Martha’s Vineyard Itinerary: Two Weeks of Activities

Martha’s Vineyard is huge for families. We have a home in Oak Bluffs, and the region’s deep-rooted black history fills me with pride. We always go there during peak weeks – the second and third weeks of August – but in reality the whole month of August is lit up. It’s all black excellence, all the time.

There are hotels on the island that people I know really like. Lambert Cove (90 Manaquayak Road) is off the beaten track, away from the hustle and bustle. Winnetu Ocean Resort (31 Dunes Rd .; from $ 325 per night) is a seaside resort town – it is the epitome of New England and offers stunning views of the water. We stayed at Oak Bluffs Inn (64 avenue du Circuit; from $ 270 per night) when we got married. It’s pink and blue and beautiful – very old Victorian architecture, very quaint. There is an observatory at the top of the hostel which is not open to the public, but if you stay there the owners will likely let you go up and see the city from the top. But generally people rent a house. I’m on a Facebook group for Oak Bluffs called the Inkwell group, and homeowners will post and say, Hey, I’m renting my house from this date to this date. You can find some really good last minute ones.

Oak Bluffs Inn

To get to the island, people take the ferry through sound. Real winemakers know that ferry bookings open around January 12, so everyone who goes to the vineyard is texting each other like, You know the ferry opens, because it will sell, especially if you want to bring your car. There is a snack bar and people usually sit at the top and enjoy the ride. It’s about 45 minutes, and it’s just beautiful. There is also a fast ferry from New York which we took a few times when we were young and childless. It’s basically the same price as the plane – around $ 250 – and takes around five hours. Once you get out of the sound you’re in open water so it’s really choppy. If you have car sickness issues, you probably don’t want to be one of them. Flying is really easy; it is only 32 minutes from New York. If I buy tickets early, I can get them for less than $ 300 per person. The airport is tiny. There is a terminal, and they put your luggage through a window.

We usually arrive around noon, and if the weather is nice, we try to go to the beach. If we are very hungry at this time, we will go and find food. I always like that my first meal is a lobster roll from Nancy’s (29, avenue du lac.). This is probably the most famous restaurant in Oak Bluffs and is said to be President Obama’s favorite on the island. Either take it home or eat outside in the dining room because it’s good for people-watching. It’s at the top of Circuit Avenue, so it’s near the water and you can see people coming from the ferry. Then there’s this bar next to the pickup window called Donovan’s Reef. Donovan is that Jamaican guy who returns every season, and he’s a city favorite. People stand in line for an hour to get a dirty banana. It’s this banana, chocolate and rum situation that everyone loves. We also source alcohol for the home from Jim’s Parcel Store (27 avenue du lac.) Where Our market (1 E. Chop Dr.), which we tend to turn to more. It’s near Nancy.

That afternoon we usually go to Inkwell (83 avenue of the sea view.). It’s a classic beach, and a lot of black families and friends tend to be there. It’s a good socializing beach for when you want to see old people and jump off blankets. There is a lot of joy between black boys and girls. The house is very close to the beach so one can walk or drive; it’s about a ten minute walk. Inkwell is right next to Town Beach, and the two are separated by a pier. Inkwell Beach is really small compared to Town, so once it fills up people flock to Town and vice versa. We usually go to the city side as it has a bit more area.


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