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Sunset Sails. Day Sails. Private Charters.

Regattas. Special Events.

General Patton's gorgeous 1939 wooden schooner is sailing out of

Key West, FL every day this Winter!

Private Charter

 

Cruise The Keys

Daysail in Key West

 

Tropical Winter Sailing

Keep in touch!

 

Day-By-Day-Updates 

Our Winter Hosts

 

Sunset Sail Key West

Book Your Perfect Key West Sailing Experience

Enjoy a day sail, or Key West's most elegant and exclusive Sunset Sail on this historic classic yacht!

Built for General George Patton in 1939, When And If is open to the public for the first time in her history.

Help raise sail, take the wheel or sit back and relax as the crew serves you a selection gourmet cheeses and any adult beverages that you care to bring. 

Click here to call Captain Dylan and enquire about chartering When and If.

We know you'll have lots of questions so don't be shy!

Private charter on When and If in NYC

Private charter on When and If in NYC

When and If sailing from Key West, FL to Havana, Cuba

When and If sailing from Key West, FL to Havana, Cuba

When and If at the Great Chesapeake Bay Schooner Race, 2015