Girls’ Getaway: THE VINEYARD

Girls’ Getaway: THE VINEYARD

Martha’s Vineyard is part of the American pop culture consciousness. It was the setting for Amity, the seaside town made famous in Steven Spielberg’s mega-epic JAWS. Lately, the 100-square-mile island is in the news as the bizarre destination for busloads of refugees from cartel-ravaged countries south of the US border.

As humorously depicted in JAWS, this Yankee enclave may tempt you to speak with exaggerated Kennedy lockjaw, as in, “The children are in the yad (rhymes with bad or cad) not fah (rhymes with nah) from the cah (rhymes with fah).” But there’s so much more to love about the Vineyard than clam chowder and souvenir saltwater taffy (although the local lobstah roll is practically a religious experience).  Since 1899, Martha’s Vineyard has been the summer playground of the Black elite. Frequent visitors, especially to Oak Bluffs, include the Obamas, Spike Lee, Oprah Winfrey, Beyonce and Jay Z,  and Wynton Marsalis.

No one is sure who the original Martha was, but the Vineyard was probably named for the mother-in-law or daughter of Bartholomew Gosmold, the first European to explore Cape Cod in 1602.  Historically, it’s been a prosperous summer colony, with summer numbers topping 200,000 (versus about 17,000 year-round residents, a number which is growing).  

Living here is heart-stoppingly expensive, with housing prices measured at 96 percent above the national average. The cost of living on the Vineyard is about 60 percent higher than the national average. Weirdly, the average weekly wage here is only about 70 percent of what people earn elsewhere in the state, although homes here are about 54 percent more expensive than elsewhere in Massachusetts.  Long story short: this is not a budget location.  And, it has to be said. Stolen ancestors were bought, sold and probated as property on the Vineyard. Thankfully, times change, and the Martha’s Vineyard African American Film Festival is one of the most prestigious in the USA.


Fly into MVY (Martha’s Vineyard airport) via Boston or NYC via JetBlue, Cape Air, American (check carriers for rates and updates). There is bus and taxi service on the Vineyard, but it’s casual– we recommend that you book a rental car in advance for convenience.

Even better: take the iconic Massachusetts Steamship Authority Ferry from nearby New Bedford or Cape Cod. The line for the ferry begins in the parking lot at Wood’s Hole, where cars line up for the trip. The ferry is the easiest way to have a car ready for adventure on the island, and there are other ferry carriers. If you can’t get a ferry slot, you can rent wheels on the other side.


Oak Bluffs (“the Bluffs”) is traditionally where it’s at for Black visitors to the Vineyard, where cute rentals abound. The town was immortalized in the 1994 movie, The Inkwell. However, Vineyard Haven, and Sengekontacket Pond are enjoying new popularity, Sengekontacket being an indigenous Wampanoag phrase for “where the stream meets the river.” If you want more privacy, go up-island to Chilmark where the Obamas usually decamp.

Check out:

Inkwell Beach Cottage, formerly Isabelle’s Beach House

Kahina, owner of Inkwell Beach Cottage

83 Sea View Avenue

Black-owned jewel of a place, a seaside collection of historic boutique inns, joining two historic properties. Porch parties spontaneously happen here. Bed-and-breakfast style. Across the street from the beach. Also check out the owners’ retail shop, Jubilee, at 42 Circuit Avenue :


Oak Bluffs Inn

Oak Bluffs Inn

64 Circuit Avenue

(508) 693-7171

Five minutes from the beach, this stately, powder-pink Victorian home was built in 1870. Although remodeled, note that the Inn does not have elevators or ADA wheelchair ramps — just stairs.

The Summercamp Hotel

Lark Hotels

70 Lake Avenue

(508) 693-6611

The largest oceanfront hotel on Martha’s Vineyard, with 95 rooms overlooking the harbor, is less charming, but convenient, especially for large groups with kids.


After Labor Day, pack a mini-umbrella, wellies (rain boots) and woolies. In October, dress for true Fall weather, meaning days in the mid-60s and cool nights in the 40s, and expect chilly rains. Grandma was right: always, always bring a down-filled vest, or a lightweight sweater you can layer under a denim jacket, even when starting out on a sparkling, sunny autumn morning. Later in the year and through April, expect snowstorms and Atlantic coast cold.

