Key West
Sailing trips & boat tours

Sailing trips & boat tours
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Key West

Key West

Our most recommended Key West Sailing trips & boat tours

From Miami: Key West Day Trip with Pickup at Selected Hotels

From Miami: Key West Day Trip with Pickup at Selected Hotels

Discover Key West on this day trip from Miami. Get picked up at most hotels in Miami Beach or Downtown Miami, and do what you want to do in Key West with 6 hours of free time. After pickup, board your air-conditioned transportation for the scenic drive to Key West. Admire the breathtaking views of the Florida Keys through the window as you take the Overseas Highway, Upon arrival in Key West, enjoy 6 hours of time to explore by yourself. Ask your guide for any activity recommendations, and take optional tours, if you like. Afterward, return to Miami for drop-off at your pickup point.

Key West: Dolphin Watching and Snorkeling Eco Cruise Tour

Key West: Dolphin Watching and Snorkeling Eco Cruise Tour

Embark on a dolphin-watching cruise from Key West and admire pods of playful bottlenose dolphins in their natural habitat from a respectful distance. Enjoy a cold beer or wine as you cruise, and stop to snorkel in the shallow waters of the Florida Keys. Hop aboard the catamaran in Key West and set off into the Gulf of Mexico on your dolphin-watching adventure. Search for the resident Key West bottlenose dolphins in the shimmering turquoise waters of the ocean. Admire the grace and beauty of the playful pods as they frolic in their natural habitat. After some time watching the dolphins, head to the Key West Wildlife Refuge to snorkel in the shallow backcountry waters. Explore a vibrant underwater world of marine creatures and coral with the snorkeling equipment provided. As you begin your ride back to the dock, enjoy a cold beer, glass of wine, or soft drink. Opt for the sunset tour and experience the world-famous Key West sunset as an added bonus to your adventure, before heading back to the city.

Key West: Afternoon Reef Snorkel Tour with Live Music & Bar

Key West: Afternoon Reef Snorkel Tour with Live Music & Bar

Spend your afternoon snorkeling in warm tropical seas surrounded by colorful fish. Enjoy expert instruction and learn about the reef’s marine wildlife from the professional crew. Your captain will select the exact location based on water and wind conditions, to give you best snorkeling in Key West. Dive into the calm waters, and see how many species of fish and coral you can find. Afterwards, grab a complimentary drink and lay on the sun deck, or cool off in the shade as you sail back to Key West. Feel the breeze in your hair and watch for dolphins playing in the ship’s wake. This trip features a live, local musician.

Key West: Sunset Sailing Trip with Open Bar, Food and Music

Key West: Sunset Sailing Trip with Open Bar, Food and Music

Join a sailing experience to get you closer to the sunset than ever before. Set sail from the historic sea port of Key West and head straight out to sea for a cruise with unobstructed views of the sunset on the horizon. During the cruise, enjoy an unlimited open bar, with a wide variety of drinks on offer including rum runners, Champagne, margaritas, and draft beer. Taste a selection of finger foods, ranging from Swedish meatballs, veggie treats, cheese and crackers, pita and hummus, and meat and veggie platters. You will be sailing on one of Key West's newest sailing catamarans, the Sandie Cat. This vessel has capacity for up to 149 passengers across 3 decks, so there will always be plenty of room onboard. Grab a drink, head to the upper deck, and dance to live music as you watch the sun go down. The captain and crew will even let you help raise the sails and you can ask to have a picture taken driving the boat.

From Miami: Key West Bus Tour

From Miami: Key West Bus Tour

Embark on a full-day tour of Key West from Miami. Feel the Caribbean atmosphere of the Florida Keys and explore at your own pace. See important sites, including Hemingway’s House, or opt to swim in the sea. Start with a 4-hour drive across 43 bridges and 31 islands to America's “Caribbean Islands,” the Florida Keys. The string of islands and islets, bordered by the Atlantic Ocean and the Gulf of Mexico, leads to Key West, the only frost-free city in the continental United States! Once in Key West, experience a Caribbean atmosphere complete with friendly street artists, lively outdoor cafés, and alfresco restaurants. Spend some time exploring Key West on your own. Book lovers might like to visit Ernest Hemingway’s House to see the former home of the famous author. Or, if you prefer, you can go to the southernmost point of the continental United States at the famous "90 miles to Cuba" Monument. Explore museums, such as the Mel Fisher Museum, the Light House Museum, or Ripley's Believe It Or Not Museum (tickets not included). Feel the pulse of Key West at Mallory Square next to the cruise ship port. You may also choose to add one of our most popular adventure activities, such as a snorkeling trip to see tropical fish, a ride in a glass-bottom boat, or the hop-on and hop-off sightseeing trolley bus (tickets not included in the price). Depart Key West at 5:30 PM for the drive back over the bridges and islands.

Key West: Dolphin Watching and Snorkeling Sunset Cruise

Key West: Dolphin Watching and Snorkeling Sunset Cruise

Climb aboard the Sunset One dolphin boat, sit back and listen to your tour guide explain where you are and where you are heading. Get ready to watch dolphins frolic in their natural playground.  Marvel as the dolphin swim closer to the boat so you can get a better view. Head out to the small islands within the boundaries of the Key West National Wildlife Refuge. Soak in this beautiful little chain of islands and jump into the gorgeous reef, perfect for snorkeling.  See fish up close and maybe some turtles. Climb back aboard and settle yourself in for the ride back to the dock with an ice cold draft beer. Watch the beautiful panoramic sunset over the crystal clear turquoise waters.

