Key West · CRUISES & BOAT TOURS
54 reviewed
Out of 54 cruises & boat tours on this site, these 15 are the ones to book. Prices, durations and the standout details are all here — choose in five minutes, then get back to the beach.
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”
Sail off Key West to the Florida Reef for easy snorkeling, see lots of fish, and enjoy an open bar on the way back.
“Very rude staff.. 10 mins of snorkeling in 30 feet water. They were in big rush.. just roamed around in the water to kill time. Very rude staff. Very bad experience. Over crowded too.”
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…”
Adults-only Key West sunset catamaran with bottomless champagne, premium wines and beers, and a gourmet cheese buffet for up to 14.
“Tip Top crew and fellow passengers. Bailey knows her stuff. Picked a good night for the weather the camaraderie and sunset”
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!”
Kayak, snorkel, and sail off Key West in a 65-foot schooner, with buffet lunch and unlimited drinks included.
“Great sailing on an actual sailboat. Captain Janet and crew were great. Also, gave us plenty of time snorkeling and kayaking”
Key West dolphin watching and snorkeling eco cruise on a 45-ft catamaran with gear, drinks, and a chance at sunset views.
“Saw dolphins and had a great time snorkeling. Absolutely recommend that tour”
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.”
Sail on a 54-foot yacht for Key West snorkeling on North America’s only living coral reef, with gear, drinks, and small groups.
“Awesome people very attentive we all had a great time would do again next time we are in the keys thank you both”
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!!!”
