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 Full-day Tours, Key West Bus Tours, Key West Private and Luxury, Key West City Tours, Key West Private Sightseeing Tours.
Duration: Around 10 hours.

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.
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.
Experience Historic Key West With A Small-Group Walking Tour Ever wondered how the island of Key West was discovered and became so rich? Explore Key West’s history, lore, and legends from the ground up with an intimate walking tour. Whether you want to learn more about the island’s first industries such as shipwrecking and cigarmaking, are curious about local history, or are looking for a fun-filled walk, Key West’s Historic Districts are waiting for you! This small-group walking tour offers both an educational experience and unparalleled delight for the lovers of history and culture. Our experienced local tour guides will lead you on an impressive stroll through the scenic streets of the Old Town where you can connect with the culture of a historic city. This unique experience is enjoyed by visitors from across the world and is a must-do while in Key West! What to bring and to wear: Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.
Known For: Key West Small Group, Key West Historical Tours, Key West Private and Luxury, Key West Cultural Tours, Key West Walking Tours.
Duration: Around 1 hour and a half.

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 Private Sightseeing Tours, Key West City Tours, Key West Full-day Tours, Key West Private and Luxury, Key West Bus Tours.
Duration: Around 8 hours.

Destination: Key West.
Join us every weekend for the Old Town Literary Walking Tour, a stroll through downtown Key West, illuminating stories of writers that have called our island home. Inspired by David A. Kaufelt’s original literary walking tour, our new tour features the former homes and favorite haunts of writers, including Tennessee Williams, Shel Silverstein, Elizabeth Bishop, and Robert Frost, and highlights tales of our lesser-known local talent.
Known For: Key West Historical Tours, Key West Literary Tours, Key West Small Group, Key West Cultural Tours, Key West Excellent Quality, Key West Seasonal, Key West Walking Tours, Key West Art Tours, Key West Private and Luxury.
Duration: Around 1 hour and a half.

Destination: Key West.
Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean waters while sipping a beverage. Take in views of Key West sights like Fort Zachary Taylor, Mallory Square, Sunset Pier and Sand Key Light Tower. Soda and water are complimentary. Two alcoholic beverages are included with your ticket. Additional beverages are available for purchase.
Known For: Key West Day Cruises, Key West Sailing, Key West Likely to Sell Out, Key West Likely To Sell Out, Key West Excellent Quality, Key West Private and Luxury, Key West Sightseeing Cruises, Key West Water Tours.
Duration: Around 1 hour and a half.

Destination: Key West.
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand Key Light Tower and more. Enjoy complimentary beverages throughout your sail along with individually plated hors d'oeuvres. Sit back and relax as your captain sails you effortlessly through the emerald green Key West waters and off toward the horizon for a quintessential Florida sunset experience.
Known For: Key West Spring Break, Key West Sunset Cruises, Key West Sailing, Key West Private and Luxury, Key West Likely to Sell Out, Key West Top Product, Key West Day Cruises, Key West Likely To Sell Out, Key West Sightseeing Cruises, Key West Water Tours, Key West Excellent Quality.
Duration: Around 2 hours.

Destination: Key West.
Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern coast of Key West. When all the sailors in Key West heard there was booty to be had, they'd get in their boats and race each other out to the reef. The first one there could claim the ship's cargo. Today, we celebrate it with the firing of the canon to start the race, and all of the schooners of Key West are on their way in a one-way race to Sand Key Lighthouse! The boat that gets there first, "wins"!
Known For: Key West Sailing, Key West Zombie Slice, Key West Half-day Tours, Key West Likely to Sell Out, Key West Adventure Tours, Key West Likely To Sell Out, Key West Zombie, Key West Private and Luxury, Key West Water Tours.
Duration: Around 3 hours.

Destination: Key West.
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the water for a Key West sunset is like being IN the sunset itself. There is nothing quite like it. Who knows, you may get lucky enough to witness that elusive green flash!
Known For: Key West Best Conversion, Key West Sunset Cruises, Key West Sailing, Key West Private and Luxury, Key West Top Product, Key West Day Cruises, Key West Sightseeing Cruises, Key West Water Tours, Key West Excellent Quality.
Duration: Around 1 hour and a half.