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The Perfect New England Getaway

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A Long Weekend Itinerary for Portland, Maine

A Long Weekend Itinerary for Portland, Maine

Portland, Maine is an underrated city in the United States that definitely deserves more recognition. Between the poetic harbors and wharfs, delicious lobster, picturesque lighthouses and the charming city, there is so much to fall in love with in Portland.

A Long Weekend Itinerary for Portland, Maine

Not to get confused with Portland, Oregon, Portland, Maine is a completely different city on the East Coast. During May 2017, my friend and I did a mini road trip to Portland to experience all of the jewels this stunning New England city is known for.

A Long Weekend Itinerary for Portland, Maine

Below is the perfect weekend itinerary for Portland, Maine.

**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.


How to Get to Portland, Maine:

A Long Weekend Itinerary for Portland, Maine

The drive from the New York City area to Portland is around 6 hours. As you drive north, you will pass by Stamford, Connecticut; Hartford, Connecticut; Worcester, Massachusetts; Portsmouth, New Hampshire and a few smaller cities and towns that you could stop in, explore and grab food. 

In addition to New York City, Portland is a great city to drive to from Boston, which is only a 2.5-hour drive; Montréal, which is a 5.5-hour drive; Québec City, which is a 5-hour drive and Providence, which is a 3-hour drive. If you are planning to drive to Portland and don’t want to use the miles on your car, it is recommended that you rent one. In addition, if you aren’t from the Northeast of the United Sates or Canada, you could fly into Portland International Jetport or Portsmouth International Airport at Pease. You could find affordable flights through Skyscanner.

Looking for an RV for your next trip, reserve here!

Where to Stay in Portland, Maine:

A Long Weekend Itinerary for Portland, Maine

When it comes to finding accommodation in Portland, I would say that most hotels in the heart of the city are on the pricier side. My friend and I stayed at Portland Sheraton at Sable Oaks in South Portland. It was about a 10 minute drive to the heart of the city. (There are Ubers and Lyfts in Portland as well. When we went out in the evening, we took either one of these services.)

In addition to hotels, you could also choose from a selection of Airbnb and HomeAway options within the Portland area. Click here to check out the hotels in and around Portland.

Day 1 in Portland, Maine:

A Long Weekend Itinerary for Portland, Maine

Dinner in Portland:

A Long Weekend Itinerary for Portland, Maine

When my friend and I arrived in Portland, we couldn’t wait to start exploring! I was also super excited for some fresh seafood. Since we arrived a little later in the day, we settled into our hotel and then headed to a warm and welcoming waterfront restaurant on Portland’s famous Commercial Street called Boone’s Fish House & Oyster Room. When we arrived in Portland, it was cold and rainy, so Boone’s was a great place to warm up since they have several fireplaces and a great selection of Portland-brewed beers. For dinner, I ate a delicious crab roll on a brioche bun and my friend had lobster mac and cheese. All of Boone’s seafood is fresh and delivered right to the restaurant.

Drinks in Portland:

A Long Weekend Itinerary for Portland, Maine

Our first night took us through history as we made our way around the cobblestoned streets. Our first stop of the night was at Vena’s Fizz House, a corner-side cocktail house with a charming turn-of-the-century atmosphere. Vena’s offers a plethora of drink options for all ages that features fresh ingredient fizz drinks that are both alcoholic and non-alcoholic along with mocktails and cocktails. The adorable bar even has a boutique that offers Vena’s mixology of syrups, infusions and other ingredients to create your own craft cocktails at home.

The best part about Vena’s is that their drinks aren’t too strong. I know everyone has his or her own drink preferences, but I cannot enjoy something when all I taste is alcohol. I ordered a Maple Syrup Switchel that consisted of rum, fresh Maine maple, molasses, ginger, coffee and aromatic bitters. I was able to savor every flavor and it was unforgettable.

After enjoying some time at Vena’s and getting to know the friendly owners, we took the party over to a local Portland bar on Commercial Street called 3 Dollar Dewey’s. This dive bar is a great place to get cheap beer and meet friendly people.

