Schooner America 2.0 in Key West

America 2.0 is the big schooner of Key West: 105 feet overall, 3,600 square feet of sail and a black hull, built in Albany, New York, in 2011 as a tribute to the schooner America, which won the 1851 race around the Isle of Wight that became the America’s Cup. Classic Harbor Line sails her in Key West from November to May and in New York from June to October. Her sunset sail is two hours with beer, wine, champagne and a plate of hors d’oeuvres for each guest; the crew does the sailing.

The sunset sail costs from $123 an adult on Viator (checked October 2026) and $123 on GetYourGuide (checked October 2026); pick a date on the calendar:

The ship

From Classic Harbor Line’s own boat pages, read October 2026.

The original America was a New York racing schooner that crossed the Atlantic in 1851 and beat the British fleet around the Isle of Wight; the cup she won was renamed after her. America 2.0 is a modern yacht in her spirit rather than a copy: a light composite hull, modern rigging and an electric motor for the harbour. She is not wheelchair accessible, though the crew can often help guests who need a hand on board.

The sails

Prices per adult on Viator (checked October 2026); they change by date and season, and tips are not included.

The sunset sail heads out of the Key West Bight along the waterfront, past Mallory Square and Sunset Pier, with Sand Key Light Tower on the horizon to the south. The day sail covers the same water in daylight, when the shallows show their colour, and is the cheapest way aboard; children sail free on the afternoon departures. The full moon sail goes out for a few evenings each month as the moon rises over the island. Classic Harbor Line also runs a stargazing cruise and holiday sails, and on race days takes guests along in the Wreckers’ Race.

Check dates for the sunset sail

The Wreckers’ Race

Key West’s wreckers once raced each other to ships aground on the reef, and the first to arrive claimed the salvage. Schooner Wharf Bar keeps the custom alive with the Wrecker’s Cup, a race series from Key West Harbor to Sand Key, 7 miles out; the 2026 series ran from 25 January to 26 April, with races on Sunday afternoons. America 2.0 races with paying guests aboard, three hours with a boxed lunch. The 2027 dates had not been published in October 2026.

Before you go

• Check-in: Classic Harbor Line’s ticket booth stands on the right side of Schooner Wharf Bar, 202 William Street, as you face the water; collect your boarding pass there 30 to 45 minutes before. The schooner leaves promptly, and a missed sail cannot be refunded or moved. The free Duval Loop bus stops at Caroline and William streets.
• Drinks: you may not bring your own alcohol on board. Cocktails can be bought on the sunset sail; the included drinks are for guests 21 and over. On Viator, a bottle of champagne or white wine with souvenir glasses is a paid upgrade (two tickets minimum), and Thanksgiving, Christmas and New Year departures carry holiday rates (checked October 2026).
• Children: ages 2 to 12 take a child ticket and under-2s an infant ticket.
• Weather: the captain decides on the day, up to an hour before sailing, and a weather cancellation gets you another date or a refund. On Viator and GetYourGuide you can cancel up to 24 hours ahead for a full refund.
• Bring: a light jacket; it is cooler on the water after sunset.

The departure points guide has the walk and the parking, and the open bar guide compares what each schooner pours.

Or another 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.