Top Key West Likely To Sell Out in 2026

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.

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.

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.

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.

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.

The glass bottom kayaks is an amazing experience with your tour guides paddling in calm shallow waterways under the stars! Your tour guides will point out sea birds and various sea-life such as different fish species, shrimp, crabs, conch shells which will be well illuminated with your high powered underwater custom LED lights. We paddle along mangrove shorelines and canals so we sometimes even see wild animals such as Racoons along the shoreline. We've also experienced manatees and dolphins on many of the tours. Definitely one of the most exciting things about your kayak tour is that we will feed fish at a certain point of our tour as well which is a blast for everyone! With very little to do at night this is an amazing rare experience under the stars that you'll never forget!

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.

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.

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.

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.

Get front row seats to a stunning Florida Keys sunset, without the hassle of chartering your own vessel, on this catamaran cruise from Key West. Sip on your choice of wine, sparkling, beer, margaritas, or sangria as you watch the sun go down over the water. As you sail, catch glimpses of the island and marvel at the views from the turquoise water.

Get ready to spend a half-day soaking up the sun and enjoying Key West’s diverse ecology during this fun sandbar and mangrove tour. Discover the backcountry waters and secluded sandbars around the busy island, all while sipping on cold drinks. This guided kayak ecotour takes you into the mangrove isles to spot dazzling marine life before heading to a sandy beach to knock back a few alcoholic or nonalcoholic beverages.

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.

It's easy to find the colorful, fun-loving side of Key West, but takes a little more effort to uncover its darker side. This walking tour offers the chance to see Key West in a completely different light. Your guide takes you to landmarks such as St. Paul's Episcopal Church and Capt. Tony's Saloon while discussing the city's spooky, sometimes grisly, history.

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.

The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour of Old Town. Our 4-hour guided experience stops at (6) locations, helping tell Hemingway’s story in Key West & Cuba. Each ticket includes guided entrance into his famed Key West home. Then eat, drink, and explore the island on foot through “Papa’s eyes”, feasting on Cuban cuisine (& 3 boozy beverages) while your knowledgeable local guide impresses with interesting stories & amazing fun facts. The adventure takes you behind the scenes of a 3rd generation family run cigar rolling factory, and into the newly remodeled Social Club at Hemingway Rum Co. for his favorite drink made with his family company’s premium rum. Then finish with a slice of our famous key lime pie! After the tour, you’ll receive a collection of exclusive recipes, recommendations on restaurants, attractions, entertainment, and cultural offerings.

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.

Enjoy a Spectacular Key West Sunset Cruise Looking for the perfect way to end your day? Join us on the Seabreeze, your 42-foot Corinthian powercat, and ride in comfort with this relaxing, catered cruise into the horizon on Key West’s gentle seas. Relax in the shade under the bimini or sunbathe on the bow to take in that last bit of sunshine. Sunset Cruises are a Key West luxury with your panoramic views of the sun melting into tropical waters – and the best way to enjoy is with good food and great drinks! Enjoy elevated hors d’oeurvres without the price tag – a typical selection includes fresh sushi, Thai appetizers, charcuterie platter (meats and cheeses), and French desserts catered by locally owned and operated restaurants. Refreshments include your complimentary selection of fine wine, premium beer, Prosecco, and soft drinks. Departure times vary with the seasons, please confirm your departure time when booking this trip.

Set sail along Key West's coast on a relaxing catamaran cruise combining dolphin watching with a front-row view of the island's famous sunset. Glide across the water aboard a spacious sailing catamaran, with wide-open views of the surrounding seascape and opportunities to spot Atlantic bottlenose dolphins along the way. With fresh fruit and water provided, and space to bring your own drinks, this is a laid-back way to spend an evening on the water.

Highlights:  Explore the world's 3rd largest coral reef, teaming with life Receive expert snorkel instruction, with all gear provided Perfect for beginners and experienced snorkelers Morning trip includes breakfast and unlimited mimosas Afternoon trip features unlimited beer, margaritas, wine and mixed drinks

Kayaking is a great way to experience the Florida Keys but your views are typically limited to what's above the surface of the water. This small-group tour provides clear kayaks that let you discover the underwater world as well. As you paddle, you just need to look below to spot starfish, tropical fish, nurse sharks, turtles, jellyfish and more.

Key West is famous for its sunsets. Rather than joining the crowds at Mallory Square, you can enjoy a more personal, uncrowded experience on this small-group sunset cruise. Aboard a custom tiki bar boat, you can toast the sunset (drinks not included BYOB) while taking in the sights as you cruise around the Key West harbor.