Have the sea to yourself with a private charter

Do you dream of the wind in your hair, the sky above, and the sea below? We get it. And we’ve got you.

When and If

Private charter day sail on When and If

Up to 32 people • Price includes 12 people
Sail into the Summer Sunset on your own private classic yacht. With capacity for up to 32 guests, When And If is the last word in comfort and elegance for cruising away those long balmy evenings or catching the breeze for a little seafaring adventure. Call to talk about extending your trip - we know that with you Massachusetts sailors two hours sometimes just isn't enough!
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When and If

Private charter sunset sail on When And If

Up to 32 people • Price includes 12 people
Sail into the Summer Sunset on your own private classic yacht. With capacity for up to 32 guests, When And If is the last word in comfort and elegance for cruising away those long balmy evenings or catching the breeze for a little seafaring adventure. Call to talk about extending your trip - we know that with you Massachusetts sailors two hours sometimes just isn't enough!
Learn More