Top Key West Half-day Tours - page 2

Discover a side of Key West some visitors miss, and immerse yourself in its beautiful scenery, on a half-day sailing tour. Board your catamaran and head to North America's only living coral barrier reef. Pass some of Key West’s top attractions on the way, then dive in to see hundreds of species of colorful fish, coral, and other sea life. This cruise includes snorkeling gear, plus beer, wine, and soft drinks.

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.

Jam to crowd favorite beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Dance the evening away or relax on the sundeck or in shaded areas as you sip on a margarita, beer, or other beverages. Unlimited drinks and light appetizers are included so you don’t need to pay extra. A great standalone evening activity or the start of a night out.

Experience the beauty of the Florida Keys on this guided 4-hour VIP tour! Travel the iconic Overseas Highway, cross the famous 7-Mile Bridge, and explore Bahia Honda State Park. Spot endangered Key Deer, visit the Blue Hole, and enjoy live commentary, island music, and breathtaking views. Hotel pickup and drop-off included. Perfect for nature lovers, history buffs, and adventure seekers!

Step onto our one-of-a-kind catamaran for an all-you-can-eat seafood boil and premium open bar! This trip promises a perfect blend of adventure, relaxation and excitement. Our catamaran is designed for comfort with speacious decks, plenty of seating and shaded areas. Ideal for lounging and enjoying the scenic views of Key West's iconic turquiose waters. Snorkel at two of Key West's prime snorkeling locations, such as Sand Key or another nearby location known for its vibrant coral and diverse marine life. Premium snorkel gear is provided and experienced guides are available for instructions perfect for all levels of experience. After snorkeling, lounge on deck and enjoy a classic Low Country boil, a classic Southern dish. Our menu typically includes shrimp, corn on the cob, potatoes, all seasoned with a magic blend of spices, cooked together. Expect a laid-back and enjoyable trip while unwinding with a cocktail served from our premium open bar.

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.

Snorkel North America’s only living coral reef, then catch an unforgettable Key West sunset, all in one trip. Jump into clear waters with provided gear and spot colorful marine life under the surface. Back on board and after you’re dried off, enjoy rum punch or other beverages on deck as reggae music sets the vibe. A perfect mix of adventure and relaxation, ideal for couples or friends.

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.

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.

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.

The main goal is to keep you safe with a SOBER driver. Let us take you on a guided golf cart tour around Key West with a seasoned and sober driver to stay out of trouble! Not only will you likely not know where you're going, but there are rules of the road in Key West for golf carts that folks do not know about and you can end up in trouble / aka: D.U.I. ! So, getting past that, Your pickup point can vary to your wish! We will gladly pick you up and drop you off at your hotel. Now the fun! We will cruise past Jimmy Buffett's studio, Mallory Square, Sloppy Joe's and Hog's Breath Saloon just to name a few of the great popular party places. Just let us know where you want to go and we will get you there (and back) safely! If you are wanting to party down we can help you get back home without the ticket!

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.

Leave the crowds behind and spend the day at one of Key West's beautiful sandbars with a maximum of just 6 guests onboard. Your local captain will choose the best location based on the day's conditions, giving you the best chance to enjoy clear, shallow water and a relaxing atmosphere. Snorkeling gear, floaties, and onboard Bluetooth music are included, so all you need to do is jump in, float, explore, and enjoy the Florida Keys at your own pace.

Experience Key West’s waterfront the way locals do—by private boat. This harbor cruise offers a more comfortable experience, complete with narration and flexibility. With a USCG-licensed captain, you’ll glide past historic forts and the Historic Seaport, Navy installations, Mallory Square, and island landmarks while hearing stories of wreckers, pirates, and poets. Choose golden-hour glow or bright daytime views, customize pace and photo stops, and savor a quiet, upscale alternative to mass tours. ✅ Explore the Historic Seaport, Mallory Square, and island landmarks ✅ See Navy installations, historic forts, and working waterfronts ✅ Learn island history from a knowledgeable USCG-licensed captain ✅ Customize the pace with photo stops, narration, or quiet relaxation ✅ Choose daytime cruises for sunshine or golden-hour evening views This is a quiet, upscale alternative to mass tours — perfect for couples, families, and small groups seeking comfort, history, and stunning harbor scenery.

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.

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

This is the only private eco boat trip that focuses exclusively on the Key West National Wildlife Refuge in such depth. Rather than hitting common tourist spots, you’ll venture into parts of the Refuge that most tours skip — winding mangrove fingers, quiet flats, and hidden inlets. With a private charter, you set the pace and direction; there’s no fixed route. Whether you want to snorkel, birdwatch, photograph or quietly drift among wildlife, this experience gives you deep access and unmatched natural beauty — all guided by permitted, knowledgeable local captains who respect the refuge’s delicate ecology. Private boat charter through Key West National Wildlife Refuge Guided mangrove, sea grass & island exploration Wildlife sightings: birds, turtles, dolphins & more Snorkel stops in calm backwaters (optional) Photography & nature immersion away from crowds

Explore the vibrant waters of Key West on this exciting Dolphin Watch & Snorkel Tour. Enjoy a family-friendly adventure as you snorkel in the beautiful backcountry waters, home to an array of marine life including tropical fish, sea turtles, and more. Spot dolphins in their natural habitat and soak in the stunning surroundings aboard a spacious catamaran. With expert guidance and all snorkeling gear provided, it's perfect for both beginners and experienced snorkelers. Relax afterwards with snacks and refreshing drinks as you share stories of the day’s adventures. - Duration of the tour is 3.5 hours, offering plenty of time for exploration. - All snorkeling equipment is included, with expert instruction available. - Enjoy complimentary snacks and drinks, including beer and soft drinks. - Limited to 36 guests for a comfortable and spacious experience.

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.

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.

Get ready for an exhilarating adventure on the vibrant waters of Key West with our private deep sea fishing charters. Led by the skilled and experienced Captain, our team is dedicated to making your fishing trip unforgettable. Reel in the fight of a lifetime as you battle magnificent mahi, king mackerel, sailfish, and more. Our knowledgeable captain and mate will guide you to the sharky hotspots and employ various techniques, including trolling and bottom fishing, to maximize your chances of landing a trophy catch. We believe in providing personalized service. Whether you're a seasoned angler or a curious first-timer, we'll tailor the experience to your skill level and preferences. We offer well-equipped vessels, clean facilities, and essential safety gear for a smooth journey

Escape the crowds and experience the best of Key West on your own terms with the Vitamin Sea Dolphin Safari. Designed for couples, families, or small groups of up to 6 guests, this 4-hour journey offers a perfect mix of adventure, relaxation, and natural beauty — all with your own captain and guide. Cruise through crystal-clear waters, spot playful dolphins in the wild, snorkel above vibrant reefs, and unwind on a remote sandbar that few ever get to see. Whether you're looking for marine life, island serenity, or picture-perfect moments, this tour delivers unforgettable coastal magic.