Coming Up This Season...

Starboard Bow Full Sail

Daysails, Sunset Sails, Deck Tours, Sea Shanties, Lobster Rolls... A long Summer Weekend in Wiscasset, ME is just what we all need! Sail away with us, buy a T-shirt, come and celebrate!

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Schooners, schooners everywhere! Join us for flags, festivities and fast sailing - Deck tours, racing and a parade of sail in Gloucester, MA

WHIF Columbia2blu

The most beautiful boats on the North Shore come together for a weekend's racing out of Marblehead, MA. Come with us as we cross the sound from Salem to join in the fun!

Check out our online store...

Our star products are our new buff/face coverings and gorgeous 2021 When And If calendars but have a look at all our fab swag and get shopping!

Click here to call 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