Sailing the Dream — Aboard the Schooner When And If
Sailing Through Time: The Schooner When And If
In 1939, General George S. Patton commissioned a schooner he dreamed would carry him around the world “when the war is over, and if I live through it.”
Crafted by John Alden and built in Maine, she was double-planked in mahogany, framed in black locust, and designed to endure. Though Patton never realized his circumnavigation dream, the vessel lived on — passing through decades of training sails, near-disasters, and loving restorations.
Today, the When And If sails strong — summers out of Salem, Massachusetts and winters in Key West, Florida.
The Seasonal Voyage
Each year, the schooner migrates like a seabird — from the cool harbors of New England to the warm tropical sunsets of the Keys.
![Map showing When And If’s annual route between Salem, MA and Key West, FL]
This dual life gives guests two distinctly different experiences: crisp autumn light on the North Shore, and fiery tropical skies off Mallory Square.
What Guests Say About Sailing Onboard
In Salem
- “The boat is 80+ years old, in perfect condition… We went out around Baker’s Island and saw a beautiful sunset.”
- “This is a must for anyone visiting Salem! The crew was incredibly friendly, helpful, and knowledgeable.”
- “Lovely piece of history, great crew. Peaceful vibe. They served wine, and it was just a lovely evening.”
![Guests sailing aboard When And If in Salem, Massachusetts]
In Key West
- “Everything was more than perfect. Beautiful historic schooner, professional and friendly Captain and crew. Delicious beverages.”
- “We had a very small group aboard… the crew took great care of us. Found lots of dolphins!”
- “Great experience, smooth sailing, stunning sunset. Could not ask for more.”
![Schooner When And If at sunset off the coast of Key West, Florida]
Why When And If Captures Hearts
- Living history – More than a tour, it’s a chance to sail aboard a dream.
- Warm, skilled crew – Guests consistently praise their hospitality.
- Atmosphere – From Salem’s lighthouses to Key West’s tropical sunsets, each sail feels like a painting come alive.
- Comfort & charm – Wine, hors d’oeuvres, and the schooner’s wood-and-sail character make every moment feel timeless.
Planning Your Sail
- Where: Salem, MA (summer/fall), Key West, FL (winter/spring)
- When: Book at sunset for the most atmospheric experience.
- What to bring: A light jacket, soft shoes, and a camera.
The dream that Patton never lived to see still sails on — carrying new generations into the horizon.