KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 13 most popular schooner sailing in Key West. What each trip costs, how long it runs, and who takes you out.
Sail on a replica Key West schooner at sunset with open bar and plated hors d’oeuvres, passing Fort Zachary and classic waterfront views.
Most Popular“Captain Janet along with her crew of Heather, Jade, and Milo we're so friendly and accommodating and efficient. Good snacks, nice wine, and a beautiful sail into the sunset.”
Sail Key West at sunset on the America 2.0 schooner. Drinks and hors d'oeuvres included, wildlife sightings, and a shot at the green flash.
Sail Key West at sunset on a classic wooden schooner with real sail work, small-group calm, and included drinks and hors d’oeuvres.
“Wonderful crew and hospitality. Appetizers were wonderful surprise and variety of drinks very good. Loved the Maine connection.”
Classic Key West schooner sunset sail with a full open bar, cocktails, snacks, and a calm small-boat ride past top waterfront landmarks.
“So much fun! Josh (our captain) and Molly were fantastic! So much fun! Highly recommend! Open bar and food. Great service and so much fun!”
Sail Key West’s coast on the America 2.0 schooner with 2 included drinks, wildlife spotting, and classic waterfront views in 1.5 hours.
“Very relaxing 2 hour, sail was not over crowded, well organized crew,”
Sail Key West at sunset on the historic schooner When and If. Help raise sails, spot dolphins and sea turtles, and enjoy beer/wine.
“Dress warm as it can be a little cooler on the water. Captain Zach was great as well as first mates Veronica and Jahn. The boat also summers in historic Salem MA. Highly recommend.”
Key West eco-sail: double-masted schooner with kayaking and snorkeling, plus lunch, snacks, and wine. Small group, 5 hours.
“Highly recommend. Great value. Lunch was fun. Activities at easy level. Scenery wonderful. Staff couldn't be nicer.”
Two hours on the Appledore schooner in Key West with a full open bar, great crew, and classic waterfront views from the deck.
“Great sunset trip crew was very fun and personable. Will definitely do again in the future. I got several amazing pictures.Thank”
Wind and Wine sunset sail in Key West: classic schooner, eight wines, premium beer, charcuterie, and sunset sailing magic.
Cruise Key West on the America 2.0. Sail past Fort Zachary Taylor, Sand Key reef, Mallory Square, and Sunset Pier with soft drinks and bar.
Sail into Key West Wreckers Race on Schooner America 2.0, race toward Sand Key Lighthouse, enjoy big views, lunch, and included drinks.
“The boat is beautiful and fast. The captain and crew are skilled sailors, but also friendly, light-hearted, and funny. They managed a full lunch and drink service effortlessly. It was a beautiful sail on a beautiful day.”
Sail Key West by night on Schooner America 2.0 for a smooth stargazing cruise with two included drinks and expert help.
“The crew was very friendly and professional. They explained everything and let us be part of the experience . Would definitely do business with them again”
A 2-hour Key West sunset sail on the Appledore Star, with champagne, top-shelf drinks, hors d’oeuvres, and hands-on sailing.
Every way to get out on the water, and every reason to stay for the sunset.
