Top Key West Private Sightseeing Tours

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.

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.

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.

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 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.

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.

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.

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.

Welcome to Key West Boat & Jet Ski Adventures! Explore Key West's Backcountry Aboard Our Brand-New Manitou Cruise with Swim Deck Set out on a half-day adventure aboard our luxurious Manitou Cruise—a spacious, smooth-riding tri-toon with a deluxe swim deck, perfect for soaking up the Key West sun in comfort and style. Guided by one of our licensed, experienced captains, your private charter explores the untouched beauty of Key West’s backcountry—customized to your pace and preferences. Cruise to local sandbars, glide through scenic mangroves, or venture farther to spots like Mud Key, Snipes Point, and the Dolphin Playground, where wild dolphins often play in their natural habitat. Swim, snorkel, relax on remote beaches, or simply enjoy the ride with a drink in hand—it’s your trip, your way. Perfect for families, couples, or small groups seeking a flexible and private escape into the real Key West.

Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the docks into some of the most colorful neighborhoods in Key West, pausing to sample locally caught pink shrimp, spiny lobster, or other just-as-delicious non-seafood options, learning about Key West history along the way. Don't forget to save room for a refreshing glass of white wine and our famous key lime pie! Exploring Key West on foot is an ideal way to soak up the vibrant atmosphere.

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.

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.

This private eco boat tour focuses on the Key West National Wildlife Refuge and its mangroves, islands, flats, and coastal habitats. Your group can prioritize wildlife viewing, photography, snorkeling, swimming, or relaxed exploration. The flexible itinerary responds to current conditions and refuge protections, giving guests a private and respectful way to experience Key West’s backcountry environment.

Have all the fun of a private tour from the comfort of your own vehicle and at your own pace to boot. Enjoy this informative self-driven tour for 100 miles, from Key Largo all the way to Key West, making as many stops along the way as you want to eat, rest, and take pictures.

Go sightseeing in the Florida Keys at your own pace with a private self-guided audio tour. Choose a northbound or southbound itinerary and learn about local landmarks, history, and more during the drive. Set out on a road trip through the Florida Keys and learn about highlights such as Seven Mile Bridge and John Pennekamp State Park along the way. Tour offline using GPS, with no cell service needed.

This 2 hour Eco Tour will take you by boat to explore the Backcountry of the Florida Keys. We will cruise through the mangrove islands that make up the Backcountry and Great White Heron National Wildlife Refuge. We will slow down and look for marine life and birdlife. Maybe see a turtle or dolphin. We will take you through "Skinny Water" and look for starfish, rays and sharks. It's a fun adventure not to be missed when visiting the Keys.

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.

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.

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.

Want to discover Hemingway's story in Key West? This tour is outside (no tickets to the Hemingway house) See the many sites he's linked to? Stop in his favorite bars for a drink? You are in luck. Our tour will begin at the Florida Keys Historical Military Memorial in Mallory Square and wind our way along storied streets and the favorite haunts of Hemingway himself, until we reach the iconic Hemingway Home and Museum and the towering Key West Lighthouse. You’ll see his bust, his favorite bar, the spot he first lived, where he ate and lived. And you’ll also hear the story of Key West along the way. Go at your own pace, stop anytime for a drink, and continue when you want. The tour never expires.

Explore an island paradise 70 miles west of Key West. Visit Fort Jefferson, a massive 19th-century coastal fort, and walk its brick walls while hearing stories about soldiers, prisoners, and shipwrecks. The tour even works on the ferry to this remote national park. Snorkel in clear blue water filled with coral, tropical fish, and sea turtles. Relax on sandy beaches and look for seabirds that nest only here. Stroll through the fort’s archways, climb to the top for ocean views, and learn how the fort defended the Gulf of Mexico. You choose what to do first—swim, explore the fort, or enjoy the beach. The tour works without internet, gives GPS directions for walking the site, and offers local tips you can keep forever. Download the tour, take the ferry or seaplane, and explore this unique national park at your own pace—where history, nature, and crystal-clear waters meet. *Download the Shaka Guide app to access the purchased tours*

Explore the vibrant spirit of the Florida Keys with the Key West Conch and Hemingway Walk. This self-guided adventure immerses you in the rich tapestry of island life where writers like Ernest Hemingway and Tennessee Williams found their muse. Navigate through charming streets, lively bars, and historic neighborhoods that showcase the unique blend of Caribbean, Cuban, and Conch cultures. As you stroll at your own pace, engaging audio narratives reveal tales of resilience, creativity, and community that define this iconic island. Discover the essence of Key West, where every corner invites you to pause, reflect, and connect with its storied past.