A Day in Series Martha’s Vineyard


Summers at the Vineyard is a thing!! Idk who’s thing, but I certainly want parts. I am still unsure about International travel with Covid-19 so I’ve been taking the time to explore all that New England has to offer. I spent some time in Rhode Island (check that post HERE) and have been rediscovering Boston (read that post HERE), and though I’ve been down to the Cape and to Martha’s Vineyard a few times, I’ll never pass up an opportunity to head back!

A few friends and I rented a home and spent a long weekend out of the city and in good company. Wanting to still abide by Covid-19 protocols, we wanted to stick to ourselves, opting for outdoor or social distance friendly activities and cooking most meals at the Airbnb if not ordering takeout or delivery!

Getting to Martha’s Vineyard? MV is only accessible by plane (airport code MVY) or ferry, with ferry being the most popular method of transportation. (Note, you can bring your car aboard the ferry for an additional charge- the Steamship Authority). The ferry runs multiple times throughout the day from either Woods Hole (1 Cowdry Road, Woods Hole, MA), Falmouth, Hyannis, or locations in Rhode Island and New York. It doesn’t make a huge difference whether you take the ferry into Oak’s Bluff or Vineyard Haven, the ports on the island, but definitely measure out the distance to your airbnb- note, not all ferry trips will go to both ports!  

D63F045F-B9B9-45DA-BC3F-C0B8FA4C2455 2

It takes approximately 40/45 minutes to travel from Woods Hole and Falmouth, about 1hr & 30 minutes from Rhode Island, or about 6 hours from NYC.

A one-way ticket from Wood’s Hole will cost you $8.50 for a passenger-only ticket- no need to reserve passenger-only tickets in advance- can purchase at the terminal. There are nearby lots available to leave your car for a small daily fee and a free shuttle to carry you from the lot to the port. Plan to arrive at least an hour before your trip to allow ample time to park, get to the port, & purchase ferry tickets. See below for more information on terminal locations, numbers for reservations and information, and daily parking rates.

Getting Around Martha’s Vineyard: The island is very walkable and also bike friendly-in addition to other transportation methods! You can rent a bike at a local shop, map out & walk to your destination, or leverage ride-sharing apps like Uber. You can also rent a car once on the island. Unless you decide to bring your car aboard the ferry, in which you can use google maps to navigate around the island. Be sure that your Airbnb or hotel offers parking & factor in any additional costs!

Where to Stay?: I am a massive fan of Airbnbs, especially when I’m traveling domestically! We stayed in this beautiful 4 bedroom, 4 bathroom house in Tisbury, MA, close to the Oaks Bluff side of the island. We were within walking distance of the Stop & Shop, local shops & eateries, and to the beach! See pictures below or check HERE for an tour! 

When choosing where to stay, the two most popular areas are Oaks Bluff , Vineyard Haven, or Edgartown. You honestly can’t go wrong with either option, but Edgartown skews more towards relaxation whereas people looking for a more lively scene with an active nightlife should head to Oaks Bluff!

HERE is the link to the airbnb that we stayed in!

Top Activities:

  • African American Heritage Trail 
  • Martha’s Vineyard African American Film Festival MVAAFF
  • Take a sunset cruise61970BA0-0FC4-4274-8472-23F0C86EFC47
  • Walk Down Circuit Ave in Oaks Bluff (Shops & Eateries)AC93979C-7681-4430-AA3E-3C1968D8472D
  • Visit the Gingerbread Cottage Village



  • Visit the Gay Head Light (East Chop)
  • Eat fresh seafood 
  • Aquinnah Red Clay Cliffs Overlook
  • Visit the Martha’s Vineyard Museum (New Location)
  • Attend Church Service at Union Chapel
  • Hang out at Ocean Park
  • Visit the Harbor View Hotel 
  • Rent a bike and ride through the streets of Edgartown to Oak’s Bluff 
  • Martha’s Vineyard Agricultural Fair 
  • Take a ride at the Flying Horses 
  • HBCU Legacy Week on the Vineyard(For My HBCU Alum)
  • Visit the beach (Inkwell, Lighthouse Beach, Meneshma Public Beach, South Beach, Sylvia State Beach)

Restaurant Recco’s

  • Black Dog
  • Back Door Donuts (Get the coconut donut)
  • Lenda Jean’s 
  • Giordano’s Pizza (So good)
  • Grace Church Lobster Rolls 
  • The Home Port 
  • Behind the Bookstore 
  • Nancy’s Snack Bar
  • Lola’s 
  • Roxana Bar 

Black in Martha’s Vineyard: If it wasn’t already (which I’m sure it was) Martha’s Vineyard became the escape for thee black elite after it was uncovered that this is where the Obamas loved to vacation. To my surprise there was a lot of black history on the island and even more culture to experience. 

If you’re looking to get or learn more about the black experience on Martha’s Vineyard it is recommended to stay in Oak’s Bluff. I outlined some top activities above, but specifically to celebrate the black culture & history on the island be sure to check out the Black Heritage Trail & the MVAAFF.


Other Fun Facts & Tips:

Best time to visit the Island would be May-September for ideal weather and optimal ocean temperature

The second Friday in August there are fireworks in Oak’s Bluff which usually brings a huge gathering 

The Obamas have a home in Chilmark on the island- I was hoping to run into them while visiting!

There is no Starbucks or McDonald’s on the island! So if this is your thing, plan ahead!

Apparently, Martha’s Vineyard is “Little Kingston” per my Uber driver(some of that rich history that I didn’t know about)! We did run into a small community of Jamaicans and it was interesting learning that there was a mini Caribbean society on the island!

We also did a mini photo shoot in the backyard of our Airbnb with the theme of Sunkissed at the Vineyard! Photos were done by @stephensonstudios (Instagram) or check their website at https://www.stephensonstudios.com/!!

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: