Martha’s Vineyard
Sailing Charter
FAQ

Your private charter aboard Our Passion includes the exclusive use of the boat and two USCG-licensed captains. Bottled water is provided. Guests should bring their own food and beverages, though a refrigerator and freezer are available on board.

We are permitted to carry up to six passengers per charter, in addition to the two captains.

Favorite stops include Edgartown and the Chappaquiddick shoreline, Lake Tashmoo, Vineyard Haven Harbor, Oak Bluffs and the Inkwell, East and West Chop lights, Menemsha, and the Gay Head cliffs. On a full day we can reach Tarpaulin Cove in the Elizabeth Islands; Cuttyhunk would require a full day with an early start. Our Martha’s Vineyard sailing charters are fully customized to your group — tell us where you want to go and we will make it happen.

Most charters depart from Vineyard Haven, Oak Bluffs, or Lake Tashmoo. In some cases, alternate pickup points may be arranged by request.

Both are destinations rather than departure points. We sail to Edgartown and Menemsha regularly on half-day and full-day charters, and can often drop guests ashore there by tender. If you are staying up-island or in Edgartown, ask us — we may be able to arrange a pickup.

A few items aren’t allowed aboard, for safety, legal, and practical reasons:

• Red wine and deeply pigmented foods and drinks — red wine, sangria, red juices, cherries, blueberries, pomegranates, beets, turmeric, red velvet cake, hot sauce and buffalo sauce, curry, and dark sodas can permanently stain the boat’s fiberglass and gelcoat. If it would stain a white tablecloth, it will stain the boat. Please leave these ashore.
• Marijuana and other controlled substances — prohibited under federal law, which governs the waters we sail. See the question below for the full explanation.
• Smoking and vaping — not permitted anywhere aboard, for the safety and comfort of all guests.

Everything else you’d bring for a day on the water is welcome. If you’re unsure about something, just ask.

Our Passion is a sailboat powered primarily by three sails: a genoa, a mainsail, and a mizzen. Depending on conditions and direction of travel, we use a combination of sails to propel the boat. Our Passion is also equipped with a 58 horsepower Westerbeke diesel engine for docking and motoring when wind conditions require it.

Yes. “Yacht” simply means a vessel used for private pleasure rather than commercial cargo or fishing, and Our Passion — our 42-foot ketch — fits that definition. Some people picture a large motorized vessel when they hear “yacht,” but sailing yachts are the older meaning of the word. Whether you call it a yacht, a sailboat, or a ketch, you’re getting the same private Martha’s Vineyard sailing charter aboard the same beautiful boat.

No. We are not permitted to operate as a fishing charter, so fishing is not an approved activity aboard. What we do offer is a full day on the water — sailing, exploring the harbors surrounding Martha’s Vineyard, swimming, and picnicking aboard — which we find is more than enough to keep guests of all ages happily occupied.

A Martha’s Vineyard to Nantucket sailing charter is one of the most memorable passages on the New England coast. This classic route has connected these two island communities for hundreds of years. The crossing takes approximately five hours each way, making a round trip a natural two-day adventure with overnight accommodations ashore. We would be happy to discuss this trip with you if it is something you and your guests would like to explore.

Martha’s Vineyard Charter Company is Black-owned and captain-operated. Captain Mason and Captain Lynne own and maintain Our Passion themselves, and one or both of them is aboard every charter. Both hold US Coast Guard 100-Ton Master licenses and lifeguard certification, with forty years of sailing between them.

Yes, guests are welcome to bring their own food and beverages. A refrigerator and freezer are provided for your use, along with bottled water.

Yes, but plan for a sailboat rather than a picnic table. When we are sailing, the boat heels and nothing stays put — open platters, charcuterie boards, and loose snacks end up in the cockpit. Pack food in individual, resealable servings you can hold in one hand, and save the bigger spread for when we drop anchor at a swim stop. On a windy day, do not arrive hungry expecting to graze; have something before you board.

No, we do not provide alcohol. Guests may bring their own beer, wine, or cocktails. Please note that red wine is not permitted, along with a few other items — review our prohibited items and foods here before you pack.

You wouldn’t be the first person to ask this if you’re wondering. While Massachusetts has legalized marijuana, boats on the water fall under federal jurisdiction, not state law — the U.S. Coast Guard enforces federal law, under which marijuana remains illegal. Because Our Passion operates on federally regulated waterways, we’re required to prohibit marijuana aboard regardless of state law. We appreciate your understanding.

We recommend bringing sunscreen, sunglasses, a hat, non-marking shoes, a light jacket or sweater, and any personal items you’d like for comfort. If you plan to swim, bring your own towels — we don’t carry guest towels aboard. Don’t forget your favorite food and beverages, but please review our prohibited items and foods here first. For a complete packing list visit our what to bring guide.

Swimming is allowed and the waters around Martha’s Vineyard offer some of the best saltwater swimming in Massachusetts. There is a swim platform on the stern, a ladder, and a hot and cold fresh-water shower for afterward. If you plan to swim, bring your own towels — we don’t carry guest towels aboard, and the fresh-water stern shower is there for when you get out of the ocean. Swimming may be restricted at the Captain’s discretion based on water conditions, boat traffic, current, or guest safety considerations. All swimmers must be confident in their ability to climb back aboard. Our Captains are certified lifeguards.

Boarding is by dock or by tender, and moving about the boat involves steps and uneven footing under way. Tell us about any mobility, medical, or sensory needs when you inquire and we will walk you through what boarding and the day would involve, so you can decide whether it is a good fit.

