Key West · HISTORIC SCHOONER DAY SAILS
15 reviewed
Tall masts and canvas still work the harbour, and a day sail on one beats any motor cruise for the ride. These are the best historic schooner sails — which raise the sails for real, which include snorkelling or drinks, and which run small enough to feel like a private charter.
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!”
Sail on the America 2.0 schooner in Key West for a 2-hour sunset cruise with drinks, hors d’oeuvres, wildlife, and a shot at the Green Flash.
“Friendly staff, clean boat, and overall great experience. Would recommend to anyone in the Key West area!”
Key West sunset sail on the Schooner Appledore with real sail raising, 360 views, and included drinks and snacks.
“This is a fun excursion. Only two hours but it fits into a schedule to see sights, have dinner, etc.”
Classic Key West schooner sunset sail with full open bar and hors d’oeuvres, gliding past Mallory Square and Sunset Key.
“Great time with a beautiful sunset! Very professional crew! The crew took great care of us the entire time.”
1.5-hour Key West sail on America 2.0 with two included drinks, free soda and water, and coast-hugging views plus dolphin and turtle spotting.
“Excellent crew. All female. Great conversations. Small group of 10. Day sail. Saw dolphins and a shark.”
Sail Key West at sunset on the historic schooner When and If. Enjoy beer and wine, spot dolphins, and help raise sail.
“So much fun! Great time on a historic ship! Would recommend this to anyone who wants to get out to see the sunset or looking for an enjoyable evening.”
5-hour Key West backcountry sail with snorkeling and kayaking, plus gourmet lunch and beer/wine on a double-masted schooner.
“Amazing. Captain and crew were amazing! Definitely would recommend this particular tour ship. Nice to not be with too many people.”
Sail Key West on the Schooner Appledore for about 2 hours with a full open bar, English guide, and classic waterfront views.
“Very enjoyable way to get out on the water. Sailing was so peaceful compared to being on a power boat. The crew was great too.”
Sail the 2-masted Appledore II for a classic Key West sunset with champagne and a hands-on sail-raising tradition.
“Beautiful sunset sail. The crew were extremely friendly and shared tons of information about the ship and gave us an unforgettable experience!”
Classic schooner Key West sunset sail with 8 wines, premium beer, and gourmet appetizers in 2 hours from Opal Key Resort.
“Loved it all. very fun, knowledgeable, and skilled crew. Would go back every evening if I could.”
America 2.0 schooner sail in Key West: 90 minutes, onboard bar drinks, soft drinks, wildlife spotting, and views of Fort Zachary Taylor.
“Wonderful young crew super friendly, knowledgeable and truly cared about their guests. Captain Rae had lots of stories to share while sailing the boat.”
Race nine miles offshore to Sand Key Lighthouse on Schooner America 2.0 during Key West Wreckers Race, with drinks and a boxed lunch.
“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.”
Two-hour Key West sunset sail on the Appledore Star with champagne, sangria, hors d’oeuvres, and a classic schooner sunset.
“Petit groupe, équipage au top, très belle autre façon de vivre the sunset à KW”
6.5-hour Key West sail and kayak with snorkeling, mangrove refuge channels, lunch onboard, and eco-guided wildlife learning.
Cruise Key West at night on Schooner America 2.0, enjoy stargazing with a laser, and get two included drink rounds for adults.
“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”
