Top Key West Half-day Tours

Picture yourself aboard our unique tiki boat, the Lazy Lady, cruising through the crystal-clear waters toward a secluded sandbar. The sun is shining bright, and the air is filled with the scent of salt and sunshine. As you approach the sandbar, the boat glides over shallow waters, revealing stretches of soft, white sand inviting you to explore. Once you anchor, the fun begins! You can jump off the boat and wade into the warm, shallow waters, where the gentle waves lap at your feet. The atmosphere is relaxed, with laughter and conversation floating through the air. Some folks might set up beach games, while others enjoy swimming or soaking in the sun. Time seems to slow down as you enjoy this little slice of paradise, surrounded by friends or newfound acquaintances. Whether you’re collecting seashells, taking a dip, or simply lounging in the sun, a sandbar trip on a tiki boat is a perfect blend of relaxation and adventure.

Get ready for fun in the sun—and leave all the planning to someone else—on this half-day sailing, kayaking, and snorkeling adventure off the coast of Key West. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef teeming with marine life. Snacks, beer, wine, and soft drinks are included.

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.

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.

Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar & Sunset Cruise! This exclusive trip takes you to a beautiful sandbar, where you can lounge on our floating lily pads while our crew turns into your personal bartenders, serving up unlimited draft beer, mimosas, wine, and champagne. For those looking to explore, grab a snorkel and discover the underwater world teeming with tropical fish, stingrays, and other marine life. As the sun starts to set, we’ll cruise through the Florida Marine Sanctuary, giving you a front-row seat to Key West’s famous sunset—keep an eye out for dolphins, sea turtles & more! Savor a taste of Key West at the sandbar! Enjoy Cuban sandwiches, veggie wraps, fresh fruit, cheese & crackers, pita with hummus & more—all paired with unlimited beer, wine, mimosas & champagne. The perfect happy hour on a boat! Whether you’re here to relax, party, or explore, this trip has it all.

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.

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

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.

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.

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.

Spend a stunning afternoon soaking up the sights of the Gulf of Mexico, chilling out at a sandbar, and watching dolphins at the Florida Marine Sanctuary. With the help of a fun and informative crew, you’ll explore the Floridian sea while your guides tell you all about the area’s history and wildlife. Enjoy lunch as well as unlimited beer, wine, and mimosas on your trip—just remember to drink responsibly.

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.

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!

Explore the best that Key West has to offer on this narrated, hop-on, hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions, with an expert guide who takes you through the history of the city. Enjoy free admission to the Sails to Rails Museum for extra sightseeing fun.

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

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.

Key West is known for its beautiful coastal scenery and its lively bar scene, but there are few opportunities to combine the two. This tour takes you out onto the crystal-clear water, traveling by a small motor boat that glides through mangrove tunnels on its way to two or three waterfront bar and restaurants.

Enjoy a private boat tour experience, without the hassle and costs of renting one yourself, on this half-day tour around Key West. The experience is fully customizable to your group’s interests, and can include relaxing on a sandbar, island hopping, snorkeling, dolphin watching, a sunset cruise or a combination of activities.

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

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.

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.

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 Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour of Old Town. Our 4-hour guided experience stops at (6) locations, helping tell Hemingway’s story in Key West & Cuba. Each ticket includes guided entrance into his famed Key West home. Then eat, drink, and explore the island on foot through “Papa’s eyes”, feasting on Cuban cuisine (& 3 boozy beverages) while your knowledgeable local guide impresses with interesting stories & amazing fun facts. The adventure takes you behind the scenes of a 3rd generation family run cigar rolling factory, and into the newly remodeled Social Club at Hemingway Rum Co. for his favorite drink made with his family company’s premium rum. Then finish with a slice of our famous key lime pie! After the tour, you’ll receive a collection of exclusive recipes, recommendations on restaurants, attractions, entertainment, and cultural offerings.