Day 2 in Portland, Maine:

Coffee and Brunch in Portland:

A Long Weekend Itinerary for Portland, Maine

Our second day in Portland was absolutely gorgeous! We wanted to take advantage of the sunny weather, so we headed back into Old Port (downtown Portland) to walk around and grab a freshly brewed cup of coffee at Coffee by Design on Congress Street (there are a few locations throughout the city).

A Long Weekend Itinerary for Portland, Maine

After walking around the neighborhoods with our coffee and admiring all of the cute New England architecture, we were starving for a delicious breakfast. Portland is known to have many great brunch spots, so we had many options to choose from. Since we were in the area, we stopped at an adorable farm-to-table gastro-pub called Little Tap House. When we walked inside, all of the furniture pieces were rustic and the decorations were colorful and charming. I savored a delicious breakfast bowl of home fries, caramelized onion, locally sourced mushrooms and peppers, scallions and topped with fried eggs with a mimosa on the side. It definitely hit the spot!

Stroll around Portland’s Promenade:

A Long Weekend Itinerary for Portland, Maine

Once we finished brunch, we were full, so a walk around the city was well needed. We walked down Congress Street, through a few neighborhoods, before we hit the Eastern Promenade – a breathtaking costal trail, built along an old rail corridor that offers beautiful views of the harbor and Casco Bay.

Since it was a gorgeous day, there were plenty of sailboats in the water, people hanging out on the lawn and East End Beach and, of course, their adorable puppies playing in the chilling water. This 2.1-mile trail allows people to bike, run, bird feed, dog walk and enjoy the day. You can even take a train ride around the promenade and learn more about this wonderful seaport city.

Admire the Picturesque Lighthouses:

A Long Weekend Itinerary for Portland, Maine

The afternoon took us over to South Portland to see the lighthouses. Even though I have spent every summer down the shore, I had never seen a lighthouse in real life prior to this trip. (There is one in New Jersey on Long Beach Island.) Over the years, I have seen lighthouses in Malta, Portugal and Delaware.

The first lighthouse we saw was the Spring Point Ledge Light, right off the Southern Maine Community College campus. The Spring Point Ledge Light is a dangerous obstruction on the west side on the main shipping channel. Unlike many of the lighthouses, this tower is built of brick instead of cast-iron and is located at the end of a 900-foot breakwater. The large pieces of rock allow you to easily walk across the breakwater to the lighthouse. Unfortunately, on the day we went, we were unable to tour the inside of the lighthouse, but it was still cool to walk up to it and enjoy the views of the harbor, pebble beaches, historic forts and the beautiful Casco Bay. I definitely recommend wearing comfortable shoes when you walk across the breakwater because there are a lot of ways you can fall and get hurt.

A Long Weekend Itinerary for Portland, Maine

After our time at Spring Point Ledge Light, we drove 15 minutes into the affluent town of Cape Elizabeth to the stunning Fort Williams Park. The beautiful park features 90 acres of rugged beauty along the Casco Bay. There are several hiking paths with beautiful cliffside views of the water crashing onto the rocks. There are many great lookouts, a rock beach, picnic areas, a playground, ball fields and more!

A Long Weekend Itinerary for Portland, Maine

As you continue to walk south, you can catch a stunning view of the symbolic Portland Head Light modeling its beauty on the coastal cliffs of Cape Elizabeth. The Portland Head Light is located at the head of the primary shipping channel into Portland Harbor. Gazing out at the lighthouse reminded us of why we chose to come to Maine in the first place.

Enjoy the Best Lobster Rolls:

A Long Weekend Itinerary for Portland, Maine

Before coming to Maine, I read on a few travel blogs that the best lobster rolls were found in a small airstream in Fort Williams Park called Bite Into Maine. Since the airstream is so small, we had a tough time trying to locate it, but it gave us the opportunity to explore the park more and interact with the locals. We finally found it and indulged in amazing fresh Maine lobster chunks on a fresh bun. There are so many types of lobster rolls for you to choose from through Bite Into Maine.

