A Weekend in Martha’s Vineyard with Vineyard Vines

This post is sponsored by Vineyard Vines

Vineyard Vines, the adorably preppy clothing line, recently celebrated its 20th anniversary on Martha’s Vineyard. As partners of the brand, my family and I were thrilled to head to the island to commemorate the occasion! (Many thanks to Vineyard Vines and The Winnetu for hosting us.)

things to do in Martha's Vineyard with kids
Family portrait in front of The Winnetu on Martha’s Vineyard Photo: Vineyard Vines

Vineyard Vines’ founders, brothers Ian and Shep Murray, grew up in Greenwich, but spent nearly every summer on Martha’s Vineyard, so the company truly has its roots there. Edgartown, one of the towns on Martha’s Vineyard, is where the brothers opened their first stand-alone store in 2005.

Whenever we travel to beachy destinations, it’s common to see fellow vacationers sporting Vineyard Vines. It might be one of their crisp baseball hats, signature t-shirts, or summery dresses. In Martha’s Vineyard, however, pride for the company is next-level! During our time there, it seemed like every other person was wearing Vineyard Vines, embracing the brand that was created to celebrate the Martha’s Vineyard lifestyle.

And what is that lifestyle exactly? Martha’s Vineyard is both laid-back and sophisticated. It’s both stylish and quaint. The historic island is a seaside paradise, complete with a majestic coastline to explore, and a distinctly New England twist. It really is a must-see, American destination. Even if your family’s only got two days to take in this picturesque island, there will be plenty of things to do in Martha’s Vineyard with kids. Here’s we recently spent two days there:

Getting to Martha’s Vineyard

Since no bridges or tunnels exist to get visitors to the island, you’ll have to take a ferry or a plane over, which makes it feel even more exclusive! If you’ve got a sea-loving little one, taking a ferry instead of a plane might even top your list of things to do in Martha’s Vineyard with kids.

things to do in Martha's Vineyard with kids
The airport that doesn’t look like an airport. Photo: Carmen Sognonvi

We took a flight there, which actually gave us a great introduction to the Vineyard. The laid-back spirit of the island is evident as soon as you land, thanks to an adorable airport that looks more like a resort. The first thing my daughter, Ella, said when we got off the plane was, “This does NOT look like an airport.” And she was right; the white and grey clapboard building looks like no airport any of us had ever seen! Right away, we felt relaxed and in vacation mode!

things to do in Martha's Vineyard with kids
Just landed on Martha’s Vineyard. Photo: Carmen Sognonvi

Where to stay in Martha’s Vineyard

We stayed at The Winnetu, at South Beach in Edgartown. The family-owned resort has single and multi- bedroom suites, private cottages, and larger vacation homes. There’s also an ocean-view restaurant called The Dunes right there onsite.

We absolutely loved our charming cottage! The Menemsha cottage, as it’s called, has one bedroom, two bathrooms, a large kitchen, and a really spacious living/dining room. It’s got three Murphy beds, so it can easily accommodate a family of five. As a parent, I loved that the Murphy beds came pre-made with sheets, blankets, and pillows. Whenever the kids were ready for bed, we didn’t have to fuss with making the beds or waiting on housekeeping to do it.

Day 1 in Martha’s Vineyard

As soon as we got to the resort, we changed into our swimwear and headed to the pool. (Like I said, we were in vacation mode right away!)

things to do in Martha's Vineyard with kids
A unicorn floatie makes everything so much more fun! Photo: Vineyard Vines
things to do in Martha's Vineyard with kids
Enjoying that cabana life. Photo: Vineyard Vines

The girls had so much fun splashing around, while Serge and I enjoyed some beers in the cabana.

things to do in Martha's Vineyard with kids
Sisters and their secrets! Photo: Vineyard Vines
things to do in Martha's Vineyard with kids
Twinning in our Vineyard Vines rashguards! Photo: Vineyard Vines

That evening, we headed out to explore Menemsha, which is often considered one of the last places where you can see the “old” Martha’s Vineyard. As a working fishing village, it’s not as prim and polished as rest of the island, but it has an authentic vibe that we loved. It’s supposedly one of the best spots on the island to watch the sun set, and from what we could tell, that’s the truth!

things to do in Martha's Vineyard with kids
The fishing village of Menemsha. Photo: Carmen Sognonvi

On that first day, we had dinner at Home Port restaurant, where we had our fill of fresh oysters (caught right there on the island), lobster and fish.

things to do in Martha's Vineyard with kids
Loved our seafood dinner at Home Port restaurant in Menemsha! Photo: Carmen Sognonvi

Afterward, we walked across the street to Menemsha Galley for ice cream, and then sat on the pier to catch that breathtaking sunset. Of all the things to do in Martha’s Vineyard with kids, we found the best ones to also be the simplest.

