Top Key West Likely To Sell Out

Watch Key West's sunset — a main island attraction — on an evening dinner cruise. Feast on a tropical-themed buffet dinner and sip provided cocktails, beer, wine, and soft drinks as you take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere, and a cash bar is also available for premium drinks.

Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you on an exhilarating, up-close adventure across crystal-clear waters, winding through lush mangroves, stopping at pristine sandbars, and exploring hidden islands that are off the beaten path. This is your chance to experience Key West like never before — in a fun, fast, and eco-friendly CraigCat boat! Perfect for All Levels: Whether you're an experienced boater or a first-time adventurer, the Craigcat is easy to handle and designed for fun and comfort. With a small, nimble design, you’ll have the freedom to explore areas that larger boats or jet skis can’t reach. Up to 4 boats per tour. 2 guests max per boat. If you have 4 people in your group please make two separate bookings to accommodate your party and so forth up to 8 guests.

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.

The whole family can learn more about sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast to try your luck spotting dolphins, stingrays, turtles, and birds while you learn more about Key West’s waters than you ever would sailing along. Then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat.

Save time and money in Key West on this all-inclusive, full-day excursion. Enjoy a day of sailing, snorkeling, and kayaking off the coast. Visit the Key West National Wildlife Refuge and explore an underwater world full of colorful fish and coral. Includes a buffet lunch with unlimited beer, wine, and soft drinks.

Explore the only living coral reef in North America on this small-group snorkeling adventure aboard a sailing yacht in Key West. You will receive instruction on how to use the equipment, but it’s recommended that participants be comfortable underwater and have the ability to swim. Common sightings include tropical fish, eels, turtles, dolphins, anemones, and urchins.

Sail to a gorgeous snorkeling spot off the coast of Key West to explore a coral reef home to rainbow-colored fish, anemones, eels, and more. On the hour-long sailing trip to the reef, sip included wine, beer, or soft drinks while watching for dolphins and sea turtles. The captain chooses the snorkeling spot according to each day’s conditions, ensuring the best experience for your group.

Getting out on the water is one of the best ways to explore Key West, but many big tours cram their boats with passengers. This private tour promises an un-crowded experience. Head out onto turquoise water aboard a unique tiki bar boat and look out for marine life such as turtles and dolphins as you cruise to a sandbar where you can swim or just soak up the sun.

Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, numbers are restricted to 24 so you have a spot at the rail when it’s time to capture photos of the setting sun.

It's the only full 2-hour jet ski tour in Key West — a longer, more complete ride than the 60–90-minute harbor loops other operators run. ✅ A full 2 hours and a 28-mile loop all the way around the island ✅ Yamaha WaveRunner VX skis — fast, stable, and comfortable ✅ 5–6 scenic stops, from the Southernmost Point to sandbars and wildlife areas ✅ Small-group or fully private options ✅ Local guides who share island history and insider tips

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.

Key West's most mind-blowing sky watch! Search for UFOs with your military-grade night vision scope as we blow your mind with tales of UFOs, UAPs, alien encounters, and the hidden history of UFOs in Key West. Small groups, local guides, little-known history, and oceanfront viewing sites make this a unique, unusual, unforgettable experience. Your $5000 night vision scope will change how you see the night sky forever. This experience is dependent on suitable viewing conditions. If we cancel you will have the option to reschedule or be refunded.

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.

Key West is known for its beautiful coastal scenery and its lively bar scene, but there are few opportunities to combine the two. This tour takes you out onto the crystal-clear water, traveling by a small motor boat that glides through mangrove tunnels on its way to two or three waterfront bar and restaurants.

Eat your way around Key West on a food tour of “mom and pop” eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and delicious key lime pie. The walking tour route takes you off typical touristy streets so you can see Key West like a local, listening to insights about the city's food, architecture, and history along the way. Tastings are enough for a hearty lunch.

Take in rare birds–eye views of Key West on a parasailing adventure over Smathers Beach. With a range of departure times offered throughout the day, this tour is a popular, flexible choice for families. Your guide, who ensures that the small group has a personalized experience, takes photos and videos available for purchase after the trip.

Florida Keys Fishing Experience for the entire family. Serious fishing serious fun! Located in Marathon Key Florida, Wet Tails Charter will give you the charter fishing experience of a lifetime. It doesn’t matter if you are looking for a sunset cruise or to land the fish of a lifetime, Wet Tails Charters is here to make it happen. We offer 4,6,8 and 10hr fishing trips. Please remember if you had a great time to take care of your deck hand who works solely for tips.

Jimmy Buffett has left his mark on Key West since he arrived 50 years ago. If you have a passion for all things Buffett and Margaritaville, this walking tour is the best way to find the locations around Old Key West that inspired his songs. Your guide will also take you to the location of his first gig, some of his favorite watering holes, bars he played in and his recording studio.

Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.

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.

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with only 17 passengers maximum. Avoid the crowds and enjoy sailing, coral reef snorkeling and the wild dolphins that live, feed and breed right along the south side of Key West. Get that yacht feeling with Champagne Service from your professional crew. Tickets are fully refundable if canceled outside of two weeks in advance!

Experience the best that Key West has to offer with this combination tour that includes a dolphin watch, snorkeling, and a view of the island’s famous sunset. Spot dolphins in their natural habitat in the Florida Keys National Marine Sanctuary and snorkel in the blue waters surrounding Key West during this family-friendly excursion.

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.