Dinner in Portland:

I was recommended by a friend to check out Gilbert’s Chowder House right off the wharf on Commercial Street. I was in the mood for a warm soup, so I was excited to give it a try! I savored a delicious New England clam chowder in a freshly baked bread bowl. It was the perfect light dinner and Gilbert’s offers a warm and welcoming atmosphere.

Drinks in Portland:

The night took us over to Bull Feeney’s a fancy Irish tavern located on Fore Street that offers something for everyone. On the bottom floor, you can grab a drink and sit down at one of their tables and talk with friends. The second story features a dance floor with a room off to the side that hosts Maine’s best cover bands. You can even get seated service and enjoy a lovely Irish brunch or dinner.

Day 3 in Portland, Maine:

A Long Weekend Itinerary for Portland, Maine

Adventure through Southern Maine’s Beaches:

A Long Weekend Itinerary for Portland, Maine

Originally, my friend and I were supposed to do a day trip to Acadia National Park in Bar Harbor, but it was further away than we thought for a day trip. (Looks like I have to make my way back up to Maine.) However, we did end up exploring the beautiful beaches south of Portland to make up for it!

A Long Weekend Itinerary for Portland, Maine

Old Orchard Beach: A half hour south of Portland is Old Orchard Beach. We started our fun day there where we grabbed breakfast, wandered around the boardwalk as well as the beach. (We enjoyed breakfast at Joseph’s by the Sea.)

A Long Weekend Itinerary for Portland, Maine

Biddeford Pool: This secluded coastal town has beautiful cedar houses and a breathtaking rock beach. Even though it was Memorial Day Weekend when we traveled to Biddeford Pool, there wasn’t a soul around! We walked around the rock beach towards the white sand beach. The cool part about these beaches is that they have a small hiking trail through the woods and meadows that you walk through to get to them. During this time, we got to see a lot of birds.

A Long Weekend Itinerary for Portland, Maine

Kennebunkport: The small town of Kennebunkport is just as beautiful as Biddeford Pool, except there were more people. I loved all of the colorful trees in the beach area. It was so breathtaking! We also enjoyed walking around the downtown area and grabbing some coffee, snacks and more before heading back to Portland.

Dinner in Portland:

Since it was our last night in Portland, we wanted to get a nice dinner on the water. We were able to enjoy a beautiful sunset and delicious lobster rolls (for one last time) at DiMillo’s on the Water. Instead of getting drinks afterwards, we ended up grabbing dessert at Gorgeous Gelato.

Day 4 in Portland:

A Long Weekend Itinerary for Portland, Maine

Donuts for Breakfast:

It was raining pretty hard during our last morning, so we wanted to get on the road early. We first stopped at The Holy Donut located in Old Port before hitting the road. Their donuts are delicious and made with locally grown potatoes. It was tasty, unique and the perfect way to end our time in Portland.

Click here to discover more to do in Portland, Maine.


A Long Weekend Itinerary for Portland, Maine

I hope you all enjoyed reading about my long weekend getaway itinerary for Portland, Maine. If you have any questions about my time in Portland, please email me at [email protected].

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., ME State Capital: Augusta

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.

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6 Comments

  1. Merrie Rodriguez on August 15, 2019 at 11:43 pm

    This is my husbands DREAM vacation!! We are hoping to get there ASAP lol!

    • Taylor Deer on August 16, 2019 at 9:17 am

      Portland is so beautiful, you guys would love it so much! If you have the time too, I recommend visiting Acadia National Park too.:)

  2. Anna on August 16, 2019 at 11:59 am

    It sounds like a wonderful way how to spend a long weekend ♥!
    And Donuts for breakfast – seriously?? That must be soo amazing :D!!!

    • Taylor Deer on August 16, 2019 at 12:38 pm

      Yes, it was quite lovely and Maine is so peaceful! lol yes, I need to do better about not having donuts for breakfast, but they are amazing! 🙂

  3. Aswani on August 16, 2019 at 2:25 pm

    Didn’t realize there is a Portland in Maine! Gorgeous picture Taylor. Makes me want to visit this place!

    • Taylor Deer on August 17, 2019 at 5:18 pm

      Yes, it’s so beautiful and the seafood is amazing! You definitely have to go at some point.

