KEY WEST BOAT TOUR FIELD GUIDE
Helm, Sails, and Sangria: Day Sailing Key West Aboard the Appledore II
A hands-on day sail aboard a 2-masted schooner — ride the Appledore II, help raise the sails, enjoy complimentary cocktails, and trace Key West’s coastline (available November–May).
Helm, Sails, and Sangria: Day Sailing Key West Aboard the Appledore II.
Step aboard the Appledore II, a two‑masted schooner operating as a passenger windjammer in Key West, and you trade a dockside crowd for the old‑school choreography of canvas and rigging. On this day sail you can take a turn at the wheel, help hoist the sails and sip complimentary cocktails as the schooner works past Key West Harbor, Mallory Square, the Navy Mole, Sunset Key and Fort Zachary Taylor — a short, sensory immersion in the coast and marine life that defines island sailing.
Highlights
Outing Highlights
A Two‑Masted Schooner with History
The Appledore II is a classic two‑masted schooner in a line of Smith family‑commissioned vessels. Built as a passenger windjammer, she carries a maximum of 49 guests on spacious, comfortable decks and blends traditional tall‑ship features with modern accommodations.
Coastal Landmarks and Marine Sightings
From the Historic Seaport the schooner sails out past Key West Harbor and Mallory Square, skirting features such as the Navy Mole, Sunset Key and historic Fort Zachary Taylor while passengers watch for dolphins, turtles and seabirds.
Hands‑On Sailing and All‑Inclusive Drinks
Guests are invited to participate in traditional sailing — helping hoist sails and taking a turn at the wheel — while enjoying complimentary homemade sangria, boutique wine, premium beer, soft drinks, water and now featured cocktails included in the price.
What the day feels like
What the Sail Feels Like
You depart the Historic Seaport under sails, trading the harbor’s bustle for warm tropical air, the hush of the ocean and intermittent wildlife sightings; crew invite passengers into the rhythm of traditional seamanship while the schooner threads past Key West’s shoreline before returning to port.
THE SHIP
A Two‑Masted Schooner with History
The Appledore II is a classic two‑masted schooner in a line of Smith family‑commissioned vessels. Built as a passenger windjammer, she carries a maximum of 49 guests on spacious, comfortable decks and blends traditional tall‑ship features with modern accommodations.
THE ROUTE
Coastal Landmarks and Marine Sightings
From the Historic Seaport the schooner sails out past Key West Harbor and Mallory Square, skirting features such as the Navy Mole, Sunset Key and historic Fort Zachary Taylor while passengers watch for dolphins, turtles and seabirds.
THE EXPERIENCE
Hands‑On Sailing and All‑Inclusive Drinks
Guests are invited to participate in traditional sailing — helping hoist sails and taking a turn at the wheel — while enjoying complimentary homemade sangria, boutique wine, premium beer, soft drinks, water and now featured cocktails included in the price.
Suitability
Who it's for
Who this sail suits — and who should check details first.
Practical planner
Details to review before reserving
Adult fares start at $49.95 (ages 12+); children ages 4–11 are $29.95; children 3 and under ride at no charge. The schooner carries up to 49 passengers.
Day sail fare includes participation in sailing activities and complimentary beverages: homemade sangria, boutique wine, premium beer, soft drinks and water; cocktails are also featured in the all‑inclusive price.
The Appledore II operates seasonally in Key West for winter months and winters in Key West as part of her year‑round schedule; confirm availability during the advertised Key West season.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
Are beverages included in the ticket price?
Yes — complimentary homemade sangria, boutique wine, premium beers, soft drinks and water are provided, and cocktails are now included in the all‑inclusive price.
How many passengers does the Appledore II carry?
The Appledore II carries up to 49 passengers, with spacious decks and modern passenger accommodations.
Can I participate in sailing the ship?
Yes — passengers are invited to help hoist the sails and may take a turn at the wheel under crew supervision.
What are the ticket prices by age?
Adult fares start at $49.95 for ages 12 and up; children ages 4–11 are $29.95; children 3 and under ride free.
What route does the sail follow?
The schooner departs the Historic Seaport and sails past Key West Harbor, Mallory Square, the Navy Mole, Sunset Key and historic Fort Zachary Taylor before returning to port.
Is the Appledore II a traditional tall ship?
Yes — the Appledore II is a two‑masted schooner in a series of historic schooners commissioned by the Smith family and operated as a passenger windjammer.