General fashion advice: do not dress to impress. The Vineyard code: less is more. The old-money Kennedy legacy still wears well here, where a preppie button-down Oxford cloth shirt (freshly laundered, but not necessarily ironed!), well-worn jeans and classic deck shoes, socks optional, are de rigeur. Be comfortable. The only signifiers of wealth: expensive sunglasses, an understated but expensive watch, and a luxury ride. Unlike the Hamptons, high heels, suits and ostentatious bling will mark you as an outsider.  DO rock your school pride in the form of a Howard or Spelman sweatshirt! And, anything nautical will flag you as a tourist, but that’s okay.


Aw shucks, let’s start with the oysters. This locally grown mollusk is revered, and slurping them raw, plump and briney on the half-shell is a favorite pastime of islanders. Oak Bluffs is packed with quaint spots to sample incredibly fresh local seafood, so let’s start there.


This is an actual oyster, clam and seaweed farm, tours available, with a floating raw bar.

(508) 299-7745


Great centrally located spot, with Maryland softshell crabs, buttermilk fried chicken, grits and greens on the menu, too.

6 Circuit Avenue

(508) 696-6040


Locals line up at the take-out window for live music and craft beers.

12 Circuit Avenue, Ace Extension

(508) 693-3420


EU certified, and they ship shellfish including littleneck and steamer clams and bay scallops nationwide! Try the BYOB tour.

(508) 299-7745

Coffee break: Black-owned MOCHA MOTTS is a favorite Spike Lee stop.

10 Circuit Avenue in the Bluffs, second location at 15 Main Street in Vineyard Haven.

(508) 696-1922, Circuit Avenue

(508) 693-3155, Main Street


1 East Chop Drive

(508) 687-9572

Take-out only. Jerk chicken, curry chicken, oxtails, meatloaf, mac ‘n cheese, beef stew. Black-owned by husband-and-wife team Lisa and Jamaican-born Winston Christie.


26 Lake Avenue

(508) 693-2033

Great for breakfast, like Nola-style blackened garlic shrimp and garlic-roasted red peppers, served over cheese grits or a cod cake, cinnamon-dusted French toast stuffed with cream cheese and berries or chocolate chips, and of course down-home biscuits and home-made sausage gravy. Black-owned.


African American Heritage Trail

Now celebrating its 25th anniversary, this historic venue is expanding as a walking, driving and shopping venue. The Trail illuminates a past rife with heroic escapes from enslavement, racial segregation and white supremacy, enriched by personal histories from the community. Truth is powerful, and it prevails. — Sojourner Truth

Just a few landmark stops along the way. Many attractions close for the winter, so check in with Vineyard Preservation Trust for updates and more listings, (508) 627-4440

Please note that as experienced world-travelers ourselves, we always recommend that you book activities directly with the specific vendor rather than working with Sorry, not sorry.

Sail on.

Cruise the waves in a gorgeous 60-foot ketch (two-masted) sailboat, the private charter Tandemeer, affording spectacular views of the lighthouses, harbor, Nantucket Sound and other iconic scenery. Especially awesome at sunset. Arrange for your own lunch or dinner.  Shaded areas as well as sun deck. Super-plush beanbag chairs for lounging.  Diving masks, snorkels, fins, and towels included.  A luxurious 2-hour experience for groups of 6, max.

Island Sailing Tours

(203) 246-1369

Seeing the Sights. How about a private, 3-hour land tour for your small group of four? A lil pricey, but you’re so worth it. Via luxury minivan. Or choose a more affordable, equally breathtaking, the all-island bus tour for your larger group. Many options.

Laid Back Tours,

Home Grown Tours, 

The Old Whaling Church

Included in the historic Walking tour in Edgartown. Skilled local shipbuilders who built the mighty whaling vessels of the past century that made the Vineyard, Nantucket and New Bedford wealthy also built this Greek Revival-style Methodist church.

Flying Horses Carousel, oldest working carousel I the USA

508-693-9481 — closing for the season in October, but make note for next summer!

Amen, Amen. Like, say, The Vatican, Union Chapel built in 1870 really is a must for visitors regardless of your current religious or spiritual affiliation. Non-sectarian. All are welcome. Seating in the round, excellent acoustics for that joyful noise!

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