Top Key West Sightseeing Tours in 2026

Head out into the open waters on this small-group kayaking and snorkeling ecotour adventure. Follow your captain through scenic mangrove tunnels and over calm waters as you make your way to one of the area's most-stunning snorkeling destinations. Learn about local wildlife before taking a dip and get an underwater look. Gear is provided on this tour that's perfect for all levels.

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

Explore Key West at your own pace with an audio-guided walk through the island's history, culture, and coastal scenery. Hear how Ernest Hemingway shaped—and was shaped by—the island, uncover tales of pirates and shipwrecks, and experience the character of its historic streets and tropical surroundings. With lifetime access to this audio tour, explore on your own schedule and enjoy revisiting the experience on future trips.

The Miami Explorer Pass by Go City is the best choice for maximum savings and flexibility when visiting Miami, Key West, Fort Lauderdale, and other locations. Choose two, three, four, or five popular attractions/activities and keep your travel budget in check. Each pass is good for 60 days; simply save your pass on your mobile device and go—no voucher redemption required!

Ideal for travelers short on time, this private tour covers the best of Key West in one day from Marathon. Highlights include stops at the Hemingway House, Mile Marker Zero, and Mallory Square at sunset. Enjoy roughly three hours of free time to explore at your own pace. Upgrade to include a sunset sail, dinner cruise, or other Key West attractions.

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.

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.

Go City's Miami All-Inclusive Pass offers you the best choice for maximum savings and flexibility when visiting Miami and South Beach. Choose between a 1, 2, 3, or 5-day pass to best suit your trip, and save up to 50 percent versus paying for individual attraction tickets. Each pass gives you access to dozens of activities and attractions. Access your pass via the Go City app and begin your Miami adventure.

Going fishing while in Key West is a must, and this deep-sea fishing tour takes you on a comfortable boat for an easy day out. Whether you’re a beginner or an experienced angler, your captain and crew assist with your fishing skills. Fish for reef species like snapper, grouper, and mackerel. A fishing license and all bait are included, and the boat features restrooms, shaded seating, and a small galley with snacks and drinks for your convenience.

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.

Experience a slice of sailing history while soaking up fantastic Key West views on a cruise aboard the *America 2.0*, a replica of the schooner that won the very first America’s Cup. Relax on decks as your captain navigates the island coastline past landmarks like Fort Zachary Taylor and Sand Key Light Tower, and sip drinks from the full onboard bar.

Naval history buffs and aspiring pirates alike are guaranteed to have a whale of a time at the Mel Fisher Maritime Museum. Your admission also includes an audio guide, which offers in depth commentary on the museum’s many artifacts. Highlights include the Spanish Treasure Galleons galleries, Slave Ship and Key West African Cemetery exhibits, and relics from the Henrietta Marie. You can even tour the museum's laboratory and see conservation firsthand.

Key West’s Most Secluded Kayak & Sandbar Adventure Escape the crowds and explore Key West’s most secluded kayak tour in the Florida Marine Sanctuary. Unlike roadside rentals, this tour transports you by boat to the untouched Mud Keys, a hidden paradise of mangrove tunnels, crystal-clear waters, and diverse marine life. What to Expect: Boat Ride to a Remote Kayaking Spot – No roads, no noise, just backcountry beauty Guided Kayak Tour – Paddle through winding mangroves and spot stingrays, tropical fish, and sea turtles Wildlife Sightings – Keep an eye out for dolphins, sharks, and exotic birds ️ Sandbar Stop – Relax in pristine waters after kayaking Drinks & Lunch Included – Enjoy unlimited drinks and a delicious meal Why This Tour is Unique: Exclusive Location – No other company goes here No Crowds, No Roads – A peaceful, off-the-grid experience Perfect for All Skill Levels – Easy and enjoyable for everyone

Take a half-day sailing adventure off the coast of Key West, Florida and observe wildlife. Sail away from the island city of Key West to the beautiful blue waters off the coast on a large catamaran. See dolphins swimming and jumping alongside the boat, then jump in for an easy shallow-water snorkel above a coral reef, shipwreck, or sponge garden, all supporting over 600 species of marine life. Relax, feel the warm sea breeze and enjoy light snacks and a variety of refreshing beverages on board the boat.

