

    Thanks for sharing a detailed Itinerary for Oahu and Maui. I have been to Oahu and would love to visit Maui someday. Love your pics.

    • Taylor Deer on May 29, 2021 at 10:30 pm

      Thank you Chirasree! You would love Maui! It is so beautiful. 🙂

  11. Suvarna Arora on May 30, 2021 at 1:07 am

    This Itinerary is great for when I plan Hawaii. That shaved ice cream had me drooling. I would refer to this when I plan my trip in the future.

    • Taylor Deer on May 30, 2021 at 8:29 pm

      Thank you Suvarna! The shaved ice truly was delicious! 🙂

  12. Lena Eriksen on May 31, 2021 at 4:44 am

    Hawaii is on the top of my long bucket list! Great itinerary and so lovely photos that make me want to pack my bags right away 🙂

    • Taylor Deer on June 1, 2021 at 10:24 am

      You would love Hawaii so much! It is such a beautiful destination! 🙂

  13. Cosette on May 31, 2021 at 11:43 am

    Great itinerary. Would love to drive the road to Hana and visit Pearl Harbor. The food also looks amazing.

    • Taylor Deer on June 1, 2021 at 10:24 am

      Thank you Cosette! The Road to Hana was my favorite part of the trip. 🙂

  14. Helena on June 4, 2021 at 8:39 am

    Such a dream of mine to visit Hawaii and do an itinerary like this! Saved for hopefully a future trip!!

    • Taylor Deer on June 8, 2021 at 10:01 am

      Yes, you definitely have to go! Hawaii is amazing!!! You would love it Helena! 🙂

  15. Lyne on June 5, 2021 at 7:32 am

    This look like a dream itinerary! The photos are so beautiful, I had never heard about pineapple wine but that sounds delicious!

    • Taylor Deer on June 8, 2021 at 10:01 am

      Thank you Lyne! It was such a great trip and the wine was absolutely delicious! 🙂

Leave a Comment





Taylor-Hana-Maui1

A woman enjoying a vacation on the Hawaiian Islands of Oahu and Maui

There is nothing like a trip to Hawaii! From an early age, visiting the Hawaiian Islands had been a dream and I was so excited to have had the opportunity to finally visit in March 2021. After incredible experiences at two Hawaiian Islands, I am excited to finally share my 10 Day Oahu and Maui itinerary!

Some fun facts about Hawaii are that there are a total of 137 islands, but only eight of them are recognized and seven are inhabited. The eight islands based on popularity are Oahu, Maui, the island of Hawaii (also known as The Big Island), Kauai, Molokai, Lanai, Niihau and Kahoolawe. The capital of Hawaii is Honolulu, which is located on the island of Oahu, it became the 50th state on August 21, 1959.

A woman enjoying her 10 day Oahu and Maui itinerary

During my 10-day trip to Hawaii, I adventured with fellow travel blogger Alex of East Coast Contessa. We spent the first half of our trip on the island of Oahu and the second half on the island of Maui, discovering West Maui and Hana. Both islands were beautiful and offered a lot of wonderful gems, but they both differed as well.

If you are planning a Hawaiian Islands trip, I recommend following along this wonderful 10 day Oahu and Maui itinerary.

**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like.


Pin the Below Image to Keep Handy

10-day Oahu and Maui Itinerary

Traveling to Hawaii in 2021:

A woman at the botanical gardens on Oahu, which was part of her 10 day Oahu and Maui itinerary

Even though Hawaii is part of the United States, there was a quarantine mandate when I traveled there in March 2021. Everyone traveling to Hawaii from mainland USA can test out of the 10-day quarantine for Oahu, Maui, Molokai, Lanai and the Big Island by following the state’s Safe Travels program. (Kauai joined the Hawaii Safe Travels Program on April 5, 2021.)

For those traveling to Hawaii and want to avoid the 10-day quarantine, you can take an NAAT PCR test from a Hawaii Trusted Traveler testing site within 72 hours from the last leg of your trip. Since I flew from Newark Airport in New Jersey to Honolulu with a layover in Los Angeles, I needed to take my test within 72 hours from when I departed LAX. (Please be mindful of the time differences.) You can see which testing sites are part of Hawaii’s Safe Travels Program. I took my test at American Family Care+ Urgent Care.

