Top 10 Sightseeing 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.
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 Nature and Wildlife Tours, Key West Sightseeing Cruises, Key West Water Tours, Key West Day Cruises.
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 Likely to Sell Out, Key West Likely To Sell Out, Key West Adventure Tours, Key West Day Cruises, Key West New Product, Key West Spring Break, Key West Water Tours, Key West Sightseeing Cruises.
Duration: Around 2 hours.

Destination: Key West.
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.
Known For: Key West Historical Tours, Key West Jet Boat Rentals, Key West Day Cruises, Key West Speed Boat Rentals, Key West Sightseeing Cruises, Key West Half-day Tours, Key West Private Sightseeing Tours, Key West Water Tours, Key West New Product.
Duration: Around 3 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 Zombie Slice, Key West Private and Luxury, Key West Water Tours, Key West Catamaran Cruises , Key West Sightseeing Cruises, Key West Zombie, Key West New Product, Key West Day Cruises.
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 Day Cruises, Key West Best Conversion, Key West Top Product, Key West Water Tours, Key West Spring Break, Key West Sailing, Key West Likely To Sell Out, Key West Likely to Sell Out, Key West Sightseeing Cruises, Key West Excellent Quality, Key West Sunset 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 Water Tours, Key West Sightseeing Cruises, Key West Private and Luxury, Key West Likely to Sell Out, Key West Likely To Sell Out.
Duration: Around 1 hour and a half.

Destination: Key West.
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand Key Light Tower and more. Enjoy complimentary beverages throughout your sail along with individually plated hors d'oeuvres. Sit back and relax as your captain sails you effortlessly through the emerald green Key West waters and off toward the horizon for a quintessential Florida sunset experience.
Known For: Key West Sunset Cruises, Key West Likely to Sell Out, Key West Spring Break, Key West Sightseeing Cruises, Key West Likely To Sell Out, Key West Day Cruises, Key West Excellent Quality, Key West Top Product, Key West Sailing, Key West Private and Luxury, Key West Water Tours.
Duration: Around 2 hours.

Destination: Key West.
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the water for a Key West sunset is like being IN the sunset itself. There is nothing quite like it. Who knows, you may get lucky enough to witness that elusive green flash!
Known For: Key West Best Conversion, Key West Sunset Cruises, Key West Sailing, Key West Private and Luxury, Key West Top Product, Key West Day Cruises, Key West Sightseeing Cruises, Key West Water Tours, Key West Excellent Quality.
Duration: Around 1 hour and a half.