Gasparilla Pirate Fest
With Pirates, Parades & Parties
5 Days | January 28 -February 1, 2027
Starting At $Flexible Pricing
Ahoy there, mateys! Get ready for swashbuckling fun at Gasparilla Pirate Fest. This annual reenactment of Tampa’s historic pirate invasion has taken place for over 100 years and features the Jose Gasparilla II and hundreds of vessels comprising the Gasparilla Flotilla sailing across the bay to secure the key to the city. Celebrate their victory with the Parade of Pirates, live music, and festivities. This tour also features great area attractions around Tampa.
Highlights
Tour Highlights:
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Tour Inclusions:
**This tours has $250 Group deposit on acceptance. **Second deposit of $250 per person is due Oct 28 at which time we need to confirm the number of Gasparilla Fest tickets you wish to guarantee. |
Itinerary
Day 1 –Thursday, Jan 28 – Tampa, FL
Arrive today in Florida, where you will enjoy four-night stay at a Tampa area hotel. Dinner on your own this evening.
Day 2 – Friday, Jan 29 – Florida Aquarium – Hyde Park Village – Tampa Bay History Center –– Sunset Pirate Cruise w/Sunset Toast
After breakfast, visit the Florida Aquarium and why The Florida Aquarium is one of the top aquariums in the country! Experience sharks, alligators, lemurs, penguins and much more! Rediscover adventure at the expanded Wetlands Trail where you will venture past alligator-infested waters to the river streams where playful otters explore. Continue your adventure up to the Aquarium’s newest exhibit, Journey to Madagascar. Filled with ring-tailed lemurs, hissing cockroaches and colorful chameleons this exhibit captures the unique Island of Madagascar and the diverse animals that call it home! Be sure to make a stop at Stingray Beach where you can touch stingrays and sharks.
Enjoy free time and lunch on your own at Hyde Park Village, a cornerstone of Tampa’s historic district, offers a distinguished blend of retail and dining within a dynamic lifestyle center. Spanning six city blocks, the Village showcases an eclectic mix of over 60 esteemed local, regional, and national retailers, including recent additions Alice & Olivia and Veronica Beard, complemented by established names like Zimmermann, rag & bone, Barry’s, Anthropologie, Warby Parker, lululemon, Sephora, Nike, Madewell, Kendra Scott, and SuitSupply. The dining scene is equally vibrant, enriched by the Michelin-rated On Swann and the contemporary sushi restaurant ro, adding to a culinary roster that features favorites like bartaco and Meat Market.
The afternoon features a visit to the Tampa Bay History Center. Discover real treasure on Water Street. Inside, three floors unfold the story of Florida and the Tampa Bay region across 12,000 years. Hands-on galleries, short films, and smart interactives invite you to slow down and follow the people and places that shaped this coast. The Touchton Map Library offers a rare look at cartography that changed how the world saw Florida.
Dinner is included this evening at a local restaurant followed by a Sunset Cruise on the pirate ship, The Lost Pearl. Set sail on a pirate adventure like no other as the Florida sun begins its golden descent over the Tampa skyline. Step aboard the Lost Pearl, an authentic interactive pirate ship, for a 1.5 hour voyage that perfectly blends swashbuckling excitement with breathtaking views. Plus, enjoy pirate games & activities and one Sunset Rum Punch Toast. (B,D)
Day 3 – Saturday, Jan 30 – Gasparilla Pirate Festival w/lunch
Enjoy breakfast and a leisurely morning at the hotel before spending the rest of the day at Gasparilla Pirate Fest. The Jose Gasparilla II, carrying hundreds of fierce pirates, sails to Tampa in search of the Key to the City. The ship and its accompanying flotilla travel north across the Bay and into Seddon Channel before they come ashore at the Tampa Convention Center. Once reaching their destination, these scallywags will raise the flags, mark their territory, and take the Gasparilla celebration on land.
The day starts with the Gasparilla Invasion. “Land Ho!” The legendary Jose Gasparilla arrives in style, sailing into the Tampa Convention Center basin along with a magnificent flotilla of hundreds of vessels and the notorious pirates of Ye Mystic Krewe of Gasparilla.