We take safety seriously and Our Passion is fully equipped with all US Coast Guard required safety equipment including an EPIRB (Emergency Position Indicator Radio Beacon), VHF Marine Radio, Type I and Type III Personal Flotation Devices, a Type IV throwable LifeSling, fire extinguishers, a first aid kit, radar, GPS, flares, and an AIS transponder. Both captains are trained to use all safety equipment aboard and hold current CPR and First Aid certification. Every Martha’s Vineyard sailing charter we offer meets or exceeds all US Coast Guard safety requirements.

Yes, Our Passion is equipped with a clean and fully functional marine restroom (head). It is private, well lit, and below deck.

Our Passion is equipped with a private marine restroom (head), a refrigerator and freezer for guest use, a stern swim platform with a swimming ladder, a hot and cold fresh-water stern shower, Starlink Wi-Fi, and multiple seating areas including the cockpit, bow, and stern. Bottled water is provided for all guests.

No. For the safety and comfort of all guests, smoking and vaping are not permitted aboard the vessel.

Yes, children are welcome. We provide U.S. Coast Guard-approved life jackets for all ages and sizes. Please let us know the age and weight of any children in advance so we can ensure the proper safety gear is available.

Yes, well behaved dogs are welcome on the vessel. The captains love dogs and would love to discuss with you the details of how we can include your dog in the charter.

The captains are used to the conditions in our local waters, and most guests are fine. If you or one of your guests does get seasick, we can stabilize the boat by reducing sail or motoring, head for the nearest sheltered harbor, or return to port. If you know you are prone to motion sickness, take your preferred remedy before boarding, not after.

Your captains work hard to ensure your safety, comfort, and enjoyment before, during and after your charter. A gratuity of 15 to 20 percent is customary and greatly appreciated. If you had a great time on the water, your crew will too.

Yes, we accept all major U.S. credit cards. We also accept Venmo and Zelle, and we recommend them — those methods are free, while credit card payments carry a 3.5% processing fee that we pass along at cost. Many guests still prefer the convenience of a card, and that’s completely fine. Whatever you choose, we’ll make it easy.

Booking your Martha’s Vineyard sailing charter usually involves two payments. A 50% deposit reserves your date, and the remaining balance is due four days before your charter. For example, if your charter is on July 5th, the balance is due by July 1st.

If your charter date is four days away or less at the time of booking, then full payment is due at the time of booking — this is what completes your reservation, since there isn’t time for a separate balance payment. We’ll always confirm the exact amount and due date when you book, so there are never any surprises.

Your charter time begins and ends at your scheduled departure time. Please plan to arrive on time as charter rates and time are not adjusted for late arrivals, missed ferries, or other transportation delays. We want to make sure you get every minute of your time on the water.

Your charter still begins at the time it was scheduled to start, and it does not extend to make up for a late arrival. If you know you are running behind, call us and we will do what we can, but please plan to arrive on time so you do not lose any of your day.

Based on weather and availability, we can accommodate pickup from a range of public docks in the area we are sailing. In some cases the exact pickup location will be confirmed shortly before your arrival so please plan accordingly. If we are unable to bring the sailboat directly to a dock, we have the ability to pick guests up from shore using our tender. Any costs for ground transportation such as taxi or rideshare will be at the guest’s expense. In some circumstances guests may be dropped off at a different location than where they were picked up. If this occurs it is rare and based on unforeseen circumstances.

Yes, though some have more parking than others. Owen Park in Vineyard Haven and Lake Street Landing at Lake Tashmoo have public parking nearby. Oak Bluffs is street parking only and can be limited at the peak of summer — allow extra time or consider a drop-off. We have selected our departure points with parking in mind and it is rarely a major issue.

If the Steamship Authority cancels your ferry, call us as soon as you know. If we can move your charter to a later slot the same day or another day, we will. If weather is bad enough to cancel the ferry, it is often bad enough that we would be cancelling too, in which case you receive a full refund. A missed ferry for any other reason is treated as a late arrival.

If you would like to extend your charter beyond the scheduled time, additional time is available at the stated hourly rate subject to the Captain’s discretion and schedule availability. Please discuss this with your Captain during the charter.

If the Captains cancel your charter because conditions are unsafe, you receive a full refund. If you cancel 14 or more days before your date, you also receive a full refund. Cancelling inside 14 days forfeits 50% of the charter fee — for most bookings that is simply the deposit already on file, so nothing further is owed. Charters booked inside four days are paid in full at booking; if one is cancelled, the fee is refunded only if we are able to rebook that time slot. In every case, if the slot is rebooked with another party, the forfeited amount is returned to you. No refunds are made for late arrivals or early departures.

Your safety and comfort are our top priorities. If weather conditions make sailing unsafe, the Captain makes the call and you receive a full refund, or we will reschedule if you prefer. New England weather changes quickly, so a grey morning does not necessarily mean a cancelled afternoon — we will stay in touch as your date approaches.

Absolutely. Both captains will ensure your trip is safe, comfortable, and enjoyable. No prior boating experience is required. You are welcome to take the helm and learn a little, or sit back and let us do the work.

Yes! Martha’s Vineyard sailing charters are perfect for birthdays, anniversaries, proposals, family gatherings, and other special events. Let us know in advance, and we’ll help make your occasion unforgettable. If you would like it to be a surprise, tell us when you book and we will keep it that way.