A beach in Maui, Hawaii

After getting my negative test results back, stating that I took it at a Trusted Traveler’s site, I had to enroll in Hawaii’s Safe Travels Program where I uploaded a PDF file of my negative test results and filled out a health questionnaire within 24 hours prior to the last leg of my trip. I then received a QR code that allowed me to hop on my flight to Hawaii. (Please make sure you follow all directions because you will only get one QR code!) Alex had to do the same thing, but she traveled from Evansville Regional Airport in Indiana to Honolulu with a layover in Dallas/Fort Worth.

Please note that when you fly United Airlines, you could save time when you arrive in Hawaii by getting “Cleared” ahead of time. All you must do is show your QR code from the Safe Travels site and your ID to the customer service desk during the last leg of your trip (so I did mine at LAX) and they will issue you a wrist band that you quickly show upon arrival in Hawaii.

A woman admiring a waterfall on the Road to Hana, part of a 10 day Oahu and Maui itinerary

In addition, since both Alex and I traveled from Oahu to Maui, we needed to take a second rt-PCR test in Oahu within 72 hours before we departed to Maui because there are inter island restrictions. Since we were only in Oahu for four days, we had to take our tests on our second day. (As of April 9, 2021, all travelers to Maui will need to take an additional test when they land in Maui to avoid a 10-day quarantine.)

We took our PCR test at The National Kidney Foundation of Hawaii at The Monarch Hotel in Honolulu. They take walk ups and it was a self-swab test. (It was super easy to do and there is someone instructing you through the entire process.)

We got our negative results via email within six hours after we took our test. Once we got our results, we uploaded them onto the Hawaii Safe Travels site again, filled out another health questionnaire within 24 hours prior to our departure to Maui and got another QR code that we needed to present upon arrival on the island.

Getting to Oahu and then Maui:

A beautiful Hawaiian sunset

Getting to Hawaii is easy. I flew from Newark Liberty International Airport in New Jersey to Honolulu International Airport in Hawaii on the island of Oahu with a short layover in Los Angeles International Airport in California. After spending 4 days on Oahu, we flew from Honolulu International Airport to Maui’s Kahului Airport where we spent the remaining 6 days on Maui. I found super affordable flights through Skyscanner!

No matter which island you visit in Hawaii, I HIGHLY recommend renting a car so that you can explore and not miss out on anything. Oahu’s TheBus is known as Hawaii’s best public transportation method and you can take it to different areas around the island. In Maui, there is also a public bus transit system that includes 13 different routes, including one that goes to and from the airport. Please note that there are no bus routes to Hana.

Both Oahu and Maui have Uber and Lyft services!

10 Day Oahu and Maui Itinerary

A woman enjoying a 10 day Oahu and Maui itinerary vacation

Oahu Itinerary:

Discover the top 10 best things to do on Oahu!

Day 1: Arrive in Honolulu

A woman horseback riding on the North Shore of Oahu, which was part of a 10 day Oahu and Maui itinerary

Arrive in: Honolulu International Airport

Where to Stay: Honolulu/Waikiki

Hotel Recommendation: The Equus Hotel

Where to Eat in Honolulu/Waikiki:

A woman at The Equus Hotel in Honolulu

Both Alex and I arrived in Honolulu later in the evening, so the only things we did on that day was check into The Equus, grab dinner at Chiba-Ken, which is a Japanese restaurant in the city, and enjoy Paniolo Bar at the hotel.

Overall, The Equus Hotel is known as Hawaii’s Best Lifestyle Hotel and it offers comfortable rooms, a welcoming bar that is open for everyone to enjoy delicious food and beverages and there is also a refreshing dipping pool to cool off in.

Day 2: Enjoy Waikiki Beach, Hike Diamond Head and Admire the Views at Nu’Uanu Pali

A woman enjoying Waikiki beach during her time on Oahu

One of the most popular beaches in the world and a popular thing to include during your 10 day Oahu and Maui itinerary is spend time at Waikiki Beach.

