Our Martha’s Vineyard Sailboat Charter: A New Family Favorite

Our family has spent years exploring Martha’s Vineyard on foot, by bike, and by car, but rarely by water. So when Captain Mason and Captain Lynne from the Martha’s Vineyard Charter Company offered to host us on a sailing trip, we were excited to say yes.

I was curious to see the island from new angles and to find out what a private sailboat charter on Martha’s Vineyard is really like for families. By the end of the day, this trip had earned a spot on our list of all-time favorite island experiences!

A family of four poses for a photo at the bow of a sailboat, with blue ocean and other boats in the background during a Martha's vineyard sailboat charter trip

Family-Friendly Fun: Our Martha’s Vineyard Sailboat Charter Experience

Before this trip, I didn’t know much about Martha’s Vineyard sailing charters, except that it’s a popular summer bucket list activity for visitors and there are a lot of companies to choose from.

When I started to research in more depth, I learned that if you want to go sailing on Martha’s Vineyard, you’ll find a huge variety of vessels here. Some are tiny and rustic, others are bigger and fully equipped for longer outings.

The background and experience of the crew can be very different from company to company. Some companies specialize in fishing charters, while others focus entirely on scenic Martha’s Vineyard sailing tours.

When I looked into the Martha’s Vineyard Charter Company, one of the things that impressed me was their focus on safety. They’re the only local charter I came across with two fully licensed captains on board.

Plus, both are certified lifeguards with First Aid and CPR (adult and child) training. As a parent, seeing that level of experience and preparedness made me feel confident bringing my kids on board.

Two children in life jackets, one pointing toward the shore, look out from the sailboat at a waterfront building labeled "DOCKSIDE.

Boat Charter Prep: Destination Decisions

Before our trip, I had lots of questions and these were all answered promptly and in great detail via email, text or phone call. Captain Mason sent over a helpful “What to Bring” list and lifejackets were provided for the kids (a relief, since I didn’t want to deal with packing or buying our own).

I’ll admit, I was pretty hands-off when it came to the itinerary. I had no idea how long it takes to sail from one town to another, or which parts of the coastline are worth seeing from the water.

Thankfully, I didn’t need to worry about this at all. I left the decisions entirely in Mason and Lynne’s hands and they came back with great suggestions.

I gave them some basic info about our family, (2 adults, 2 kids under 10) told them we prefer cooler temps, so a morning sail was ideal, and that with kids onboard, we’d need plenty of interesting sights to keep them engaged.

A deep blue sailboat docked at a marina under a bright sun and clear sky, with people on the dock preparing it for sailing.

Pickup Logistics: Meeting the Boat

The pickup for our trip was at 9am at Owen Park Beach in Vineyard Haven, one of their preferred spots because of its easy dock access.

They also pick up in Edgartown Harbor, or Oak Bluffs, but I’d recommend Vineyard Haven if you’re driving. There’s a small parking lot right at the dock with a few 4-hour spots, which worked out perfectly for our half day charter.

If you’re planning a longer daysail, getting a cab or the bus might be a better option, since most downtown areas don’t offer extended parking and it’s much harder to find a spot.

A woman fastening a life jacket on a young girl holding a book while standing on a wooden dock beside a sailboat before embarking on a private sailboat charter on Martha's Vineyard

Captain Mason and Captain Lynne greeted us with a wave at the end of the dock, fitted the kids with their lifejackets and welcomed us aboard their 42ft sailboat, “Our Passion”

On Board: First Impressions

Once on board, Captain Lynne gave us a tour of the interior: two bedrooms, a full galley kitchen, TWO bathrooms (yes, really!), and a spacious dining/sitting area.

The boat is beautiful and I could see how you could comfortably spend long periods of time on board.

All the facilities mean that you can spend the day swimming and enjoying a relaxing sail, then shower, change and get ready to go straight to dinner when your excursion is over.

One of the big benefits to this boat is its size. It never felt crowded, even with our family of four and both captains on board. We passed by some smaller boat charters on our trip and I really noticed how cramped they looked with six passengers plus crew in one small seating area.

