Schooner When and If in Key West
Schooner When and If in Key West: George Patton's 1939 Alden schooner, her wreck and rebuild, the sunset sail, what is poured, the season and which dock.
When and If is a 63.5-foot wooden schooner designed by John G. Alden and built in Wiscasset, Maine, for George S. Patton, who named her for the voyage he planned “when the war is over, and if I live through it.” He died in 1945 without making it. Her operator, Sunset Sail Key West, 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 sail is two hours with select beer and wine, a champagne toast at sunset, included on the Viator booking, and a turn at the wheel, from $117 an adult on Viator (checked October 2026).
Her story
| Year | |
|---|---|
| 1938 to 1939 | Launched in November 1938 at F. F. Pendleton’s yard in Wiscasset, Maine, and delivered to Patton in 1939: double-planked in mahogany on black locust frames |
| 1945 | Patton dies; the family keeps the schooner |
| 1972 | The Patton family gives her to the Landmark School, which uses her for training sails |
| 1990 | A nor’easter drives her onto the rocks at Pride’s Crossing, Massachusetts, with a hole in her port side |
| 1994 | Relaunched from Gannon and Benjamin on Martha’s Vineyard after a rebuild |
| 2011 to 2017 | A second rebuild and a new teak deck; her captain, Seth Salzmann, refits her, leases her and becomes her owner |
From the schooner’s own site and Sunset Sail Key West’s pages, read October 2026.
She spends the summer in Salem, Massachusetts, and the winter in Key West, and carries up to 28 guests on a shared sail.
The sunset sail
Two hours under sail at sunset, with select beer and wine, soft drinks and bottled water, a champagne toast at sunset, included on the Viator booking, and a restroom on board; bottle service is an extra. The crew handles the sails, and anyone who wants to can take the wheel or help raise them. Children sail at a lower fare and must come with an adult; children 6 and under wear a lifejacket on board. Sunset Sail Key West also welcomes guests to bring their own drinks, with coolers of ice provided.
On the Viator calendar the sail leaves:
| Dates | Leaves | Sunset |
|---|---|---|
| November | 4:00 pm | 5:39 to 5:48 pm |
| 1 to 15 January | 4:15 pm | 5:50 to 5:59 pm |
| 16 January to 5 February | 4:30 pm | 6:00 to 6:15 pm |
| 6 February to 3 March | 4:45 pm | 6:15 to 6:31 pm |
| 4 to 13 March | 5:00 pm | 6:31 to 6:35 pm |
| 14 March to 7 April | 6:00 pm | 7:36 to 7:46 pm |
| 8 April to 9 May | 6:15 pm | 7:46 to 8:00 pm |
| From 10 May | 6:30 pm | 8:00 pm and later |
Departures from the Viator schedule (checked October 2026); December showed no open dates when it was read. Sunset at Mallory Square from the NOAA solar equations; clocks go forward on 14 March 2027.
Which dock
This is the one thing to check. Sunset Sail Key West’s own site puts her departures at the Perry Marina on Stock Island, 7001 Shrimp Road, about 6 km east of Old Town, a marina with bars and restaurants. Her Viator listing meets at the end of E dock on the Key West Bight boardwalk, in front of the Waterfront Brewery, with check-in at the boat 15 to 30 minutes before. Go by the dock on your booking confirmation, and if it names the Perry Marina, ask about parking when you book and allow for the drive out of Old Town.
Who she suits
Key West Sunset Sail on the Schooner When and If
Patton's schooner, 28 guests at most, a champagne toast at sunset and the wheel if you want it.
Check dates →Key West Sunset Sail on the Schooner Appledore
The Appledore, a wooden windjammer from the end of William Street: help raise the sails, with cocktails and hors d'oeuvres.
See the Appledore →Key West Sunset Sail on the Schooner America 2.0
America 2.0, the 105-foot schooner from Schooner Wharf, with a plate of hors d'oeuvres each.
See America 2.0 →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.
- Weather: the captain checks the weather before every sail, and a captain’s cancellation is refunded in full. On Viator you can cancel up to 24 hours ahead for a full refund.
- Season: her operator gives Thanksgiving to Memorial Day; her Viator calendar opens dates from 1 November, shows none in December and runs into the first week of June (read October 2026). In the summer she is in Salem, Massachusetts.
- Other boats: Sunset Sail Key West also sails the 1930 Alden schooner Malabar X from the Perry Marina, and the sloop High Tide from Schooner Wharf Bar.
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 When and If at Sunset
Two hours on George Patton's 1939 wooden schooner, with select beer and wine, a champagne toast at sunset and a turn at the wheel.
Check dates on Viator