This beautiful beach features two miles of white sand beaches, comforting aqua blue waters and high-rise beachfront hotels. Other great things to do at Waikiki Beach is to take a surfing lesson, watch professional surfers, enjoy an event and walk around Ala Moana Regional Park that surrounds the beach area.

Not too far from Waikiki is Diamond Head. This beautiful mountain is a volcanic cone, located in the most popular State Park of Hawaii. Hiking Diamond Head will take you to the edge of the 300,000-year-old crater. This hike includes a 1.8-mile, easy to moderate trail and it costs $1 USD per walk-in visitor and $5 USD per vehicle to enter Diamond Head State Monument. It is also heavily trafficked.

A woman enjoying the views at Nu'Uanu Pali, which was part of a 10 day Oahu and Maui itinerary

Another epic thing to do on the second day (or first full day) of your 10 day Oahu and Maui itinerary is enjoy the panoramic views at Nu’Uanu Pali Lookout. It is free to get into this area and it costs $3 USD to park your vehicle. It’s an amazing spot for sunrise!

For dinner, head over to one of the best Thai restaurants in Honolulu called Maile’s Thai at Ward. Both the food and drinks are unbelievable!

Day 3: Tour Pearl Harbor, Adventure around the North Shore, Attend a Hawaiian Luau

Pearl Harbor on Oahu

A 10 day Oahu and Maui itinerary would not be complete without paying a visit to Pearl Harbor. Visiting Pearl Harbor on Oahu is both a somber and educational experience.

During a tour through Pearl Harbor, stories will be told of those who were there on December 7, 1949, when the bombing took place. A tour through Pearl Harbor will also take you on a boat ride to the Peace Memorial. While you’re on the boat, you will see plaques sticking out of the water, indicating where ships sank on December 7, 1949.  The actual Peace Memorial stands above the USS Arizona, which is the only ship that sank that wasn’t taken out of the water.

Fumi's Shrimp Truck on the North Shore of Oahu

After exploring Pearl Harbor, head to the North Shore that features beautiful beaches, breathtaking waterfalls, awesome food trucks and more!

Check out Waimea Falls on the North Shore before having lunch at Fumi’s Shrimp Truck; it is beautiful! Even though there are a plethora of food trucks ranging from traditional Hawaiian to poke and fresh seafood to shaved iced, Fumi’s Shrimp Truck is one of the best along the North Shore! (The coconut shrimp and buttered garlic shrimp are bomb.)

A woman horseback riding at Hawaii Polo Club on the North Shore

When you’re finished with lunch, head over to Hawai’i Polo Club to enjoy a lovely horseback ride along the beach in Waialua. You can admire all of the stunning views of the aqua blue ocean and nearby mountains. On certain days, you can even see sea turtles, whales and even Hawaiian monk seals.

Later in the day, it is fun to attend a traditional Hawaiian luau such as Ka Moana Luau at Sea Life Park. At a luau you can enjoy and dance to live music, watch cultural performances and savor traditional hula cuisine such as poi, pulled pork, poke, coconut pudding and more.

Day 4: Visit Ho’omaluhia Botanical Garden and Byodo-In Temple and Relax at Lanikai Beach

Exploring Ho'omaluhia Botanical Garden on Oahu, which is part of a 10 day Oahu and Maui itinerary

A stunning gem and place that takes your breath away on Oahu is Ho’omaluhia Botanical Garden. Located on 400 acres, these gorgeous gardens represent botanical collections from the Philippines, Malaysia, Tropical America, Polynesia, India, Sri Lanka and Africa.

Overall, Ho’omaluhia Botanical Gardens is one of the most beautiful spots on Oahu and it should most definitely be on your 10 day itinerary for Oahu and Maui. You can also go fishing, set up a campsite, enjoy a picnic, walk around and do so much more at this spot!