Leave a Comment





DSC_0035

The Perfect New England Getaway

Pin the Below Image to Keep Handy

A Long Weekend Itinerary for Portland, Maine

A Long Weekend Itinerary for Portland, Maine

Portland, Maine is an underrated city in the United States that definitely deserves more recognition. Between the poetic harbors and wharfs, delicious lobster, picturesque lighthouses and the charming city, there is so much to fall in love with in Portland.

A Long Weekend Itinerary for Portland, Maine

Not to get confused with Portland, Oregon, Portland, Maine is a completely different city on the East Coast. During May 2017, my friend and I did a mini road trip to Portland to experience all of the jewels this stunning New England city is known for.

A Long Weekend Itinerary for Portland, Maine

Below is the perfect weekend itinerary for Portland, Maine.

**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.


How to Get to Portland, Maine:

A Long Weekend Itinerary for Portland, Maine

The drive from the New York City area to Portland is around 6 hours. As you drive north, you will pass by Stamford, Connecticut; Hartford, Connecticut; Worcester, Massachusetts; Portsmouth, New Hampshire and a few smaller cities and towns that you could stop in, explore and grab food. 

In addition to New York City, Portland is a great city to drive to from Boston, which is only a 2.5-hour drive; Montréal, which is a 5.5-hour drive; Québec City, which is a 5-hour drive and Providence, which is a 3-hour drive. If you are planning to drive to Portland and don’t want to use the miles on your car, it is recommended that you rent one. In addition, if you aren’t from the Northeast of the United Sates or Canada, you could fly into Portland International Jetport or Portsmouth International Airport at Pease. You could find affordable flights through Skyscanner.

Looking for an RV for your next trip, reserve here!

Where to Stay in Portland, Maine:

A Long Weekend Itinerary for Portland, Maine

When it comes to finding accommodation in Portland, I would say that most hotels in the heart of the city are on the pricier side. My friend and I stayed at Portland Sheraton at Sable Oaks in South Portland. It was about a 10 minute drive to the heart of the city. (There are Ubers and Lyfts in Portland as well. When we went out in the evening, we took either one of these services.)

In addition to hotels, you could also choose from a selection of Airbnb and HomeAway options within the Portland area. Click here to check out the hotels in and around Portland.

Day 1 in Portland, Maine:

A Long Weekend Itinerary for Portland, Maine

Dinner in Portland:

A Long Weekend Itinerary for Portland, Maine

When my friend and I arrived in Portland, we couldn’t wait to start exploring! I was also super excited for some fresh seafood. Since we arrived a little later in the day, we settled into our hotel and then headed to a warm and welcoming waterfront restaurant on Portland’s famous Commercial Street called Boone’s Fish House & Oyster Room. When we arrived in Portland, it was cold and rainy, so Boone’s was a great place to warm up since they have several fireplaces and a great selection of Portland-brewed beers. For dinner, I ate a delicious crab roll on a brioche bun and my friend had lobster mac and cheese. All of Boone’s seafood is fresh and delivered right to the restaurant.

Drinks in Portland:

A Long Weekend Itinerary for Portland, Maine

Our first night took us through history as we made our way around the cobblestoned streets. Our first stop of the night was at Vena’s Fizz House, a corner-side cocktail house with a charming turn-of-the-century atmosphere. Vena’s offers a plethora of drink options for all ages that features fresh ingredient fizz drinks that are both alcoholic and non-alcoholic along with mocktails and cocktails. The adorable bar even has a boutique that offers Vena’s mixology of syrups, infusions and other ingredients to create your own craft cocktails at home.

The best part about Vena’s is that their drinks aren’t too strong. I know everyone has his or her own drink preferences, but I cannot enjoy something when all I taste is alcohol. I ordered a Maple Syrup Switchel that consisted of rum, fresh Maine maple, molasses, ginger, coffee and aromatic bitters. I was able to savor every flavor and it was unforgettable.

After enjoying some time at Vena’s and getting to know the friendly owners, we took the party over to a local Portland bar on Commercial Street called 3 Dollar Dewey’s. This dive bar is a great place to get cheap beer and meet friendly people.

