Top Key West Day Cruises

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 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.

Soak up sunset views from the water's edge, and admire a perspective many visitors miss, on this Key West sailing tour. Sample up to eight different wines and/or five different beers as you sail, and indulge in a selection of gourmet hors d'oeuvres to accompany them. As you go, learn more from your crew, and enjoy a festive and celebratory way to toast to your trip.

Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.

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.

Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, numbers are restricted to 24 so you have a spot at the rail when it’s time to capture photos of the setting sun.

Get ready for fun in the sun—and check off two top experiences in just one trip—on this dolphin-watching and snorkeling tour off the coast of Key West. Departing Key West, look out for dolphins swimming alongside the boat, then jump in for a shallow-water snorkel at the Key West National Wildlife Refuge with many different species of marine life. Relax, feel the warm sea breezes, and select from a variety of refreshing beverages on board the boat.

For the aquatic adventure of a lifetime, cruise to North America's only living coral barrier reef. No need to go diving or snorkeling for this great view—see tropical fish, sharks, turtles, colorful coral, and other sea life from the deck of the glass-bottom boat. Opt for an evening departure to enjoy a glass of Champagne as the sun sets into the Gulf of Mexico.

Watch Key West's sunset — a main island attraction — on an evening dinner cruise. Feast on a tropical-themed buffet dinner and sip provided cocktails, beer, wine, and soft drinks as you take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere, and a cash bar is also available for premium drinks.

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Skipjack Resort & Marina, this serene 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 region. Our spacious 52’ catamaran provides a smooth, comfortable ride — perfect for couples, families, and small groups seeking relaxation with panoramic ocean views. 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, ensuring you experience the most spectacular sky colors possible. Your confirmed departure time will be reflected in your booking confirmation.

Set sail for a full-day escape to the hidden gems off Key West’s coast—where pristine beaches and secluded islands await. Whether you're soaking up the sun, taking in the coastal views, or just unwinding with your group, this experience blends the excitement of the open water with the comfort of premium onboard amenities. Perfect for history lovers and adventure seekers alike, this guided journey offers something for everyone.

Key West is famous for its sunsets. Rather than joining the crowds at Mallory Square, you can enjoy a more personal, uncrowded experience on this small-group sunset cruise. Aboard a custom tiki bar boat, you can toast the sunset (drinks not included BYOB) while taking in the sights as you cruise around the Key West harbor.

Experience a slice of sailing history while soaking up fantastic Key West views on a cruise aboard the *America 2.0*, a replica of the schooner that won the very first America’s Cup. Relax on decks as your captain navigates the island coastline past landmarks like Fort Zachary Taylor and Sand Key Light Tower, and sip drinks from the full onboard bar.

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.

The whole family can learn more about sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast to try your luck spotting dolphins, stingrays, turtles, and birds while you learn more about Key West’s waters than you ever would sailing along. Then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat.

Experience a relaxing start to your day on a spacious 53’ luxury catamaran as you cruise through the clear waters surrounding Marathon. Enjoy a complimentary morning mimosa as the crew guides you along scenic coastlines with views of the Atlantic Ocean, Boot Key, and the iconic Seven Mile Bridge. Take a refreshing swim in calm, shallow waters and explore the sandy bottom for shells and sea life. With plenty of space on board, comfortable seating, and friendly local crew, this tour offers a peaceful and memorable way to experience the beauty of the Florida Keys.

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.

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.

Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.

Ready for the most beautiful 2 hours of your Florida Keys vacation? Forget crowded piers and noise—imagine yourself drifting peacefully as the sun melts into the beautiful water of the Florida Keys. Our 2-Hour Sunset Tiki Cruise transforms the spectacular Keys sunset into a private, moving masterpiece just for you. The Magic of the Sunset Cruise: Front-Row Seat to Nature’s Show: Glide across the tranquil, crystal-blue waters as the sky ignites in a breathtaking palette of reds, oranges, and pinks. You'll have the best, unobstructed view of the legendary Keys sunset from the comfort of your floating tiki bar. A Toast to Paradise: Whether you're celebrating a special occasion or simply savoring a perfect day, the sunset hour is magical. Bring your favorite beverages to toast the end of a perfect day as the stars begin to appear over the horizon. Secure your spot now and create a memory that will glow long after the sun goes down!

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.

Get front row seats to a stunning Florida Keys sunset, without the hassle of chartering your own vessel, on this catamaran cruise from Key West. Sip on your choice of wine, sparkling, beer, margaritas, or sangria as you watch the sun go down over the water. As you sail, catch glimpses of the island and marvel at the views from the turquoise water.

Combining the fun of a tiki bar with the serenity of being out alone at sea, this private tiki boat experience gives you the best of both. Reserved exclusively for your group, your captain will take you around Key West waters. Bring your own snacks and drinks to party under the covered bar or relax on the floating mat with a cocktail in hand.