A woman admiring the peacefulness at Byodo-In Temple on Oahu, which is part of a 10 day Oahu and Maui itinerary

Another amazing spot to visit on Oahu is Byodo-In Temple. Hawaii has a lot of Japanese influence and there is a Buddhist temple, located at the bottom of Ko’olau Mountain in the Valley of the Temples Memorial Park, to walk around and admire.

Byodo-In Temple was made in memory of the first Japanese immigrants to Hawaii. This temple on Oahu is a smaller replica of the Byodo-In Temple in Uji, Kyoto, Japan. There is a lush garden, a koi pond, meditation area and so much more.

Charcoal pancakes from Basalt in Waikiki

After checking out the gardens and temple, head back to Waikiki to enjoy brunch at Basalt. This award-winning restaurant features an incredible brunch and dinner menu along with a great happy hour and wine list. For brunch, their signature charcoal buttermilk pancakes and French toast with coco-macnut crunch are two popular staples to try! The French pressed coffee and guava mimosa did not disappoint as well.

Once you’re finished with brunch, get ready to head to the beach! Known as Oahu’s “most beautiful” beach, Lanikai in Kailua is a favorite amongst many.

A woman enjoying a beach day at Lanikai Beach in Kailua

At Lanikai Beach, you can relax on the warm sand, swim in the stunning blue waters, go on a hike, have fun on a rowboat and/or kayak plus, grab food in town and shop! No matter what, you MUST put Lanikai Beach on your 10 Day itinerary for Oahu and Maui. (If you’re looking for great ice cream in Kailua, head to Banan in town. They have delicious ice cream and you can even enjoy a sundae in a pineapple!)

For dinner, make reservations for Duke’s Waikiki. It is a great Hawaiian restaurant that is known for its wonderful dishes and amazing hula pie for dessert!

Maui Itinerary:

A woman enjoying her 10 day Oahu and Maui itinerary

Discover more about West Maui and the best spots on Road to Hana in detail.

Arrive in: Kahului Airport

Where to Stay: Days 5-7, stay at Napili Kai Beach Resort in Lahaina and Days 8-10, stay at Hana Maui Resort in Hana

Where to Eat in West Maui:

Where to Eat in Hana:

Day 5: Fly to Maui

A woman enjoying her stay at Napili Kai Beach Resort in West Maui

After enjoying one last breakfast on Oahu, head over to the airport to fly to Maui, the next island to explore on your 10 day itinerary!

After landing in Maui, we rented another vehicle and drove around an hour to Napili Kai Beach Resort in West Maui. This beautiful beach resort is located in Lahaina and it is perfect for those on a family vacation, honeymoon/couples’ getaway, girls’ trip and more.

A woman sitting on a rock in Lahaina

When you first arrive and check into the hotel, I recommend enjoying the resort and relaxing. Napili Kai has its own beach on Napili Bay where you can relax and sunbathe on the beach as well as stand up paddle board, swim, surf and boogie board in the ocean. There are also four pools and two hot tubs to enjoy, a spa, various events and more at this great resort!

For dinner on your first night in West Maui, I recommend eating next door to Napili Kai at Merriman’s, which is located at Kapalua Resort. 90% of everything served at Merriman’s are locally grown or caught, using sustainable methods. When you go out to dinner at Merriman’s, you can enjoy a 4-course prix-fixe dinner or choose a meal from the amazing bar menu.

Day 6: Soak Up the Sun at Lahaina Beach and Explore Dragon’s Teeth

A woman enjoying the waves at Dragon's Teeth, which is part of a 10 day Oahu and Maui itinerary

On your second day in West Maui, enjoy breakfast at Napili Kai’s Sea House Restaurant. You can savor everything from an all-American breakfast to cinnamon rolls and Korean fried rice to frittatas. After breakfast, relax at the beach! The beaches in Lahaina are so beautiful.

A cool spot to enjoy in Maui and a bucket list item on a 10 day Oahu and Maui itinerary is Dragon’s Teeth at Makaluapuna Point. This epic spot features cool rock formations and is a great place to watch giant Pacific waves crash along the cliffs. The unique rock formations at Dragon’s Teeth were formed when the lava from the West Maui volcano went into the ocean. Heavy winds and waves forced it back and it cooled into black teeth-looking rocks. There is also a labyrinth at Dragon’s Teeth!

