I know I travel a lot, and that it often looks like all I do while on the road is vacation—bear in mind, I’m my own best marketer, producer of a well-curated highlights reel of my own life—but the majority of trips I take are typically work-related. So it was doubly nice being on pure uninterrupted vacation in Massachusetts last month: going somewhere not on an assignment or campaign, staying in a friend’s house that I neither had to review or do a site inspection of, logging off my laptop for the majority of the trip, no meetings on the docket, just girl time and the opportunity kick up my feet and relax.
Which could be precisely why Martha’s Vineyard was one of my favorite vacations I’ve taken in years. Make that ever.
While I’d been fortunate enough to visit for a quick day back in 2011, I didn’t really have enough time to get a feel or context for the Vineyard prior to this trip. Alex told me I would love it, and given that we share a disposition for Zumba, diving, inversions, and pretty much anything precarious, active or downright insane, I figured she knew me well enough to suss out my destination preferences, too.
She was absolutely spot on.
Truth be told, a dedicated New England summer vacation had simply never occurred to me when plotting out adventures in the past. Even during the stint I lived in New York, I was jetting off every chance I could get: to California to see my long-distance beau (now husband), to Florida for summer trips with my family, to Tennessee for 500 weddings a year, to Europe for assignments whenever I could get them.
My Vineyard vacation made me realize that, in a sense, I wasted those years living in New York by always trying to, well, get out of New York.
For as long as I’ve traveled, I’ve been more of the bikini-on-the-beach, stay-immersed-in-the-water kind of traveler. I like cities, sure, but what I really want is warm weather, a drink in my hand, the ability to lay out for eight hours at a time (with the help of SPF 30, of course).
Martha’s Vineyard is not necessarily that place—OK, other than the whole drink-in-hand part of the equation (we did plenty of that).
While Alex tells me there are stretches in the summer when it’s warm enough to tip-toe in, other than few hours when the sun came out on the Saturday of our long weekend on the Vineyard, it was barely warm enough to remove our cardigans.
And you know what? That was actually fine by me. After the stifling 100+ degree heat we’ve had in Tennessee all summer, the brisk Massachusetts air felt refreshing, welcoming even.
But, more importantly, I know you’re wanting to know what all we ate and drank, right? Do I know you guys or what?
Alex has a much more comprehensive guide to Martha’s Vineyard on her site, but here are some of my favorites as a total newbie:
Eat + Drink
Slice of Life. This quaint cafe on Circuit Avenue was our first stop on the Vineyard after arriving on Friday afternoon. Our stomachs rumbling, Slice of Life was the perfect lunch spot with plenty of seating, quick and friendly service, and a bevy of sandwich, salad and soup options (a turkey Reuben and truffle fries for me, please).
Art Cliff Diner. This elevated diner concept is one of the island’s most popular spots. As such, we didn’t even try to go on a weekend—Alex says the lines are long and undesirable—and saved it for a Monday morning instead. It’s got all your typical diner dishes, like heavy egg combos, omelets and hashes, in addition to fancier fare like crepes, but I opted for the peanut butter, fluff and banana panini and was not regretting my decision one bit.
State Road. This is one of her go-to spots on the island and she said she just knew we’d love it, too. And indeed we did. This farm-to-table West Tisbury joint combined a big-city restaurant experience with the charm of a bucolic setting right smack in the middle of the island.
The Red Cat Kitchen. The Red Cat Kitchen was the only dinner we ate out; the other two we dined in at our gingerbread house. The restaurant describes itself as whipping up “soulful cuisine,” and the menu is peppered with surf and turf options such as pork rib chop, pan-roasted halibut and “big-ass scallops.” I had a fried chicken meal that was excellent, but truth be told, we didn’t have the best service experience. Alex had made a reservation, but when we arrived, we were seated on the porch, where it was so so hot out there, despite the 50 degrees outside, that we all about melted and were downright miserable for part of it. We waited to get moved inside, but it never happened. But if you can nab an indoor table, you’re in for a treat.
Sharky’s Cantina. Sharky’s is not where you settle in for a fancy meal, it’s where you go for margaritas the size of your head and to indulge your Mexican whims. While it’s no fine-dining and it’s a tad pricey for what it is, it’s also super fun and a must-experience for any first-timers to the Vineyard.
We did not have enough time—or stomach space—to try the following restaurants, which were all on the short list, as well: 20byNine, Biscuits, Atria Cellar, Porto Pizza, Smoke n’ Bones, Down Island and Back Door Donuts (the line was insane!). Other than a late night at the Lampost, we also got a bit lazy when it came to heading out for cocktails—plus, Alex came armed and ready with a full case of wine—so we didn’t make it to Port Hunter, Beetlebung or The Shanty, which were all on our initial itinerary, too.
Other things I did not try: lobster ice cream. I’ll leave it at that.
Oak Bluffs. We made our base in Alex’s mom’s house in the charming 300-home Campground of Oak Bluffs, and I loved the walkability of the entire town; there are so many places to eat and shop that we simply couldn’t squeeze them all into three days. This would be my first choice for a place to stay if given the option. Bonus: The main car ferry arrives in and departs from the heart of downtown.
Edgartown. There’s no better way to describe Edgartown than “Instagrammable from every angle.” Following the Campground of Oak Bluffs, it is, without a doubt, the (second) cutest part of the Vineyard. And don’t even get me started with the shopping–let’s just say, I came home with two new dresses and a trio of necklaces (and nothing cost me more than $100 either, shockingly).
Vineyard Haven. Vineyard Haven is the next sizable town over from Oak Bluffs, and we went there to do a little retail therapy, see a movie and get our workout on at the gym. It’s definitely worth a couple hours of exploration, whether you’re staying nearby or not (there’s also another ferry option that arrives and departs from there).
Summercamp Hotel. If you aren’t fortunate enough to nab one of the six weeks a year that Kathryn rents out her gingerbread cottage, then I’d highly suggest checking out the whimsical Summercamp right in the heart of Oak Bluffs. We swung by to see some of Alex’s friends who happened to be on the Vineyard at the same time we were, and I wanted to move into this bright-and-airy themed hotel.
Due to the weather, the “do” portion of our itinerary was constantly in flux. We couldn’t really go to the beach because of the rain. We opted not to ride bikes around East Chop due to the irritable skies. It was too foggy to see the Aquinnah Cliffs. We missed our Cape Poge Lighthouse tour because they had the wrong time listed on their site.
But the weather and change of plans didn’t matter one bit. We still had a blast.
What we did do was a little fitness—Zumba at the Mansion House and yoga at Yoga Barn were both great fun—a Jane Austen movie complete with an emcee at the charming MV Film Center, a bit of shopping—check out Alley’s General Store in West Tisbury, Portobello Road in Edgartown and basically every boutique in Vineyard Haven—and a tad bit of eating. OK, A LOT of eating.
You could also check out the Not Your Sugar Mamas Chocolate Factory. While we didn’t actually take the tour, I did stock up on plenty of their raw chocolate bars to bring home with me. I’m also a bit sad I didn’t head over to Bad Martha’s Brewery, which will be the first stop I make upon my return.