A ritual that spans a decade

In 2019, a friend invited me to share a house on Martha’s Vineyard for a week. I had no idea I was being initiated into what would become my favorite week of the year.

Five trips since — sometimes a group of 8, sometimes 11 of us — and now? Nobody wants to miss it.

Why this island, of all islands

Martha’s Vineyard hits different for me, and this why.

The Wampanoag people have called this island Noepe for centuries. And for Black Americans, it’s been a sanctuary for generations. When so much of the mainland was openly segregated mid-century, Inkwell Beach in Oak Bluffs became one of the few places on the East Coast where Black families could gather freely. Folks summered here. They bought homes. They built community.

You don’t read about it in the visitor brochures. You feel it walking down Circuit Avenue.

And then there’s the Polar Bears. The early-morning swim group that gathers at Inkwell every day between Memorial Day and Labor Day — 7:30 a.m., rain or shine, for prayer, community, and water aerobics. The story goes that back in 1946, summer workers coming over from the mainland couldn’t swim during their workday, so they’d show up at dawn, swim from one point to the pier and back, and start their shift wet and salty. Their group is still going. Eighty years later.

(I tried it last summer. The water is freezing. I’d absolutely do it again.)

Where we stay

We’ve rented in both Vineyard Haven and Oak Bluffs — VRBO, Airbnb, local rental companies, all of it. We’ve stayed in modern, beautifully renovated homes. We’ve also stayed in older houses that were charming but very… vintage. Both have their case.

Here’s how I’d break it down:

Vineyard Haven — homes tend to be larger, more modern, more updated. But it’s a hike into the action of town. Plan for that.

Oak Bluffs — most rentals put you walking distance to everything. The homes are generally older though, less recently renovated. You’re trading polish for proximity.

Edgartown — beautiful, manicured, walking distance to town, the most “put-together” of the three. Usually pricier.

In 2026, four of us are switching things up. We’re staying at the Summer Camp Hotel in Oak Bluffs, right across from the wharf. First time I’m doing the Vineyard from a hotel instead of a rental. I’m curious what changes and what doesn’t. (I’ll report back.)

Our annual rotation

Every trip has the same shape, more or less.

Arrival day is always lunch at Nancy’s on the Oak Bluffs wharf, where Donovan makes a cocktail that looks like a craft project. At least one morning, we meet Christopher for beach yoga at Inkwell — a class that’s somewhere between meditation, exercise, and church. At least one Friday, we get lobster rolls and prosecco from Grace Church. (If you know, you know.)

And at least once a day — unfortunately — we end up at Back Door Donuts. I have no defense.

For dinner: Lookout Tavern in Oak Bluffs is always a favorite — easy, no-fuss, gets the job done. Atria in Edgartown is the must-book reservation, where you order the things you’d never make at home. The Seafood Shanty in Edgartown has rooftop tables and is exactly what a vacation dinner should feel like. For breakfast, Art Cliff Diner in Vineyard Haven, hands down. And Sweet Life Café in Oak Bluffs is just one of those places.

The last evening — every trip — ends with the sunset at Menemsha Beach. People bring chairs, blankets, dinner, wine. When the sun finally dips below the horizon, everyone claps. Show up early. Bring something to share. Make some new friends. That’s the move.

The thing nobody tells you

The best part of Martha’s Vineyard isn’t a house or a restaurant or a beach. It’s the people you bump into.

We’ve been lounging on Chappaquiddick and looked up to see someone from high school. I’ve been walking down Circuit Avenue and heard someone shout my name — turned out to be a young man I mentored years ago, all grown up, on vacation with friends. Every August, I’ll post a Story on Instagram and within an hour someone will text: “You’re on the Vineyard? So am I — let’s meet.”

It’s a small island. The same people — and the same kind of people — keep finding their way back. That’s part of why we go.

The August math

We always go in August. The vibe is right. The weather is kind. The calendar is loaded: African American Film Festival, Comedy Fest, the Book Festival, Legacy Week, Illumination. If you want a Vineyard week that feels alive, August is it.

It’s also the most expensive month. Plan for it.

Here’s what I actually spent last August — 7 days, group of 11:

• Flight (business class): $1,335. Yes, I treat myself. That’s my business.
• House share (one bedroom in a 4-bedroom rental, $20,127 total split 11 ways): $1,830
• Linen and beach gear rental (sheets, towels, beach chairs): $68
• Eating out (including one big dinner at Atria): around $600
• Groceries for the house: under $100
• Taxis / Ubers / airport rides: about $65 total
• Week-long bus pass: $30

All in: a little over $4,000 for the week.

(Without the business-class flight, knock about $800 off. The house share is the house share — there’s no real way to do an August week for meaningfully less and still get the vibe.)

What to actually wear

The Vineyard has a dress code nobody tells you about and everybody follows: casual but pulled-together. Linen. Layers. Straw hats. Low heels or no heels — you’ll walk everywhere. Tailored shorts and a nice t-shirt are fine. A simple sundress is fine. Bring a cardigan or a wrap for cooler nights, because the ocean breeze always shows up after dinner.

You don’t need to dress up. You just shouldn’t show up at Atria in flip-flops.

Black-owned MV — where I actually shop

Part of what makes the island matter to me is the Black-owned community. Some of my personal favorites:

• Michael Johnson’s Vineyard Haven Gallery — serious art, and one of the best places I’ve found anywhere on the island to bring a real piece home
• Island Life Studio — where some of my favorite pieces I own came from
• C’est La Vie in Oak Bluffs — for everything from gifts to souvenirs

For the full directory — restaurants, shops, services, places to stay — check out blackownedmv.com. That’s the resource I wish I’d had on my first trip.

Is the Vineyard your vibe?

Martha’s Vineyard is for grown folks. If you’re over 40, you value community, you love a chill rhythm, you can handle moderate weather (yes, you’ll want a sweater some August evenings), and you appreciate being around people who get it — you’re gonna love it.

It’s also wonderful for families with kids, but I’d skip August for that. June or July is calmer, less crowded, and the weather is just as good.

It is not for you if you’re looking for nonstop nightlife, beach clubs, live music until 4 a.m., or that warm Caribbean-blue water. The Vineyard’s water is North Atlantic cold — bracing, beautiful, but cold. (Save that itch for Curaçao. I’m writing about that one next.)

Five summers in seven years. Same friends, mostly, plus their friends. We’ve cooked together, held heated debate, learned the latest line dances until midnight together. We’ve cried, we’ve run into people we hadn’t seen in twenty years, we’ve sat on Menemsha beach in a row of chairs and clapped when the sun went down. The houses change. The rituals stay.

If you’ve been thinking about Martha’s Vineyard — especially if you’re a woman in your 50s, 60s, or 70s looking for the kind of trip you come back from feeling reset instead of depleted — this is your sign.

Go. And then go again next August.

Drop a 🌊 in the comments if you’ve been to the Vineyard — or if this just made you want to book it.