An Hawaiian shaved ice from Coconut Caboose in Maui

For an afternoon snack, I recommend checking out Coconut Caboose, which is a fun food truck that sells Hawaiian shaved ice, located off of Honoapiilani Highway that overlooks Honokahua Bay.

Everything that Coconut Caboose offers is vegan and organic and all of their shaved ice is made out of frozen coconut water from coconuts hand-picked earlier in the morning. In addition to Hawaiian shaved ice, Coconut Caboose also has raw coconut gelato, fresh coconuts, popsicles, juices and more!

After watching the sunset at Napili Kai, enjoy a lovely seafood dinner at the resort’s Sea House Restaurant. They also have great tropical drinks as well.

Day 7: Day Trip to Wailea and Sunset Dinner at Whaler’s Village

A woman enjoying a beach day in Wailea, which is part of a 10 day Oahu and Maui itinerary

Another great spot to add to your 10 day Oahu and Maui itinerary is Wailea, which features stunning beaches!

On day 7, drive a little over an hour to Maluaka Beach, which is also known as Turtle Town in Wailea-Makena. This specific beach is free to relax at, swim and even spot sea turtles if you’re lucky! The sand is soft, the water is a clear aqua blue and there are breathtaking views all around.

In addition to the beach, there are also great restaurants, shops, golf courses and hiking trails to enjoy in Wailea! Check it all out if you have time.

Hula pie from Hula Grill in Maui

Later in the day, head back to West Maui and enjoy a sunset while watching the surfers at Black Rock Beach, located at the north end of Ka’anapali Beach. Overall, Black Rock Beach is great for sunbathers, surfers, boogie boarders and snorkelers.

During your time at Black Rock Beach, also grab dinner at Hula Grill in Whaler’s Village. Both Duke’s, which I talk about above in Oahu, and Hula Grill are owned by the same parent company and feature delicious Hawaiian cuisine. An evening at Hula Grill would not be complete without enjoying a Hula pie for dessert. (I recommend sharing it because it is huge!) It is made with macadamia nut ice cream, hot fudge, toasted macadamia nuts and whipped cream and it includes an Oreo cookie crust! It’s delicious!

Day 8: Snorkel at Molokini Crater

On your last morning in West Maui, I recommend grabbing breakfast in the town of Lahaina at Cruzin’ Café. This quaint breakfast spot and coffee shop offers locally roasted Hawaiian coffee, Italian sodas, breakfast sandwiches, hoagies, shaka dogs (which are hog dogs in a Hawaiian sweet roll) and Hawaiian shaved ice.

Molokini Crater in Maui

One of the most memorable day excursions in Hawaii that you must include on your 10 day itinerary for Oahu and Maui is to go snorkeling at Molokini Crater with GetYourGuide. During this three-hour snorkeling excursion with Maui Snorkeling, you will take a boat from Maalaea Harbor to Molokini Crater.

During the sail to Molokini Crater, you will enjoy breathtaking views and even see a few whales. Overall, Molokini Crater is a crescent-shaped atoll and it was formed from a volcanic eruption that happened around 230,000 years ago. You can enjoy snorkeling and diving at this wonderful location and during your adventure, you can even spot different fish, coral, nurse sharks and more!

A woman snorkeling at Molokini Crater, which is part of a 10 day Oahu and Maui itinerary

The overall experience visiting Molokini Crater with GetYourGuide was a lot of fun. There was also a packed lunch available for us and they even set up an inflatable water slide that you could take from the top deck of the boat into the ocean. It was loads of fun!

After your epic day of snorkeling, head over to Hana Maui Resort. I recommend driving over to the resort as soon as your tour ends because it takes around two hours to get there and you will need to drive the Road to Hana since that is where Hana Maui is situated.

