Top 10 Day Cruises in Key West

Destination: Key West.
Max 6 people. Explore the waters around Key West. This versatile boat let's you plan your own adventure. Snorkel the reef, explore an offshore island, look for dolphin and other marine life or simply relax on a sandbar with your toes in the sand! A favorite for families!
Known For: Key West Full-day Tours, Key West Likely to Sell Out, Key West Day Cruises, Key West Likely To Sell Out, Key West Sightseeing Cruises, Key West Half-day Tours, Key West Private Sightseeing Tours, Key West Water Tours.
Duration: Around 3 hours and a half.

Destination: Key West.
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.
Known For: Key West Private Sightseeing Tours, Key West Day Cruises, Key West Full-day Tours, Key West Private and Luxury, Key West Water Tours.

Destination: Key West.
Our US Coast Guard licensed captains have decades of combined excursion experience in the Middle Keys and look forward to sharing our lovely paradise with you! Your captain will provide all the tips to have you exploring our local sea-life in no time. We hold ourselves to a high standard and run a quality operation. With your enjoyment in mind, our boats are clean and comfortable offering multiple seating options, and maintained regularly. After your 2 hour excursion, you’ll fall in love with the Keys! Florida Mom owned, voted Best in Marathon 2023, 2024
Known For: Key West Sightseeing Cruises, Key West Day Cruises, Key West Nature and Wildlife Tours, Key West Water Tours.
Duration: Around 2 hours.

Destination: Key West.
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.
Known For: Key West Day Cruises, Key West Sightseeing Cruises, Key West Half-day Tours, Key West Private Sightseeing Tours, Key West Water Tours.
Duration: Around 4 hours.

Destination: Key West.
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.
Known For: Key West Spring Break, Key West Adventure Tours, Key West Likely to Sell Out, Key West Day Cruises, Key West Likely To Sell Out, Key West Sightseeing Cruises, Key West Water Tours, Key West New Product.
Duration: Around 2 hours.

Destination: Key West.
Come see for yourself why Marathon Mermaid is voted the #1 thing to do in Marathon! Watching the sunset by water is a must-do when visiting the Keys!
Known For: Key West Sunset Cruises, Key West Day Cruises, Key West Zombie Slice, Key West Water Tours, Key West Catamaran Cruises , Key West Sightseeing Cruises, Key West Zombie, Key West New Product.
Duration: Around 2 hours.

Destination: Key West.
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.
Known For: Key West Likely To Sell Out, Key West Nature and Wildlife Tours, Key West Full-day Tours, Key West Spring Break, Key West Water Tours, Key West Sailing, Key West Day Cruises, Key West New Product.
Duration: Around 2 hours.

Destination: Key West.
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy a guided tasting of fine wines from around the world, along with a selection of craft and domestic beers and light hors d'oeuvres including crudites, meats, cheeses, crackers, fruit, and chocolate. With small group sizes, there’s plenty of space to move around and enjoy the view without the crowds. It’s perfect for a romantic date or a fun evening with friends—upscale, but never uptight. What really sets this trip apart is the crew. They’re fun, welcoming, and passionate about what they do—ready to pour your next glass, share a story, or make sure you’re having a great time. Add in a Key West sunset, and you’ve got one of the most unique and enjoyable evenings on the water!
Known For: Key West Best Conversion, Key West Excellent Quality, Key West Likely to Sell Out, Key West Likely To Sell Out, Key West Sailing, Key West Water Tours, Key West Spring Break, Key West Top Product, Key West Day Cruises, Key West Sunset Cruises, Key West Sightseeing Cruises.
Duration: Around 2 hours.

Destination: Key West.
Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean waters while sipping a beverage. Take in views of Key West sights like Fort Zachary Taylor, Mallory Square, Sunset Pier and Sand Key Light Tower. Soda and water are complimentary. Two alcoholic beverages are included with your ticket. Additional beverages are available for purchase.
Known For: Key West Day Cruises, Key West Sailing, Key West Likely to Sell Out, Key West Likely To Sell Out, Key West Excellent Quality, Key West Private and Luxury, Key West Sightseeing Cruises, Key West Water Tours.
Duration: Around 1 hour and a half.

Destination: Key West.
This trip combines sailing, snorkeling, kayaking, and local insight in a laid-back, small-group setting. You'll sail on an authentic schooner into the calm, protected waters of the Key West National Wildlife Refuge—a remote area only accessible by boat. With group sizes limited to 20 guests, the experience feels personal, spacious, and relaxed! Our crew truly sets us apart. They’re knowledgeable, passionate, and always ready to share the history, wildlife, and ecology of the Keys in a fun, engaging way. Whether you're in the water or relaxing on deck, they’re there to guide, support, and make everyone feel welcome—regardless of experience level. Snacks, beer, wine, soda, and water are included onboard, adding to the comfort of your time at sea. If you join the afternoon trip, you'll also enjoy a beautiful sail back to Key West timed with the sunset, making the day even more memorable.
Known For: Key West Top Product, Key West Half-day Tours, Key West Day Cruises, Key West Full-day Tours, Key West Water Tours, Key West Best Conversion, Key West Excellent Quality.
Duration: Around 4 hours and a half.