SAILING WORLDWIDE
The best days on the water.
The 11 most popular key west sailing trips. What each sail costs, how long you are on the water, and which crews run it well.
Sail Key West at sunset on a spacious catamaran with live music, open bar, and hearty hors d’oeuvres. 2 hours, great views.
Most Popular“Great staff, fun apps and delish drinks. Boat is nice and big with plenty of room up top and the covered down below”
Half-day Key West snorkel sail on a 69-foot catamaran with reef time, gear included, and beer/wine plus cocktails on the return.
“Crew was great, we had a wonderful time. The boat was clean and equipment was in great working order.”
Key West small-group sunset sail with wine and hors d’oeuvres: up to eight wines, five beers, and a calm, romantic 2-hour cruise.
“Small group, really personal and quiet! It was perfect for a sunset cruise! Good amount of wine and beer and little charcuterie skewers to round out a great time, for sure.”
A 2-hour Key West catamaran sunset party with live music, unlimited drinks, and appetizers, plus prime water views and quick return for dinner.
“Not your usual review as our sunset cruise was cancelled by a freak raging windstorm. Just wanted to thank the team there at the pier that handled everything so professionally and quick. Rescheduling was offered but we had opt for cancellation as it was our last night in town.”
Key West sunset sail with beverages included. Small group, attentive crew, harbor views, and a front-row look at the night celebration.
“I do not have a rating on this. Unfortunately, our trip was cancelled due to high winds. I can say that the cancelation was done early enough that we could make other plans. Maybe next time.”
Sunset sail on America 2.0 in Key West: beer, wine, champagne, plated hors d'oeuvres, and views of Fort Zachary from the water.
“Highly recommends to those who appreciate a quiet sail vs a powerboat. Crew was kind and accommodating , drinks were robust and plentiful! We thought appetizers were also fresh and delicious!”
Full-day kayak, snorkel and sail from Key West with a 65-foot schooner, wildlife refuge stops, and an all-inclusive buffet lunch.
“Great staff well organized the food and drinks worked well. On time and an easy sign in. lot of fun for anyone who likes the water or sailing.”
Small-group Key West sunset sail with dolphin watching, premium wine, and chef-selected tapas on a luxury catamaran.
“Very enjoyable sailing and ocean experience with personalized service and attention to detail on behalf of captain & assistant”
Sail Key West’s Historic Harbor on a champagne sunset catamaran with included drinks, captain-led viewing spots, and ocean views.
“Had an amazing time, crew is happy and attentive, saw tons of dolphins and saw an amazing sun set. Can’t beat the value!”
Small-group Key West snorkeling from a 54-foot sail yacht with sanitized gear, reef wildlife, and drinks included. 3 hours, $79.
“It was a great tour. We were worried about the weather, but the captain decided to go on the Thanksgiving day with only 5 people on the boat. Very appreciate the decision! The staff was so nice and provided the best service and help us to prepare for snorkeling. Saw beautiful fishes and good amount…”
Full-day catamaran trip from Key West to Dry Tortugas: Fort Jefferson tour, snorkeling with gear provided, and breakfast/lunch included.
“snorkeling was wonderful It was very hot so the water was amazing. Dry Tortegas was ok. Something I would only want to do once.”
The sailing ports worth the trip, grouped by the sea they sit on.
