Step aboard the Appledore II in Key West for a tall ship sailing experience that combines historic rigging, vibrant marine life, and refreshing cocktails. Discover coastal landmarks and marine wildlife as you sail in style.
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Difficulty
easy
Duration
3–4 hours
Fitness Level
Basic mobility needed to move around decks and participate in raising sails; suitable for beginners and families.
Wildlife
History
The Appledore II inherits the design legacy of the Smith family's series of schooners known for circumnavigating and bridging northern and tropical waters for over a century.
Conservation
Appledore emphasizes sustainable tourism practices by limiting passenger counts and encouraging respect for local marine wildlife and habitats.
Appledore - Key West
Step aboard the Appledore II in Key West for a tall ship sailing experience that combines historic rigging, vibrant marine life, and refreshing cocktails. Discover coastal landmarks and marine wildlife as you sail in style.
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.
Wear Non-Slip Shoes
Decks can get wet—choose shoes with good grip to stay steady while moving around the schooner.
Bring Sun Protection
Wide-brim hats and sunscreen are crucial for midday sails on open water under Florida’s strong sun.
Arrive Early
Give yourself time to check in and get oriented before departure at Key West’s Historic Seaport.
Motion Sensitivity
If prone to seasickness, consider taking preventive medication—waves on the Atlantic side can be choppy.
Non-slip deck shoes
Protects your footing on wet, moving decks.
Sunglasses with UV protection
Reduces glare and protects eyes from intense sun.
summer
Light windbreaker or layered jacket
Keeps you comfortable during cooler mornings and breezy sails.
spring
Water bottle
Stay hydrated during the sunny day on the water.