Top Florida Holidays

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.

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.

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.

Combine two activities into one tour and save with this Key West sunset snorkel sail. Not only will you get to relax and listen to the music as you cruise on the Atlantic Ocean during sunset, but you’ll also get to snorkel in a nearby coral reef. Beverages and snorkel equipment are included for added convenience.

PLEASE NOTE: Booking 1 Traveler = 1 row that can seat up to 4 people. Book 2 travelers for groups of 5 - 8 people and you will get 2 rows! Get into the holiday spirit on a trolley tour of St. Augustine’s popular, annual Nights of Lights Festival! Traffic is heavy and crowds are thick for this high demand, often sold-out activity so book ahead to secure your preferred date and time and avoid disappointment! Hop on the trolley, sit back, pop on your 3-D glasses and enjoy a fully immersive holiday experience from more than 3 million lights along the city’s Historic District. After your trolley tour, enjoy a holiday cookie and a cup of hot apple cider.

Do you still believe in holiday magic? Discover it again at the return of Mickey’s Very Merry Christmas Party at Magic Kingdom® Park! Join Mickey and the gang as they host the happiest holiday party of the season. The holiday magic shines bright on select very merry nights during Mickey’s Very Merry Christmas Party at Magic Kingdom Park, November 7–December 21!

See St. Augustine’s spectacular Nights Of Lights Christmas celebration from a different perspective with this fun boat tour. This is an excellent way to see the city shine without being confined in a small vehicle or needing to walk. Float by the Bridge of Lions, see the Old Fort, and marvel at the Old City lit up with holiday cheer.

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! PLEASE NOTE: Your party may be split between more than one boat when booking our public cruise. This is only for the ride to/from Crab Island, and you will be able to go between boats while anchored. If you would like to guarantee that your group stays together, please inquire about our private charters.

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.

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.

Take time out from the daily grind and enjoy wine, beer, prosecco, and frozen cocktails on this two hour cruise along Miami’s coastline. Relax as the sun sets over Miami and then enjoy Miami’s spectacular nighttime skyline light up before you. You get 2 hours of relaxing music, unlimited drinks, and beautiful sights to unwind and de-stress with your family or friends. Seats are limited so make sure to book early. Please note this is not a party cruise, it is a way to relax after a hard week and enjoy the beautiful sights with an eclectic mix of music.

Cruise the stunning waters of Destin on a private 3-hour adventure to Crab Island aboard the Tiki Pub. This unique floating Tiki bar, equipped with a waterslide and bathroom, sets the stage for a fun, social atmosphere. Bask in the sun, keep an eye out for playful dolphins, and enjoy the crystal-clear waters as you sip your favorite drinks. Perfect for groups looking to relax and create lasting memories in a vibrant setting. - 3-hour private cruise to Crab Island on the Tiki Pub with up to 6 guests - Enjoy a floating tiki boat with a waterslide and onboard bathroom - Spot dolphins and soak in the beautiful Destin waters - Bring your own drinks for a personalized experience

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

Limited to an intimate number of passengers, this small-group sunset sail includes an up-close look at dolphins and views of Key West landmarks like Mallory Square, Sunset Key, and Fort Zachary Taylor. Relax on the luxury catamaran to watch the sunset while enjoying tapas such as shrimp cocktail served with wine, champagne, and other alcoholic beverages included in the price.

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.

Escape to the wilderness of Florida's Everglades on this guided, full-day adventure from Fort Lauderdale. This exciting small-group tour includes an airboat ride through Everglades National Park, a drive through Big Cypress National Preserve, a nature walk through a cypress forest, and a scenic boat ride through Everglades National Park in search of a variety of wildlife.

Gather round goblins, gargoyles, ghosts and all! Mickey’s Not-So-Scary Halloween Party is making its return to Magic Kingdom® Park! Join for a ghoulishly good time filled with everything from a themed parade and spelltacular stage show to favorite Characters, a festive fireworks extravaganza and plenty of sweets for all trick-or-treaters. Choose from select nights August 7 – October 31, 2026. Come on...Let’s Boo This! ** Capacity for this event is limited, so get your tickets soon.

St. Augustine’s original “frightseeing” tour provides an evening of fear and fun. Board Ghosts and Gravestones' Trolley of the Doomed for a spooky ride through St. Augustine's sinister past. Listen to stories of the ghosts and ghouls believed to still wander the town’s streets as you pass supposedly haunted hot spots, and visit Potter’s Wax Museum. Expect a tour so scary, it comes with a warning: not recommended for under-13s.

Cool off in Key West on a half-day water sports tour that features 10 different water activities for you to try, from jet skiing to parasailing to banana boat rides to snorkeling, and much more. Enjoy lunch and draft beer on the way back to the marina for those over the age of 21.

Make sure you tick off the most important highlights of the Everglades with an experienced guide in the lead when you book this Everglades airboat tour. Race through the River of Grass listening to in-depth commentary on the local environment and wildlife. Plus, round-trip transport from Fort Lauderdale is provided for a stress-free adventure.

Travel from Fort Lauderdale to Key West with ease on this full-day tour. Drive across the famous 7 Mile Bridge straddling the Gulf of Mexico and Atlantic Ocean on your ride into the Keys, and then explore the island on your own or get out on the water with optional activities that you can add upon booking, including snorkeling, trolley, and a glass-bottom boat tour.

Swim among coral and tropical fish in Key West's living reef on this snorkeling excursion. Sit back and relax on a custom-built boat, and sail to the reef where a professional crew is on hand to provide snorkeling instruction and guidance. After your swim, enjoy included beer, soft drinks, and water on the boat for your ride back. All snorkeling equipment is provided.

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.