Schooner Appledore in Key West
Schooner Appledore in Key West: Appledore II and the Appledore Star, sunset, open-bar, day and eco sails, prices, departure times, the booth by Western Union.
The Appledore is two ships. Appledore II is an 86-foot wooden windjammer built in Maine and launched in 1978, which sailed round the world on her maiden voyage and still spends her summers in Camden, Maine; the Appledore Star is a 65-foot bugeye schooner built by hand in 1983, the last of her kind. Key West Schooners sail both from the Key West Bight between November and May, may put either on a given sail, and let guests help raise the sails and take the wheel. The sunset sail costs from $99 an adult on Viator (checked October 2026).
Key West Sunset Sail on the Schooner Appledore
Two hours at sunset: cocktails, beer, wine and champagne, and the chef's hors d'oeuvres with cocktail shrimp.
Check sunset dates →Key West Schooner Sunset Sail with Open Bar
Two hours at sunset on a classic schooner with a full open bar of cocktails, beer, wine and champagne; no food listed.
See the open-bar sail →Key West Day Sail on the Schooner Appledore with Open Bar
Two hours under sail from 1:30 pm with a full bar for guests 21 and over. No stops.
See the day sail →Key West Schooner Eco Sail with Kayaking and Snorkelling
Five hours on the Appledore Star to the mangrove islands of the wildlife refuge, with lunch.
See the eco sail →Prices, ratings and review counts from the Viator listings (checked October 2026). Operators price by date and season, so treat the figures as the shape of the market, not a quote.
Two Appledores
| Appledore II | Appledore Star | |
|---|---|---|
| Built | 1978, Gamage Shipyard, Maine | 1983, by hand, by Jim Richardson of Lloyds, Maryland |
| Length | 86 feet overall, 65 on deck | 65 feet overall, 49 on deck |
| Draft | 10 feet | 4 feet 10 inches |
| Rig | Two-masted schooner, a windjammer | Two-masted bugeye schooner |
| Story | Sailed round the world on her maiden voyage; owned by the McKean family since 1988 | The last known bugeye built; came to Key West in late 2015 |
| Sails on | The Windjammer sunset sail (up to 45 guests) and the afternoon day sail | The Schooner Champagne Sunset Sail (up to 22) and the backcountry eco tour (up to 20) |
From Key West Schooners’ own pages, read October 2026.
Twice a year Appledore II makes the 2,000-mile offshore passage between her summer home in Camden, Maine, and Key West. The Appledore Star is the smaller, shallower boat, drawing under 5 feet to Appledore II’s 10, and she is the one that takes the eco tour out to the mangrove islands. The McKean family has run the Key West operation with Sebago Watersports since 2003, so the Appledore sails are also sold by Sebago.
On deck
The Appledores are the hands-on schooners of Key West. The crew raises the sails on the way out of the harbour and invites guests to take a halyard; once under way you can take a turn at the wheel. The sunset sail heads out past the Historic Seaport, Mallory Square’s Sunset Celebration, the Navy Mole where the cruise ships dock and Fort Zachary Taylor, and comes back after the sun has gone. There are no stops. Each ship has a head; there is no restroom at the check-in booth.
When she sails
On the Viator calendar the Appledore sunset sail runs from 1 November 2026 to 31 May 2027 (checked October 2026), and leaves:
| Dates | Sunset sail leaves | Sunset |
|---|---|---|
| 1 November to 14 February | 4:30 pm | 5:39 to 6:21 pm |
| 15 February to 6 March | 4:45 pm | 6:21 to 6:32 pm |
| 7 to 14 March | 5:45 pm | 6:33 pm; 7:36 pm on the 14th |
| 15 March to 11 April | 6:00 pm | 7:36 to 7:47 pm |
| 12 April to 16 May | 6:15 pm | 7:48 to 8:03 pm |
| 17 to 31 May | 6:30 pm | 8:04 to 8:11 pm |
Sunset at Mallory Square from the NOAA solar equations; clocks go forward on 14 March 2027. Your booking confirms the exact time.
The afternoon day sail leaves at 1:30 pm and the eco tour at 10:30 am. Boarding begins 30 minutes before departure.
The eco sail
The backcountry eco tour takes the Appledore Star out to the uninhabited mangrove islands of the Key West National Wildlife Refuge, five hours in all: a sail out, then the day split between a guided kayak tour and guided snorkelling in warm, shallow water, a lunch from the company’s own kitchen, and beer, wine and sangria on the way home, from $119 (checked October 2026). All snorkelling is done before anyone drinks. To climb back aboard you step onto a platform just below the waterline and up a ladder, so it suits guests with a moderate level of fitness. The sunset, day or eco sail guide compares it with Danger Charters’ trips.
Where to check in
The check-in booth is at the very end of William Street, just to the right of the Western Union sign. From Elizabeth Street, keep the water on your left and follow Lazy Way Lane past the shops, with the Marker Resort on your right and Schooner Wharf Bar on your left; the booth is on the left. The nearest parking is the Key West Bight lot at William and Caroline streets. The departure points guide has the rates.
Before you go
- Drinks: you must be 21 and carry photo ID to be served. Guests under 18 sail with a parent or guardian.
- Children: welcome on the Windjammer sails; the smaller Appledore Star sunset sail is pitched at couples and charges children the adult fare.
- Weather: if the captain cancels for weather you get a full refund or another date. On Viator you can cancel up to 24 hours ahead for a full refund.
- Which ship: the sail you book names a ship, and Appledore II or the Appledore Star may stand in for each other.
Other Key West Sails with Open Dates
More Key West Boat Trips with Open Dates
Sunset sails, schooners and snorkel trips, with live availability. Times and cancellation terms are on each listing.
Sail the Appledore at Sunset
Two hours on a two-masted wooden schooner from the Key West Bight: help raise the sails, with cocktails, beer, wine and hors d'oeuvres with cocktail shrimp.
Check dates on Viator