Top Key West Adventure Tours - page 2

Experience premier snorkeling in the Florida Keys aboard the Island Pearl, a 50-foot classic vessel with modern comforts and a colorful past as the liberty boat for the USS Roosevelt. Set off on a scenic excursion past Marathon’s iconic landmarks while we share fascinating stories of the Keys’ historic past. Then, explore vibrant reefs teeming with marine life, or simply relax on the water and take in the views. Even if you’re less adventurous or prefer to stay dry, there’s plenty to enjoy—this is a tour that truly lets everyone in your group experience the magic of the Keys. This unique adventure is quickly becoming a Florida Keys tradition for visitors who want history, scenery, and unforgettable snorkeling.

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.

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.

A Sunset Cruise with a Twist aboard the Island Pearl Wrap up your perfect day in the Keys aboard the Island Pearl, a 50-foot classic vessel with modern comforts and a colorful past as the liberty boat for the USS Roosevelt. Set out on a relaxing evening cruise through the heart of Marathon as we share the rich history surrounding the Seven Mile Bridge, Pigeon Key, and other landmarks that shaped the Middle Keys, with relaxing island music to enhance the vibe. Bring your favorite beverage and toast the day as the sky glows with color over the island waters. There’s even a chance you’ll spot playful dolphins along the way! Whether you’re soaking in the history, the views, or just the laid-back Keys atmosphere, this cruise offers something special for everyone on board. This one-of-a-kind experience is quickly becoming a Florida Keys tradition for visitors who want to end their day with scenery, storytelling, and a truly memorable time on the water.

Kick back, drop your line in the water and enjoy a relaxing day in the Florida Keys, trying your hand at a catch that may include sailfish, wahoo, mahi mahi, tuna, snapper, grouper, king mackerel, and shark. This private charter includes exclusive use of a 30-foot (9-meter) open fishing boat with shade, instruction for beginners or advanced tips for the pros, and all the equipment you need.

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands in the Key West National Wildlife Refuge. Keep an eye out for dolphins, sea turtles, manta rays and many other wildlife that call the Refuge home. Your captain knows where dolphins are frequently seen and will let you know if he spots any. Upon reaching the mangrove islands, the schooner anchors and your exploration begins. Your day is divided between guided kayaking tours and guided snorkeling tours. The warm, shallow water is calm, sheltered by the uninhabited mangroves, making kayaking a breeze. After your tours, come back aboard and wash off with our fresh water rinse, and relax on deck. Choose from plenty of complimentary cold drinks – frosty cold beer, wine, homemade sangria, chilled sodas and filtered water. This is the best of laid-back island living.

Pretend that you and your friends are a pod of dolphins and leap over the waves of Key West during this small group jet ski adventure. Each jet ski can fit you plus one, which allows members of your group to alternate driving and riding the surf. This guided tour takes your group around the entire Key West island where you’ll see mangrove creeks full of wildlife and a former base of the U.S. Navy.

Get ready to spend a half-day soaking up the sun and enjoying Key West’s diverse ecology during this fun sandbar and mangrove tour. Discover the backcountry waters and secluded sandbars around the busy island, all while sipping on cold drinks. This guided kayak ecotour takes you into the mangrove isles to spot dazzling marine life before heading to a sandy beach to knock back a few alcoholic or nonalcoholic beverages.

The glass bottom kayaks is an amazing experience with your tour guides paddling in calm shallow waterways under the stars! Your tour guides will point out sea birds and various sea-life such as different fish species, shrimp, crabs, conch shells which will be well illuminated with your high powered underwater custom LED lights. We paddle along mangrove shorelines and canals so we sometimes even see wild animals such as Racoons along the shoreline. We've also experienced manatees and dolphins on many of the tours. Definitely one of the most exciting things about your kayak tour is that we will feed fish at a certain point of our tour as well which is a blast for everyone! With very little to do at night this is an amazing rare experience under the stars that you'll never forget!

Kayaking is a great way to experience the Florida Keys but your views are typically limited to what's above the surface of the water. This small-group tour provides clear kayaks that let you discover the underwater world as well. As you paddle, you just need to look below to spot starfish, tropical fish, nurse sharks, turtles, jellyfish and more.

One of the only Adult Only experiences offered in Key West, our excursions are top-notch, with the vessel, all equipment, food and beverage service being set to premium standards! We offer a more intimate experience with less crowded excursions for the comfort of all of our guests.

The Florida Keys are one of the best places in the US to fish, with yellowtail, snapper, tarpon, grouper, barracuda, and sharks just waiting to be caught. Prebook this Florida Keys Marathon Inshore Fishing Charter Experience and go with a guide who knows exactly where to fish to have the best time on the water. You can book this experience for two to four people in a variety of different duration times.

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

Explore the vibrant waters of Key West on this 4-hour dolphin watch and snorkeling tour aboard a luxurious catamaran. Encounter playful dolphins in their natural habitat and dive into the colorful coral reefs, guided by experienced crew. After snorkeling, indulge in a delicious Taste of Key West menu featuring local specialties like conch fritters and shrimp ceviche, complemented by an open bar of refreshing cocktails. With professional instruction and a maximum group size for personalized service, this tour promises a unique blend of marine exploration and culinary excellence. - 4-hour tour featuring dolphin watching and guided snorkeling - Chef-prepared menu with local favorites and an open bar - Professional crew with extensive knowledge of local ecosystems - Maximum group size ensures personalized attention and comfort

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Sparky’s Landing in Marathon, this relaxing 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 Keys. Our spacious 52’ catamaran provides a smooth, comfortable ride — perfect for couples, families, and small groups looking to unwind while taking in panoramic views of the surrounding waters. 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, helping ensure the best possible experience on the water. Your confirmed departure time will be reflected in your booking confirmation.

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.

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 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.

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.

Discover the Great Florida Reef while visiting the Florida Keys on this private snorkel excursion. Board a private boat and depart from Big Pine Key towards Looe Key, where you can jump in the water and explore the extensive coral reef system. Snorkel alongside your captain and learn about the various species you encounter such as barracuda, parrotfish, and rays.