Gasparilla Pirate Festival weekend – one of the most fun events in the United States! As Captain Jack Sparrow of Pirates of the Caribbean said, “Not all treasure is silver and gold mate.”

One of the top USA destinations to visit during the winter is Florida. Every year, a giant pirate festival takes place during the last weekend of January. (The actual event takes place on a Saturday, but festivities and parties go on all weekend long.)

During January 2014, I traveled south to Sarasota, Florida to visit a friend who was living there at the time.

2014 boasted one of the most brutal NYC winters and it was nice to do a four-day weekend getaway to Florida’s beautiful Gulf Coast to relax on their sugar-fine white sand beaches and attend Gasparilla weekend.

Discover the top things to do on Florida’s Gulf Coast, outside of Sarasota, and read all about my experience during Gasparilla weekend when I attended in 2014.

**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

Traveling to Florida’s Gulf Coast:

When I traveled to the Gulf Coast of Florida for Gasparilla weekend, I flew from Newark Airport to Tampa Airport. I found affordable flights through Skyscanner. (There is also an airport in Sarasota called Sarasota-Bradenton International Airport, but it is easier to find more affordable and convenient flights into Tampa.)

Since Sarasota is around an hour south from Tampa, I took an Uber from the airport. Since I was visiting a friend, we had her car to get around, but I recommend renting a car otherwise.

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

Where to Stay in Sarasota and Tampa:

Throughout the Gulf Coast are numerous hotels and resorts both on the beach and within the cities. You could choose an accommodation based on your budget and there are a variety of Airbnb and Vrbo options as well.

Because I was visiting my friend during Gasparilla weekend, I stayed at her apartment in Bradenton. Just outside of Sarasota are Coquina Beach, Longboat Key and Siesta Key. There are also great hotels to choose from in Tampa as well.

Hotels in Sarasota:

Luxury Option – The Ritz Carlton, Sarasota

Boutique Option – The Sarasota Modern, a Tribute Portfolio Hotel

Mid-Budget Option – Hyatt Regency Sarasota

Budget Option – Comfort Suites Sarasota – Siesta Key

Hotels in Tampa:

Luxury Option – Epicurean Hotel, Autograph Collection

Boutique Option – Hotel Haya

Mid-Budget Option – Hampton Inn & Suites, Ybor City Downtown

Budget Option – Holiday Inn Express & Suites Tampa/Rocky Point Island

What to do on Florida’s Gulf Coast:

Enjoy a Beach Day at Coquina Beach and Long Boat Key:

During a Gasparilla Pirate Festival weekend, I highly recommend exploring more of the Gulf Coast because the beaches are absolutely stunning!

Florida’s West Coast typically tends to draw a retirement community as compared to the party-central East Coast of the state, but it was nice to be able to sit on the beach in both Coquina Beach and Longboat Key in peace and quiet when I visited in 2014.

I let the sun hit my face while I read a book. It was the perfect way to begin a vacation!

Both Coquina Beach and Long Boat Key feature miles of shoreline, powdery white sand and beautiful palm trees.

There are specific beach areas for hotels, condos and private properties, so we stayed on the public area, which I liked better since we didn’t get views of tall hotels and apartment complexes.

One side of the beach was the Gulf of Mexico and the other side was beautiful palm trees and sea grass paths. It was gorgeous!

Explore Downtown Sarasota:

Sarasota is a beautiful city filled with stunning beaches, amazing restaurants, wonderful shops and so much more! It is definitely a MUST visit during a Gasparilla weekend.

During our first night in Sarasota, my friend and I enjoyed Japanese hibachi at Tsunami Sushi & Hibachi. Afterwards, we went to a great island-inspired bar called Tommy Bahama Restaurant & Bar. 

The next day, we grabbed breakfast and then went into historic St. Armand’s Circle that is nestled between the beautiful blue waters of the Sarasota Bay and Gulf of Mexico.

This charming and quaint circle is the vision of its founder – circus magnate John Ringling. In St. Armand’s Circle, you can stroll around the “Circus Ring of Fame”, shop at one of the high-end stores or enjoy a holiday extravaganza!

The day we went to St. Armand’s Circle was beautiful and luckily, it wasn’t too crowded!

