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.

Valentine's Day on When and If

 

Every loved-up pair receives a half bottle of sparkling rose wine, 4 pieces of delicious cupcake sushi to share, and a single red rose.

All for just $199 per couple!

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