Top Key West Private and Luxury - page 5

Set sail for the sunset on your own private evening cruise with a captain to show you some of the most scenic spots around Key West, Florida. Listen as your guide tells you fun facts about the area and its waters, while you soak up views of islands and waterfront mansions. Keep your eyes peeled for marine wildlife like dolphins during this private experience.

Experience two distinct Florida Keys environments in one outing with this snorkel and sandbar combo from Marathon. Visit a protected reef area known for marine life and shallow depths, then continue to a calm sandbar ideal for relaxing and exploring clear waters. This tour balances active snorkeling with downtime, making it a practical choice for confident swimmers who want variety without booking separate excursions.

Key West is a wonderfully walkable island that deserves just as much exploration under the moonlight as it does under the sun. Avoid crowded group tours with this private self-guided ghost tour. Using your smartphone, you’ll explore Key West’s allegedly haunted sites and hear their grizzly histories. Go at your own pace, taking breaks or visiting other Key West attractions as you continue your adventure.

Experience a relaxing start to your day on a spacious 53’ luxury catamaran as you cruise through the clear waters surrounding Marathon. Enjoy a complimentary morning mimosa as the crew guides you along scenic coastlines with views of the Atlantic Ocean, Boot Key, and the iconic Seven Mile Bridge. Take a refreshing swim in calm, shallow waters and explore the sandy bottom for shells and sea life. With plenty of space on board, comfortable seating, and friendly local crew, this tour offers a peaceful and memorable way to experience the beauty of the Florida Keys.

Imagine gliding over gentle waves aboard the Lazy Lady, a 53-foot, one of a kind tiki boat. Soak in the vibrant colors of an iconic Key West sunset - hues of orange, pink and purple. Sip on ice-cold beverages prepared by your friendly crew while the warm sea breeze carries the sounds of island music and laughter. The atmosphere is relaxed and festive, perfect for making new friends or sharing moments with loved ones. Expect a laid-back and enjoyable trip while unwinding with a refreshing beverage from the bar. As the last sliver of sun disappears below the water, watch for the green flash, an enchanting touch of magic. Sail back to Key West Harbor under the star-filled sky, creating a Key West memory to last a lifetime.

Key West is famous as mainland America’s Caribbean resort town. Here, time slows down as the island vibes take over. But, as you’ll soon find out on this walking tour, there’s more to this island than umbrella drinks and warm breezes. On this tour, travel writer and tour guide Gregg Squeglia will share stories of some of the island’s more famous residents and some lesser-known tales that have given Key West its unique place in American culture and history. He'll tell you about Key West’s incredible history, from its origins as a maritime village that profited heavily from salvaging wrecked ships along the Great Florida Reef to the hilarious creation of the ‘Conch Republic’. You’ll also find out how, soon after its creation, this micro-state declared war on the United States for a full minute. On this self-paced tour, you’ll also visit the island’s major landmarks and lesser-known treasures.

This private tour is ideal if you want to see it all in Key West, but are not a fan of crowded group tours. In the company of just your group and a guide, hit the streets and stroll to all the top attractions, including the Southernmost Point and Mallory Square. Best of all, the tour can be customized to your own interests.

Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose our popular 3-hour Day Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailboat rides feature the perfect blend of natural beauty, maritime history, and the thrill of the open sea. Don't forget your camera – this is a photo opportunity you won't want to miss! Book your spot now and get ready to create memories that will last a lifetime.

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.

Swap crowded bus tours for a private tour of Key West on a comfortable and unique tiki bike. Your driver will pedal you around the streets of Old Town and the Historic District to top attractions and places that cannot be reached by bus.

If you’re curious about finding out more about Ernest Hemingway’s links to Key West, then this tour saves you hours of research time. Set off with a guide on an expertly planned route that showcases some of Hemingway’s old haunts, including places he both worked and played. Along the way, the guide entertains you with stories about Hemingway that you’d miss out on otherwise.

Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings that celebrate the island’s unique mix of Cuban, Caribbean, and Floridian influences. Start with a refreshing iced coffee before biting into golden, crispy conch fritters—a true island classic. Savor authentic Cuban cuisine that reflects Key West’s cultural heritage, then indulge in rich chocolate-covered Key lime pie, the city’s most famous dessert. Along the way, your guide will share stories of pirates, poets, and island life, bringing the history and charm of Key West to life. To end, you’ll taste our exclusive Secret Dish, a surprise that makes the experience truly unforgettable. This is Key West beyond the postcard—an authentic taste of its food, culture, and soul. As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience.

Key West is filled with rich and spooky history, but ghost tours often lose some of their haunting atmosphere when guests are crowded together in a group. This private walking tour is exclusively for your party so you'll enjoy your guide's undivided attention as they lead you to at least five haunted mansions and two haunted bars.

See as much as Key West as possible from the thrilling seat of a Jet Ski on this guided tour. You’ll launch from Stock Island and ride around the coastline, gazing at Key West’s sites like the buoy marking the Southernmost Point of the Continental USA. Cruise at your preferred speed: those looking for a fast ride can go full throttle while those hoping to take in the sites will enjoy a relaxed viewing of Key West Harbor.

Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll through the narrow, historic streets, you'll hear chilling tales of ghostly encounters, from restless spirits who never left to eerie legends passed down through generations. We’ll pass by the famous haunted landmarks, including the Key West Cemetery, where some say the dead still walk at night, and the eerie corners of Old Town, known for their strange, unexplainable occurrences. With the breeze in your hair and the moonlight casting long shadows, prepare for a spine-tingling ride into the heart of Key West’s most mysterious and supernatural stories. Buckle up, it's going to be a night you won't forget!

Join me, a true seventh-generation local captain for a personalized Key West adventure on my private boat. Spend the day exploring the stunning turquoise waters and hidden islands of the Florida Keys, with opportunities to snorkel, search for dolphins, visit a sandbar, enjoy light fishing, or simply relax and take in one of Key West’s world-famous sunsets. Every trip is fully private and tailored to what you want to experience — whether it’s adventure, leisure, or a bit of both. Departing conveniently from Garrison Bight Marina, your journey promises incredible views, local insight, and unforgettable memories on the water.

Join us on a 2-hour private, exclusive walking tour through the dark and untold stories of Key West. Our tour will begin at St. Paul’s Episcopal Church, where we will share stories of its haunted past and the intriguing legend of Robert the Doll. Next, visit The Artist House, where we will delve into the bizarre true story of Carl and Elena, followed by Dean-Lopez Funeral Home and Crowne Plaza Key West-La Concha, which have a dark and chilling past. At Marrero’s Guest Mansion, explore the eerie story of Enriquetta and other ghostly legends associated with this haunted yet historic mansion. Moving on to 322 Duval St, uncover the mysteries of Captain Watlington’s Haunted House and share bone-chilling stories of the haunted past and present of Key West. Our journey concludes at the Audubon House & Tropical Gardens and the infamous Capt Tony’s Saloon, discovering their dark histories and encounters with the paranormal.

27 Miles and 90 Minutes of pure exhilarating watersports bliss. Your Key West Island Jet-ski Tour starts in the shallow cove, The Ibis Bay Resort dock area. From the Gulf of Mexico to the Atlantic Ocean.....and back to the Gulf of Mexico. From sea to Ocean and back again. After your exhilarating 90-minute adventure, many guests celebrate their experience with a drink and the freshest seafood at the Stoned Crab Restaurant.

Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring with stops like Fort Zachary Taylor Historic State Park, U.S. Coast Guard Cutter Ingham Maritime Museum, Smathers Beach, Southernmost Point of your list.

Some big boat tours in the Florida Keys can feel crowded and impersonal. This private tour instead offers a personalized and customizable experience of the Lower Keys. Where you go and what you do is largely up to you, whether it's snorkeling, kayaking, dolphin-watching or simply chilling out on the water.

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Skipjack Resort & Marina, this serene cruise includes a complimentary champagne toast and seasonal local seafood appetizers such as fresh Florida stone crab or shrimp (when in season), offering an authentic taste of the region. Our spacious 52’ catamaran provides a smooth, comfortable ride — perfect for couples, families, and small groups seeking relaxation with panoramic ocean views. Enjoy island music, warm breezes, and vibrant sunset colors as the day fades into tropical paradise. Departure times adjust seasonally to align with the actual sunset, ensuring you experience the most spectacular sky colors possible. Your confirmed departure time will be reflected in your booking confirmation.

Discover the enchanting beauty of the Florida Keys with Island Girls Excursions. This adventure combines relaxing sandbar experiences with stunning sunset cruises. Unwind on your spacious 52’ catamaran, complete with complimentary snacks and drinks while soaking up the sun or exploring the crystal-clear waters. Your experienced crew will ensure a smooth sailing experience, showcasing the best spots in the area. Perfect for groups seeking relaxation, celebration, or exploration, this tour promises unforgettable memories in paradise. - Enjoy a leisurely sandbar trip with paddleboarding and floats - Experience breathtaking sunset views while sipping drinks - Spacious and comfortable 52’ catamaran with Wi-Fi - Friendly and knowledgeable crew dedicated to your safety and enjoyment

Combining the fun of a tiki bar with the serenity of being out alone at sea, this private tiki boat experience gives you the best of both. Reserved exclusively for your group, your captain will take you around Key West waters. Bring your own snacks and drinks to party under the covered bar or relax on the floating mat with a cocktail in hand.

Explore the crystal-clear waters and pristine sandbar islands that surround the Florida Keys. This private sandbar charter is fully customizable—whether you’re looking to relax with a drink in hand, explore the local marine sanctuary, or simply enjoy a laid-back day on the water. Your captain will tailor the experience to your preferences, taking you to the best sandbar spots and providing everything you need for a carefree day in paradise. Enjoy sunshine, calm waters, and unforgettable views of Key West’s natural beauty. This is the ultimate way to experience the islands—your day, your way, in the heart of the Florida Keys.