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A Key West sunset cruise is a vacation must-do that adds an unforgettable experience to any Key West visit. Choose a graceful sailing schooner, a sleek modern catamaran, or a roomy dinner cruise liner with live music and all the trimmings – this curated selection of the best Key West sunset cruises offers good times set against one of nature’s grandest spectacles.

Depart the harbor in the late afternoon to enjoy an evening on the water, or combine dolphin watching, snorkeling, or a glass-bottom boat tour with sunset and the perfect end to another day in paradise. Key West sunsets are famous for highlighting nature’s grandeur as the sun sinks below the broad ocean horizon and brings on dramatic color changes of a range and intensity not seen on land. The unobstructed fetch of the light, atmospheric moisture, and other refractory factors combine to produce awe-inspiring natural beauty. Add a chilled beverage and a loved one to share the occasion and the result is sublime. Click on a selection below to learn more about the most popular Key West Sunset Cruises.

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Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Key West Sunset Cruises?

A: According to verified reviews on Cool Key West and TripAdvisor, the best Key West Sunset Cruises are:

Q: What Key West Sunset Cruises are taking additional safety precautions?

A: The following activities in Key West experiences are providing additional COVID-19 safety measures (to read the specific policies please click the activity name and read the "Keeping you safe during COVID-19" section located underneath the booking calendar):

Q: What type of boats are used for Key West Sunset Cruises?

A: The diversity of available sunset cruise vessels is one of the things that make Key West Sunset Cruises so special. Guests who enjoy sailing can choose a 65-foot skipjack schooner with authentic lines that replicate the sailboats used by 19th century Florida Keys fishermen and wreckers. Or a modern sailing catamaran with the stability, speed, and generous deck space these craft are known for. Power catamarans are fast and smooth, perfect watersports or dolphin-watching platforms. And of course, enjoying a buffet dinner and cocktails aboard a 65-foot custom party catamaran should be on everyone’s bucket list. For a wedding, anniversary, or other special occasion, try a private charter to have a sail or power yacht all to yourself.

All the boats used for these popular Key West Sunset Cruises are top-of-the-line designs built for safety, comfort, and fun on the waters around Key West. The United States Coast Guard regularly inspects every Key West Sunset Cruise boat, and all required safety equipment is aboard and properly updated at all times. This is luxury sunset cruising at its best, with expert local captains and crew members, high-tech navigation gear, and the latest in quiet, efficient, low-emission engines. Plus, there are those added touches to enjoy like room for cocktail and wine service, deck space for top local musicians to perform, and even a bit of space to dance on some cruises.

Q: What makes a Key West Sunset Cruise so special?

A: Something about sunset in a tropical island location inspires people to a greater appreciation for what is normally a simple daily event. The famous and elusive Waikiki sunset “green flash” draws hundreds of camera-toting tourists to the Kalakaua Avenue beach walk each evening. Maui has Mt. Haleakala, the “House of the Sun” with sunsets worth an hour drive up the mountain. Beach bar decks in Phuket Thailand get packed as early evening comes on. And sunset in Key West is definitely a big deal whether seen from land or water.

Mallory Square and the nearby anchorage waters have been a hub of activity in Key West for over two hundred years, and when hippies arrived in town during the late 1960’s, they discovered that Mallory Pier offered a perfect wide-open view to the west. The custom of celebrating the amazingly colorful ocean sunsets took hold, and now Mallory Square and the Key West sunsets are both world famous.

Visitors have been boarding boat tours out of the harbor near today’s Mallory Square since the mid-19th century. With quiet, unobstructed on-deck views, the blazing orange, red, and purple clouds along the horizon and the awesome disc of the sun visible as it slides out of sight captured attention very early on. Now, modern vessels are able to provide visitors with a nice range of specialized sunset-watching cruises to suit any taste, and the best way to find out why Key West Sunset Cruises are so special is to come aboard and try one (or more).

Q: Which Key West Sunset Cruise is best for me?

A: The only easy choice among the many popular Key West Sunset Cruises is deciding to go on one. After that, the variety of attractive options may easily lead a visitor to decide that the only solution is to enjoy more than one sunset on the water! But if a choice of just one (or two) must be made, the best strategy is to consider what you like best and who is joining you for what could easily be the highlight of any Key West visit.

Naturally, the idea of gliding smoothly over turquoise water under sail while toasting a perfect day with a cold beer, glass of wine, or cocktail is very tempting. A Sunset Sip & Sail or Premium Sunset Sail with Hors D’oeuvres and Full Bar will provide a perfect happy hour start for a couple planning an evening on the town.

