Key West Schooner

A schooner is a sailing ship with two or more masts and fore-and-aft sails, the working rig of the American coast in the nineteenth century, and Key West keeps a small fleet of them for visitors. Four sail public trips from the old harbour the locals call the Key West Bight, or a few blocks from it: America 2.0, a 105-foot schooner launched in 2011 in honour of the yacht that won the first America’s Cup; the Appledore, in fact two wooden schooners of that name; When and If, the wooden schooner built for George Patton in 1939; and the Jolly II Rover, an 80-foot square-rigged topsail schooner with red sails. Danger Charters adds four schooners of 48 to 57 feet for wine sails and trips to the backcountry.

The short answer

For one sail, take America 2.0 at sunset: two hours under 3,600 square feet of sail with beer, wine, champagne and soft drinks, and a plate for each guest of cheese and crackers, vegetables and dip and shrimp cocktail. It costs from $123 an adult on Viator, rated 4.9 from 893 reviews on Viator and Tripadvisor (checked October 2026), and the same sail is on GetYourGuide from $123 (checked October 2026). Check in at Classic Harbor Line’s booth on the right of Schooner Wharf Bar, 202 William Street, as you face the water; you must be 21 to drink.

Check dates for America 2.0

If you would rather haul on a line yourself, or sail with fewer people, one of the other three suits you better.

Pick your schooner

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.

The four schooners

America 2.0 (guide) is the largest and the most polished. Classic Harbor Line had her built in Albany, New York, in 2011, a black-hulled tribute to the schooner America that won the 1851 race around the Isle of Wight; she is certified for 85 passengers and has two bathrooms. The crew sails her while guests sit back with a drink. She spends November to May in Key West and June to October in New York, and besides the sunset sail runs a 90-minute day sail with two drinks for adults, from $79 on Viator (checked October 2026), when children sail free on the afternoon departures.

The Appledore (guide) is the hands-on one, and there are two of her. Appledore II is an 86-foot windjammer built at the Gamage Shipyard in Maine 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 by Jim Richardson of Lloyds, Maryland. Key West Schooners sail both and may swap one for the other. Guests help raise the sails and take the wheel, and the sunset sails pour cocktails, beer and wine with hors d’oeuvres and cocktail shrimp.

When and If (guide) is the one with the story: a 63.5-foot wooden schooner designed by John G. Alden and built in Wiscasset, Maine, for George Patton, who meant to sail her round the world “when the war is over, and if I live through it.” She was wrecked in a nor’easter in 1990, rebuilt and relaunched in 1994. Her own site puts her departures at the Perry Marina on Stock Island, east of Old Town, while her Viator listing gives a dock in the Key West Bight, so go by your booking confirmation.

The Jolly II Rover is the square-rigger: red sails, cannons, no band, and a crew who let you hoist sail and steer. She sails all year from the Historic Seaport, with her ticket booth on the dock beside Conch Republic Seafood Company at Greene and Elizabeth streets.

Sunset, day or eco sail

Most people sail at sunset, but the schooners also go out by day and further afield. A day sail is cheaper and brighter, with the water at its clearest; a full moon sail on America 2.0 goes out after dark; and two operators take a schooner into the mangrove islands of the Key West National Wildlife Refuge to kayak and snorkel: Key West Schooners’ five-hour eco sail on the Appledore Star and Danger Charters’ half-day trip, whose afternoon departure sails home at sunset. The sunset, day or eco sail guide sets them side by side.

When the schooners sail

America 2.0, the Appledores and When and If are winter visitors: America 2.0 sails Key West from November to May, the Appledore’s Viator calendar runs from 1 November 2026 to 31 May 2027, and When and If’s operator gives her season as Thanksgiving to Memorial Day, while her Viator calendar opens dates from 1 November, shows none in December and runs into the first week of June (read October 2026). The Jolly II Rover and Danger Charters sail all year, weather permitting. The sunset sails leave earlier in winter and later in spring, so that the sun goes down while you are out:

Departures from each schooner’s Viator schedule, read October 2026; sunset at Mallory Square from the NOAA solar equations, within two minutes of the U.S. Naval Observatory’s tables. Clocks go back on 1 November 2026 and forward on 14 March 2027. America 2.0’s times appear only on its booking calendar; your confirmation gives the exact time.

Where they leave from

Three of the four check in within a minute’s walk of each other at the Key West Bight: America 2.0’s booth by Schooner Wharf Bar, the Appledores’ at the far end of William Street to the right of the Western Union sign, and the Jolly II Rover’s at Greene and Elizabeth streets. Danger Charters’ schooners leave from Opal Key Resort on Front Street, by Mallory Square, and When and If from Stock Island. The departure points guide has a close-up map and the parking.

What is included

America 2.0 and the Appledore sunset sails come with the drinks and the food; Key West Schooners also sell a sunset sail with a full open bar and no food listed; When and If pours select beer and wine, with a champagne toast at sunset included on the Viator booking; the Jolly II Rover’s fare covers ice, cups, water and snacks but no alcohol. The open bar, champagne and food guide sorts them, with each price.

The Western Union

Visitors still ask for the Western Union, the schooner launched at Key West in 1939 that laid and mended undersea telegraph cables until 1973. She is not offering public sails as far as can be confirmed, and since 1 July 2026 she is no longer Florida’s official state flagship: the Legislature passed the title to the S.S. American Victory in Tampa.

Who should pick something else

• A party with a band: the schooners are quiet. The big sailing catamarans of Key West carry the open bars and the live music.
• Wine before anything: Danger Charters’ Wind and Wine sail is a guided tasting on a small schooner, ages 13 and up, from $135 (checked October 2026).
• Summer: America 2.0 is in New York from June to October, Appledore II in Maine and When and If in Massachusetts; the Jolly II Rover and Danger Charters’ schooners stay and sail all year.