I suppose without realizing it, I wrote a blog post in the form of an email to someone who wanted to pick my brain about visiting one of the world’s most beautiful islands. I’m posting the information below just in case you’re making plans to visit.
“As far as the Vineyard goes, they have a really inexpensive and efficient bus system that makes it easy to cover the island in a day. There are also Jeep and scooter rentals as well.
Not sure what ferry you’re taking, but if it’s docking in Oak Bluffs, sort of the island’s main hub, I wouldn’t miss the Flying Horses, which is the oldest operating carousel in the country (this may be more of a nostalgic thing for me since I’ve ridden it as a kid, but if it’s just you and your parents, you might want to just take a look and then move on…haha). The famous gingerbread cottage village is also in Oak Bluffs and definitely worth a walk-through. The town is very walkable and full of unique shops and restaurants. (There are no chains on the island save for a couple reduced-sized grocery stores.)
Here are some food recs:
Mad Martha’s ice cream (OK, my sister swears by Ben & Bill’s, which is also delicious, but you can get it on the mainland. Either way though, you can’t go wrong.)
MV Gourmet Cafe and Bakery (THE APPLE FRITTER OMG)
Nancy’s (you can sit on the harbor and they have excellent seafood)
Of course, you’ll want to see some Jaws shooting locations. You’ll probably recognize a lot of the Amity Island town scenes in Edgartown, and if I remember correctly, you can see the infamous bridge/pond (from the terrifying scene with Brody’s son) from one of the bus routes, since the bridge is on the road that connects Oak Bluffs and Edgartown.
I also love Vineyard Haven (again, not sure which ferry you’re taking, and it might dock here too), which is the home of the original Black Dog restaurant. Whether or not the food is actually excellent or if it’s more of a tourist trap is debatable, but it’s basically a shack on the beach and is a cool experience IMO. The last time I was there I remember my food being delicious. There’s always a crazy wait though.
That’s what I’m most familiar with, but of course there’s tons more. There are plenty of biking paths, organic farms, lighthouses, beaches, etc. that you can explore. They have plenty of guides and tourist information should you need it too. There’s a pretty big art/film scene too, which I imagine you’ll enjoy. Also, if I think of anything else, I’ll pass it along.
Oh, and keep your eye out for celebs! My sister has talked with Maggie Gyllenhaal, and of course the Obamas and Clintons have vacationed there. My dad has seen David McCullough a bunch of times. Also, Carly Simon has a shop in Vineyard Haven.
Overall, wherever you go (at least on the Vineyard anyway), it’ll be walkable and beautiful with plenty of interesting, non-chain places to check out. Hope that helps! Didn’t mean to write a book…haha. Excited for you guys! The Cape is a beautiful place.”