Hana Maui Resort in Hana, Hawaii

One of the most important things to bring on a journey around the Road to Hana is a map/GPS. Please make sure to download directions on your phone when you have service because there is barely any cell phone reception on the Road to Hana. I also recommend bringing proper hiking clothing, an optional change of clothes (I brought a dress for pictures), cash, comfortable hiking shoes or sneakers, bug spray, sunscreen, motion sickness medication (if you get car sick easily), an umbrella or poncho, a water bottle, a swimsuit for the beaches, sunglasses, a hat and hand sanitizer (since some of the restrooms along the road don’t have soap containers).

Once you arrive at Hana Maui and check in, I recommend grabbing dinner at Hana Ranch Restaurant, which features farm-to-table Hawaiian cuisine and great drinks.

Day 9: Drive the Road to Hana

A woman enjoying a drive along Road to Hana in Maui, which is part of a 10 day Oahu and Maui itinerary

A MUST do during a 10 day Oahu and Maui itinerary is drive the Road to Hana. I recommend waking up early to start your adventure because there is so much to see and do along this amazing road! I also don’t recommend driving Road to Hana at night since there are no streetlights and everything closes at a certain time. You definitely don’t want to miss out on anything and you don’t want to put yourself in danger!

Our day exploring Road to Hana in Maui was a self-guided driving tour with our own vehicle. There are numerous guided tours that you can take around Road to Hana and you can download the Shaka Guide, which is a Road to Hana app that guides you on a tour for a small price.

Hana Lava Tube on Road to Hana

For breakfast, I recommend savoring fruit bread and a freshly brewed cup of coffee at Nahiku Café. After you fuel up, explore the Hana Lava Tube! At $12 USD per person (cash only), you will be given a flashlight and can head into the caves to explore. Before you enter the cave itself, there are beautiful gardens with stunning plant life for you to admire.

The cave at Hana Lava Tube was formed a little less than a thousand years ago because of molten lava coming up from underground and flowing towards the ocean. As the lava was draining out, that was when the tunnel was formed. It will take you around 40 minutes to walk through and explore Hana Lava Tube. It is a cool experience!

Coconut Glen's vegan ice cream on Road to Hana in Maui

After exploring Hava Lava Tube, cool off to some vegan ice cream at Coconut Glens. This colorful food truck offers organic and vegan ice cream in a variety of different flavors and it’s delicious!

As you continue on, explore the beautiful Hanawai Falls, the waterfalls at Pua’a Ka’a State Wayside Park, Makapipi Falls and admire the stunning views at all of the overlooks. When you drive along the Road to Hana, you will come across numerous areas where you can pull over.

A woman enjoying Road to Hana on a 10 day Oahu and Maui itinerary

In the afternoon, visit Ka’enae Peninsula, which is a traditional Hawaiian village that suffered devastation after a tsunami that happened in 1946 without warning. Overall, there are beautiful viewpoints along Ka’enae Peninsula for you to enjoy! If you’re hungry, head over to Aunty Sandy’s Banana Bread for delicious banana bread, a smoothie, sandwich or coconut candy.

The last spot to stop at along the Road to Hana before turning around to make your way back to Hana Maui Resort is Bamboo Forest at Haleakala National Park. It will cost you $30 USD to get into the National Park and they also accept the America the Beautiful pass.

Before you go, make sure there is no flash flooding because that is when this specific hike can be dangerous. Overall, the hike isn’t too hard and you will see stunning waterfalls, bayan trees, natural pools and more!

A woman walking on a black sand beach on Road to Hana

On your way back to the resort, your last stop along the Road to Hana should be the Black Sand Beach in Wai’anapanapa State Park. Known as the closest spot to Hana Maui Resort, Wai’anapanapa State Park costs $5 USD to enter and $10 USD to park your vehicle.

The scenery at Wai’anapanapa State Park is beautiful. You can sit and relax at the black sand beach or do an easy hike to see the ocean caves, sea arches, blow hole and more.

Day 10: Taste Pineapple Wine at Maui Wine

A woman enjoying Maui Wine, which is part of a 10 day Oahu and Maui itinerary

On your last day in Maui, I recommend grabbing breakfast at Hana Ranch Restaurant before hitting the road for your next adventure.

