I’ve never been to Martha’s Vineyard, but my friend from Southeastern Europe has never even heard of the place.

When it comes to the popular vacation destination, there are a couple of overarching topics that routinely come up: it’s simultaneously known as a classy, family getaway, President Obama lives here part-time, and Jaws was filmed on the island. (More on that later). But in the middle of our conversation, my friend would randomly send grape emojis. I was perplexed. Was he trying to be random for the sake of being silly? That is, before I realized that he assumed there were actual vineyards on the island. It makes sense: with a name like Martha’s Vineyard, you would think it was awash in every kind of grape, growing every which way: a Sonoma of the east. Alas, there’s not a single vineyard on the island. Though there are plenty of places to grab a drink, even in the early autumn.

 

We’ve arrived on the Island and land at its small, homey airport (literally, its terminal is the size of a house), before quickly finding myself at the front door of the Hob Knob. Located in the neighborhood of Edgartown, the hominess of the airport matches the coziness of this boutique hotel. It’s a Gothic Revival Inn, and since revivals are all the rage these days on television and in film, it only makes sense to also stay in one. Inside are glorious Bed and Breakfast vibes, right down to multiple spacious living and dining rooms downstairs and comfortable quarters upstairs. Its porch, meanwhile, is so impressively shiny you could practically see your reflection staring back at you. Legend has it that John F. Kennedy once stayed here, in town for a regatta.

 

 

The heart of town, and nearby water, is only a couple of blocks away, so we saunter down the street; tempted by the multiple shops that hawk both fudge and ice cream (hallmarks of any good diet). We wind up at The Seafood Shanty, a bustling waterside eatery that boasts every kind of fish and shellfish your heart desires. The Bloody Mary here is the star; a delectable conflagration they dub The Best Damn Bloody Mary Evah! (Emphasis on the Evah, to be said in a thick Boston accent). What makes it the best, you ask? Aside from being perfectly balanced, it’s a meal in a glass that boasts two plump, juicy shrimp proudly sticking out from the rim.

 

After an afternoon at the beach (and sometime gawking at the picture-perfect Edgartown Harbor Lighthouse), we’re aimlessly walking when we find what seems like a mirage in the distance. It’s the immaculate Bettini restaurant at the Harbor View Hotel. Aside from views of the water (are you sensing a theme?), the dining room is dimly lit except for a lone light on a bouquet of flowers in the middle of the room. We also witness the waitstaff running plates of high-end food back and forth. What to order when you’re in such a top-flight environment? A Martini, of course, which they make with Nikka Coffey Gin.

 

Forgoing food at our earlier place, our next stop is the highly-recommended Atlantic Restaurant for some grub. Here the soundtrack is blasting pure Yacht Rock (think “Escape (The Pina Colada Song)” by Rupert Everertt and “Sailing” from none other than Christopher Cross) and the drinks are just as jolly. Aside from requesting a plate of mussels, it’s also time for another Martini and luckily Atlantic menu is littered with ‘em, whether their namesake concoction (made with Lemon-Basil Belvedere), a French Martini (with Chambord, Prosecco, and Pineapple) or, what I order, a Sexual Chocolate Martini, which boasts Godiva White and Dark Chocolate Liquor. It’s as smooth as chocolate milk.

 

Before we stumble back to the Hob Knob, it’s time to pop into The Wharf, a classic neighborhood bar packed with revelers. Here, the Bud Lights are plentiful, as is something called Boom Sauce, an IPA from Lord Hobo brewing. Sitting at the narrow bar, one can assume that’s all to the space: but in the back and to the right you’ll find an expansive other room. Tonight, there’s a live band and we have no choice but to dance.

 

We decide to make the long walk (above five miles) from Edgartown to nearby Oak Bluffs, with ocean views and quaint forests along the way. We also walk over the Jaws bridge; an overpass over a waterway where Jaws was filmed in the ‘70s, a claim-to-fame for the community. (Luckily no actual sharks have been spotted. At least not yet anyway). After some more beach time and miles of walking, we find ourselves at Noman’s; a cavernous place near a local golf course that boasts local beers, fried chicken sandwiches and an array of cocktails perfect for a day outdoors. Yes, that includes an Aperol Spritz; because when the weather is perfect, you need a cocktail in hand to match. Served in a plastic cup, its blazing color doubles as a liquidy ray of light.

 

 

After exploring Oak Bluffs, including its array of small, colorful homes dubbed the Gingerbread Houses and getting some shopping in, we strut into the aptly named Offshore Ale Co, an eatery that leans into the aquatic theme with boats and canoes strung up on the ceiling and all beers brewed in house. I wash down the ribs (with a homemade sauce made with their in-house stout) with a couple beers, as well as a horseradish-forward Bloody Mary, all hitting the spot after a long day.

 

With our Martha’s visit about to be in the rearview, we make our way toward what bills itself as a sailor-bar-dive: The Ritz, a longtime community staple. Dead quiet when we walk in, it quickly fills up with all sorts of characters from town and way beyond. Ferraris are passed around (for those uninitiated, that’s a tongue-smacking Campari and Fernet Branca shot). It’s an appropriate way to cheers my welcome to this island. No vineyards? No problem.