Julee Wilson’s Two-Week Family Trip to Oak Bluffs, Martha’s Vineyard

Photo-Illustration: The Strategist; Photo: Julee Wilson Everyone knows that person who spends weeks sniffing around travel blogs, going deep down into Tripadvisor rabbit holes, collecting Google docs from friends of friends, and creating A Beautiful Mind–style spreadsheets to come up with the best vacations and itineraries possible.

The Oak Bluffs Inn Prices May Vary Booking.com Buy Prices May Vary TripAdvisor Buy 11 a.m.: Take the ferry from Woods Hole To get to the island, people take the ferry across the sound. Real Vineyarders know that ferry reservations open up around January 12, so all the people who go to the Vineyard are texting each other like, You know, the ferry is opening, because it’ll sell out, especially if you want to bring your car. There’s a snack bar, and people usually sit at the top and enjoy the ride.

1 p.m.: Jump off Jaws Bridge After that, I go back home and order sandwiches from Tony’s , a small market where you can buy groceries. They also have a deli stand inside, where you can get sandwiches and chicken fingers and fries. Then we pack up the car by noon, and we’re on the beach by 12:30. We’ll reach out to friends and ask where everyone is going to, but we go either to Inkwell/Town or Joseph Sylvia State Beach in Edgartown, which we just call State Beach. We love State Beach.

Day 4 12 p.m.: Have a picnic in Aquinnah Aquinnah is where the famous clay cliffs that everyone photographs are. It’s just breathtakingly beautiful. It takes about 45 minutes to an hour to go up there, and it’s all winding country roads. There’s not one stoplight. We go to Moshup Beach . It’s on the ocean side of the island, so the waves are big, the sand is like dust, and the water is stunning. It’s my favorite place to take pictures.

Day 6 1 p.m.: Eat at Dapper Dan’s favorite diner On Fridays at 3 p.m., Grace Church in Vineyard Haven sells the best lobster rolls. They’re big and succulent, and there’s no filling — no celery and shit. Just a little bit of mayo and seasoning. There’s also the Agricultural Fair. It happens in West Tisbury from August 19 to 22, and it’s fun. There are rides and all of that, but there are also livestock and pig races. The kids can go into the barn and touch the sheep and feed the chickens.

Day 11 6 p.m.: Eat lobsters at Atria Hennessy throws its annual party at my favorite restaurant, Atria , on Thursday night of the second week. It’s invite-only and D-Nice DJs it every year. It’s kind of a who’s who party, but once you get invited, you’re kind of on the radar. If you’re not invited, Atria is worth going to another time; the restaurant is stunning indoors and outdoors. It has a swing hanging from a tree branch outside on the front lawn.

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