SAILING WORLDWIDE
The best days on the water.
The 15 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“The crew were friendly and on top of filling our drinks. The music was good and he took requests. Our experience was great.”
Half-day Key West snorkel sail on a 69-foot catamaran with reef time, gear included, and beer/wine plus cocktails on the return.
“It was exactly as we anticipated. There were a lot of people on the boat, but the staff was great and well prepared. The equipment they provided was in good condition, but I felt the water wasn't that clear and I had a hard time seeing a lot on the reef.”
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.
“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.…”
A 2-hour Key West catamaran sunset party with live music, unlimited drinks, and appetizers, plus prime water views and quick return for dinner.
“Overall good. Drinks were decent. Surprised there wasn’t a rum drink. Margs were decent for venue. Staff was attentive and friendly. Food was ok also for venue. Served veggies and pin wheel wraps and cheese and crackers and a few other things. The band was very good.”
Key West sunset sail with beverages included. Small group, attentive crew, harbor views, and a front-row look at the night celebration.
“Great night of sailing with a gracious captain and crew. They took great care of us making sure we had everything we needed! It was a lovely night.”
Sunset sail on America 2.0 in Key West: beer, wine, champagne, plated hors d'oeuvres, and views of Fort Zachary from the water.
“First, this tour took off right on time. Check in at least 15 minutes ahead of departure time- we had not checked in and got a call- I thought that was a nice touch. Captain Rae was amazing- she was so personable and explained a lot about sailing to us during the trip. The crew…”
Full-day kayak, snorkel and sail from Key West with a 65-foot schooner, wildlife refuge stops, and an all-inclusive buffet lunch.
“This was so much fun! We took our two teenage grandkids and made some great memories. Kayaking with sharks and sea turtles was the highlight of the day! The crew was amazing and made sure we all had what we needed. The only downside was the colder temperatures but it was still worth every penny.…”
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.
“OK this is take 2 because I use talk to text and I had said some absolutely fantastic words that now I will have to try to recreate in a nutshell it my experience was absolutely phenomenal the staff was absolutely wonderful they were very friendly bubbly enthusiastic and accommodating they spoke to you by…”
Small-group Key West snorkeling from a 54-foot sail yacht with sanitized gear, reef wildlife, and drinks included. 3 hours, $79.
“I would NOT recommend this place at all, flew down to enjoy a birthday getaway from out of state was very much looking forward to getting some sun time and exploring the reefs we get a call 1 hour before our reef departure and was told because we only have a small amount of people…”
Full-day catamaran trip from Key West to Dry Tortugas: Fort Jefferson tour, snorkeling with gear provided, and breakfast/lunch included.
“Incredible Day spent at this National Park, Wonderful history and learned so much about the British and other foreign invaders. Amazingly scenery and incredible weather. A superb day trip, The staff aboard the Catamaran were fantastic. Thank you all for a memorable day and well worth the money.”
Parasail 300 feet above Key West for an 8–10 minute flight, mostly dry, with optional ocean dip and digital photo options.
“This was our first time parasailing for our group of five and it was such an awesome experience. Tony and Abbey were great—super friendly, easygoing, and made us feel safe the whole time. The ride itself was beautiful and way more fun than we expected. We would definitely do it again and recommend Fury Parasailing…”
Snorkel Key West’s living coral reef, enjoy rum punch and reggae on a catamaran, then watch the sunset from spacious decks.
“Great experience. Travelled with 5 and 8 year old. Was perfect for them, saw dolphins, turtles and stingrays”
Sail the America 2.0 schooner on a Key West sunset cruise with drinks, hors d’oeuvres, wildlife spotting, and a shot at the Green Flash.
“The sunset sail was wonderful. We saw a beautiful sunset on our cruise. We were treated to dolphin sightings. The crew was knowledgeable and it was such a thrill to watch them hoisting and lowering the sails. Drinks and snacks were provided. Highly recommended!”
Sail Key West at sunset on the Sandie Cat with live music, an unlimited open bar, and snack appetizers for a fun 2-hour cruise.
“It was a great experience! The sunset was beautiful. Great music and drinks were great too! Not too crowded so plenty of room for everyone to enjoy. We enjoyed it!”
The sailing ports worth the trip, grouped by the sea they sit on.
