Top Key West Whale Watching

Set sail from Key West on a 60-foot catamaran and enjoy the clear blue waters and Atlantic bottlenose dolphin sightings. Afternoons are when dolphins are the most active so you’re sure to see the adorable creatures jumping and swimming around the boat. You’ll also see some Key West landmarks from the water and enjoy the sea breeze.

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.

Not only is Key West a playground paradise for adults, it is for dolphins, too. See how many of these playful creatures you can spot on this small-group sailing tour. You’ll board Our SQUID, we designed and built SQUID from scratch to ensure our guests, and the animals, have the best wildlife experience possible. This catamaran will take you and a crew trained by biologists into the waters around Key West. After watching dolphins swim, you’ll jump into the water and snorkel around the coral reefs to view other marine life.

This isn’t a packed tourist boat — it’s a true small-group adventure with a maximum of 6 guests. You’re not watching dolphins from far away; you’re close enough to feel that electric moment when they swim right next to the boat. Our captains know the dolphin pods by territory and behavior, so you spend more time with them and less time searching. After the dolphin encounter, we take you to hand-picked spots that big boats can’t access: clear, shallow water, quiet backcountry reefs, and hidden sandbars. Beginners feel safe, families feel relaxed, and experienced snorkelers get genuinely good underwater visibility. Personalized, unhurried, and run by a local crew that actually cares — that’s what sets this trip apart.

Experience Marathon’s ultimate adventure with our exclusive Trifecta: reef snorkeling, sandbar relaxation, and a breathtaking sunset cruise—all in one! Our premium location means you get to the reef and sandbar faster than anyone else, so you’ll enjoy more time in the water and less time traveling. Discover vibrant marine life while snorkeling at Marathon’s top reefs, unwind at a pristine sandbar, and finish your day cruising into a stunning Florida Keys sunset. Our vessels are well maintained, fully insured, and operated by a professional crew led by a local Florida mom. Voted Best in Marathon for 2023 and 2024, we’re proud to offer unmatched experiences and friendly service. Book now and see why travelers love our 3-in-1 adventure!

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with only 17 passengers maximum. Avoid the crowds and enjoy sailing, coral reef snorkeling and the wild dolphins that live, feed and breed right along the south side of Key West. Get that yacht feeling with Champagne Service from your professional crew. Tickets are fully refundable if canceled outside of two weeks in advance!

Take a half-day sailing adventure off the coast of Key West, Florida and observe wildlife. Sail away from the island city of Key West to the beautiful blue waters off the coast on a large catamaran. See dolphins swimming and jumping alongside the boat, then jump in for an easy shallow-water snorkel above a coral reef, shipwreck, or sponge garden, all supporting over 600 species of marine life. Relax, feel the warm sea breeze and enjoy light snacks and a variety of refreshing beverages on board the boat.

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unobstructed view of the surrounding seascape. We will search for our resident Atlantic Bottlenose Dolphins and then head to the best seat in the house to witness a world-famous Key West sunset. Watch as the sky erupts in a spectacle of color from the peaceful vantage point of the water. Organic fruit and filtered water will be provided to keep you refreshed, and you're welcome to bring your own adult beverages to toast to a successful day. Join us for a relaxing and memorable evening that celebrates the serenity of sailing, the wonder of marine life, and the breathtaking beauty of a Key West sunset.

Escape the crowds and discover hidden sandbars on a private eco tour through Key West’s backcountry waters. Swim, snorkel, or simply relax on pristine beaches only accessible by boat, with a flexible itinerary customized just for you. • Watch wild dolphins in their natural habitat • Private eco-friendly tour, just for your group • Cruise Key West’s beautiful backcountry waters • Flexible departure times to fit your schedule • Learn about marine life from a local guide

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.

THE ONLY 2 DESTINATION TRIP IN MARATHON. Snorkel at the iconic Sombrero Reef and relax at the secluded Molasses Key Sandbar, perfect for a day of marine exploration. This 3.5-hour tour invites you to discover the vibrant underwater world of the 3rd largest barrier reef, where you can swim among tropical fish and coral. Enjoy the convenience of snorkeling gear, a floating mat, and a power catamaran led by a licensed captain. Cooler and ice are provided for your refreshments, ensuring a comfortable outing on the water. - Explore the renowned Sombrero Reef, teeming with marine life - Unwind at the exclusive Molasses Key Sandbar, away from crowds - Includes snorkeling gear and a power catamaran with a licensed captain - Convenient cooler and ice provided for your snacks and drinks

Join this combo Key West adventure, where you’ll be up close with dolphins, either watching them from the boat or snorkeling with them, and also getting off the boat to check out some local attractions. All the logistics are taken care of for you, so you just need to grab a drink at the open bar, then relax into the tour. Cap it off with a trip to the Sails and Rails Museum for a history lesson.