For an active family, or anyone who enjoys the water, taking an afternoon snorkeling trip that winds down with a beautiful sunset (and beverages) offers the best of both worlds. A Key West Sunset Snorkel Sail is just the ticket. Nature lovers should try a Glass-Bottom Boat Tour Sunset Combo or take the Dolphin Watch Sunset Snorkel Cruise.

Looking to party with some reggae or just enjoy live music and a cocktail hour at sunset? Take a look at Rum n’ Reggae or the Sunset Party Cruise. The award-winning Key West Wind & Wine Sunset Sail is notable for its pairing of fine wines and craft beers with gourmet appetizers. Special occasions (and every Key West sunset is special) call for a Sunset Champagne Cruise or Dinner Cruise. And for the ultimate in luxury, gather family and friends or just one significant other on a 65-foot schooner and sail away on a Key West Wind & Wine Private Charter.

Q: What kind of wine is served on the Key West Wind & Wine Sunset Sail?

A: Looking for a sunset cruise with a focus on fine wine to go with the fine view? The Key West Wind & Wine Sunset Sail is a legend with locals and visitors alike. This elegant and awesome sunset cruise has pulled down top ratings on Trip Advisor for several consecutive years in addition to earning a Top Sunset Cruise designation (one of the top 2 in North America) from Coastal Living Magazine. The Wind & Wine is a cruise that stands above the rest because it is one of very few sailing excursions in the United States that offers a selection of “real” fine wines from America and around the world.

A small group will gather on deck beneath the billowing sails to enjoy an intimate atmosphere, tropical music, and the incredible Key West sunset along with 8 different wines from around the world and 5 types of domestic and imported beer. There are usually 4 red and 3 white wines plus a champagnoise open for the tasting. The charcuterie and cheese board goes far beyond simple sailors’ rations to deliver the perfect wine pairings with Dill Havarti, Smoked Gouda, fresh Mozzarella, and Brie cheeses. Caprese skewers, summer sausage, honey-drizzled green apple slices, fruit, water crackers and more make for the ultimate water-borne wine tasting session.

Q: Skipjack schooner or catamaran – which one is best for a sunset cruise?

A: Sailing schooners and sailing or powered catamarans are the two most popular Key West sunset cruise vessels. In fact, these are the most commonly used craft for all types of Key West water tours from Backcountry snorkeling and kayak tours to glass-bottom boat rides. The reason for this is simple – skipjack-style schooners and catamarans are both shallow-draft boats that are well-suited to navigating the sandbar- and reef-filled waters around Key West.

Skipjack schooners were originally designed for harvesting oysters in shallow Chesapeake Bay. Adopted for use by 19th-century Florida Keys wreckers, sailors who would race out to salvage cargo from ill-fated ships caught on the reefs around the Keys, skipjacks became very common in local waters as general working and fishing boats. Modern catamarans are adaptations of ancient Polynesian boat designs used by sea-going peoples who lived on tropical islands ringed by shallow coral reefs and lagoons. The ability to skim through the shallows and land directly on the beach was critical. Known for their stability and versatility, today’s catamarans are the fastest and shallowest-running boats on the water.

Both types of vessel provide a safe, comfortable ride and can take guests to the best places to sightsee and play in Key West waters. Do you enjoy a touch of history and the romance of a tall ship under sail? Then a schooner would be a good choice. These classic ships have been sailing out of Key West for over 200 years, and guests who come aboard a Key West schooner today are in for an award-winning luxury sunset cruise.

Catamarans also move very gracefully under sail, but a key difference is that the cat’s deck remains level at all times because the vessel does not heel (lean over under the wind power) like a single-hull sailboat. A catamaran can also offer more wide-open deck space between the two hulls. This allows for seating at tables, live music and dancing, and ease of movement around deck for enjoying the view and taking pictures. The broad, flat deck also makes the catamaran a great play boat for an afternoon of watersports and sunbathing.

Schooners and catamarans are both a lot of fun on the water, so the choice between them is mainly about a guest’s personal preference. Planned activities for the sailing trip as well as any physical limitations and the need for ease of movement should also be considered. Of course, many Key West visitors end up going out on both types of vessel to enjoy not only beautiful sunset cruises but the many other opportunities for fun on and in the water that have made Key West a world-famous tropical vacation destination.