Top Key West Sailing Tours

Watch the sun set over Key West from the deck of a traditional schooner on an evening sailing experience with a full open bar. Settle into the rhythm of the water as the crew sails offshore, taking in unobstructed Gulf views while bartenders serve cocktails, wine, and spirits throughout the cruise. Combining classic sailing with an easygoing onboard atmosphere, this is a memorable way to experience Key West at sunset.

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.

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.

Set sail from Key West aboard a spacious catamaran for a morning snorkeling cruise combining relaxation and adventure. Glide across the waters where the Gulf of Mexico meets the Atlantic Ocean before stopping at a secluded snorkeling location. Enjoy a gourmet breakfast and unlimited mimosas on board, offering a convenient way to experience Florida’s coastal scenery before the rest of your day begins.

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.

Witness orange, gold, and pink-hued skies as you set sail from the island city of Key West on this evening sailing experience. Experience views of the city as you sail by, including the historic seaport, the Navy Mole, and Mallory Square—keeping an eye out for the square’s sunset celebration—while relaxing on deck with a beer or cocktail.

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.

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.

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.

Limited to an intimate number of passengers, this small-group sunset sail includes an up-close look at dolphins and views of Key West landmarks like Mallory Square, Sunset Key, and Fort Zachary Taylor. Relax on the luxury catamaran to watch the sunset while enjoying tapas such as shrimp cocktail served with wine, champagne, and other alcoholic beverages included in the price.

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.

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.

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.

Snorkel North America’s only living coral reef, then catch an unforgettable Key West sunset, all in one trip. Jump into clear waters with provided gear and spot colorful marine life under the surface. Back on board and after you’re dried off, enjoy rum punch or other beverages on deck as reggae music sets the vibe. A perfect mix of adventure and relaxation, ideal for couples or friends.

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.

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 the Florida Keys from the open water aboard a 50-foot sailboat departing from Marathon. This small-group daytime cruise travels through the Florida Keys National Marine Sanctuary, offering a chance to take in the area’s coastal scenery and enjoy the feel of sailing along the Keys. Combining natural beauty with a taste of maritime adventure, it’s a relaxing way to experience this stretch of Florida’s picturesque coastline.

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.

Leave the tourist crowds of Key West behind for the evening and head out on the water on the historic and elegant schooner built for General Patton in the late 1930s. Cruise around the coast with the boat’s crew looking after you the whole time, 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.

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. The tour departs from the Key West Historic Seaport at 201 William St, near South Beach on Duval Street.

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands in the Key West National Wildlife Refuge. Keep an eye out for dolphins, sea turtles, manta rays and many other wildlife that call the Refuge home. Your captain knows where dolphins are frequently seen and will let you know if he spots any. Upon reaching the mangrove islands, the schooner anchors and your exploration begins. Your day is divided between guided kayaking tours and guided snorkeling tours. The warm, shallow water is calm, sheltered by the uninhabited mangroves, making kayaking a breeze. After your tours, come back aboard and wash off with our fresh water rinse, and relax on deck. Choose from plenty of complimentary cold drinks – frosty cold beer, wine, homemade sangria, chilled sodas and filtered water. This is the best of laid-back island living.

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.

Set sail along Key West's coast on a relaxing catamaran cruise combining dolphin watching with a front-row view of the island's famous sunset. Glide across the water aboard a spacious sailing catamaran, with wide-open views of the surrounding seascape and opportunities to spot Atlantic bottlenose dolphins along the way. With fresh fruit and water provided, and space to bring your own drinks, this is a laid-back way to spend an evening on the water.