KEY WEST
Ranked by traveller popularity
The 10 most popular schooner cruises in Key West. Here's what they actually deliver, who runs them, and what they cost.
Key West sunset on America 2.0: beer, wine, champagne, and plated hors d’oeuvres as you pass Fort Zachary and Mallory Square.
“Captain Janet and crew were fantastic. Great experience. The food and drinks were great. We also had a spectacular sunset.”
Sail Key West on a classic schooner at sunset with drinks, hors d’oeuvres, dolphin sightings, and a shot at the Green Flash.
“Very good food ❤️ The captain let us drive the ship. Amazing experience!”
Sail Key West at sunset on the classic Schooner Appledore: real sailing, small group vibes, and drinks plus hors d’oeuvres included.
“Fantastic crew, informative and friendly. Good quality of drinks ( although would be better if the upcharge for prime wine states in beginning) apps nice. The lack of large crowd and no music was a huge plus and the weather was fantastic.”
Small-group Key West schooner sunset sail with full open bar, tasty hors d’oeuvres, and iconic bay views.
“Loved the trip. Great experience and would highly recommend. Shout out to Joe and Vitale. Well done!”
Sail Key West aboard America 2.0, a classic schooner-style day sail with Fort Zachary and Mallory Square views, plus two drinks included.
“Very relaxing 2 hour, sail was not over crowded, well organized crew, very clean sail boat, had wonderful time”
Two-hour Key West sunset sail on a historic schooner. Spot dolphins and turtles, sip beer and wine, help raise sail, small group.
“The boat was beautiful, the sunset cruise was awesome and crew was very friendly. The only hiccup was the time shown on this site (Trip Advisor), whom we booked it through was completely off…by about 1hr 45mins. Trip advisor needs to update the time so that individuals won't have to wander around wondering where the…”
Sail and snorkel with a small crew in Key West. Kayak the backcountry, enjoy lunch onboard, and explore the National Wildlife Refuge.
“. It was a fantastic experience, the guides were very good and kind, and they were very attentive to our needs throughout the trip. We felt very safe at sea. I would recommend to others not to miss this trip with Joe and Cristina.”
Sail Key West on the Appledore for 2 hours with a full open bar and English crew, passing Mallory Square and the Historic Seaport.
“Great experience! Friendly tour group and very informative. We really enjoyed it. Felt very safe. Highly recommended.”
Sail past Key West icons on the Appledore II at sunset with included champagne and sangria, plus a hands-on sail-raising tradition.
“Beautiful sunset sail. The crew were extremely friendly and shared tons of information about the ship and gave us an unforgettable experience!”
Sail Key West at sunset on a classic schooner with global wines, cold beer, and gourmet appetizers from Opal Key Marina.
“Loved it all. very fun, knowledgeable, and skilled crew. Would go back every evening if I could.”
