Policies and Frequently Asked Questions

Charters may be scheduled between the hours of 10 am through 8 pm daily. As the sun begins to set earlier throughout the summer season, our hours of operation end earlier in the evening.

*Requests for time outside of our normal operating hours will be considered based on availability and will incur an additional fee.  Email us at office@sailthevineyard.com for information.

We offer monohull sailboats for our Martha's Vineyard sailing excursions for day sails, sunset sails, marriage proposals, weddings, bachelorette parties, birthday celebrations, and anniversary celebrations from June 1 - October 10.  We also offer sailing instruction aboard our 44-foot monohull sailboat in Martha's Vineyard.

We also offer 7-10 day liveaboard catamaran sailing vacations in the Caribbean, Tahiti, and other exciting worldwide destinations from December 1 - April 30.

Yes, our dual-licensed Captain offers sailing lessons for all levels of experience aboard our vessels or yours.  Email captain@sailthevineyard.com for details.

All of our sailing excursions include a licensed Captain and a crew person to run the boat.  We welcome guests to be involved with all of the sailing activities as much as they would like.

All of our private sails are based on up to 6 guests.  If your group is is larger than 6, please call 508-493-8767 for options.

Private sailing excursions are solely for you and anyone you choose to bring with you, typically up to a maximum of 6 people.  

A "Public" Sail is a sailing excursion in which you buy a ticket to come aboard and share the experience with other people who have also bought a ticket.  We offer these trips on specific days and times, currently including some sunset sails and a brunch sail.  These trips are also small-group focused, with a typical maximum of 6 total guests aboard. 

Your sailing excursion time begins and ends at your schedule charter time. Round trip transportation time from the dock to the sailboat is part of your total excursion time. 

Charter rates and time are not adjusted for late arrivals, including missed ferries or or other transportation issues, so please plan ahead for an on-time arrival.

Yes, of course!  Our sails are arranged in 2-hour increments. If you'd like to add 1 hour to your trip, please call to inquire about additional sailing time.

Guests are welcome to bring alcoholic beverages (with the exception of red wine which is prohibited) and drink in moderation while aboard for our PRIVATE SAILING EXCURSIONS.  Guests may not bring their own alcohol aboard for the public sailing excursions.

Excessive alcohol use, as identified by the Captain while underway, is not permitted as it poses a safety hazard to guests and crew, and will result in an early and immediate end to the sail.

 We have an alternate location we can use for pick up if this is the case for you.  This must be pre-arranged with the Captain.  Call us at 508.493.8767 for assistance with this. 

Our sailing excursions require guests to be able to step from the dock into a smaller, inflatable boat to be transported to the sailboat.  Upon reaching the sailboat, it is necessary to climb up onto the sailboat using upper body strength to help pull up and lower body strength to step up onto the deck.  This is easily achieved by the majority of people with basic fitness. 

There are several options for preventing sea sickness, both medication based and natural remedies.  Some people find relief bands to be very helpful. There are inexpensive pressure-point types and more expensive ReliefBank pressure-point bands that emit a small electrical pulse.  Ginger chews, lozenges or gum can be helpful as well.  Medication options, which you should discuss with your doctor, include prescription scopolamine patches and over-the-counter medications such as Dramamine.