Top Florida Seasonal & Special Occasions

Experience a famous Florida Keys sunset from a boat with this private tour. Bring up to six people for a private cruise into Key Largo Bay. Keep an eye out for local wildlife including dolphins, manatees, and birds during the tour. Slow down and watch the sunset from a fresh perspective during this cruise.

Limited to an intimate number of passengers, this small-group sunset sail includes an up-close look at dolphins as well as views of Key West landmarks like the legendary Mallory Square, Sunset Key, and historic Fort Zachary Taylor. Then, relax on the luxury catamaran to watch the sunset as nibble on tapas such as shrimp cocktail served with wine and champagne.

Take a daytime or evening cruise around Clearwater, Florida aboard the Calypso Queen. A lunch or dinner buffet, as well as an open bar featuring rum punch, wine, and beer, is included. A full bar and dessert available for purchase. The evening cruise includes a DJ and dancing.

Spice up any Florida vacation with a cruise on the Gulf of Mexico. Beginning in St. Petersburg, enjoy a beautiful sunset (depending upon the time of year) and listen to live music on board the elegant 'StarLite Sapphire' yacht. Choose from the open-air observation deck or the climate-controlled cabin inside. Either way, the view is spectacular. Then dance the night away or take a romantic stroll along the deck.

Cruise into the sunset on St. Augustine’s sole all-inclusive sunset sail with unlimited beer, wine, and margaritas (non-alcoholic options available) on a luxurious catamaran. As you sip your drink and enjoy complimentary snacks, live music will accompany the colorful setting sun on the water, for an unforgettable night. See the historic city and its landmarks bathed in beautiful colors from the water.

Watch the sun set and the moon rise off the coast of Key West on this relaxing sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer, and soft drinks are included.

Enjoy a one-of-a-kind Florida Keys experience as you cruise across crystal blue waters aboard a floating, palm-thatched Tiki bar. You can swim, vibe to tunes of your choosing, and watch for marine life as the sun paints the sky with breathtaking hues. Your bar comes with almost everything you need for the perfect day: bottle openers, solo cups, a cooler with ice, and an iPad for streaming music. Just bring your own drinks!

Soak up sunset views from the water's edge, and admire a perspective many visitors miss, on this Key West sailing tour. Sample up to eight different wines and/or five different beers as you sail, and indulge in a selection of gourmet hors d'oeuvres to accompany them. As you go, learn more from your crew, and enjoy a festive and celebratory way to toast to your trip.

Spend a few hours out on the water off Panama City Beach's coast on this sightseeing cruise. Get your captain's assistance in spotting local marine wildlife such as dolphins, manta rays, manatees, and sea turtles. This family-friendly cruise includes the chance to play games and dance on the deck on the way back to land.

Ahoy mateys... You have been captured by the pirates for a night of frivolity and fun in Orlando! Join your fellow hostages for a feast fit for a king. Enjoy a swash-buckling, side-splitting musical aboard a fully rigged pirates galleon. Pirate's Dinner Adventure in Orlando is the world's largest and most interactive dinner show!

Whether you’re on Spring break with your girlfriends or backpacking solo, this sunset booze cruise in Fort Myers is the perfect end to a day in paradise. It’s a bring–your-own-booze party boat, so you supply the tipples and your awesome crew take care of the rest – ice buckets, tunes, party games and, with some help from Mother Nature, that glorious Floridian sunset. Come away with lasting memories and some new drinking buddies.

Party on the Florida waters with your pals during this floating BYOB tiki bar experience off Fort Myers Beach. Whether you’d rather sip and sunbathe or mix and mingle with new friends over party games, there’s plenty to enjoy while you float along on the crystal blue sea. All while your crew is on-hand to make sure everyone is staying safe while you have fun.

Planning a night out in Key West with entertainment can add up quickly. This Key West cruise saves you money by combining an open bar with musical entertainment as you sail the waters keeping an eye out for views of the sunset. Plus, it ends early enough to leave you enough time to bar hop afterward if you’d like.

Experience Destin’s top-rated 3-hour Crab Island Sandbar Cruise aboard the Tiki Pub! This floating Tiki bar features a waterslide, onboard bathroom, and a fun, social atmosphere. Enjoy crystal-clear waters, dolphin sightings, and great vibes. Bring your drinks, relax, and make unforgettable memories. The best way to experience Crab Island—book now!

Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.

Experience Key West’s dark side on this fun yet frightening haunted bar crawl. Hear tales of known paranormal activity from your local guide and visit the most eerie bars in Old Town Key West – located in two haunted mansions and repurposed morgue. By the end of the 2‐hour tour, you’ll see ‘Bone Island’ in a different (and profoundly spookier) light.

Clearwater has some of the best voted beaches in the United States and this exciting tiki tour is a great way to experience the Gulf waters. Hop aboard the only U.S. Coast Guard certified tiki boat in Clearwater Beach for a fun day under the sun. Perfect for celebrations, this cruise can hold over a dozen people for a party. An open bar with beers and cocktails is included.

This wine tasting experience offers a structured yet approachable way to build your understanding of different varieties. Guests develop practical tasting skills and gain insight into wine production, helping improve future wine selection. The guided format ensures clear takeaways for all levels, while the small-group setting supports conversation and shared learning. With five wines and paired bites included, it provides a social experience in a convenient historic location.

Cruise the beaches of Destin and ride the waves aboard the world's largest jet ski. See dolphins up close in there natural habitat as our boat is down closer to the water than most. Our experienced captain and crew will stop the boat for photo opportunities and answer any questions you may have through out the tour to the best of their knowledge. Also cruise by and see Crab Island on the tour. The tour is just 1 hour so it will not take up much of your vacation time. Tour is for ages 5 and up due to Coast Guard height restriction

Step aboard an evening cruise for dinner and drinks while you take in views of St. Pete Beach. Watch over the landmarks of St. Pete and munch on food from the tropical-themed buffet. Open bar means you won't go thirsty while jamming to island music from the onboard DJ and other entertainment.

Relax on the water and enjoy stunning views of Naples Bay on a sunset cruise. The boat seats six guests, letting you skip the crowds and enjoy a more personalized experience. You may also see local wildlife such as dolphins, manatees, ospreys, and more. You don't need to worry about bringing anything, since snacks and drinks come with the cruise.

Witness orange, gold, and pink-hued skies as you set sail from the island city of Key West on this evening sailing experience. Experience views of the city as you sail by, including the historic seaport, the Navy Mole, and Mallory Square—keeping an eye out for the square’s sunset celebration—while relaxing on deck with a beer or cocktail.

Check out Crab Island in style on this tiki hut-inspired pleasure cruise. Let your captain steer you and your group to their favorite spot on the sandbank where you can kick back, relax, take a dip, and sip a drink in the crystal blue water. And don’t worry, there’s a restroom on board.