Day 2 in Martha’s Vineyard

The following morning, we stayed at The Winnetu for breakfast. The dining room is bright and airy. The breakfast selection is a simple buffet of continental options, like pastries, fruit, and cold cuts. There’s also an omelet station where you can add hot options.

things to do in Martha's Vineyard with kids
Visiting the Vineyard Vines store in Edgartown, where it all started! Photo: Vineyard Vines

Next, we drove to Edgartown to visit the Vineyard Vines store. Though the store is not in its original location (the new store is much bigger than the original), it still feels very much like visiting Vineyard Vines’ mothership.

things to do in Martha's Vineyard with kids
Sean and Ella playing cornhole with the Vineyard Vines mascot. Photo: Carmen Sognonvi

The girls were excited to meet the Vineyard Vines whale mascot, who said hello to all of the kids.

things to do in Martha's Vineyard with kids
Meeting Shep and Ian, the founders of Vineyard Vines. Photo: Vineyard Vines

Serge and I were honored to meet founders, Shep and Ian, who came by to chat with all of the families who came out. (And yes, they are just as laid-back and down-to-earth as you’d expect!)

things to do in Martha's Vineyard with kids
Exploring Edgartown. Photo: Vineyard Vines

Afterward, we explored Edgartown for a bit before heading to lunch at The Seafood Shanty, a great waterfront restaurant. Just about all of us ordered one of the delicious lobster rolls on the menu! (Insider tip: The best views are from the roof deck.)

things to do in Martha's Vineyard with kids
On board the water taxi. Photo: Vineyard Vines

One of the best things to do in Martha’s Vineyard with kids is to take the water taxi through Katama Bay. The kids loved checking out boats of all sizes, while we loved seeing estates not visible from the road.

things to do in Martha's Vineyard with kids
Sean became instant besties with the other kids on the trip! Photo: Vineyard Vines

When we docked, there was a surprise waiting for us. The Winnetu owns an antique fire truck, and they brought it out to the dock so that we could ride it back to the hotel. The kids had so much fun with this, especially since they all got to take turns ringing the big golden bell!

things to do in Martha's Vineyard with kids
Getting to ride on The Winnetu’s antique fire truck was definitely a highlight of this trip! Photo: Vineyard Vines

After we got back to The Winnetu, we headed to the beach, which is about a 5-10 minute walk from the main building of the resort.

things to do in Martha's Vineyard with kids
Sean and Serge enjoying the ocean. Photo: Vineyard Vines

Though the water was too choppy for swimming, Sean and Ella had a great time building sand castles, while Serge and I relaxed on our beach chairs.

things to do in Martha's Vineyard with kids
Excited for the clam bake! Photo: Vineyard Vines

Then it was time for the big clam bake, which was one of the things I was most looking forward to.

things to do in Martha's Vineyard with kids
Serge playing cornhole with the girls. Photo: Vineyard Vines

This event takes place on Wednesday evenings throughout the summer with clam chowder, lobsters and dessert.

things to do in Martha's Vineyard with kids
Bubbles are a must for outdoor fun! Photo: Vineyard Vines

With family-friendly entertainment and a sunset s’mores party, this was the highlight of our trip! It was definitely one of our favorite things to do in Martha’s Vineyard with kids.

Why we’ll be back to Martha’s Vineyard

While two-day trips are always too short, this time around was really memorable. Martha’s Vineyard is a beautiful destination that feels both a little bit rustic and little bit chic. On our recent trip, we only scratched the surface. With so many fabulous things to do with kids in Martha’s Vineyard, we can’t wait to go back and explore more!

Top Flight Family received complimentary airfare, accommodations, meals and activities. All opinions are our own.

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About Carmen Sognonvi

Carmen Sognonvi is a luxury family travel and lifestyle digital influencer at Top Flight Family. Her insights on travel have been featured in Wanderlust Travel Magazine, TravelPulse, HOTELS Magazine, Seatrade Cruise News and more. Carmen firmly believes that you can (and should) travel with your kids from a young age. She offers families practical solutions for travel, as well as tips on how to travel in luxury for less. She lives in New York City with her multiracial and multicultural family of four. Follow her on Instagram, FacebookTwitter and Pinterest.

Click here to read Carmen's articles

Looking for things to do in Martha's Vineyard with kids? Here's a 2-day itinerary for families visiting Martha's Vineyard.

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