Travel Tuesday with Taylor to Florida’s Gulf Coast

Posted on Social Impact, Travels with Taylor November 14, 2017 by Taylor Deer

From the Beaches of Sarasota to Gasparilla Pirate Festival

by Taylor Deer

“Not all treasure is silver and gold, mate.” – Captain Jack Sparrow of Pirates of the Caribbean

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It’s 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!

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Throughout my college years, I saw several people attend the famous Gasparilla Pirate Festival in Tampa, FL. Every year, I would see fun pictures on Facebook and from that, I knew I wanted to make my way there at some point. The winter after I had graduated from college, I decided to book a four-day weekend getaway to Florida’s beautiful Gulf Coast to relax on their sugar-fine, white sand beaches and attend Gasparilla.

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During January 2014, I was working in NYC during one of the city’s most brutal winters. I could remember how I needed to cover every inch of skin on my body as I walked down 42nd street to my old job. After almost getting frostbite, I knew I had to get away to a warm destination and figured it was a good time to visit my great friend Courtney who was living in the Sarasota area.

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As I departed from Newark Airport at the crack of dawn on a Thursday morning, I was more than ready to put on one of my sundresses and flip-flops. The flight from the Greater New York City area to Tampa is a little less than two hours. I arrived early in the morning so that I could enjoy four full days in Florida. My friend Courtney picked me up from Tampa and we drove 45 minutes south to the Sarasota area where she was living. During the drive, there were countless palm trees off the side of the Interstate and beautiful blue waters all around. It was night and day compared to snowy New Jersey!

(Please don’t mind the quality of the pictures in this post. I went on this trip almost four years ago and being a travel blogger was not on my mind during that time of my life. I guess it is true when they say that all of the best things in life come when you least expect it.)

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After arriving at Courtney’s old apartment and settling in, we got ready to hit up Sarasota’s famous beach towns of Coquina Beach and Long Boat Key. I was so excited to visit Long Boat Key specifically because my grandparents used to live there during the winter when my nana was alive. (They were snowbirds.) I always wanted to go and stay with them during my spring break, but because I was a competitive dancer, I unfortunately never made it to their place because of competition season, so it was amazing to finally experience it!

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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 peace and quiet and let the sun hit my face while I read a nice book. (Talk about a perfect way to start off a vacation!)

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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 were beautiful palm trees and sea grass paths. It was gorgeous!

After our beach day, we headed back to Courtney’s apartment and then got ready for dinner and drinks in downtown Sarasota. Both Courtney and I LOVE hibachi, so we went to a delicious restaurant in Sarasota called Tsunami Sushi & Hibachi Grill. I enjoyed shrimp hibachi, while Courtney got the vegetarian dinner. It was so good and it hit the spot!

When we were finished with our meal, it was time to pick up our other good friend from college, Dorothy! At the time, Dorothy was living in North Carolina, so she flew separately to meet us and enjoy the weekend. Dorothy was lucky enough to get a flight that flew directly into Sarasota’s airport. (Unfortunately, it is almost impossible to find a flight into Sarasota from the Greater New York City area.)

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Since the three of us were back together after not seeing each other for a while, we couldn’t wait to have the time of our lives like we did in college! We went back into downtown Sarasota where we went to a great island-inspired bar called Tommy Bahama Restaurant & Bar. We were all exhausted from traveling, so we stayed for a drink or two before we headed back to Courtney’s apartment to rest up before our next adventure.

The next day, we went to a breakfast place that offered the same southern hospitality I used to receive when I went to brunch in my dining hall during my college years. Unfortunately, I don’t remember the name of this place, but there are so many breakfast and brunch places in the Sarasota area, you won’t have trouble finding a nice restaurant.

After we fueled ourselves up, we 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 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 to Daiquiri Deck to enjoy one of their many flavors of frozen drinks. Since it was January when we went to the Gulf Coast area, the weather wasn’t boiling hot, which was nice, but it may have been a little chilly for a daiquiri. I personally didn’t care since I was just way too excited to enjoy a tropical drink in Florida. I got Electric Lemonade, Courtney got Mangorita and Dorothy had the Strawberry daiquiri. They were all delicious and colorful! I also loved how our table was outside where we got amazing views of St. Armand’s Circle!

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When we were finished with our daiquiris, we strolled around the Circle where we window shopped, strolled 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.

Later on, we made our way to the world-famous Siesta Key Beach – home to the best white sand beach in America. Prior to going to the Gulf Coast, my grandparents told me that Siesta Key was one of their favorite beaches in Florida and boy, do I know why! Similar to the first two beaches I went to in the Sarasota area, 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!

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We hung around Siesta Key Beach for a while; walking up and down the shore line, making sand art, sunbathing and reminiscing over college memories. We loved this beach so much that we ended up staying there for a while and even saw the most beautiful sunset!

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Throughout my travels, I have seen gorgeous sunsets on the seas in California, Greece, Italy, the Jersey Shore and in the Blue Ridge and Rocky Mountains, but this sunset at Siesta Key Beach was probably the hardest to top. Since we were on the Gulf Coast, which is the West Coast of Florida, the sun set on the water, making it very peaceful. It was probably one of the most serene places I had been to.

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Later on in the evening, we got ready to head up to our hotel in downtown Tampa. We decided to go there at night so that we could avoid the traffic in the morning. We also heard Tampa had a fun downtown area, so we wanted to enjoy a night out as well.

After we settled into our hotel and got ready, we hit up Ybor City – Tampa’s historic downtown area. For a downtown area in the city of Tampa, this district was super cute! The streets were all lit up in Christmas lights (I love that!), the Southern architecture was charming and the liveliness got us all excited!

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

After having a good night sleep, we woke up refreshed and ready to enjoy the highlight of the trip – Gasparilla Pirate Festival. As I have mention in a previous blog post about my favorite events, Gasparilla definitely outdid itself. It was probably one of the most fun days of my life!

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The day of the event was gorgeous – not a cloud in the sky, the temperature was in the high 70s, everyone was friendly and in a good mood 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!

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

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We got to dance, laugh, sing, eat, drink and have fun all day long. We started the day at a fun pirate brunch (I don’t remember the name) 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 here in the US and it was the perfect way to end our amazing four-day weekend in Florida.

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Overall, I had an amazing time with my best friends on this trip. I hope you all enjoyed reading about my fun and relaxing time in the Gulf Coast area of Florida. Gasparilla will be taking place on Saturday, January 20, 2018. Now is the time to make your plans to go to Gasparilla and enjoy a warm winter getaway. Since most of our team is from Florida, we can help you plan the perfect Gulf Coast getaway this January and February. Contact me at or call our team to book your reservations today!

Happy Travels!


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