Massachusetts: Martha’s Vineyard

Massachusetts: Martha’s Vineyard

New England Summer Vacation

Fly in/out: Martha’s Vineyard (MVY)

Recommended ages: 4 and up

Ball Park Price: $1700/person for 4 travellers (airfare not included)

Best Season: Summer

Pace: Moderate

Time EST


Nantucket Island
Nantucket Island

DAY ONE: Flew into Boston and transferred to Cape Air or Jetblue to Martha’s Vineyard airport (MVY) and rented from Hertz. Checked into rental in Oak Bluffs.

DAY TWO: Rent bikes in Oak Bluff and get an orientation of the island. View gingerbread village, stop at the Flying Horses carousel. Stop at Scottish Bakehouse for take out food.

Gingerbread Houses, Oak Bluff
Gingerbread Houses, Oak Bluff

DAY THREE: Take kite surfing lessons and spend the day at the beach. Stop at Black Dog restaurant for lunch and shopping.

DAY FOUR: Take a deep sea fishing charter with Menemsha Blues Charter. Have lobster dinner at Nancy’s.

DAY FIVE: Rent paddleboards, kayaks and boogie boards at the beach. Take a kayak tour with Island Spirit. Go to “Jaws/jumping” beach where kids jump off bridge.

DAY SIX: Take a one-hour ferry to Nantucket for the day. Visit Nantucket Whaling Museum.

DAY SEVEN: Depart Martha’s Vineyard airport home via Cape Air.


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Cliffs of Aquinnah
Cliffs of Aquinnah

Vacation Highlights

  • A warm summer vacation in Martha’s Vineyard offered something for everyone. It was so great to see the kids decompress together on this quaint and elegant island.
  • We enjoyed staying in Oak Bluffs with local shopping and restaurants. We also loved exploring the other towns, Vineyard Haven, Edgartown, Aquinnah, and Menemsha.
  • We explored Nantucket and followed a list of things to do from’s Nantucket History.

Soak Up Martha's Vineyard

Great Excursions

  • We really enjoyed our day fishing with Menemsha Blue Charters. They provided a great day of kid-friendly fishing lessons and we caught huge fish every 15 minutes.
  • Our kayak and paddle board tours with Island Spirit were really fun for all kids’ age ranges.


Places to Stay

Places to stay

There are six little towns on Martha’s Vineyard. Oak Bluffs offers shopping, attractions and local restaurants within biking and walking distance. We loved the option of lobster and seafood takeout to enjoy in our rental home occasionally. We received helpful service from Karen M. Overtooms, Martha’s Vineyard Real Estate.

Menemsha Fish Market
Menemsha Fish Market



  • Beaches on Martha's VineyardWe appreciated the time saving by flying directly into Martha’s Vineyard versus taking the sometimes long ferry wait. We felt we did need a rental car to explore the whole island.
  • There is sometimes temperature variation in June, bring layers and windbreakers for the boat rides.
  • The kids loved the downtime walking and swimming on some of the beautiful beaches. The south side of the island that have waves for boogie boarding and the northern side offers calmer waters for kayaking and paddleboarding.
  • We liked the freedom of having a rental. We would need to book two rooms at a hotel and found this option just as economical. We liked the option of having food take out.
  • Bring lots of sunblock and sun gear!

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