One of our first stops in St. Armand’s Circle was Daiquiri Deck to enjoy one of their many flavors of frozen drinks as well as a seafood lunch.

I got an Electric Lemonade daiquiri and it was absolutely delicious. (All of their drinks are so colorful!) I also loved how our table was outside where we got amazing views of St. Armand’s Circle!

When we were finished with our daiquiris, we strolled around the circle where we window shopped and made our way into a beautiful jewelry store, pasta place, coffee shop, gelato stand and more!

In St. Armand’s Circle, you can find people enjoying the day by bike riding around the area; tourists from all over the world shopping in designer boutiques; top-of-the-line restaurants offering amazing cuisine and lively nightlife that everyone enjoys! I definitely recommend coming to this area if you are in the Gulf Coast vicinity.

Watch the Sunset at America’s Favorite Beach:

After wandering through Downtown Sarasota, we made our way to the world-famous Siesta Key Beach, which is home to the best white sand beach in America.

Similar to the first two beaches I went to outside of Sarasota, Siesta Key had a beautiful path full of palm trees. When we got onto the beach, the sand was absolutely amazing! It had a very light powder texture that made it feel so soft on the souls of my feet. I loved it!

We hung around Siesta Key Beach for a while; walking up and down the shoreline, making sand art, sunbathing and reminiscing.

My friends and I loved this beach so much that we ended up staying there for a while and even caught one of the most beautiful sunsets!

Throughout my travels, I have seen breathtaking sunsets in Indonesia, Greece, California, Sicily and the Jersey Shore. Siesta Key has definitely made its way to one of the top.

Gasparilla Weekend in Tampa

Everything to do during Gasparilla Weekend:

Have Fun in Downtown Tampa:

During one of our evenings on the Gulf Coast, we all got ready to head up to the hotel we were staying at in Tampa. We went to Tampa at night rather than the morning of Gasparilla so that we could enjoy the nightlife and make a full weekend out of it.

After we settled into our hotel and got ready, we hit up Ybor City – Tampa’s historic downtown area. Prior to going to Tampa, I didn’t really know much about the city.

I was actually surprised by how cute it was when we were there. The streets were all lit up in Christmas lights, the Southern architecture was charming and the liveliness got us all excited!

Ybor’s 7^th Avenue is the main commercial street that features countless bars and clubs, restaurants, hotels, art museums and more!

After grabbing pizza at a stand on the street, we started the night at a jazz bar and then spent the rest of our evening dancing at Club Prana – Ybor’s premier nightclub that features five levels, all with a different theme. In addition to that, Prana also has a nice rooftop bar that overlooks the entire city of Tampa. We had a blast!

Gasparilla Pirate Festival:

On the day we went to Gasparilla, we had absolutely gorgeous weather in Tampa and we couldn’t wait to start the celebrations! The event took place right alongside Tampa Bay, which made it even more awesome.

Gasparilla is similar to New Orlean’s Mardi Gras, except everyone dresses up as a pirate. There is a huge parade that goes down the main boardwalk area along the bay where people throw beads.

All of the houses surrounding the bay had open parties; the local bars and restaurants had great specials going on and we met several new friends that day!

The history behind the Gasparilla events celebrate the legend of José Gaspar (also known as Gasparilla), a mythical Spanish pirate who supposedly operated in Southeast Florida in the early 1800s.

During Gasparilla weekend, we got to dance, laugh, sing, eat, drink and have fun all day long.

We started the day at a fun pirate brunch and then ended the night having an amazing tapas dinner at Ceviche Tapas Bar & Restaurant. It was one of the best Spanish restaurants I’ve eaten at in the United States and it was the perfect way to end our amazing four-day weekend in Florida.

Ps. If you are staying longer in Tampa and want to visit a fun amusement park, Busch Gardens is definitely the place to go!

Overall, I had an amazing time having fun at Gasparilla and relaxing on the beaches of the Gulf Coast.

If you have any questions about my Gasparilla weekend or my time on Florida’s Gulf Coast, please email me at info@browneyedflowerchild.com.

Make sure to pin this post if you find it useful!

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., FL State Capital: Tallahassee, Time Zone: Eastern Standard Time

Looking for the best agency to book your next bespoke travel experience? Contact Crawford Concierge!

*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 Gasparilla Weekend Look: