Key West · SUNSET SAILS FROM MALLORY SQUARE
35 reviewed
Nothing says Key West like casting off as the sky turns tangerine. Here are the best sunset sails from the Historic Seaport and Mallory Square — the quiet champagne schooners, the full-on party catamarans, and everything between — with prices, what’s poured, and how to match the boat to your crowd.
Sail into Key West sunset on a 60–70 ft catamaran with an open bar, live local music, and hearty hors d’oeuvres for about 2 hours.
“Staff is very attentive and customer service oriented! The appetizer were very good. Music was also fun. A lovely evening!!”
Key West sunset dinner cruise with tropical buffet and unlimited drinks. Live music on a 65-foot yacht for a 2-hour sunset sail.
“It was a blast. Great crew, great music, excellent fun vibe....all around great experience and the best lemon drop I've ever had from the young blonde bartender on the upper deck”
Key West small-group sunset sail with wine tasting, beer, and hors d’oeuvres on a schooner-like boat for about two hours.
“Go on the sunset sail! You won’t regret it! Our friend group of 6 went on a sunset sail with captain Mary, Lexi, and Connor. It was the highlight of everyone’s Key West trip! The crew was amazing. You could tell that they absolutely love what they do and truly care about their passengers experience. I’m sure that they could cater to any age group and make any sailing experience worthwhile. We loved the way that they served wine and appetizer courses. The appetizers were creatively served skewer style, but still kept taste in mind by pairing things such as fig and cheese, mozzarella and tomato, as well as apples…”
Key West sunset sail on a 65-foot catamaran with live music, unlimited margaritas and appetizers, plus views over Mallory Square.
“Great time from start to finish. Good band, food and open bar. It was all really fantastic. A must do.”
A small-group Key West sunset sail with drinks included. 90 minutes on the water, great views, and service that keeps things easy.
“It was fabulous! This is my fourth time sailing with you guys and it was great! Great music, drinks, and conversation. So relaxing.”
Key West sunset on the schooner America 2.0 with beer, wine, champagne, and plated hors d’oeuvres plus views of Fort Zachary and Mallory Square.
“Great staff, fun and beautiful Can’t beat the views and the staff were engaging and a knowledgeable!”
Key West sunset sail with dolphin watching plus premium wine and chef’s tapas. Small group, landmark views, and an easy 2.5-hour plan.
“The sunset cruise was a lot of fun. We enjoyed the views, the beautiful sunsets, and the dolphins. The appetizers were delicious and the staff were knowledgeable and fun!”
A 69-foot Key West catamaran at sunset with captain-led views, included champagne-style drinks, and a laid-back 1.5-hour sail from the harbor.
“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. The crew was amazing and on point attending to any needs we had. Highly recommend this cruise.”
See North America’s only living coral reef on a Key West glass-bottom catamaran, with an optional sunset cruise and champagne.
“Perfect sunset night travel. Enjoyed the education about the coral reef and our crew was a delight during the trip.”
3-hour Key West dolphin watching and snorkeling sunset cruise with snorkel gear, beer, and reef time near Cottrell Key.
“Excellent adventure & fantastic staff! Snorkeling, watching a pod of dolphins playing, and a breathtaking sunset. Great memories!!!”
Key West reef snorkeling on a roomy catamaran with drinks after your snorkel and an optional sunset sail with rum punch.
“We very much enjoyed the snorkeling/sunset cruise! The crew was fun and helpful, and ran everything very smoothly. Definitely a great deal and worth the money!”
A 2-hour Key West catamaran sunset cruise with unlimited open bar, appetizers, and live music on the water at historic harbor.
“Free food and beverages live music and of course the sunset!”
Snorkel Key West’s living coral reef, then cruise into sunset on a catamaran with reggae and rum punch. 3 hours, $59.95.
“Reef snorkeling did not disappoint. We actually had more time than advertised and the crew made sure we had our fill of rum punch afterwards.”
Sail on the America 2.0 schooner in Key West for a 2-hour sunset cruise with drinks, hors d’oeuvres, wildlife, and a shot at the Green Flash.
“Friendly staff, clean boat, and overall great experience. Would recommend to anyone in the Key West area!”
Sail the Sandie Cat on a 2-hour Key West sunset cruise with live music, unlimited open-bar drinks, and snacky appetizers for $72.
“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.”
