Top Key West Private and Luxury

Picture yourself aboard our unique tiki boat, the Lazy Lady, cruising through the crystal-clear waters toward a secluded sandbar. The sun is shining bright, and the air is filled with the scent of salt and sunshine. As you approach the sandbar, the boat glides over shallow waters, revealing stretches of soft, white sand inviting you to explore. Once you anchor, the fun begins! You can jump off the boat and wade into the warm, shallow waters, where the gentle waves lap at your feet. The atmosphere is relaxed, with laughter and conversation floating through the air. Some folks might set up beach games, while others enjoy swimming or soaking in the sun. Time seems to slow down as you enjoy this little slice of paradise, surrounded by friends or newfound acquaintances. Whether you’re collecting seashells, taking a dip, or simply lounging in the sun, a sandbar trip on a tiki boat is a perfect blend of relaxation and adventure.

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.

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.

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.

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.

Explore Key West through the eyes of a local on a craft cocktail tour that stops at six off–the–beaten–path establishments for drinks and food tastings, from a historic mansion to a boutique hotel that was once a hospital. In addition to navigating for you, your guide uses the city’s bar scene to give you an overview of its history and culture. The tour includes five craft cocktails and two gourmet food tastings.

Paddle a kayak through mangrove creeks and shallow water on a Key West kayaking tour that offers an up-close look that this unique coastal environment. This guided tour is the perfect way to spot Florida wildlife in a natural habitat.

Discover 28 miles (45 kms) of the Floridian coast on a 1.5-hour Jet Ski tour. With several daily tours, you can easily find a time that fits with your schedule. The tour is priced per Jet Ski, so you can ride tandem with a friend at no additional cost. Your guide is on hand at all times to lead the way on your aquatic adventure.

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 best that Key West has to offer on this narrated, hop-on, hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions, with an expert guide who takes you through the history of the city. Enjoy free admission to the Sails to Rails Museum for extra sightseeing fun.

Pedal through the charming streets of Old Town Key West on a guided bike tour, perfect for first-timers exploring the island. Along the way, you’ll uncover its rich history and stop at iconic spots like Mallory Square, Mile Marker Zero, and the Southernmost Point Buoy. With morning and afternoon tour options, it’s easy to soak in panoramic ocean views and experience Key West at your own pace.

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.

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.

Jam to crowd favorite beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Dance the evening away or relax on the sundeck or in shaded areas as you sip on a margarita, beer, or other beverages. Unlimited drinks and light appetizers are included so you don’t need to pay extra. A great standalone evening activity or the start of a night out.

Explore the best that Key West has to offer on this narrated tour aboard a miniature train. See Key West’s top attractions and learn about the Conch Republic’s history and residents, including Ernest Hemingway and Harry Truman. Get to know Old Town Key West, from the Front Street Depot to Mallory Square, and learn the stories behind the sights from the live on-board commentary.

One of the only Adult Only experiences offered in Key West, our excursions are top-notch, with the vessel, all equipment, food and beverage service being set to premium standards! We offer a more intimate experience with less crowded excursions for the comfort of all of our guests.

Get ready for fun in the sun—and leave all the planning to someone else—on this half-day sailing, kayaking, and snorkeling adventure off the coast of Key West. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef teeming with marine life. Snacks, beer, wine, and soft drinks are included.

Discover some of Key West’s deepest, darkest secrets on a ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of what is said to be one of the most haunted cities in the US. Travel down the narrow, dark streets of the Old Town at night. The wooden houses still bear the secrets of their former inhabitants. This tour is narrated by an actor playing a gravedigger.

After a long day of work or sightseeing, treat yourself to a relaxing 2-hour sunset cruise in Key West. Climb aboard the 47-foot catamaran and set sail along the scenic Floridian coast as the sun sinks into the water. Enjoy unlimited South Florida craft beer, California wine, and hand-crafted cocktails for the duration of the tour.

Key West is famous for stunning sunsets, and this dinner cruise offers the perfect way to enjoy them. Savor breathtaking views as the sky transforms, while indulging in a tropical buffet, live music, and incredible vibes. It’s an unforgettable evening on the water. Relax on a luxury catamaran with an open-air sundeck and fully air-conditioned lower cabin. Grab a drink from the open well bar as live tropical music sets the mood. Every moment is filled with beauty, flavor, and celebration as you soak in Key West’s legendary charm. This popular cruise often sells out, so book your spot today! Don’t miss your chance to experience the best of Key West – sunsets, music, and memories await on this unforgettable adventure.

Visit the only Breadfruit Grove in Continental United States! While here, discover the rich history of Grimal Grove and its legendary founder, Adolf Grimal, on a 75–90-minute tropical fruit hunting tour. This engaging experience takes you through the grove where you'll learn about its 70+ year journey of restoration and resilience. Depending on the season, guests may even have the chance to pick ripe fruits directly from the trees. The tour includes a scenic walking exploration, followed by a delightful tasting session in an outdoor tasting room featuring prepared exotic fruits. - 75–90-minute tour revealing the history of Grimal Grove - Guided walking tour with opportunities to pick fruit (seasonal) - Outdoor tasting experience with a variety of exotic fruits - Learn about the 70+ years of restoration and resilience at the grove

Navigate through the stunning Mangrove Tunnels on this engaging 2-hour kayak tour in Key West. Ideal for all ages and skill levels, this adventure allows you to explore diverse ecosystems while searching for fascinating wildlife like manatees, nurse sharks, and playful dolphins. Led by knowledgeable guides, every excursion provides a unique experience filled with insights about the local flora and fauna. With single and double kayaks available, gather your family or friends for an unforgettable journey through the mangroves. - Tour duration: 2 hours, suitable for ages 6 and up - Max group size of 35, ensuring a personalized experience - Spot wildlife including manatees, sea stars, and birds - Essential gear: sunscreen, water, and waterproof items recommended

Experience Key West’s tropical blue waterways on this Jet Ski tour along the Atlantic Ocean and/or the Gulf of Mexico. Enjoy panoramic island views and watch for dolphins, stingrays, sea turtles, manatees, and more while gliding over warm ocean water. Bring a waterproof camera to capture this southernmost point in the continental United States.