Day 2 in Portland, Maine:

Coffee and Brunch in Portland:

A Long Weekend Itinerary for Portland, Maine

Our second day in Portland was absolutely gorgeous! We wanted to take advantage of the sunny weather, so we headed back into Old Port (downtown Portland) to walk around and grab a freshly brewed cup of coffee at Coffee by Design on Congress Street (there are a few locations throughout the city).

A Long Weekend Itinerary for Portland, Maine

After walking around the neighborhoods with our coffee and admiring all of the cute New England architecture, we were starving for a delicious breakfast. Portland is known to have many great brunch spots, so we had many options to choose from. Since we were in the area, we stopped at an adorable farm-to-table gastro-pub called Little Tap House. When we walked inside, all of the furniture pieces were rustic and the decorations were colorful and charming. I savored a delicious breakfast bowl of home fries, caramelized onion, locally sourced mushrooms and peppers, scallions and topped with fried eggs with a mimosa on the side. It definitely hit the spot!

Stroll around Portland’s Promenade:

A Long Weekend Itinerary for Portland, Maine

Once we finished brunch, we were full, so a walk around the city was well needed. We walked down Congress Street, through a few neighborhoods, before we hit the Eastern Promenade – a breathtaking costal trail, built along an old rail corridor that offers beautiful views of the harbor and Casco Bay.

Since it was a gorgeous day, there were plenty of sailboats in the water, people hanging out on the lawn and East End Beach and, of course, their adorable puppies playing in the chilling water. This 2.1-mile trail allows people to bike, run, bird feed, dog walk and enjoy the day. You can even take a train ride around the promenade and learn more about this wonderful seaport city.

Admire the Picturesque Lighthouses:

A Long Weekend Itinerary for Portland, Maine

The afternoon took us over to South Portland to see the lighthouses. Even though I have spent every summer down the shore, I had never seen a lighthouse in real life prior to this trip. (There is one in New Jersey on Long Beach Island.) Over the years, I have seen lighthouses in Malta, Portugal and Delaware.

The first lighthouse we saw was the Spring Point Ledge Light, right off the Southern Maine Community College campus. The Spring Point Ledge Light is a dangerous obstruction on the west side on the main shipping channel. Unlike many of the lighthouses, this tower is built of brick instead of cast-iron and is located at the end of a 900-foot breakwater. The large pieces of rock allow you to easily walk across the breakwater to the lighthouse. Unfortunately, on the day we went, we were unable to tour the inside of the lighthouse, but it was still cool to walk up to it and enjoy the views of the harbor, pebble beaches, historic forts and the beautiful Casco Bay. I definitely recommend wearing comfortable shoes when you walk across the breakwater because there are a lot of ways you can fall and get hurt.

A Long Weekend Itinerary for Portland, Maine

After our time at Spring Point Ledge Light, we drove 15 minutes into the affluent town of Cape Elizabeth to the stunning Fort Williams Park. The beautiful park features 90 acres of rugged beauty along the Casco Bay. There are several hiking paths with beautiful cliffside views of the water crashing onto the rocks. There are many great lookouts, a rock beach, picnic areas, a playground, ball fields and more!

A Long Weekend Itinerary for Portland, Maine

As you continue to walk south, you can catch a stunning view of the symbolic Portland Head Light modeling its beauty on the coastal cliffs of Cape Elizabeth. The Portland Head Light is located at the head of the primary shipping channel into Portland Harbor. Gazing out at the lighthouse reminded us of why we chose to come to Maine in the first place.

Enjoy the Best Lobster Rolls:

A Long Weekend Itinerary for Portland, Maine

Before coming to Maine, I read on a few travel blogs that the best lobster rolls were found in a small airstream in Fort Williams Park called Bite Into Maine. Since the airstream is so small, we had a tough time trying to locate it, but it gave us the opportunity to explore the park more and interact with the locals. We finally found it and indulged in amazing fresh Maine lobster chunks on a fresh bun. There are so many types of lobster rolls for you to choose from through Bite Into Maine.

