Sunset Cruise: Key West's Twilight Views

Embark on a premium sunset sail in Key West aboard Sebago’s modern sailing catamaran. Sip sparkling wine, indulge in shrimp cocktail, and enjoy live music while admiring the painted sky.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • 205 Elizabeth St - Join the Key West Sunset Sail at the Key West Historic Harbor. Step aboard the Marquesa, a contemporary 70’ sailing catamaran, and meet the captain and crew. As the vessel departs, enjoy a drink of your choice to kick off the evening. Options include champagne, beer, wine, sangria, or a cocktail from the open bar.
What's Included
  • Open liquor bar with champagne, sangria, boutique wine, premium beer, and cocktails
  • Soft drinks and filtered water
  • Chef’s selection of hors d’oeuvres
  • Live music from local Key West musicians
  • Dual spacious bathrooms for guest comfort
What's Not Included
  • Gratuities
Meal Options
  • Shrimp Cocktail -
  • Toasted crustini with savory spread
  • Antipasti skewer with tomato, mozzarella and olives
  • Seasonal mini tart selection
Additional Information

Relish the magnificently coloured sky on this high-end Key West sunset cruise. Make unforgettable moments aboard one of Sebago’s state-of-the-art sailing catamarans, while enjoying a glass of bubbly or a cocktail of your choice and indulging in a shrimp cocktail heading towards the prime sunset vantage point. Experience the dusk vistas of the island as…

