Set sail aboard the historic Appledore Star for a private day adventure exploring Key West's iconic waters. Enjoy snorkeling, sunbathing, and expert sailing in an unforgettable Florida Keys experience.
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Difficulty
easy
Duration
4–6 hours
Fitness Level
Suitable for all fitness levels as the sailing is relaxed with opportunities to rest on deck.
Wildlife
History
Key West has a rich maritime history, once serving as a strategic naval base and thriving fishing port dating back to the 19th century.
Conservation
Appledore promotes eco-friendly sailing practices to protect coral reefs and marine habitats in the Florida Keys National Marine Sanctuary.
Appledore - Key West
Set sail aboard the historic Appledore Star for a private day adventure exploring Key West's iconic waters. Enjoy snorkeling, sunbathing, and expert sailing in an unforgettable Florida Keys experience.
Appledore - Key West operates traditional schooner sails and themed cruises from Key West, Florida. The company features two primary vessels, the Appledore II and the Appledore Star, offering a range of departures that include champagne sunset sails, classic day sails, morning Bloody Mary sails, and specialized eco excursions.
Trips combine authentic sailing traditions with modern comfort: guests can help raise sails, enjoy roomy seating, and watch coastal wildlife like dolphins and pelicans. The fleet’s scheduled experiences range from relaxing evening cruises with gourmet hors d'oeuvres and premium beverages to active backcountry adventures that include kayaking through mangrove islands and snorkeling at sponge gardens as part of the Bugeye Backcountry Eco Tour.
Appledore - Key West lists limited-capacity departures and small-group options to preserve an intimate onboard experience and provide personalized attention. Event participation includes seasonal evenings such as the Lighted Boat Parade, offered on select dates with reserved seating and curated beverage selections. Crews are trained to guide sailing activities and support snorkeling and kayaking components where included.
All itineraries are presented with clear descriptions so visitors can choose the appropriate trip—whether seeking a romantic sunset, a family-friendly day sail, or an eco-focused exploration of Key West waters. Operating from Key West, Florida, the Appledore offerings highlight regional maritime heritage through historic schooner sailing and curated coastal experiences.
Location
Key West, FL
Sails depart from Key West harbors.
Tours Offered
6 tours
Sunset, day, morning, and eco options.
Vessels
Appledore II & Appledore Star
Historic two-masted schooners in operation.
Special Events
Lighted Parade Participation
Seasonal boat parade event seating available.
Reserve limited seats for champagne sunsets, day sails, or the backcountry eco tour and secure a memorable Key West experience.
Bring reef-safe sunscreen
Protect your skin and marine life by using reef-safe sunscreen during your sail.
Stay hydrated
Bring a reusable water bottle to stay hydrated throughout the day on the water.
Wear non-slip shoes
Choose non-slip footwear to stay safe while moving around the wet deck.
Bring a light jacket
Evenings on the water can get breezy, so a light jacket will keep you comfortable.
Reef-safe sunscreen
Protects your skin and the delicate marine ecosystem during sunny sailing days.
summer
Polarized sunglasses
Reduces glare from water making it easier to spot marine life and navigate.
Swimsuit
Ideal for swimming or snorkeling when the boat anchors in calm bays.
summer
Light windbreaker
Useful in cooler breezes, especially during early morning or late afternoon sails.
spring