The excitement is palpable when the ship docks at precisely 1:00 P.M., and the captain meets the Mayor of Tampa to make his final demand for the key to the city. It’s a thrilling spectacle that you won’t want to miss!
The afternoon features the Gasparilla Parade of Pirates. The City of Tampa is under pirates’ control! These merry pirates have once again conquered the city with a triumphant invasion, and now it’s time to celebrate! They will march down Bayshore Blvd for a victory parade that follows a 4.5-mile journey along the beautiful Hillsborough Bay through downtown Tampa. Presented by Ye Mystic Krewe of Gasparilla annually since 1904, the parade features approximately 140 units of krewes, floats, marching bands, and social organizations.
Groups will have seating included for the event, with the best views of every passing pirate, parade float, and performance. Lunch will also be included today (boxed lunch or buffet depending on seating choice) (A bus pass for drop-off and pick-up at the seating area is also included)
Seating Options
- First Mate Seating, reserved folding chairs in the first two rows (with a boxed lunch) is included.
- You can upgrade to the Scully Hospitality Tent for an additional $125 per person, it includes:
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- Lunch buffet
- Two drink tickets, followed by a cash bar
- On-site restrooms
- Access to both bleacher and chair seating
Following the parade, enjoy Pirate Fest on your own. Rock pirate style! Seminole Hard Rock Gasparilla Pirate Fest features live music stages along the Tampa Riverwalk. There is live entertainment before and after the parade at Curtis Hixon Waterfront Park (at Ashley and Twiggs Street) and MacDill Park (at Ashley and Whiting Street).
Dinner will be on your own at Pirate Fest. There are 100+ Food, Beverage, and Novelty vendors located on the festival site. (B,L)
Day 4 – Sunday, Jan 31 – Tampa Electric’s Manatee Viewing Center – Sarasota – Ringling Museum of Art – Circus Museum – Bayfront Gardens – Dinner Cruise
After breakfast, head to Apollo Beach, FL and the Tampa Electric’s Manatee Viewing Center (Available Nov-April). Manatees love warm water. And by a stroke of POWERful luck, Tampa Electric can provide it to them! The Big Bend Power Station in Apollo Beach circulates water from Tampa Bay for cooling, then sends the water flowing clean and warm back into the bay. In the winter months, the manatees leave colder waters to return to this warm and welcoming refuge.
Next, head to Sarasota, FL where you enjoy the afternoon at The Ringling. Your admission includes entry to the Museum of Art, Circus Museum, and Bayfront Gardens. Lunch will be on your own at the museums.
The Ringling Museum of Art’s collection represents a vast range of cultures, mediums, techniques, and stories. From ancient Indian sculpture to early photography to immersive contemporary installations to Baroque masterpieces, come discover what sparks your interest.
At the Circus Museum, immerse yourself in circus history, be wowed by incredible human and animal feats, study the amazing logistics of circus management, or try your hand at walking the wire. The Circus Museum’s vast and varied collections are on view throughout two different buildings: the Historic Circus Galleries and the Tibbals Learning Center. Read on to learn more about what you’ll discover in each space.
While visiting The Ringling, you are welcome to explore the vast 66-acre grounds at your leisure. As awe-inspiring as any work of art, the Bayfront Gardens are a living treasure that will awaken all your senses. Relax under the shade of a banyan tree, feel the cooling breezes coming off the bay as you walk along the promenade, and smell the intoxicating perfumes of flowers in bloom. The Bayfront Gardens offer many different plants, trees, sculptures, and trails for you to enjoy all year long.
Returning to Tampa, enjoy a dinner cruise to end the day. Discover spectacular views of Downtown Tampa while enjoying a delicious meal aboard America’s first 3-Diamond-rated dining yacht. After dinner, let the music carry you to the open-air top deck to dance all night with DJ entertainment. (B,D)
Day 5 – Monday, Feb 1 – Depart for Home
After breakfast, depart for home. (B)