A cozy sailboat cabin interior with rich wood paneling, a navy couch decorated with nautical-themed pillows, and a foldable table.

“Our Passion” is full of thoughtful features that would make a big difference on long charters or warm days.

There’s a swim platform for jumping off the boat at the back, a freshwater outdoor shower with hot and cold water for rinsing off afterwards, an outdoor grill for onboard cooking, and comfortable folding chair cushions with built-in backrests.

I’d never seen those before but the kids immediately claimed them as their own, hauling them around the boat until they found the perfect spot to relax and enjoy the views.

I particularly liked the light-filled yet fully covered seating area which meant we were protected from the sun no matter where it was in the sky.

A smiling couple poses together on the bow of a sailboat, surrounded by other docked sailboats in a harbor.

Meeting the Captains

Mason and Lynne have decades of sailing experience between them and a wealth of knowledge about Martha’s Vineyard and Cape Cod.

Captain Mason is what I’d call a boat geek (in the best possible way). He clearly loves the technical side of sailing, eagerly sharing details about other vessels we passed, and explaining the ways their own boat had been upgraded extensively over the past season.

But what stood out most was how passionate he is about introducing kids to sailing – not just as a fun activity, but as a potential career path.

As a Black sailboat captain, he’s aware of how uncommon it is to see someone who looks like him at the helm. He talked about how important it is for Black children to see that representation early, whether at sailing summer camps or just out on the water, so a maritime career feels like something that’s accessible.

A young girl stepping onto the sailboat from the dock as adults wearing headsets guide her, with a young boy waiting behind her.

On past sailing trips, I’ve found it a little stressful to watch the crew rushing around the boat, clearly under pressure to get things done quickly. However, on this trip, the calm energy brought by Captain Lynne, created a much more relaxing atmosphere.

Lynne seemed to know exactly what needed to happen, moving around confidently with no rush. At the same time, she fielded rapid-fire questions from our children about everything from how the toilet worked to what kind of fish lived in these waters, answering every one with an impressive level of knowledge and patience.

Captain Lynne also regularly checked in with the kids, asking if they wanted to see a new part of the boat, take a turn pushing a button, or pointing out an interesting bird or landmark.

I really appreciated how much she involved them in the experience, making sure the trip was as unforgettable for them as for the adults.

A classic white lighthouse with a black top stands on a lush green hill beside a rocky shoreline, flanked by charming coastal homes overlooking the water. The foreground features choppy blue ocean waves under a clear summer sky.

Our Half Day Sail: Touring the Island Coastline

The sail itself was calm and beautifully scenic. Our route took us from Owen Park, past Vineyard Haven Harbor to Oak Bluffs and back. I noticed that Captain Mason purposefully avoided sailing at high speeds or in a way that would cause a lot of spray so that our kids would feel safe and comfortable during the whole trip.

Along the way, we cruised past the East Chop Lighthouse (a Vineyard landmark that’s even more striking from the water) and took a spin around Oak Bluffs Harbor. Familiar spots like Nancy’s and the restaurants along the marina all look so different from the water!

We got to appreciate the dramatic bluffs and stunning houses along West Chop as we looped back to Vineyard Haven. The kids enjoyed seeing the Black Dog tall ships up close and passing by the Steamship Authority ferries which seem enormous when viewed from the water.

A tall white schooner with two masts and a black dog flag sails near the coast with a tree-lined shoreline in the background.

On a longer full-day sail, there’s the option to visit destinations like Nantucket, Cuttyhunk and the Elizabeth Islands, or to sail to Menemsha for lunch. After enjoying our short trip so much, this is something we will definitely plan for another time.

For someone who’s spent years visiting Martha’s Vineyard, it was really enjoyable to get a new perspective and see the island’s picturesque coastline up-close.

As we turned for home, we decided to have lunch. This is one detail I wish we had planned a little better. I would recommend deciding in advance roughly what time you want to eat, so the Captains can navigate to a calm spot or a quiet cove.

A picnic-style lunch setup on a wooden boat table featuring crackers, cheeses, salami, pretzels, buns, pickles, and drinks.

