KEY WEST
Every trip has one spare afternoon in it. These 15 key west sailing tours are the ones that earn it, priced and timed so you can decide in minutes.
Key West sunset sail review with open bar, live music, shrimp, spacious catamaran decks, practical tips, value, weather advice, and FAQs.
“The sunset was absolutely divine. We sat outside on the bow, drank wine, and took it all in. The crew were attentive and the company was a good time. 10/10 would do again.”
Review of Key West’s 3-hour reef snorkel sail, with catamaran details, drink policy, value, crowding, safety, and practical tips.
“Not cruise ship friendly. If you're traveling on a cruise ship, they dropped us off far from our port and made it a difficult boarding. At least let me know, so I can plan accordingly. Because I would not have selected this experience.”
Review of Key West’s small-group sunset sail with eight wines, beer, hors d’oeuvres, friendly crew, and practical booking tips.
“Very attentive staff on the boat! Generous wine pouring. Nice variety. Beautiful cruise. Check in process was slow.”
Key West sunset sail review with live music, unlimited drinks, appetizers, sunset views, practical tips, pricing, and who should book.
“Amazing sunset cruise, great music, good food and drinks! Fantastic end to our week in Key West/birthday celebration with family and friends!”
Sail from Key West Harbor aboard a small boat, sip included drinks, and watch the famous sunset with attentive crew and room to relax.
“Very relaxing, smaller group makes it feel much more personal. The captain and his first mate were great. My husband & I very much enjoyed it.”
Review of Key West’s America 2.0 sunset sail, with sailing views, open drinks, hors d’oeuvres, practical tips, and honest value advice.
“Sunset was enchanting and the crew was super accommodating! Captain Dan also added historical tid bits that enhanced the Key west experience. Great trip!”
Sail, snorkel, and kayak through Key West’s wildlife refuge with lunch, drinks, and a small-group crew for one active day at sea.
“Amazing time!! Staff was amazing! Experience was once in a lifetime. Checked off swimming with a sea turtle off of my bucket list!!”
Key West sunset sail review with dolphin watching, wine, champagne, tapas, landmark views, practical tips, pricing, and honest drawbacks.
“Wonderful experience, excellent hors d’oevres, drinks, beautiful sunset, well worth the price - would have liked to be under sail instead of engine for the trip”
Review of Key West’s small-group reef snorkel and sail, with yacht details, wildlife, price value, safety, timing, and booking advice.
“The captain and deck hand were wonderful! We had a wonderful boat ride and saw a lot of marine life.”
Key West Rum and Reggae combines reef snorkeling, drinks, music, and sunset views for a lively three-hour outing at $59.95.
“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 aboard the America 2.0 at sunset with drinks, hors d'oeuvres, wildlife sightings, and a chance to see the Green Flash.
“The best way to watch the sunset in the Keys! Every member of the crew was amazing!💖”
Review of Key West’s 2-hour sunset catamaran sail with live music, open bar, appetizers, practical tips, value advice, and honest drawbacks.
“Fun live music and a sunset sail. The captain, crew, and live musician were great. Open bar and light snacks were provided”
Review of Key West’s two-hour sunset catamaran cruise with open bar, appetizers, live music, sailing, and practical booking tips.
“This cruise was over the top. The food the drinks the entertainment and the sunset a very memorable trip!”
Review of Key West’s Jolly II Rover sunset sail, with red sails, cannon fire, island views, snacks, practical tips, and honest drawbacks.
“It’s the perfect romantic date or wedding proposal having the sunset and getting to propose in the captains spot and they helped by taking our picture it was amazing everyone one was super sweet and helpful”
Review of Key West’s two-hour Appledore sunset sail, with classic sailing, open views, drinks, snacks, practical tips, and honest value advice.
“This is a fun excursion. Only two hours but it fits into a schedule to see sights, have dinner, etc.”
Pick a rig, a coast or an afternoon.
