Winter in the Keys

A gorgeous Key West Sunset. George S. Patton's stunning historic schooner yacht. Perfect!

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Winter in the Keys

A gorgeous Key West Sunset. George S. Patton's stunning historic schooner yacht. Perfect!

Book your Key West Winter sail on When and If here!

See our daily schedule of sunset sails and daysails, or call us to enquire about a private charter or special event.

Race to Cuba on a beautiful classic yacht!

 

24th January - 3rd February 2017

 

Race When and If across the Straits of Florida to arrive in the resort town of Varadero before experiencing the delights of Havana. Viva Cuba!

We're back for the world-famous Key West Wreckers' Races!

Once a month, everyone who's anyone in Key West races out to the reef in remembrance of the folks who salvaged ships foundering there in years gone by. 

It's a fun day of the hardest sailing the wind will allow, and includes race lunch, cold drinks and snacks, and afterparty tickets.

Click here to call Captain Seth 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