KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 15 most popular evening experiences 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“The staff was excellent as well as the entertainment! They made sure you had a great time and the appetizers were perfect. The captain was skilled and made sure everyone was safe and comfortable.”
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”
Half-day Key West sailing with mangrove kayaking and snorkeling in protected waters, with wetsuits, drinks, snacks, and a sunset option.
“This was out second time with Danger, and we really enjoyed both outings. Smaller crowds, lovely boat, informative guides, and great time on the water. I appreciated the use of wet suits, it was a thoughtful addition to the experience.”
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!”
Adults-only Key West sunset cruise on a small Echo catamaran with champagne-inspired drinks, gourmet cheeses, and Moët upgrades available.
“This was such a wonderful experience. Having a small group made it even more special. The sunset was beautiful. The captain and crew were knowledgeable and hospitable. If you’re wondering if you should book this trip- you definitely should!”
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.
“Very relaxing, smaller group makes it feel much more personal.”
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.
“Very enjoyable sailing and ocean experience with personalized service and attention to detail on behalf of captain & assistant”
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.…”
Glass-bottom boat over Key West’s living coral reef, with narrated marine life and optional sunset champagne cruise. Air-conditioned comfort.
“Very relaxing trip out to the reef. Staff was professional and knowledgeable. I highly recommend this trip.”
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.
“Saw many fish, small but beautiful! A group of over 50 fish right in front of me, they were not scared at all. A very exciting experience. Will come back to do it again, but probably not in January again. The water was not cold but it was cold after coming out of water.”
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.
“Fun live music and a sunset sail. The captain, crew, and live musician were great. Open bar and light snacks were provided”
Every way to get out on the water, and every reason to stay for the sunset.
