Where to meet a man, get a tan and embrace the MV spirit

I’m practically giddy with excitement to write this article, and that’s because Martha’s Vineyard is one of my top three favorite places on the planet. Although it isn’t technically summer time yet, think of this post as my gift to you, because this is one trip you need to plan for in advance. Read on to find out why you should go, how you’ll get there and what kind of men you’ll meet. Just in case you were wondering, I can guarantee that none will be wearing Speedos

For those of you who are currently scratching your heads with monkey-like confusion, Martha’s Vineyard is actually a tiny, tiny island off the coast of Massachusetts. Although political royalty like the Kennedys and Clintons have summer compounds there and the Obamas seem to love the spot, it’s nowhere near as pretentious or preppy as you’d assume. Sure, a small element of snobbery is still present on parts of the island, but when you set off for a weekend on ‘The Vineyard’ or ‘MV’,  you won’t be gawping at any extreme opulence or wishing you were a baller. In fact, you’ll be more likely to fully chill out and do nothing more pressing than getting drunk, getting a tan and, more likely than not, getting laid.


The Vineyard is divided up into six towns and spans about 20 miles in total. Of these six wee little areas, three are ‘wet’, which means that you’re shit out of luck when it comes to finding booze on approximately half of the island. The wet towns are Oak Bluffs, Edgartown and Vineyard Haven (also called Tisbury). The ‘dry’ areas are Chilmark, Aquinnah and West Tisbury. However, given that you’re going to meet men, my guess is you’re going to want to stick to the places where alcohol is freely flowing. So what — and who — will you find in each area?


If Edgartown were a person as opposed to a place, it would probably be wearing a whale belt, khaki shorts and a popped-collar pink shirt. The guys that hang out here are aggressively preppy. They say things like ‘brah’ (without irony, sadly), were probably in a frat at some point in their lives and tend to go for expensive-looking blondes that wear Lilly Pulitzer. I lived on MV for six summers, and although I loathed Edgartown with the passion of unwarranted reverse snobbery, nowadays it’s where I prefer to hang out post-sunset. Sure, you’ll still get your ‘brosef types’, but not everyone is a complete DB, I swear.

Where to go: The Wharf is a pretty standard weekend spot. There’s usually a live band, and, with three separate rooms, it’s big enough that you can dance, have an intimate conversation or simply camp out at the bar doing shots of Jack. Across the street is my hands-down favorite E-town bar, the Atlantic. The crowd is a bit older, a bit better looking and way more established. If the 28+ set isn’t your thing, don’t come here.

If you want something a bit less populated, roll on over to Alchemy, where you can play pool whilst drinking swanky cocktails, or Atria, which is damn expensive but good for celebrity-spotting (my favorite night: George Clooney and Matt Damon. Together. ‘Nuff said.) The Newes From America is a straight-up pub and chock-full of good-looking dudes, but it isn’t really meant for late nights, so instead, head there for an early dinner or to catch a game. There’s also David Ryan‘s, which is my least favorite bar in the area because it typically caters to the 40+ set, and, finally, The Seafood Shanty. The Shanty is an interesting hangout, because it seems to be the most popular of the Edgartown bars nowadays. There’s live music, an outdoor patio and relatively cheap drinks — which makes it the easiest spot to become the ‘last woman standing’ of Edgartown. Meaning, if you’re trying to pick someone up without him throwing up, this is probably your best bet.


Oak Bluffs is a beast. I mean, it isn’t literally a hoofed, snarling, fanged animal, but you might feel that way after a night out here. OB has a vacation-friendly atmosphere that’s conducive to languid conversations, endless cocktails and very little common sense. Because this is the only town where there are ferry ports and bars, it tends to become pretty overpopulated in the high season. You’ll find your summer boys, but you’re also going to be surrounded by tourists, children and daytrippers. But back to the guy situation. OB is the anti-Edgartown, so if normal guys are more to your liking, head here.

Where to go: There are a string of bars along the harbor, but the Sand Bar is easily the best. It’s the biggest, there’s usually live music and there are always hot guys loafing around. Fishbones and Coop de Ville, also located on the waterfront, are pretty casual in comparison, and are more popular with older tourists and island residents. Next door to the Sand Bar is Nancy’s, which has been made famous by its floral-shirt wearing Jamaican bartender, Donovan. Regardless of Donovan’s mix-master abilities, this isn’t a spot that’s ever floated my boat. I swear to you I’m not a woman scorned when I tell you that the guys who tend to hang out here are mostly assholes. Just saying. Moving right along, if you want some speciality margaritas and  relatively inexpensive Mexican food, Sharky’s Cantina is your place of choice. Similarly, if you’d prefer beer and peanuts, check out the homemade brews at Offshore Ale House. Offshore is refreshing because its a bit off the beaten path; residents tend to find relief here from the ever-present sexual shenanigans occurring on OB’s main street, Circuit Ave.

Speaking of sex, look no further than The Lampost if you want some quick and easy ass. This bar terrifies me. It’s the only island ‘bar’ that has cages and dance contests, thus, making it very un-Martha’s Vineyard-like. They have a ‘Christmas in July’ party every year, and it shouldn’t be any surprise what you’re going to find when you sit on Santa’s lap… For more bump ‘n grind action, head on down the street the Island House. If five minutes in either place makes you yearn for a remedy, run in the opposite direction towards the Oyster Bar, which is as classy and devoid of co-eds as the ‘Post is trashy. This, like Atria in Edgartown, is also a prime celeb-seeking spot.


Vineyard Haven just became a wet town a few years back, and although some of its restaurants are ace,  I wouldn’t even attempt to have a night out here unless your idea of a wild and crazy night is popcorn and a movie. Stick to Edgartown or Oak Bluffs for your kicks and keep to VH for its shopping. Hot surfers get their gear at the Green Room on Main Street; they are often South African or Australian, if you like that kind of thing (which I do).