Our kids started to get hungry right as we entered some choppy waters. It was a little difficult to get everything set up and hold on to everything as we bumped over the waves.

I also had assumed I needed to bring plates, cutlery, cups etc with me but found that all of this is provided on the boat and they even take the trash afterwards. You just bring what you want to eat and drink.

A young girl wearing a blue life jacket and pink cap reaches forward at the helm of a sailboat while a boy stands behind her, both appearing focused on the water ahead.

Who Should Book This Private Sailboat Charter?

Sailings are available from June 1st through October 1st each year but if the weather is right in May, you can book for Memorial Day weekend!

low-key bachelorettes, sorority reunions or birthday parties

This sailing charter on Martha’s Vineyard is a great fit for small groups of family or friends who want something private, relaxed, and tailored exactly to your group’s needs. You can even fly your college/company/team flag from the mast!

This isn’t the right pick for party-heavy groups who want to drink excessively. Mason and Lynne are welcoming, and happy to accommodate guests celebrating an occasion, but they prioritize creating special experiences that are more about relaxation and connection.

Despite the large size of “Our Passion”, there is a strict, 6-passenger limit (coast guard regulations) so if you’re planning a larger gathering, this boat wouldn’t be suitable for your group.

Families with young Children

This boat is also ideal for families with young kids. Having a bathroom onboard (rarely available on smaller vessels) is essential in my opinion, especially if you are out for 4 hours or more.

Other pros for families are the fully covered seating area, attention to safety and the kids getting to take the wheel and steer!

Groups seeking a bespoke experience at an Accessible price

This isn’t a charter for people looking for a fully catered or ultra-luxurious experience. The boat is comfortable and spacious but you’ll need to organize your own food, drinks, and whatever else you want to bring.

And while the captains are friendly and incredibly attentive, they aren’t hovering in the background with trays of hors d’oeuvres. It’s hands-off in that sense, but not in a bad way, just something to know before you book.

The upside to this is that compared to other local operators, a full or half-day private sail with the Martha’s Vineyard Charter Company is one of the most reasonably-priced Martha’s Vineyard sailboat charters available right now. Don’t sleep on this because it’s unlikely to be that way for long!

Two children wearing life jackets sit at the bow of a sailboat, looking toward a docked ferry as the boat approaches shore.

Day-Trippers who don’t really want to go home

I regularly hear from those visiting Martha’s Vineyard on a day-trip that the day is just too short and they hate having to rush away to get the last boat home.

This charter is perfect for day trippers who want more control over their time. Come over using the regularly scheduled ferry, enjoy your day then charter this boat for your return to the mainland.

You can even time your return trip to make it a sunset sail so you can enjoy the brilliant colors of Martha’s Vineyard sunset on your way home. This is one of the only charter options I’ve found that caters so well to day trippers looking for something beyond the typical land-based itinerary.

Boat Owners or those thinking of Purchasing.

Finally, if you have your own boat elsewhere, want to brush up on your skills (or learn some new ones) or you’re considering taking the leap into ownership, you should book this charter. Mason and Lynne’s level of technical expertise and enthusiasm is invaluable for anyone looking to get more involved in sailing.

A smiling family sits around a wooden table on a sailboat enjoying lunch, with plates of sandwiches, crackers, and juice boxes.

Final Thoughts on our Martha’s Vineyard Sailing Charter

Spending the morning on a sail aboard “Our Passion” felt less like a tour and more like an outing with friends. The boat had everything we needed, the captains were warm, professional, and knowledgeable, and we thoroughly enjoyed the experience.

If you regularly take a vacation to Martha’s Vineyard and are looking for something that will show you the island in a new way, I definitely recommend booking a private sailboat charter on “Our Passion”.

On this trip, the cost of our sail was covered by the Martha’s Vineyard Charter Company. All other expenses (transportation, food/drinks and incidentals) were covered by us. As always, all opinions in this post are my own and I’m sharing an honest account of what the experience was actually like for our family.

Got questions? Post them in the Martha’s Vineyard Travel Tips group on Facebook and I’ll be happy to share more about our Martha’s Vineyard boat charter experience!