Policies and Frequently asked questions

Gratuity for the Captain and crew is not included in charter pricing. While always discretionary, gratuities are customary in the yachting and hospitality industry and are based on your experience aboard. Typical gratuities range from 15–25% of the charter price based on your experience aboard.

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 offer 7+ 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 vessel or yours.  Email captain@sailthevineyard.com for details.

All of our sailing excursions include a licensed Captain and crew to run the boat.   Guests are welcome to take part in the sailing of the vessel as much or as little as they would like.

All of our sailing excursions are based on up to 6 guests.  If your group 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.  These trips are also small-group focused, with a typical maximum of 6 total guests aboard. 

Yes. We offer private charters for celebrations, ceremonies, proposals, and custom experiences.

Yes, children are welcome on most private charters when accompanied by an adult. Some specialty events may be adults-only. 

Unless prior arrangements are made, all trips begin and end in Vineyard Haven. We do offer trips to or from other harbors; contact us for more information.

There is limited 2-hour parking across the street from the ferry ticket office and limited 4-hour parking one block up, on Main Street.  Due to the limited nature of parking, we recommend an Uber or the  VTA bus.  In an effort to reduce traffic and help the planet, Martha's Vineyard island has established a fee-free bus system, which drops off directly in front of our dock.  The #13 bus makes a loop between Vineyard Haven, Oak Bluffs and Edgartown approximately every 15 minutes during peak season. 

 We recommend sunglasses, sunscreen, and a light jacket or sweater, as it can be cooler on the water. Please apply sunscreen before arrival and bring lotion only (no spray) aboard for reapplication.

 Comfortable, layered clothing is best. We are a shoeless vessel, so footwear should be easy to remove and appropriate for a marine environment. 

Yes, on most private charters. Some specialty experiences may include curated food or beverage service, so check your booking details.  We also offer catering options.

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.

Not at all. Your captain and crew handle everything. You’re welcome to relax or get involved as much or as little as you’d like.  

 Yes. Guests are welcome to participate in the hands-on activity of sailing the vessel as much or as little as they would like. 

 No two sailing experiences are ever exactly alike. Wind, weather, sea conditions, lighting, and the rhythm of the water all combine to make each trip unique. 

Every sailing excursion is shaped by the natural conditions of the day. If wind conditions are light, the vessel may operate under auxiliary power to ensure a smooth and comfortable experience on the water.

No. Every sail is unique and shaped by the wind, weather, tide, sea state, and overall conditions of the day.

Swimming opportunities depend on weather conditions, location, timing, and the specific experience reserved. Please contact us in advance if swimming is important to your group.

Yes—our vessel is equipped with a marine restroom for guest use.  However, for your comfort, we recommend using the restroom located inside the Steamship Ferry Ticket office prior to boarding the vessel. 

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.  

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.  

This is rare and most people feel great while aboard. However, if this is a concern for you, 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 ReliefBand 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. 

We are a smoke-free vessel.

No. Although certain states have legalized the recreational use of some substances, our vessels operate under federal maritime regulations and therefore prohibit the use of recreational drugs aboard at all times.

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. 

We are happy to extend your sailing excursion if there is availability in our schedule.

Safety always comes first. Although rain itself does not mean we will cancel, we want you to have fun and enjoy your time aboard. Weather cancellations are made at the sole discretion of the Captain. If conditions are unsafe, trips are rescheduled or refunded according to our weather policy. 

Because each sailing time is reserved exclusively for your group and cannot be replaced on short notice during our limited season, our cancellation policy is structured around time-based rebooking feasibility.

• 14+ days before departure: full refund of deposit 
• 7–13 days before departure: deposit is non-refundable unless we are able to rebook the reserved time 
• Less than 7 days before departure: deposit is non-refundable and the remaining balance of the charter may be charged unless we are able to rebook the reserved time 
• Less than 48 hours: full charter value may be charged due to limited rebooking opportunity 
• No-shows: considered a full forfeiture of the reservation. The deposit is retained and the remaining balance of the charter will be charged in full 

We always do our best to rebook cancelled reservations whenever possible.

Certain specialty events, custom experiences, and multi-vendor charters may be subject to separate cancellation terms discussed at the time of booking. 

Yes. We offer intimate weddings and vow renewals aboard our sailboats for couples seeking a unique and unforgettable Martha’s Vineyard experience. Please contact us to discuss details, availability, and custom arrangements. 

Absolutely. We specialize in unforgettable proposal experiences aboard our sailboats and are happy to help coordinate details such as timing, flowers, champagne, photography, music, and other special touches to help create the perfect moment. 

 In some cases, yes. Decorations or customized setup requests must be arranged in advance and may require additional reserved time aboard depending on the scope of setup involved. Please contact us in advance to discuss your plans.