I'm heading to Martha's Vineyard and will be staying in Edgartown, MA. Where are some cool local hotspots? (applies to Boston as well)

When you are at Martha’s Vineyard you MUST go to the beaches at Aquinnah. They are beautiful. They bump up against these huge clay cliffs. At the top of the cliffs is a Wampanoag family restaurant that serves yummy fish and chips. It is so relaxing and serene.

When you are in Boston check out the South End for bars and restaurants. It is a pretty cool neighborhood.

Both Edgartown and Oak Bluffs have main streets that are chock full of restaurants and coffee houses. The places aren’t that big, so it won’t be hard to find them. Dump your car somewhere and walk around. There’s not a lot of around to walk. You’ll find your thing in those places. Elsewhise you can go down the road and watch the secret service guard the road to the house where the POTUS is staying.

You have to have a reservation to bring a car onto Martha’s Vineyard. There are places to rent a car, mopeds, bicycles… and I’d suggest having a vehicle of some sort to see all of the island.The red clay cliffs at Gay Head are awesome…and people are nude on the beach. Do the Duck Boat Tour in Boston…Quack, Quack.

While in Boston, you can pick from whichever suits your interests, the Science Museum, the Museum of Fine Arts, the Aquarium. Anthony’s Pier 4 is great for good seafood and not terribly pricy. To just hang out, the North End is cool for open-front restaurants, particularly Italian food, and well situated if the day’s agenda includes either the Science Museum or the Aquarium.

When in the city, park the car in an outer lot where rates are reasonable and take the T everywhere you go. If you have a laptop with you, Google Maps will show you the shortest T route point to point and give you travel instructions if you swithc its mode from driving to Public Transportation.

I wouldn’t bother bringing a car onto Martha’s Vineyard. When I was there, I got around fine by foot and using the Vineyard’s public bus company. I bought a 3-day visitor’s pass for the buses. Also, lots of people rent bicycles to get around.
As for Boston—I’d also recommend crossing the Charles River to hang out in Cambridge! Take the T’s redline, get off in Harvard Square and do some people-watching.

@answerjill‘s note on transit passes reminded me, when in Boston, there is a Day Pass or 3-Day Pass for the T. Much better than trying to drive in harrowing traffic and bewildering city layout, and finding no place to park at each stop. There is a 90 Minute Ferry from Provincetown on the Cape to Boston near the Aquarium. So if you can find transit to Provincetomwn, grab that to come to Boston.