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 and crew were fantastic. Great experience. The food and drinks were great. We also had a spectacular 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.
“Our experience aboard the Schooner Appledore was fantastic! Crew members Joe, Mary, and Christina were AMAZING; they were prepared with stories and anecdotes of their time at sea, and it was so fun to learn about their adventures. Drinks were great, apps were yummy, and they were appropriately careful of my spouse’s shellfish allergy. We…”
Classic Key West schooner sunset sail with a full open bar, cocktails, snacks, and a calm small-boat ride past top waterfront landmarks.
“Great outing. Service and experience were at the center of everything Captain Josh and Christina did. Safe loading of passengers, a ‘to the point’ safety overview, almost immediate serving of tasty cocktails/water/etc, and tasty treats (shrimp cocktail, key lime tart, smoked fish with crackers). The boat was nice having padded seating, toilet below deck, and…”
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.
“Captain and crew made it a fun experience! We had a beautiful day for sailing and enjoyed the short tour from the water.”
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.
“. It was a fantastic experience, the guides were very good and kind, and they were very attentive to our needs throughout the trip. We felt very safe at sea. I would recommend to others not to miss this trip with Joe and Cristina.”
Two hours on the Appledore schooner in Key West with a full open bar, great crew, and classic waterfront views from the deck.
“Great experience. Crew was great!! Weather was amazing and sailing experience was wonderful. Crew was knowledgeable”
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.
“This was a great experience. The crew was friendly and fun, but also very competent. This is a special boat--beautiful and well-maintained.”
Sail Key West by night on Schooner America 2.0 for a smooth stargazing cruise with two included drinks and expert help.
“We’ve been to Key West many times over the years, always looking for something new to do for fun. We booked this tour with family, which are all adults. The gentleman on the cruise was very knowledgeable about the stars and used a laser to point where they were located in the sky. I’m always…”
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.