Located near the start/end of Road to Hana is Maui Wine, which is a renowned winery on the island. Overall, Maui Wine produces wines made from estate grown grapes, pineapples and raspberries. (It will take you around two hours to drive from Hana Maui Resort to Maui Wine and please be mindful that you will be going in the opposite direction from when you drove on your Road to Hana adventure the day before. The opposite side of Road to Hana is definitely rougher and will require more patience and awareness.)

Pineapple wine tasting at Maui Wine

During a visit to Maui Wine, you have to do the pineapple wine tasting and also try the pineapple champagne, especially if you love pineapple! The food is also tasty.

When you arrive back to Hana, check out the food truck park located next to Hana Maui Resort. This food truck park includes a Thai restaurant, a BBQ joint, places to get tropical fruit bowls and coffee, plus more.

Day 11: Fly Home

A woman enjoying her 10 day Oahu and Maui itinerary

On day 11, wake up at a decent time to head back to Kahului Airport to fly home or to your next destination. It will take you around two hours to drive from the resort to the airport and you will need to take the Road to Hana to get there!


A woman enjoying sunrise at Hana Maui Resort

I hope you all enjoyed discovering the best 10 day itinerary for Oahu and Maui. If you have any questions, please email me at [email protected]

(Alex’s mom made us beautiful, homemade flower crowns and seashell headbands for our Hawaii adventure. Click here to get one for your Polynesian trip!)

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., HI State Capital: Honolulu, Time Zone: Hawaiian-Aleutian Standard Time

Click here to join my private blog sharing Facebook group.

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

Shop my Hawaii Look:

30 Comments

  1. Kim Deer on May 28, 2021 at 6:53 pm

    What an awesome Itinerary for Oahu and Maui ~ You really provided awesome options for touring and eating! So many fabulous things to do there and so many great authentic restaurants to eat at! Your photos are amazing and brings everything to life ~ felt like I went there with you. Dad and I will get back there soon again! And I will definitely use this guide ~ Great blog and beautiful photos of those two breathtaking islands.
    Love you,
    Mom xoxo <3

    • Taylor Deer on May 28, 2021 at 6:58 pm

      Thank you mom! It sure was an incredible trip. I want to go back. <3 love you too!

  2. Sarah Blevins on May 28, 2021 at 7:16 pm

    This has so much great information! Thank you! We have been wanting to get to Hawaii – especially Maui for a long time and I am inspired to really start planning a visit.

    • Taylor Deer on May 29, 2021 at 1:21 am

      Thank you so much Sarah! You would love Hawaii. It is so beautiful! Maui was amazing. 🙂

  3. Erin on May 28, 2021 at 7:58 pm

    The temple looks so beautiful, and I’m really craving a shaved ice from the Coconut Caboose. (If only I could hop on over to Hawaii to satisfy my craving! lol) I love that you lived up to your flower child title with all of the flower crowns in this post. 🙂 Looks like a fantastic trip!

    • Taylor Deer on May 29, 2021 at 1:22 am

      Thank you so much Erin! It really was a great trip. I honestly didn’t want to leave lol. Coconut Caboose truly did have the best shaved ice! 🙂

  4. Sharyn on May 29, 2021 at 4:50 am

    This is such a great itinerary. I love visiting Hawaii but mostly stay in Oahu. Next trip I will head to Maui.

    • Taylor Deer on May 29, 2021 at 10:22 pm

      Thank you Sharyn! Hawaii is so beautiful and I hope to visit Kauai and the Big Island next time. 🙂

  5. Ha on May 29, 2021 at 5:45 am

    Your trip to Oahu and Maui looks amazing! The beaches are so clean and I’m in love with the sunset scene too. I’d love to try charcoal pancake as well. Yummy!

    • Taylor Deer on May 29, 2021 at 10:23 pm

      It really was an incredible place! I loved the beaches as well and the pancakes at Basalt were amazing! 🙂

  6. Jennifer Connarn on May 29, 2021 at 11:58 am

    This looks like the trip of my dreams! What an incredible experience, it sounds like you girls stayed busy and eat/saw so much! I’ve never been to Hawaii but if I ever plan a trip there, I will refer back to some of your tips in this post. So fun!

