THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
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.
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.
Book with Appledore - Key West
Verified experiences and guided adventures in the surrounding area.
Operated by Appledore - Key West · Key West, Florida
Set against the sunlit, salt-tinged backdrop of Key West, Appledore - Key West offers a rare window into maritime heritage aboard the iconic Windjammer Classic Day Sail. This 2-masted schooner, the Appledore II, traces its lineage to schooners of the 19th century but delivers modern comfort for up to 49 passengers. Departing from the Historic Seaport, the ship glides past landmarks like Mallory Square, Fort Zachary Taylor, and the Navy Mole, weaving history with the stunning natural coastline.
Key West’s coastal waters are renowned for vibrant marine ecosystems; aboard the Appledore II, passengers often spot dolphins frolicking alongside or turtles gliding below the surface. Overhead, ospreys and pelicans scan and swoop, adding dynamic wildlife moments to the cruise. The schooner’s large, open decks provide multiple vantage points, encouraging guests to take part in raising sails or steering, lending hands-on connection to traditional sailing techniques.
What sets this experience apart is the blend of adventure and refined hospitality. Complimentary crafted cocktails, including signature Bloody Marys and Dark & Stormies, refresh as the sails snap taut in the tropical breeze. The small passenger capacity allows for a relaxed, less crowded atmosphere compared to typical charters.
The Appledore II spends summers sailing Maine’s rugged coast but winters in the Florida Keys, making Key West its seasonal home and a unique hub for classic tall ship cruises. This seasonal migration itself is emblematic of the schooner’s storied history and adds to its narrative authenticity.
For visitors seeking a meaningful maritime outing in Key West, the Windjammer Classic Day Sail offers a tangible link to nautical traditions combined with the vivid natural beauty of the Keys. It’s a standout sailing adventure that captures both spirit and place, inviting travelers to engage actively in the rhythms of the sea just beyond the island’s shores.
easy.
3–4 hours.
Basic mobility needed to move around decks and participate in raising sails; suitable for beginners and families.
Children aged 4 and older can book a ticket; children under 4 ride free but must be accompanied by an adult.
The sail includes complimentary cocktails and non-alcoholic beverages, but no full meals; you may bring light snacks if desired.
Due to the historic design and layout of the schooner, wheelchair access is limited and not recommended.
Yes, guests are encouraged to help hoist sails and even take a turn at the wheel under crew supervision.
Tours may be rescheduled or refunded in the event of unsafe weather conditions; the crew prioritizes passenger safety.
Bring sun protection, comfortable shoes, and a light jacket; cameras are encouraged for the scenic views.
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.
Appledore emphasizes sustainable tourism practices by limiting passenger counts and encouraging respect for local marine wildlife and habitats.
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.
Book with Appledore - Key West