Dinner in Portland:

I was recommended by a friend to check out Gilbert’s Chowder House right off the wharf on Commercial Street. I was in the mood for a warm soup, so I was excited to give it a try! I savored a delicious New England clam chowder in a freshly baked bread bowl. It was the perfect light dinner and Gilbert’s offers a warm and welcoming atmosphere.

Drinks in Portland:

The night took us over to Bull Feeney’s a fancy Irish tavern located on Fore Street that offers something for everyone. On the bottom floor, you can grab a drink and sit down at one of their tables and talk with friends. The second story features a dance floor with a room off to the side that hosts Maine’s best cover bands. You can even get seated service and enjoy a lovely Irish brunch or dinner.

Day 3 in Portland, Maine:

A Long Weekend Itinerary for Portland, Maine

Adventure through Southern Maine’s Beaches:

A Long Weekend Itinerary for Portland, Maine

Originally, my friend and I were supposed to do a day trip to Acadia National Park in Bar Harbor, but it was further away than we thought for a day trip. (Looks like I have to make my way back up to Maine.) However, we did end up exploring the beautiful beaches south of Portland to make up for it!

A Long Weekend Itinerary for Portland, Maine

Old Orchard Beach: A half hour south of Portland is Old Orchard Beach. We started our fun day there where we grabbed breakfast, wandered around the boardwalk as well as the beach. (We enjoyed breakfast at Joseph’s by the Sea.)

A Long Weekend Itinerary for Portland, Maine

Biddeford Pool: This secluded coastal town has beautiful cedar houses and a breathtaking rock beach. Even though it was Memorial Day Weekend when we traveled to Biddeford Pool, there wasn’t a soul around! We walked around the rock beach towards the white sand beach. The cool part about these beaches is that they have a small hiking trail through the woods and meadows that you walk through to get to them. During this time, we got to see a lot of birds.

A Long Weekend Itinerary for Portland, Maine

Kennebunkport: The small town of Kennebunkport is just as beautiful as Biddeford Pool, except there were more people. I loved all of the colorful trees in the beach area. It was so breathtaking! We also enjoyed walking around the downtown area and grabbing some coffee, snacks and more before heading back to Portland.

Dinner in Portland:

Since it was our last night in Portland, we wanted to get a nice dinner on the water. We were able to enjoy a beautiful sunset and delicious lobster rolls (for one last time) at DiMillo’s on the Water. Instead of getting drinks afterwards, we ended up grabbing dessert at Gorgeous Gelato.

Day 4 in Portland:

A Long Weekend Itinerary for Portland, Maine

Donuts for Breakfast:

It was raining pretty hard during our last morning, so we wanted to get on the road early. We first stopped at The Holy Donut located in Old Port before hitting the road. Their donuts are delicious and made with locally grown potatoes. It was tasty, unique and the perfect way to end our time in Portland.

Click here to discover more to do in Portland, Maine.


A Long Weekend Itinerary for Portland, Maine

I hope you all enjoyed reading about my long weekend getaway itinerary for Portland, Maine. If you have any questions about my time in Portland, please email me at [email protected].

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., ME State Capital: Augusta

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.

6 Comments

  1. Merrie Rodriguez on August 15, 2019 at 11:43 pm

    This is my husbands DREAM vacation!! We are hoping to get there ASAP lol!

    • Taylor Deer on August 16, 2019 at 9:17 am

      Portland is so beautiful, you guys would love it so much! If you have the time too, I recommend visiting Acadia National Park too.:)

  2. Anna on August 16, 2019 at 11:59 am

    It sounds like a wonderful way how to spend a long weekend ♥!
    And Donuts for breakfast – seriously?? That must be soo amazing :D!!!

    • Taylor Deer on August 16, 2019 at 12:38 pm

      Yes, it was quite lovely and Maine is so peaceful! lol yes, I need to do better about not having donuts for breakfast, but they are amazing! 🙂

  3. Aswani on August 16, 2019 at 2:25 pm

    Didn’t realize there is a Portland in Maine! Gorgeous picture Taylor. Makes me want to visit this place!

    • Taylor Deer on August 17, 2019 at 5:18 pm

      Yes, it’s so beautiful and the seafood is amazing! You definitely have to go at some point.

Leave a Comment





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