Key West: Sandbar Excursion & Kayak Tour with Lunch & Drinks

Key West: Sandbar Excursion & Kayak Tour with Lunch & Drinks

Explore Key West’s Florida Marine Sanctuary on a sandbar and kayak eco-adventure. Hop on a boat and cruise through the crystalline waters of the Atlantic Ocean as you head toward the marine sanctuary. Be on the lookout for dolphins and sea turtles, participate in water activities, and savor lunch with unlimited drinks. Start with a guided kayak tour through the mangrove islands, exploring the local marine wildlife and mangroves. See as much local wildlife as possible with 500 marine species in the area. Next, venture further into the wildlife sanctuary to a secluded sandbar. Select your lunch with options such as fresh local Cuban sandwiches, fried chicken tenders, veggie wraps, fruit and veggie trays, cheese and cracker platters, and pita and hummus platters. Take advantage of unlimited draft beer, wine, and soft drinks that will be available after lunch. At the sandbar, you'll have the chance to either explore with a paddleboard or kayak, go snorkeling, or just sit back and relax while you grab a drink in the secluded oasis.

From Miami: Key West Tour with Choice of Water Activities

From Miami: Key West Tour with Choice of Water Activities

Join this exciting excursion to the southernmost point of Florida. Travel to amazing landmarks like the Overseas Highway 1 and unwind on the warm shores of Key West. After pickup at your hotel in Miami, head across Key Largo and the magnificent Overseas Highway 1 Key West. Cross famous bridges, including the Seven Mile Bridge Arrive at Key West before noon and enjoy ca. 5 hours on the island. Choose from various activities such as a dolphin spotting snorkel tour by boat, a snorkel tour with drinks, a glass bottom boat tour or simply enjoy the six hours of free time at your own pace.

Key West: Old Town Trolley 12-Stop Hop-On Hop-Off Tour

Key West: Old Town Trolley 12-Stop Hop-On Hop-Off Tour

Enjoy the sun, charming setting, and clear waters of Key West on this Old Town Trolley Hop-On Hop-Off Tour, and recieve complimentary admission to the "Sails to Rails" Museum This tour covers the entire city. You can avoid the trouble of driving and parking in a new place. The trolley tour is also designed so that you can hop-on and off and explore on your own, on any of the 13 stops. Your ticket is valid for all day, so you can tour at your own speed. There are frequent pick-ups at all of the 13 stops so you’ll never have far to walk. And the Old Town Trolley conductors will be there to guide you through this tropical paradise on one of the distinctive orange and green trolleys. Be sure to take advantage of the complimentary ticket to the Sails to Rails Museum for a comprehensive overview of the Florida Keys and Key West history. It is one of Key West's top attractions and located near Stop 2. There are 13 Stops conveniently located close to many places of interest in Key West: 1) 400 Wall St: Mallory Square1a) Whitehead/Caroline St: Presidential Gates2) 280 Margaret St: Mac’s Sea Garden3) Corner of Greene/Simonton St: Simonton Row4) 430 Duval St: La Concha Hotel5) Whitehead/Petronia: Bahama Village6) 2400 N. Roosevelt Blvd: Fairfield Inn7) 3840 N. Roosevelt Blvd: Roosevelt Station8) 3755 S. Roosevelt Blvd: Hampton Inn9) 3501 S. Roosevelt Blvd: East Martello10) 1500 Reynolds St: Casa Marina11) South/Simonton St: Southernmost Trolley Stop12) Corner of Truman/Duval St: Truval Village13) Corner of Angela/Duval St: Angela Street Depot

Key West: Jet Ski Island Tour

Key West: Jet Ski Island Tour

Climb on a brand new jet ski and set off on a thrilling island jet ski adventure. With your experienced guides, navigate through mangrove islands, stop at a local sandbar for a dip in the crystal clear waters, get a picture of the southernmost point from the water, and more. Each tour has 2 guides to ensure the complete safety of riders. The first guide sets the pace at the front, allowing all riders who want to go fast the opportunity to floor it. The second guide brings up the back, allowing the riders who want a more leisurely tour to go at their own pace. This tour has been voted the best jet ski tour in Key West. Get a great deal with a free second rider on each jet ski.

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What people are saying about Key West

Overall rating

3.9
(307 reviews)

The sunset sail was wonderful. We saw a beautiful sunset on our cruise. We were treated to dolphin sightings. The crew was knowledgeable and it was such a thrill to watch them hoisting and lowering the sails. Drinks and snacks were provided. Highly recommended!

Was great, top luck with Captain John and Sparkles as our guides. We saw a dolphin family, sting rays and good amount of corals. Simply good!

Everything was great, very helpful staff, great spot for snorkeling and delicious drinks.

The guides were just awesome! So friendly and entertaining. We had a blast!

Great experience. Sebago was fantastic, great crew!