Sunset Sails. Day Sails. Private Charters. Regattas. Special Events.

General Patton's gorgeous 1939 wooden schooner is sailing out of Salem, MA every day.

Book your North Shore sunset sail here

COMING SOON:

When And If returns to  MA as Salem's hottest new bar!

Daysail in Salem, MA

 

Breezy Summer Sailing

Sunset Sails in Salem, MA

 

Historic North Shore Sailing

Our Summer Hosts

 

Sunset Sail Salem

Book online or call to enquire
Summer sailing in Salem
book sunset tickets here
Visit sunset sail Salem

Book Your Perfect North Shore Sailing Experience

Enjoy a day sail, or Salem'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 beverages from our onboard minibar. 

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.