    • Taylor Deer on May 29, 2021 at 10:27 pm

      It was definitely the trip of my dreams! We had such a great time. You would love Hawaii once you have the opportunity to go. 🙂

  7. Brittany on May 29, 2021 at 3:37 pm

    This is such an awesome guide for Oahu and Maui, Taylor! I’m dying to visit Maui now after my trip to Oahu. Snorkeling at Molokini Crater sounds like an incredible experience. I’d also love to try the pineapple wine. It sounds delicious!

    • Taylor Deer on May 29, 2021 at 10:28 pm

      Thank you so much Brittany! You would absolutely love Maui! I hope to get back as well as see more islands. 🙂

  8. Anna on May 29, 2021 at 4:19 pm

    Looks like such an amazing trip! I would love to get out to Hawaii maybe next year so I’ll be sure to use this and help plan my trip. 🙂

    • Taylor Deer on May 29, 2021 at 10:29 pm

      It really was Anna! I never wanted to leave. 🙂 You would totally love Hawaii!

  9. Rachel H Beland on May 29, 2021 at 4:53 pm

    Pineapple wine!?? Um yes please! The only time I went to Hawaii I was a kid, I need to go back…. just for the wine 😉 Amazing post and a great initerary.

    • Taylor Deer on May 29, 2021 at 10:30 pm

      Yes, the pineapple wine was absolutely delicious! Thank you Rachel, you would love Hawaii as an adult. 🙂

  10. Chirasree Banerjee on May 29, 2021 at 9:36 pm

    Thanks for sharing a detailed Itinerary for Oahu and Maui. I have been to Oahu and would love to visit Maui someday. Love your pics.

    • Taylor Deer on May 29, 2021 at 10:30 pm

      Thank you Chirasree! You would love Maui! It is so beautiful. 🙂

  11. Suvarna Arora on May 30, 2021 at 1:07 am

    This Itinerary is great for when I plan Hawaii. That shaved ice cream had me drooling. I would refer to this when I plan my trip in the future.

    • Taylor Deer on May 30, 2021 at 8:29 pm

      Thank you Suvarna! The shaved ice truly was delicious! 🙂

  12. Lena Eriksen on May 31, 2021 at 4:44 am

    Hawaii is on the top of my long bucket list! Great itinerary and so lovely photos that make me want to pack my bags right away 🙂

    • Taylor Deer on June 1, 2021 at 10:24 am

      You would love Hawaii so much! It is such a beautiful destination! 🙂

  13. Cosette on May 31, 2021 at 11:43 am

    Great itinerary. Would love to drive the road to Hana and visit Pearl Harbor. The food also looks amazing.

    • Taylor Deer on June 1, 2021 at 10:24 am

      Thank you Cosette! The Road to Hana was my favorite part of the trip. 🙂

  14. Helena on June 4, 2021 at 8:39 am

    Such a dream of mine to visit Hawaii and do an itinerary like this! Saved for hopefully a future trip!!

    • Taylor Deer on June 8, 2021 at 10:01 am

      Yes, you definitely have to go! Hawaii is amazing!!! You would love it Helena! 🙂

  15. Lyne on June 5, 2021 at 7:32 am

    This look like a dream itinerary! The photos are so beautiful, I had never heard about pineapple wine but that sounds delicious!

    • Taylor Deer on June 8, 2021 at 10:01 am

      Thank you Lyne! It was such a great trip and the wine was absolutely delicious! 🙂

Leave a Comment





Related posts

Best Cabin Weekend in Broken Bow, Oklahoma

During late April 2021, I was excited to have scratched off another U.S. state off my bucket list – Oklahoma!...

What to do with One Day in Dallas

Dallas, Texas is a thriving city located in Northeastern Texas. It is the 9th largest city in the United States...

Top Peninsula Papagayo Exclusive Resort

Peninsula Papagayo is located on Costa Rica’s Pacific Coast and it is known as Latin America’s ultimate and exclusive coastal...