Location
205 Elizabeth St
Elizabeth Street
Unit #1; Office located on Lazy Way Lane between Conch Republic and Schooner Wharf. Please arrive 30 minutes prior to departure for check-in.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.7
(3534 Ratings)
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1 star
Tebay
Jan 16, 2026
See my review for highlights. - We visited Key West Florida twice, once three years ago and then about 10 months ago. We are Alaskans, who snowbird for almost 6 months in Florida. Key West is one of our favorites. It is the southernmost point in Florida, famous for its lively atmosphere, rich history (Conch Republic, Hemingway), unique wildlife (chickens, Key Deer), vibrant nightlife on Duval Street, delicious Cuban/seafood cuisine, Key Lime Pie and water activities. I hated to leave Key West the last trip, but we had to take off for Homestead in order to make our hotel reservations there. We do Key West in four-night stays, two there, one going south and the other going north. We live in Central Florida on the Atlantic around Oak Hill. Two beautiful days here in paradise. I'm providing a picture of the scene from our balcony, just before sunset the last night. Did a whole two days of touring. Did two 1.5-hour tours of the island on the hop-on-hop off. Plus did the Hemingway house this time, and the Sails to Rails Museum. We wanted to do at least one more museum, there were about a dozen more we thought we would like, but we were exhausted. Got back to the Inn and that free margarita was waiting down by the pool, it really hit the spot. They said 59 cats live in the Hemingway home; you better believe it. Cats were everywhere, but they didn't bother me a bit, maybe I'm getting over my allergy, or outgrowing it. One interesting and ironic aspect of Hemingway's most famous novel "The Old Man and the Sea" was that a picture in his home shows him and his fishing buddy, Gregorio Fuentes. Many believe that Hemingway used Fuentes when developing the character. Like "Santiago", Fuentes was gaunt and thin, had blue eyes, and had a long, battle-scarred history as a fisherman. Fuentes was the captain of Hemingway’s boat and the two frequently talked about the novel. But, for an old man, when Hemingway wrote the book in 1952, Fuentes went on for another 50 years, he died at age 110. Hemingway was only 62 when he killed himself. But years of hard living had taken its toll. He was in two airplane crashes, World War 1 battlefield accidents where he got shot, suffered at least 9 concussions, was a hard-core boxer and a boxing fan, hard core drinker, maybe even an alcoholic, four wives. On our first trip down to Key West the morning we before we left Oak Hill we had frost on the grass and roof. So, we decided to head south further. Neither of us had ever been down on the Florida Keys. We booked into the Double Tree Inn at Key West. On the way down the first trip, we stayed overnight in Florida City, which is the jumping off point where the Keys begin. Quite an interesting drive across all these small islands. "The Florida Keys are a coral cay archipelago located off the southern coast of Florida, forming the southernmost part of the continental United States. They begin at the southeastern coast of the Florida peninsula, about 15 miles (24 km) south of Miami, and extend in a gentle arc south-southwest and then westward to Key West, the westernmost of the inhabited islands, and on to the uninhabited Dry Tortugas. The islands lie along the Florida Straits, dividing the Atlantic Ocean to the east from the Gulf of Mexico to the northwest, and defining one edge of Florida Bay. At the nearest point, the southern part of Key West is just 90 miles (140 km) from Cuba. The Florida Keys are between about 24.3 and 25.5 degrees North latitude." Not counting the US Territory of Guam, which is just 900 miles north of the equator at 13 degrees north, the south tip of the big Island in Hawaii is the southern most point in the US 50 States, at 18.9 degrees. A lot of folks don't realize no part of Florida is in the "tropics", like all of Hawaii is. Hawaii's northern island of Kauai is at 22 degrees. The Tropic of Cancer is at 23.26 degrees. But when we got up the first morning, in Florida City, and looked out the window, there was a grove of Coconut Trees. The southern portion of Florida actually has Coconut Palms and later on when in Key West, green coconuts were in all the trees outside our balcony. The temperatures there, approached 80 F degrees. After we got into Key West, we immediately decided to extend our stay anther night.
Review provided by Tripadvisor
Ajnr911
Jan 15, 2026
Beautiful views - Enjoyable sunset cruise! The music was great and everyone was friendly! The food was nothing to rave about, but you’re not really going for the food! Highly recommend!
Review provided by Tripadvisor
Heidi_j
Jan 14, 2026
Great trip! - Great trip with a fun staff. We weren’t going to have a sunset due to the clouds, but we went anyway. So glad we did. The hors d’oeuvres and drinks were fantastic. Our entertainer was very good. The shop was clean and not overcrowded. We would definitely do this again.
Review provided by Viator
Mark_r
Jan 13, 2026
Great sail, great crew - Come ready to have fun. Crew was attentive, friendly, fun and went out of their way to serve and make sure everyone was taken care of
Review provided by Viator
Adventurer759208
Jan 12, 2026
Wonderful Key West Sunset Sail Adventure! - My wife and I celebrated the New Year vacationing in the Florida Keys, including Key West, and chose this Sunset Sail adventure as part of our trip. It was a wonderful experience from start to finish. The crew was friendly and attentive, the boat was comfortable, and the live music added a great atmosphere. The hors d’oeuvres and beverage selection were varied and enjoyable. The crowd size felt just right, the sail duration matched what was advertised, and everyone on board—coming from many different places—was clearly there to relax and have a good time. We were lucky with perfect weather, gentle waves, and cooling breezes, and the sunset views were absolutely beautiful. We would definitely do this again and highly recommend it to others looking for a fun, relaxing way to enjoy Key West.
Review provided by Tripadvisor
Michael_r
Jan 12, 2026
Great cruise, drinks and... - Great cruise, drinks and staff were amazing and the staff outgoing. The finger food was not very impressive though.
Review provided by Viator
Thomas_b
Jan 11, 2026
A True Highlight of out Key West Trip - The sunset cruise was on a nice boat that well accommodated the 50 or so participants. The captain and staff were super friendly. I recommend taking the option to upgrade to the premium liquor, and you get a plastic cup to use and keep. The hors d'oeruvres were varied, delicious, and plentiful. The musician on the boat kept the people well entertained. We will definitely do this activity again on our next trip to Key West.
Review provided by Viator
Jeanhervey23
Jan 11, 2026
Awesome Sunset Cruise! - We had a terrific time on the boat! The captain, crew and entertainment were excellent. The punch was really good too! I highly recommend this tour, and this crew. Finally, the entertainment was excellent. He sang a variety of genera’s including country, pop-rock and oldies, on request. Great personality, ability to bring the crowd together and fine vocalist. We loved it and would highly recommend.
Review provided by Tripadvisor
Michael_s
Jan 13, 2026
good food, bad tunes - appetizers were very good. music was horrible. crew was fun. bathroom got stinky by the middle of the cruise.
Review provided by Viator
Discover135587
Jan 11, 2026
Beautiful Sunset Weak Drinks - Fun cruise but not sure they were actually serving liquor in the drinks. No way we could drink as much as we did and not even feel it. A bit disappointed with the appetizers. Not what I expected. Beautiful sunset and people were nice. The main guy yelled orders so loud I could not make out anything he said.
Review provided by Tripadvisor
From $79
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).