After the energy of Boston, we took a ferry to Martha’s Vineyard for a slower-paced, small-town adventure. The island offered us a chance to reset with beach walks, arcade games, bike rides, and evenings on the porch.
This stop was all about simple pleasures. Here’s what stood out to each member of our crew, according to the kids (and a little from the grown-ups too).
Sam’s Pick: The Arcade in Oak Bluffs
Tucked in the center of Oak Bluffs, the arcade became Sam’s favorite hangout. It was packed with skeeball machines, racing games, claw machines, and just enough nostalgia to make us smile too. He returned almost every evening, determined to win more tickets than the day before.
Andrew and Paige’s Pick: Walkability of Oak Bluffs
Andrew and Paige both loved how easy it was to get around Oak Bluffs. From our rental house, we could walk to the beach, the ferry dock, the arcade, and a dozen ice cream shops. With sidewalks everywhere and lots of people strolling or biking, Oak Bluffs gave the kids the freedom to explore without feeling overwhelming.
Mom and Dad’s Favorites: Bikes, Home-Cooked Meals, and Lobster Rolls
We rented bikes and explored beyond Oak Bluffs, pedaling past beaches, through shaded neighborhoods, and along open coastal roads. One of our favorite evenings was cooking dinner together at the Airbnb with the doors open and music playing.
And of course, we could not leave without trying a lobster roll. The one from Lookout Tavern hit the mark perfectly. Fresh lobster, buttery bun, and a table overlooking the harbor made it a true Vineyard moment.
If You’re Planning a Trip to Martha’s Vineyard
Getting there is half the fun. Most visitors take the ferry from Woods Hole, which is scenic and easy to navigate. Once you’re on the island, many people rely on bikes, walking, or local shuttle buses to get around. Oak Bluffs is especially walkable and great for families.
Helpful travel resources:
Final Thoughts
Martha’s Vineyard invited us to slow down and savor the moment. The kids found joy in everyday rituals like arcade games and ice cream runs. We embraced long bike rides, porch dinners, and seafood with a view. It was the kind of trip that fills your camera roll and your memory bank.
According to the kids, it was the most relaxing stop yet.
