Travel Guide: Martha's Vineyard

The island has two parts, up-island and down-Island. Up-island refers to the elevation being higher and is on the west side of the island where the towns of Aquinnah, Chilmark, and West Tisbury are. This is a much quieter part of the island and has winding roads through forest, meadows, and around picturesque views of different harbors. Down-Island is on the east side where the towns of Edgartown, Vineyard Haven, and Oak Bluffs are located. These parts of the island are more populated and where there are more restaurants, bars, and activity. Chappaquiddick (or "Chappy") is now a separate island on the far east side (it used to be connected via the beach on the South but has since eroded).

{Get There/Get Around}
Getting to the island takes some doing, but that’s part of what has made it feel so removed from the hustle and bustle. The easiest way to get there is to fly. There are direct commercial flights from several NYC airports as well as DC. Cape Air also provides service to the island. Taking the ferry is another great way to get to Martha’s Vineyard and likely the most economical, though the fees to take your car on the ferry are not insignificant. Once on the island you can easily get around with a combination of Uber/Lyft and the local VTA bus system, but renting or having a car would afford you more flexibility.

We stayed at the Harbor View Hotel in Edgartown which I would unfortunately not recommend. Nothing about the property was particularly outstanding and there were a number of rather unfortunate negatives. That said, there are dozens of cute Airbnb and B&B options across the island. I’d check out The Charlotte Inn, Hob Knob, Winnetu, Summer Camp Hotel,

{See & Do}
Edgartown Lighthouse is at the far edge of Edgartown and features beautiful views  
Cliffs at Gay Head in Aquinnah boast incredible views of the island, Aquinnah clay cliffs, and a stunning lighthouse. Perfect spot to watch the sun set in the west!
Menemsha Beach in Chilmark is a small fishing village where you can see the local fishing operations. This is also one of the most popular spots for sunset viewing
Chappaquiddick Island requires a short (5min) ferry to visit, which leaves from downtown Edgartown. Much of Chappy requires a season or daily permit to explore.
Martha's Vineyard Camp meeting Association in Oak Bluffs is a cool neighborhood of historical small houses or "gingerbread cottages" around Trinity Park in Oak Bluffs
South Beach in Edgartown is a large beach along the south side of the island
Morning Glory Farm just outside of Edgartown is a local farm with a small grocery store and deli

{Eat & Drink}
Espresso Love is tucked away cafe in the heart of Edgartown with great sandwiches and coffees and plenty of outdoor seating
Isola is right beside Espresso Love and has a great menu of pizzas and casual Italian. They also have takeout.
Among the Flowers is right by the water in Edgartown and serves up a delicious breakfast or brunch. Tip - go early, the line gets long!
Rosewater Market has delicious sandwiches, salads and coffee to takeaway or eat in the airy shop which is chock full of local goodies and design finds.
Behind the Bookstore is a cosy cafe and coffee shop tucked behind the Edgartown Bookstore. The menu has something for everyone and the outdoor bar makes it a perfect spot for an impromptu afternoon cocktail.
Seafood Shanty huge back deck overlooking the harbor in Edgartown
Port Hunter is a rustic local restaurant right in Edgartown that usually has live music and fun vibe
Backdoor Donuts in Oak Bluffs is an institution and worth a stop for any donut fans.
l'étoile is a delicious and slightly more upscale option

The Grey Barn and Farm
Ally’s General Store
Bunch of Grapes Bookstore   
Edgartown Bookstore
Edgar
Vineyard Vines!

{What to Pack}
While the days are warm in summer, the evenings can get either quite cool or very muggy so bring a few options to suit either.