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.

Book your Key West sunset sail here

COMING SOON:

Wreckers Race Sailing 2020!

Daysail in Key West, FL

 

Tropical Winter Sailing

Sunset Sails in Key West

 

Winter in the Keys!

Our Winter Hosts

 

Sunset Sail Key West

Book online or call to enquire
Winter sailing in Key West
book sunset tickets here
Visit sunset sail Key West

Book Your Perfect Florida Keys 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 still or sparkling water - BYOB!

reservations

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!

An Historic Vessel

Welcome Aboard!

Sailing Schedule

Private charter on When and If in NYC

WHEN AND IF, NYC from Caleb Seppala on Vimeo.

Private charter on When and If in NYC

WHEN AND IF, NYC from Caleb Seppala on Vimeo.

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

Key West to Cuba from Caleb Seppala on Vimeo.

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

Key West to Cuba from Caleb Seppala on Vimeo.

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

When And If from Caleb Seppala on Vimeo.

When And If from Caleb Seppala on Vimeo.