Top 10 Private and Luxury in Key West

Destination: Key West.
Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. This is way more than just a shuttle service. HIGHLIGHTS • See the sights in Key West • Stay for the Key West sunset • Plenty of Free Time • Stops of your choosing along the way • Designated Driver • Narrated Tour Do what you want in Key West! We're doing the driving! During your free time we recommend to sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail. There's so much to do! Sit back & enjoy the scenery as we drive down to Key West. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide. It's more like a road trip than a tour - ask questions, point out wildlife, stop to visit the Florida Keys landmarks of your choosing and more!
Known For: Key West Private Sightseeing Tours, Key West City Tours, Key West Bus Tours, Key West Full-day Tours, Key West Private and Luxury.
Duration: Around 10 hours.

Destination: Key West.
Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or an evening out with family and friends. Departing in the evening as the moon comes up over Key West, enjoy star gazing opportunities and a moonlit sky as the boat glides through the majestic waters at night.
Known For: Key West Sailing, Key West Water Tours, Key West Likely to Sell Out, Key West Likely To Sell Out, Key West Night Cruises, Key West Private and Luxury, Key West Night Tours.
Duration: Around 1 hour and a half.

Destination: Key West.
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. Enjoy a festive hot cocoa and holiday treats as we glide along with water for a fun night in Key West. Our beautiful 105-foot Schooner America 2.0 in full holiday decor that's sure to get you into the Christmas spirit in Key West harbor.
Known For: Key West Private and Luxury, Key West Adventure Tours, Key West Likely to Sell Out, Key West Seasonal, Key West Likely To Sell Out, Key West New Product, Key West Music Tours, Key West Sailing, Key West Christmas, Key West Water Tours, Key West Art Tours.
Duration: Around 1 hour and a half.

Destination: Key West.
Experience an Unforgettable Fishing Adventure in Key West! Join us for an exhilarating private deep-sea fishing adventure on the vibrant waters of Key West. Led by a skilled and experienced captain, our charters cater to both seasoned anglers and first-timers, ensuring an unforgettable experience. Reel in magnificent mahi, wahoo, sailfish, and more. Our knowledgeable crew will guide you to prime fishing spots, employing techniques like trolling, reef, or wreck fishing and many more to maximize your chances of landing a trophy catch. Choose from flexible charter options: 1/2-day, 3/4-day, full-day, or extended 10-12 hour trips tailored to your preferences. Our 36-foot Hatteras "Cowboy" offers comfort and safety with clean facilities, restrooms, , a flybridge, and state-of-the-art equipment. Book now and discover why our private charters are the ultimate choice for a thrilling day on the water in Key West.
Known For: Key West Private Sightseeing Tours, Key West Day Cruises, Key West Full-day Tours, Key West Private and Luxury, Key West Water Tours.

Destination: Key West.
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.
Known For: Key West Private and Luxury, Key West Water Tours, Key West Likely To Sell Out, Key West Sightseeing Cruises, Key West Adventure Tours, Key West New Product, Key West Likely to Sell Out, Key West Spring Break, Key West Day Cruises.
Duration: Around 2 hours.

Destination: Key West.
Paddle through the serene waters of Geiger Key at your own pace, with a private guided kayak/Paddleboard tour that immerses you in the natural beauty of the Florida Keys. Paddle through tranquil mangroves where your expert guide highlights local wildlife and ecological wonders, from tropical bird habitats to vibrant sea turtles. This eco-friendly adventure is suitable for all skill levels, ensuring a relaxing time as you navigate the peaceful waterways. Discover hidden gems and soak in the lush surroundings, all while enjoying small group sizes for a personalized experience.
Known For: Key West New Product, Key West Water Tours, Key West Private and Luxury, Key West Private Sightseeing Tours, Key West Eco Tours, Key West Kayaking Tours, Key West Nature and Wildlife Tours.
Duration: Around 2 hours.

Destination: Key West.
Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy unobstructed views of the sweeping night sky and a fun adventure in Key West at night. Please note there are different options for this experience. Select departures will have live narration from a seasoned local astronomer, or a local guide sharing nautical superstitions with Key West's most famous ghost stores. Select options accordingly at check-out.
Known For: Key West Sailing, Key West Water Tours, Key West Likely to Sell Out, Key West Likely To Sell Out, Key West New Product, Key West Night Cruises, Key West Private and Luxury, Key West Eco Tours, Key West Night Tours.
Duration: Around 2 hours.

Destination: Key West.
Come see for yourself why Marathon Mermaid is voted the #1 thing to do in Marathon! Watching the sunset by water is a must-do when visiting the Keys!
Known For: Key West Sunset Cruises, Key West Zombie Slice, Key West Private and Luxury, Key West Water Tours, Key West Catamaran Cruises , Key West Sightseeing Cruises, Key West Zombie, Key West New Product, Key West Day Cruises.
Duration: Around 2 hours.

Destination: Key West.
Meet The Locals, On Foot, At Eye Level If you’re like us, you think of travel as more than just “going places.” You crave experience and discovery, not just monuments and museums. You want to understand what’s behind the touristic façade that most people never penetrate. That’s why the Southernmost Walking Tour is the best way to immerse you into the history and culture of Key West! When you’re on foot, the world can’t slide past you faster than you can absorb it. You’ll have time – and proximity – to get up close to the region’s culture and natural history. Start your tour at the famous Cuban sandal factory - Kino Sandals before heading off toward the Southernmost Point of the continental United States. Along the way, our incredibly knowledgeable and well-connected local guides will show you the most popular landmarks and introduce you to local culture. By the time you’re finished, you’ll have a uniquely fun perspective of our tiny island!
Known For: Key West Walking Tours, Key West Adventure Tours, Key West Excellent Quality, Key West Private and Luxury, Key West Cultural Tours, Key West Small Group, Key West Historical Tours.
Duration: Around 2 hours.

Destination: Key West.
Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS • See the sights in Key West • Stay for the Key West sunset • Plenty of Free Time • Designated Driver • Narrated Tour Do what you want in Key West! We're doing the driving! Sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more! Sit back & enjoy the scenery as we drive down to Key West. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide. See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory Square It's more like a road trip than a tour - ask questions, point out wildlife, make new friends.
Known For: Key West Bus Tours, Key West City Tours, Key West Full-day Tours, Key West Private and Luxury, Key West Private Sightseeing Tours, Key West Excellent Quality.
Duration: Around 8 hours.