The Perfect New England Getaway: 1 Week in Martha's Vineyard

Advisor - Erica Charles
Curated By

Erica Charles

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  • USA

  • Luxury Travel

  • Boutique Travel

  • Food & Wine

  • Off-the-Beaten-Path Travel

  • Nature Escapes

  • Road Trip Travel

  • Beaches

  • Couples Travel

  • Summer

  • Fresh Seafood

  • Beach Town

lighthouse in the distance of a overgrown field with blue sky and ocean beyond
Curator’s statement

Just off the coast of Cape Cod and adjacent to its better known island counterpart - Nantucket, Martha's Vineyard is the perfect escape from city life. Although Martha's Vineyard can be enjoyed year round, the best time to visit is between early May through the end of September. Spanning just about 100 square miles, this island is home to ample protected land, quaint town centers, and a wonderful restaurant scene; this destination has something for everyone.

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Insider knowledge

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Where to stay

Harbor View Hotel

An exclusive Martha's Vineyard resort highlighted by top-tier dining and breathtaking views of the Edgartown Harbor.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Hob Knob

This 100-year old boutique hotel and spa is a classic Gothic Revival inn with modern amenities, charming décor, and convenient Edgartown location.

Fora Perks
  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.


Designed as a nod to Oak Bluffs’ history as a summer "camp" destination, this whimsically renovated historic hotel invites you to come be a kid again.

Advisor - Erica Charles

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Day 1: Arrive on Martha's Vineyard

view from grassy shore of large ferry in a harbor and other smaller boats

Getting there

The easiest and most convenient way to arrive is by plane; fly into the local airport in West Tisbury (relatively central point to touch down!) *Jet Blue has plenty direct flights in the summer from JFK!

Another common way to arrive is by car and ferry; you can drive from wherever you hail, and book a car ferry to the island out of Woods Hole or Hyannis (great option if you would like to do some exploring and have your own car!). You can also drive to any of the ferry docks on the mainland (Woods Hole, Hyannis, Providence) and ride a ferry as a passenger! I love the ferry rides - go up on the top deck to take in the fresh air and waterline views, read a book and grab a coffee on board!

Get checked in!

Find your house rental or hotel and get settled. Highly recommend the Harbor View Hotel in Edgartown.

Dinner in town

Make your way to Bettini for dinner - waterfront views, relaxed, warm environment with a chef inspired menu featuring the season’s freshest offerings from local farms, fishing boats, foragers and markets.

Day 2: Adventure day

view from on a sailboat of the shore with white houses with docks and american flag waving

Start your day by walking over to your breakfast spot of choice...Espresso Love for fresh baked pastries, bagels, breakfast sandwiches and of course coffees and lattes, Among the Flowers for smoothies and lighter morning fare, or Toccopuro Coffee for the best coffee on the island in my opinion - strong and lots of flavors/options!

Rent bikes in Edgartown and hop on The Chappy ferry across to Chappaquiddick. Ride down the island roads to the Royal and Ancient Par 3 course for activity! You can rent clubs or bring your own, as well as bring your own drinks or buy a bucket of beers. Such a fun, walkable course for family and friends.

Post golf, ride around Chappy and return to Edgartown. Head back to your hotel, shower and change!

Do some shopping in town; wonderful boutiques line the streets of Edgartown. Then head to dinner at The Covington or The Atlantic.

Day 3: Beach day

large sandy beach with grass and houses in the distance

Enjoy a slow morning and grab breakfast + lunch to go at one of the spots I mentioned for Day 1 that you did not try yesterday, and load up for the beach...there are so many wonderful options for beaches that you can explore during your time on the island. State Beach (home of the Jaws Bridge!), Inkwell Beach, Menemsha (wonderful for sunset + don't forget to grab a fresh lobster roll on your way to set up!), South Beach (probably the best "classic beach day" option! has parking along the water, and the option to deflate tires to do some sand driving!).

Post beach day, head to Nomans for a casual dinner! This spot has lawn games and open air dining - perfect for winding down after a day in the sun.

Day 4: More of the island + boat day

charming houses decorated like gingerbread houses in red white and blue colors with american flags in the front yard

Up and at 'em today! Get an early start and head to Grey Barn - such an ethereal, bucolic start to your day! Chickens and bunnies roam free, with horses and cows in the distance. Willow trees and gardens line the walk up to the farmhouse, where you can get your hands on some of the best croissants and honey buns known to man - they go quick, so must get there early! They also have fresh cheeses, meats, spreads, and produce for a killer charcuterie board.

Once you have your morning fuel, head to Oak Bluffs - explore the historic Gingerbread houses, Main St (Fat Ronnie's are fabulous burgers if you are looking for a classic fix!), and Ocean Park.

Head to Vineyard Haven and pick up sandwiches at Waterside Market for a day on the water. You can rent a boat for the day and be picked up at the Vineyard Haven Marina. Such a great day to see more of the island and enjoy the great outdoors!

For dinner, highly suggest Lambert's Cove. A wonderful hidden gem tucked in the woods up island. They have a beautiful outdoor set up with twinkly lights and fresh island menus during the summer. Very romantic!

Day 5: Another adventure day

natural cliffs over the ocean with crashing waves on a clear sunny day

Drive out to view the Cliffs at Aquinnah + Lighthouse - a classic vineyard view! Then head to the Katama Airfield for lunch and a bi-plane ride; you can hear more island history while getting a sky-high lay of the land, whilst also spotting wales, seals and the tricks tour to do some loop-de-loops in the sky!

Need to Know

If you continue your stay through a full week, or beyond, there are so many more wonderful beaches, hikes/walks, areas to explore. Vineyard Haven, Edgartown and Oak Bluffs have every type of food, bars, stores, markets you could need during your stay. I also always make sure to have a few days with no plans...sleep in, relax, amble around and soak up island life!

For more travel tips, check out Fora Advisor Nicole Sansone's guide, The Key to a Family Holiday in Cape Cod, Massachusetts.

Advisor - Erica Charles

Travel Advisor

Erica Charles

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