Gasparilla-1

From the Beaches of Sarasota to a Pirate Festival

Pin the Below Image to Keep Handy

Gasparilla Weekend on the Gulf Coast of Florida

Gasparilla Weekend on the Gulf Coast of Florida

Gasparilla Pirate Festival – 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.” As I write this on the last day of summer, I am realizing it is that time of the year to start thinking about winter getaways and there isn’t a better and easier place to go to than sunny Florida during the month of January. (Gasparilla Pirate Festival will take place on Saturday, January 25, 2020.)

Gasparilla Weekend on the Gulf Coast of Florida

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.

Gasparilla Weekend on the Gulf Coast of Florida

Discover the top things to do on Florida’s Gulf Coast, outside of Sarasota, and read all about my experience at Gasparilla.

**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.


Gasparilla Weekend on the Gulf Coast of Florida

Getting to the Gulf Coast:

Gasparilla Weekend on the Gulf Coast of Florida

When I traveled to the Gulf Coast, I flew from Newark Airport to Tampa. I found affordable flights through Skyscanner. 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:

Gasparilla Weekend on the Gulf Coast of Florida

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

What to do on Florida’s Gulf Coast:

Gasparilla Weekend on the Gulf Coast of Florida

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

Gasparilla Weekend on the Gulf Coast of Florida

Florida’s West Coast typically tends to draw more of 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. I let the sun hit my face while I read a book. It was the perfect way to begin a vacation.

Gasparilla Weekend on the Gulf Coast of Florida

Both Coquina Beach and Long Boat Key feature miles of shoreline, powdery white sand and beautiful palm trees. Certain beach areas were for hotels, condos and private property so we stayed in 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:

Gasparilla Weekend on the Gulf Coast of Florida

Sarasota is a beautiful city filled with stunning beaches, amazing restaurants, wonderful shops and so much more! 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

Gasparilla Weekend on the Gulf Coast of Florida

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!

Gasparilla Weekend on the Gulf Coast of Florida

One of our first stops in St. Armand’s Circle was to 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!

Gasparilla Weekend on the Gulf Coast of Florida

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:

Gasparilla Weekend on the Gulf Coast of Florida

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!

Gasparilla Weekend on the Gulf Coast of Florida

We hung around Siesta Key Beach for a while; walking up and down the shoreline, making sand art, sunbathing and reminiscing. We loved this beach so much that we ended up staying there for a while and even caught one of the most beautiful sunsets!

Gasparilla Weekend on the Gulf Coast of Florida

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.

Everything to do in Tampa and Gasparilla:

Gasparilla Weekend on the Gulf Coast of Florida

Have Fun in Downtown Tampa:

Gasparilla Weekend on the Gulf Coast of Florida

During one of the evenings, we all got ready to head up to the hotel we were staying at in Tampa. We went to Tampa at night rather than in the morning of Gasparilla so that we could enjoy the nightlife.

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!

Gasparilla Weekend on the Gulf Coast of Florida

Ybor’s 7th 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 night 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:

Gasparilla Weekend on the Gulf Coast of Florida

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 Weekend on the Gulf Coast of Florida

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!

Gasparilla Weekend on the Gulf Coast of Florida

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.

Gasparilla Weekend on the Gulf Coast of Florida

During Gasparilla, 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!


Gasparilla Weekend on the Gulf Coast of Florida

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 Gasparilla or Florida’s Gulf Coast, please email me at [email protected].

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., FL State Capital: Tallahassee

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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2 Comments

  1. Aswani on September 24, 2019 at 8:12 pm

    This sounds so much fun Taylor! I need to visit Florida ASAP!

    • Taylor Deer on September 24, 2019 at 11:29 pm

      It really was a blast! Florida has a lot to offer (including Disney). 🙂

Leave a Comment





Gasparilla-1

From the Beaches of Sarasota to a Pirate Festival

Pin the Below Image to Keep Handy

Gasparilla Weekend on the Gulf Coast of Florida

Gasparilla Weekend on the Gulf Coast of Florida

Gasparilla Pirate Festival – 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.” As I write this on the last day of summer, I am realizing it is that time of the year to start thinking about winter getaways and there isn’t a better and easier place to go to than sunny Florida during the month of January. (Gasparilla Pirate Festival will take place on Saturday, January 25, 2020.)

Gasparilla Weekend on the Gulf Coast of Florida

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.

Gasparilla Weekend on the Gulf Coast of Florida

Discover the top things to do on Florida’s Gulf Coast, outside of Sarasota, and read all about my experience at Gasparilla.

**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.


Gasparilla Weekend on the Gulf Coast of Florida

Getting to the Gulf Coast:

Gasparilla Weekend on the Gulf Coast of Florida

When I traveled to the Gulf Coast, I flew from Newark Airport to Tampa. I found affordable flights through Skyscanner. 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:

Gasparilla Weekend on the Gulf Coast of Florida

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

What to do on Florida’s Gulf Coast:

Gasparilla Weekend on the Gulf Coast of Florida

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

Gasparilla Weekend on the Gulf Coast of Florida

Florida’s West Coast typically tends to draw more of 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. I let the sun hit my face while I read a book. It was the perfect way to begin a vacation.

Gasparilla Weekend on the Gulf Coast of Florida

Both Coquina Beach and Long Boat Key feature miles of shoreline, powdery white sand and beautiful palm trees. Certain beach areas were for hotels, condos and private property so we stayed in 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:

Gasparilla Weekend on the Gulf Coast of Florida

Sarasota is a beautiful city filled with stunning beaches, amazing restaurants, wonderful shops and so much more! 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

Gasparilla Weekend on the Gulf Coast of Florida

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!

Gasparilla Weekend on the Gulf Coast of Florida

One of our first stops in St. Armand’s Circle was to 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!

Gasparilla Weekend on the Gulf Coast of Florida

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:

Gasparilla Weekend on the Gulf Coast of Florida

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!

Gasparilla Weekend on the Gulf Coast of Florida

We hung around Siesta Key Beach for a while; walking up and down the shoreline, making sand art, sunbathing and reminiscing. We loved this beach so much that we ended up staying there for a while and even caught one of the most beautiful sunsets!

Gasparilla Weekend on the Gulf Coast of Florida

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.

Everything to do in Tampa and Gasparilla:

Gasparilla Weekend on the Gulf Coast of Florida

Have Fun in Downtown Tampa:

Gasparilla Weekend on the Gulf Coast of Florida

During one of the evenings, we all got ready to head up to the hotel we were staying at in Tampa. We went to Tampa at night rather than in the morning of Gasparilla so that we could enjoy the nightlife.

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!

Gasparilla Weekend on the Gulf Coast of Florida

Ybor’s 7th 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 night 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:

Gasparilla Weekend on the Gulf Coast of Florida

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 Weekend on the Gulf Coast of Florida

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!

Gasparilla Weekend on the Gulf Coast of Florida

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.

Gasparilla Weekend on the Gulf Coast of Florida

During Gasparilla, 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!


Gasparilla Weekend on the Gulf Coast of Florida

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 Gasparilla or Florida’s Gulf Coast, please email me at [email protected].

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., FL State Capital: Tallahassee

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.

2 Comments

  1. Aswani on September 24, 2019 at 8:12 pm

    This sounds so much fun Taylor! I need to visit Florida ASAP!

    • Taylor Deer on September 24, 2019 at 11:29 pm

      It really was a blast! Florida has a lot to offer (including Disney). 🙂

Leave a Comment





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Wyoming is a beautiful state located in the American West. It is known for its natural wonders, Old West history...

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