These three towns are referred to collectively as ‘up-island’, and they’re typically hippie-heavy locales. You’ll find your surfers at Long Beach in West Tis, your  green-thumbed gardeners in Aquinnah and your wealthy vacationers in, well, all three. However, Jake Gyllenhaal and his family have a home in Chilmark, so do with that information what you will. The up-island towns are harder to get to without a car (there are buses, but who wants to be on a schedule in paradise?) but well worth the trip, even if you do have to hitchhike to get there. Clearly, these three towns aren’t hardcore party places. You’ll be more likely to find a BBQ than a keg-heavy rager.

While you’re there, make sure to check out Menemsha, a tiny fishing village in Chilmark, for one of the best sunsets you’ll ever see. If you do have a quickie vacation romance, its pretty much the height of romanticism if he brings you to Menemsha for a make-out and wine session.

And on that note, I should probably mention the Vineyard’s one lone nudist nook, Moshup Beach. Weirdly, it’s the ‘darker’ half of a real family area. Trust me, though, no hotties hang out  in the buff – you’ll be more likely to run into paunchy old pervs than a young stud who bares it all. Fun fact: Aquinnah was formerly known as ‘Gay Head’. Fun fact #2: The cliffs at Gay Head are made of clay that you can play in. Fun fact #3: I rhymed.


The season officially starts over Memorial Day weekend, but the most shenanigans occur in late July/early August. I prefer the Vineyard in early September when the crazy crowds have died down, the heat isn’t as oppressive and the overly impressed college kids have been sent packing.


MV does have an airport but beware — it’s tiny. You’re going to have to hold on for dear life while your baby plane-let whips around the sky via a connecting flight from Boston. JetBlue is the only carrier with a pretty consistent schedule to MV as of 2011, but driving out to Woods Hole on Cape Cod and taking a ferry over is another, less terrifying option. Fast ferries also run from NYC, Point Judith, RI and New Bedford, Mass.


Tip #1 If you’re looking for some beachy party action in preparation of the night to come, South Beach is your spot. Although you’re more likely to hear reggae than anything electronic a la South Beach in Miami, you’re going to find just as many attractive guys and gals in heat. Volleyball and beer happen here…a lot.

Tip #2 The island bars do their last call at 12:30 and kick you out by 1 (SHOCKING, I know) but, luckily, MV is the home of the afterparty. Make sure you meet some perfect strangers before closing time so you don’t have to go home horny and disappointed.

Tip #3 Rent a house. It’s expensive to stay on MV, so get a huge group together for the weekend and agree to ‘rough it’ by sleeping either a) on top of one another or b) rotating bedrooms so that not all of you are constantly stuck on blow-up mattresses or in sleeping bags.

Tip #4 This is more of an FYI than a tip: there is one — count it — one strictly live-music venue on the entire island. Nectar‘s, which has a sister spot in Burlington, Vermont, is a pain in the ass to get to (it’s out by the airport in the middle of nowhere, and you’ll have to cab it there) but on big concert nights it is the one place you must go if you are in search of the hottest guys. Trust.

Tip #5 MV cab drivers are hot. You’ll see what I mean when you get there.

Here is my last, and most useful piece of advice for you: if you have the will, there is a way. To simplify this statement, what I mean is that if you have a vagina, you will hook up. If you build it (or if you have it) they will come. If you put yourself out there, then you will have one hot summer romance. Thats a promise.

– Laura Schreffler

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13 Responses
  1. Carolyn says:

    Hey girl! This brought back so many awesome memories of our weekend in MV together! If anyone knows what’s up in MV, it’s The Love Trekker!!! I speak from personal experience.

  2. Amy says:

    I am so happy you included the Lampost, you know that was part of our stomping grounds!!! I loved those summers!

  3. Apteka says:

    Thanks for a nice post.

  4. I’m really interested and i also wants to share this with my college students, can I create pdf version for them?

  5. We have some questions. May I ask here or perhaps is it much better I ask on email address? Appreciate your time and energy. Then one more point, it’s difficult to read your site on tablets.

  6. [...] it ain’t, but 2011 can be your summer of love – especially if you’re an avid festival-goer. What better way to spend a sultry summer [...]

  7. [...] it is a LoveTrekker tradition to watch the fireworks from a boat in Edgartown harbor on Martha’s Vineyard, the display there is more of a nostalgia thing for me than an actual appreciation of the fireworks [...]

  8. [...] year for the past 11 years, regardless of where I happen to be living at the time, I have been on Martha’s Vineyard, Mass. for 4th. Not so this year. But while I could have been sitting sadly at home in Santa Monica, [...]

  9. [...] had the great pleasure of spending the past weekend on Martha’s Vineyard with one of my best friends in the world, Katie. We were celebrating her engagement to Brad, the man [...]

  10. Kate Hughes says:

    Wow Love Trekker!
    This Post about MV is so right on, thoughtful, and well written!!

    I spent 3 summers out there. And went back and forth for 2 more summers as I just could never leave the Vineyard once I was there.
    One of my friends was a bartender at Sharky’s. I would religiously wait for her to get out of work and our nightly adventures would begin.
    I love the vineyard while I was a bit Outta Control down there those summers truly shaped me into the woman I have become! And I actually met my fiance out there 2 summers ago while visiting! It is truly a magical place! k*

  11. [...] go to the places I love most in the world. I’d sit on Lucy Vincent beach in the sleepy town of Chilmark on Martha’s Vineyard at dawn. I’d head to Primrose Hill in London and watch the world catch fire at sunset. I’d [...]

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