Top Florida Holidays

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.

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.

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.

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.

Catch the thrill of fishing while enjoying the stunning waters of Destin on our party boat. Sweet Jody Fishing offers a unique fishing adventure that combines family fun with the excitement of deep-sea and bottom fishing. Our experienced crew, led by Captain Aaron Finkley, is dedicated to ensuring you have a memorable experience on the Gulf of Mexico. Suitable for anglers of all ages, each trip is designed to be enjoyable and educational, perfect for both beginners and seasoned fishers alike. Join us in the ‘World’s Luckiest Fishing Village’ for a day of fishing and laughter with loved ones.

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.

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!

Enjoy a memorable evening on the water with Keylypso's Craft Beer & Wine Sunset Cruise. Glide along the Intercoastal as the sun sets over Palm Beach, providing stunning views of Peanut Island and luxurious waterfront estates. Sip on an array of craft beers and wines while relaxing in a spacious covered seating area. Soft music enhances the ambiance as you create unforgettable memories with friends or that special someone. This 2-hour cruise is perfect for any occasion, making it an ideal way to unwind and appreciate the beauty of Florida's coastline. - Duration: 2 hours of relaxation on a spacious catamaran - Enjoy craft beer, wine with great company - Maximum capacity of 34 guests for an intimate experience - Witness breathtaking views of the sunset and coastal scenery

Sail along St. Augustine’s picturesque coastline—and indulge in a number of generous wine samples—during this two-in-one tour. Make your own way to the dock, hop aboard the pontoon boat, and get comfortable: as you set off, you’ll see landmarks like the Castillo de San Marcos, the Bridge of Lions, and more. You’ll also taste six different wines, and will have access to the on-board bar.

The Moonshine Mixology Class is an island-themed experience where you'll learn to craft 2 tropical cocktails using signature Moonshine. The class includes: A hands-on lesson to make 2 signature cocktails A tasting flight of 6 craft island rums Led by expert mixologists, you'll discover the techniques and secrets behind making perfect island-inspired drinks.

Experience Fort Lauderdale and Hollywood, Florida aboard a narrated water taxi that takes you to 20 different stops, where you can get on and off as you like. Discover historic landmarks such as the Stranahan House and vibrant hubs including Las Olas Boulevard. Enjoy waterfront dining at 15th Street Fisheries, explore the elegant Hilton Marina, cruise by Bahia Mar and the International Swimming Hall of Fame, and much more.

Step into a ready-made party on this adults-only night cruise in Miami. Skip planning a bar or club crawl, and board a comfortable boat to dance and party on Miami’s waters. Sip two included cocktails as a live DJ pumps out top hits on the lighted dance floor; and lose yourself in the upbeat vibe. Take time out when needed to savor further drinks (extra cost) from the bar and soak in the skyline views—the perfect party backdrop.

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.

Discover a side of Key West some visitors miss, and immerse yourself in its beautiful scenery, on a half-day sailing tour. Board your catamaran and head to North America's only living coral barrier reef. Pass some of Key West’s top attractions on the way, then dive in to see hundreds of species of colorful fish, coral, and other sea life. This cruise includes snorkeling gear, plus beer, wine, and soft drinks.

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.

Travel deep into Everglades National Park on a private airboat tour and wildlife encounter at Sawgrass Recreation Park. Experience the unique subtropical ecosystem on your own airboat, going deeper into the Everglades than on typical public rides. Skim across the grassy water at high speeds while looking for alligators, fish, turtles, and wading birds. This tour includes entrance to the park and admission to the Reptile and Glades exhibits.

Avoid busy bars and clubs and get out on the water with this Miami boat party. Don’t worry about expensive bar tabs, as this is an all-inclusive party, with an open bar that’s stocked with whiskey, vodka, rum, tequila, and soft drinks. During the trip, access beautiful views of the Miami skyline, take part in dance contests, and enjoy great music from a live DJ and MC.

Enjoy a comfortable and flexible way to explore the best of St. Augustine on this narrated Old Town trolley tour. See dozens of points of interest, such as the Old Jail, Flagler College, and Spanish colonial neighborhoods. Along the way, discover more about America’s oldest city, founded in 1565, from your conductor, and listen as they share in-depth narration about St. Augustine's history.

Harken back to yesteryear on a fun Fort Lauderdale sightseeing cruise aboard the Carrie B paddlewheeler. Sail past yachts, mansions, and cruise ships along the New River, Intracoastal Waterway, and Port Everglades. Spend time on the open sun deck, sit outside under a canopy, or in air-conditioned comfort on the main deck. The captain narrates the tour and a full-service bar and light snacks are available to purchase.

St. Augustine is no stranger to spirits, spectors, and somethings that go bump in the night. As the oldest continuously occupied colonial city in the United States, it has a bloody real-life history that’s inspired ghostly tales. Decide for yourself whether or not some of the Ancient City’s landmarks are resting places for the undead during this exciting pub crawl. You’ll visit bars and restaurants where the employees and patrons report ghostly encounters.

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.

Rent a jet ski in Ft. Lauderdale and head out to discover the intracoastal waterways. Check out the mansions and yachts that line the waterways during this excursion. Feel the exhilaration of the jet ski while exploring the area at your own pace. Life jackets and water-tight bags for your belongings are provided.