Key West is famous as mainland America's Caribbean resort town. Here, time slows down as the island vibes take over. But there is more to this island than umbrella drinks and warm breezes. Key West has an incredible history, from its origins as a maritime village that profited heavily from salvaging wrecked ships and crews along the Great Florida Reef a few miles offshore, to the creation of the micro-state known as the Conch Republic. While in Key West, you will want to visit many of the sites that make the island distinct such as the Key West Lighthouse, the Hemingway House, the Little White House, and Southernmost Point. On this tour, you will visit all of these and more, stopping for refreshments along the way at many of the island's signature restaurants and bars. You will hear stories of some of the island's more famous residents along with some lesser-known tales that have given Key West its unique place in American culture and history.

Set sail for a full-day escape to the hidden gems off Key West’s coast—where pristine beaches and secluded islands await. Whether you're soaking up the sun, taking in the coastal views, or just unwinding with your group, this experience blends the excitement of the open water with the comfort of premium onboard amenities. Perfect for history lovers and adventure seekers alike, this guided journey offers something for everyone.

Cruise alongside Key West’s picturesque waterfront in style during this private sunset tour aboard a charactered tiki bar boat. Enjoy BYOB drinks in a floating, thatched bar, complete with private restroom, bluetooth-equipped television and stereo, and padded bar stools. Head past attractions like Sunset Pier, Mallory Square, Wisteria Island, and Trumbo Point, with cruises timed to capture the coastline’s famous sunsets.

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.

This self-guided audio tour takes you through the Key West Cemetery, a unique graveyard filled with characters that shaped the island's bohemian past. Join Frank Everhart, a nearly 30-year Key West resident, on a walking tour where you'll uncover the secrets of legendary figures, millionaires, and families. As you stroll among crumbling graves, spot descendants of Cuban cockfighting roosters and sun-bleached iguanas. Hear stories of the 1846 hurricane, the Freemasons, and the USS Maine Memorial, whose victims' deaths sparked the Spanish-American War. The 75-minute tour starts at the main entrance, passing through the Jewish B'Nai Zion Cemetery, where you'll learn to decipher gravestone symbols.

Explore the waters of Key West on a private boat charter with a captain, offering a flexible way to spend time on the water. Travel to sandbars, beaches, and clear-water spots only accessible by boat. With space for small groups (up-to six people) and onboard shade, this boating experience provides a comfortable and customizable way to enjoy the Florida Keys at your own pace.

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"!

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour through the beautiful Florida Keys mangrove back country. Stop at various sandbars to paddle board, snorkel, or just hang out. Watch for wildlife throughout the trip such as dolphins, sea turtles, fish, birds, and much more! A cooler filled with ice and bottled water will be provided. Feel free to bring any food or alcoholic beverages.

Hey there, I’m Captain Zak; just a guy with a boat who loves showing off Key West and sharing good times on the water. Whether you’re into sandbar hopping, snorkeling, or soaking up one of those legendary Key West sunsets, I’m all about creating the perfect day for you and your crew. Let me know what you’d love to do while you’re here, and together we’ll design a sandbar cruise that’s completely personalized, relaxed, and unforgettable. From hidden sandbars to vibrant reefs, it’s all about seeing my backyard playground—The Fabulous Florida Keys—like a local. Climb aboard the Casual Monday and let’s make some memories in paradise. See you on the water! Captain Zak

Experience a classic Florida Keys sandbar adventure on a comfortable 53’ catamaran. Cruise through Boot Key Harbor and past scenic landmarks as your crew shares information about the local area and points out interesting sights along the way. Once you arrive at the sandbar, step into shallow turquoise water perfect for swimming, floating, and relaxing. Use the provided water floats and noodles, or simply unwind on deck and enjoy the sunshine and music. This relaxed and family-friendly tour offers plenty of space to move around the boat, shaded seating, onboard restrooms, and a cooler with ice, soda, and water. Ideal for couples, families, and groups, this experience lets you enjoy Marathon’s sandbars the way locals do—easygoing, fun, and surrounded by the natural beauty of the Keys.