The scene is festive and light; the food is Tex-Mex with portions large enough for leftovers. There is southern charm in the form of cuisine available on the island as well. Fried pickles at Smoke-N-Bones can remedy even the worst hangover, and biscuits with gravy at Biscuits cafe are true to its down-home roots.
Nancy's restaurant on Circuit Avenue is synonymous with the town of Oak Bluffs. Fresh seafood and views of the yacht-filled marina are added bonuses, but the real treat comes in the form of Jamaican-born bartender Donovan at Nancy's outdoor bar. Reggae songs from the '90s fill the air, although often drowned out by Donovan's own booming voice, adding his special take on the tune.
Locals and tourists don't seem to mind, which might have to do with his heavy-pouring hand that swiftly concocts rum punch and his signature drink, the Dirty Banana. It adds to the laid-back feel of the spot. And, if you close your eyes for a second, you could mistake this mellow vibe for the Caribbean.
Continuing along the marina will lead to a few food options, including a sushi bar to take in the sunset and boats headed to and from Cape Cod and Nantucket.
If desserts are your weak spot, you may find nirvana at the Oak Bluff's Back Door Donuts. At this local favorite, full of croissants, honey-dipped donuts and buttercrunch cakes, the real secret is, indeed, at the back door.
After 7 p.m., pedestrians can walk to the back parking lot of the bakery and stand in line at a screened door that leads to a kitchen where the magic happens. Here, huge fresh-out-the-deep-fryer fritters, decorated with mounds of tart apples and moist sugar cinnamon bread for $3.75, are prepared for a hungry line of devoted fans. You have until the clock strikes midnight to experience this ridiculously delicious treat.
The best way to see the island on a budget is by renting a bike. The rental will run about $25 for a full day. And, with a free day and conviction to take in as much as possible, viewing most of the island is possible in half the time. Enjoy a sandwich from the island's sandwich shop, Skinny's Fat, and take in the view along the way at one of the islands many beaches.
Aquinnah, located on the Western tip of the island, may not be as easily accessible by bike if you are staying in Vineyard Haven or Oak Bluffs. But a car or taxi ride is definitely worth the visit.
Grab a cup of clam chowder from a small shack called the Bite in the next door fishing village of Menemsha. Walk across the dirt road to the fresh seafood market, pick out a lobster.
Head down to the beach, just footsteps away, and watch a burnt-orange sun sink into a fushcia- and aqua-colored sky.
Now, you understand why both presidents and tourists alike keep coming back. There's magic in the air.