Top Key West Sailing Tours

Explore the only living coral reef in North America on this small-group snorkeling adventure aboard a sailing yacht in Key West. You will receive instruction on how to use the equipment, but it’s recommended that participants be comfortable underwater and have the ability to swim. Common sightings include tropical fish, eels, turtles, dolphins, anemones, and urchins.

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.

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, this small group experience ensures you have a spot at the rail when it comes time to capture photos of the setting sun.

Escape to the still waters off the coast of Key West on this small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers. Also included is a gourmet cheese buffet and other appetizers, like summer sausages, water crackers with brie, green apples with a honey drizzle and more. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.

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.

If you’re looking to snorkel in Key West, but don’t know where to plan your experience, this Key West snorkeling cruise makes things easy. Just prebook this experience, and enjoy a cruise over to a coral reef area—perfect for snorkeling and spotting tropical fish. Plus, all equipment, as well as lessons, breakfast, showers, and a beer or soda is provided for you.

Experience a sunset you’ll never forget on this 2-hour catamaran cruise in Key West. Sip on your choice of wine, champagne, beer or sangria as you watch the sun go down over the water. As you sail you’ll catch glimpses of the island and marvel at the views from the turquoise water. Cocktails are also available at a cash bar on board.

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 unlimited drinks from the full onboard bar.

While most boat tours travel on small private vessels or luxury yachts, this sunset cruise takes travelers around Key West on Jolly II Rover, the only square-rigged, topsail schooner in the area. Board your ship at the historic Seaport at the corner of Elizabeth and Greene streets and sail out to see some of Key West’s best sights, including the Man O War Harbor, Christmas Tree Island, Fort Taylor, and others.

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.

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.

Planning a night out in Key West with entertainment can add up quickly. This Key West cruise saves you money by combining an open bar with musical entertainment as you sail the waters keeping an eye out for views of the sunset. Plus, it ends early enough to leave you enough time to bar hop afterward if you’d like.

Enjoy a day of fun in the sun on the Island T’ing adventure off the coast of Key West. Sail away from the island city of Key West to the beautiful blue waters of the Gulf of Mexico on a large catamaran. Hop in a kayak and enjoy a paddle around a natural stand of mangrove. Look for dolphins, stingrays, sea turtles, manatees and more on this full-day adventure. A full breakfast and buffet lunch, plus beer, wine, soft drinks and homemade sangria are included.

Experience the best that Key West has to offer with this combination tour that includes a dolphin watch, snorkeling, and a view of the island’s famous sunset. Spot dolphins in their natural habitat in the Florida Keys National Marine Sanctuary and snorkel in the blue waters surrounding Key West during this family-friendly excursion.

Sail to a gorgeous snorkeling spot off the coast of Key West to explore a coral reef home to rainbow-colored fish, anemones, eels, and more. On the hour-long sailing trip to the reef, sip included wine, beer, or soft drinks while watching for dolphins and sea turtles. The captain chooses the snorkeling spot according to each day’s conditions, ensuring the best experience for your group.

Combine a snorkel session on North America's only living coral reef with a Key West sunset during this catamaran cruise. Listen to lively reggae beats, snorkel using the provided equipment, and watch the sunset with a rum punch in hand.

Explore the patch reefs, mangrove islands, and waterways of Key West on a 6-hour cruise and snorkeling tour aboard a wooden sailing schooner. Take a hand at the wheel on your way across the Gulf of Mexico, kayak through the mangroves, then snorkel through patch reefs and sponge gardens. This 6-hour tour includes lunch and access to an open bar on the return sail to Key West.

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.

Enjoy the sunset from the water on this Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, pass by sights such as Mallory Square with its Sunset Celebration and the Navy Mole, where big ships dock. Hors d'oeuvres and unlimited drinks are included onboard. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.

Enjoy the Key West sunshine on a full-day catamaran excursion, and take part in a range of watersports, too. As you cruise around the alluring Gulf of Mexico, gaze out at the scenery and spot local marine life. Choose from a range of activities from snorkeling and kayaking to adrenaline-fuelled parasailing or Jet Skiing. Breakfast and lunch are served on board.

Set sail on the schooner Appledore for a scenic cruise from Key West!.  Join the crew to raise the sails, take a turn at the wheel, or just soak up views of the gorgeous Florida coast with a cocktail.. Choose a day sail for maximum sunshine, or opt for a sunset sail in the early evening, then enjoy a selection of drinks during your time on the water.

Combine two activities into one tour and save with this Key West sunset snorkel sail. Not only will you get to relax and listen to the music as you cruise on the Atlantic Ocean during sunset, but you’ll also get to snorkel in a nearby coral reef. Beverages and snorkel equipment are included for added convenience.

Leave the tourist crowds of Key West behind for the evening and head out on the water on the historic and elegant When And If!, built for General Patton in the late 1930s. Cruise around the Florida coast with the boat’s crew looking after you the whole time, providing a complimentary cheeseboard and even letting you take the wheel if you want to try your hand at boating. Watch the sunset from the ocean before heading back.