Limited to an intimate number of passengers, this small-group sunset sail includes an up-close look at dolphins as well as views of Key West landmarks like the legendary Mallory Square, Sunset Key, and historic Fort Zachary Taylor. Then, relax on the luxury catamaran to watch the sunset as nibble on tapas such as shrimp cocktail served with wine and champagne.

You’ll see more than swimmers playing in the tropical waves of Key West. Hop on this boat cruise and watch pods of dolphins leap from the waters just off the coast of the Florida Keys. When the boat slows, it’s time to strap on your snorkel equipment and dive down to the reef system. Spot more sea life as you glide across the water back to shore, enjoying your fill of unlimited beer and soft drinks.

Swim among coral and tropical fish in Key West's living reef on this snorkeling excursion. Sit back and relax on a custom-built boat, and sail to the reef where a professional crew is on hand to provide snorkeling instruction and guidance. After your swim, enjoy included beer, soft drinks, and water on the boat for your ride back. All snorkeling equipment is provided.

The Experience: Don't miss your chance to experience a luxury charter in the Florida Keys, versatile enough for any on-water activity you can envision. Whether you're interested in snorkeling, light tackle fishing, sandbar hopping, sunset cruises, dolphin watching, sightseeing, trips to the intercostal from key west to miami, we do it all! Fun for the entire family! We also offer poker runs, with our 36 Contender powered by triples give us a whopping 1,050 hp YOUR day, YOUR way: Probably the best thing about our boat service is we don't do cookie-cutter trips. Every trip is personalized to who and what is important to you. As a bareboat/demise charter, this vessel offers ultimate freedom—the itinerary is entirely up to you. With endless possibilities in the Keys, our seasoned team, in conjunction with the captain you choose, will tailor the journey to your dream day's desires. We'll provide you with a curated list of recommended captains, ensuring a seamless, expert-guided adventure.

Explore the waters of Key West on a private boat charter with a captain, offering a flexible way to spend time on the water. Travel to sandbars, beaches, and clear-water spots only accessible by boat. With space for small groups (up-to six people) and onboard shade, this boating experience provides a comfortable and customizable way to enjoy the Florida Keys at your own pace.

Hey there, I’m Captain Zak; just a guy with a boat who loves showing off Key West and sharing good times on the water. Whether you’re into sandbar hopping, snorkeling, or soaking up one of those legendary Key West sunsets, I’m all about creating the perfect day for you and your crew. Let me know what you’d love to do while you’re here, and together we’ll design a sandbar cruise that’s completely personalized, relaxed, and unforgettable. From hidden sandbars to vibrant reefs, it’s all about seeing my backyard playground—The Fabulous Florida Keys—like a local. Climb aboard the Casual Monday and let’s make some memories in paradise. See you on the water! Captain Zak

The Keys are at their most beautiful at sunset. Experience them from the water on this comfortable cruise that includes a glass of sparkling wine to toast the setting sun. Savor winding mangroves and local landmarks like Boot Key Harbor, Sombrero Beach, East Sister Rock Island, and more, culminating in the Seven Mile Bridge.

* US Coast Guard licensed Master Captain and Mate provided for your safety & comfort * Open bow and comfortable cushioned perimeter seating * Lots of shade available* Premium Bluetooth marine sound system with island vibe music * Enjoy cruising the Keys waters in comfort * Beautiful Florida Keys sunset from the water * Enjoy the relaxing Sandbar * Family friendly / fun for all ages * Make everlasting memories!

We provide some of the best inshore and offshore fishing key west has to offer. All of our excursions are specialized to our customers satisfaction. We provide half day 3/4 day and full day fishing charter excursions in key west florida. We catch almost every species of fsih key west has to offer, form the beginner to the expert we take everyone for a great day of fishing on the water.

Explore the only living barrier reef in America with Southpoint Divers on eco-friendly dive trips tailored for certified divers. Begin your day at your air-conditioned dive shop near the Hyatt Centric, where you’ll be equipped with top-of-the-line SCUBAPRO gear. Cruise past stunning views of Sunset Key and Fort Zachary Taylor Beach as you head to the reef. Dive into vibrant coral gardens teeming with tropical fish, turtles, and rays. With PADI-certified instructors ensuring safety and personalized attention in small groups, your underwater adventure also supports vital conservation efforts in the Florida Keys.

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you to create your own adventure. Connect with Key West's abundant wildlife as you cruise the waters in search of our resident coastal dolphins. From there, we'll head to a secluded sandbar, a pristine shallow-water oasis where you can unwind and enjoy the tranquility. This tour is ideal for those who prefer to relax and socialize. Spend your time floating, swimming, or simply lounging with a cold beverage in hand. While snorkeling is an option, it is not a guided activity on this trip, making it perfect for guests who are more interested in a leisurely day on the water than a structured snorkel excursion. We'll provide a snack of fresh, organic fruit from Date & Thyme, and the trip is BYOB so you can bring your favorite drinks.