Share an evening harbor sail as the light shifts over the water
2 Hours
Settle in for a shared evening sail across the harbor. Take in changing coastal light while the crew shares local history and fun facts.
Cancel 14 or more days before departure for a full refund of the deposit. Cancellations 7–13 days before departure are refundable only if the time is rebooked. Within 7 days, the deposit is non-refundable and the remaining charter balance may be charged unless rebooked. Within 48 hours, the full charter value may be charged. No-shows forfeit the full reservation.
Product ID: 4YDQ8E
Yes. Ages 18+ only.
No pets are allowed aboard the vessel.
This excursion may not be suitable for travelers with impaired mobility. Special accommodations may be available for physical limitations.
Small wooden dock at the Steamship Ferry terminal, 1 Water Street, Vineyard Haven, MA 02568
We celebrated my Mom’s 71st birthday with Captain Wendy and first “femate” Cassie and it was an amazing experience. They took care of everything and it was such a relaxing sail. Highly recommend for those who want to be out on a safe sailboat and celebrate with some drinks, snacks, laughs and fun.
peschke66
August 14, 2026
We celebrated my Mom’s 71st birthday with Captain Wendy and first “femate” Cassie and it was an amazing experience. They took care of everything and it was such a relaxing sail. Highly recommend for those who want to be out on a safe sailboat and celebrate with some drinks, snacks, laughs and fun.
peschke66
August 14, 2026
Discover Martha’s Vineyard’s iconic cliffs and villages on a flexible private tour.
A fishing-ready center console with rod holders and a live well
Take the helm of a 19-foot center console with fishing-ready features
Set sail on a private classic sloop tailored to your group
Raise the sails or take the wheel on Martha's Vineyard waters
Raise the sails or take the wheel aboard a historic schooner
Sail Vineyard Sound with lighthouse views and secluded swim options