KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 15 most popular sunset sails & cruises in Key West. What each trip costs, how long it runs, and who takes you out.
Sail Key West at sunset on a large catamaran with an open bar, live local music, and filling hors d’oeuvres. Depart from Elizabeth St.
Most Popular“Sunset was beautiful. Music and food were good. Dancing was fun. Would recommend to a friend. The time of the excursion was perfect.”
Key West sunset dinner cruise with a tropical buffet, unlimited drinks, and live music on a 65-foot yacht. See sunset from the water.
“We had a group of sixty people and they boarded first fed first and whenl it was our tern to eat. They increased the speed for return making very rough”
Key West small-group sunset sail with up to eight wines, beer, and hors d'oeuvres on a schooner. Intimate, romantic start to night.
“Great experience on the Key West Sunset Sail and Wine Tasting. Beautiful sunset and smooth sailing. The crew was professional and attentive. The wine selection was good and paired well with simple hors d”oeuvres. We’d book again with Danger Charters!”
A 2-hour Key West catamaran sunset sail with live music, unlimited drinks, and appetizers—plus views of Mallory Square and more.
“Third trip with Fury & all were an excellent experience! We can hardly wait for our next excursion with Fury.”
Key West sunset sail with included drinks. Small-group 90 minutes from Hyatt Centric; champagne, wine, margaritas, craft beer.
“Amazing! Eric and Carlos are incredible hosts. The sunset was incredible! And seeing dolphins was an added bonus.”
Sail on a replica Key West schooner at sunset with open bar and plated hors d’oeuvres, passing Fort Zachary and classic waterfront views.
“Captain Janet and crew were fantastic. Great experience. The food and drinks were great. We also had a spectacular sunset.”
Key West sunset sail with dolphin watching, premium wine, champagne and tapas on a luxury catamaran, small group max 50.
“Captain Daniel and John were outstanding and very accommodating. The tapas were exceptional, much more than we anticipated and would give the chef 5 stars!”
Sail Key West’s harbor to chase the champagne sunset from a 69-foot catamaran, with included drinks, a restroom, and great photo views.
“You may want a sweatshirt or light jacket after the sun sets. The wind is fairly strong and the temperature gets a little cooler. We booked a 1.5 hour champagne cruise but it didn’t sail that evening so we were given a complimentary upgrade to the 2 hour sail with live music and hors d’oeuvres.…”
A 3-hour Key West dolphin watching and snorkeling sunset cruise with snorkel gear, draft beer, and possible reef sightings at Cottrell Key.
Snorkel Key West’s living coral reef, then sail into sunset with reggae, rum punch, and free sunscreen on a spacious catamaran.
“Super fun, super crazy ! What an experience ! It was a little intimidating but over all it was super fun.”
Sail Key West at sunset on the America 2.0 schooner. Drinks and hors d'oeuvres included, wildlife sightings, and a shot at the green flash.
Sail Key West at sunset on a modern 3-deck catamaran with live music, unlimited open bar, and light appetizers for about 2 hours.
“It was exactly as expected....drinks and sunset on a big catamaran. Fortunately, it was not super crowded. The staff was great and the boat was clean.”
A 2-hour Key West sunset sail on the Sandie Cat with an open bar, finger foods, and live music on the upper deck.
“The crew did a great job! The pictures do this excursion justice!”
Sail Key West at sunset on a vintage topsail schooner with red sails, classic sights from the water, plus snacks and bottled water.
“This was the best boat tour we’ve been on down here! The crew was super fun and kept us entertained. Capt Harley, Carl, Jeremy and Simone were very friendly and knowledgeable. Carl set off several cannon shots at other boats after some good natured taunting between us. Gorgeous sunset also! Will do this again when…”
Sail Key West at sunset on a classic wooden schooner with real sail work, small-group calm, and included drinks and hors d’oeuvres.
“Our experience aboard the Schooner Appledore was fantastic! Crew members Joe, Mary, and Christina were AMAZING; they were prepared with stories and anecdotes of their time at sea, and it was so fun to learn about their adventures. Drinks were great, apps were yummy, and they were appropriately careful of my spouse’s shellfish allergy. We…”
Every way to get out on the water, and every reason to stay for the sunset.
