A Girlfriend Getaway to Martha’s Vineyard

If I was missing the island life after leaving Maui, the sensation didn’t last long. A week after landing back on the East Coast, I was on my way to the new family retreat on Martha’s Vineyard. This was a super exciting weekend for me — I was hosting my two childhood besties Michelle and Kristin there for the first time ever! I couldn’t wait to show them this place that had such a huge part in my childhood,  and now has such a big part of my future.

Our weekend got off to a bumpy start when we almost didn’t land a ferry reservation — and then almost missed the one we managed to nab. Never could I have imagined how much time and mental energy ferry schedules take up in the collective Baackes existence these days. With limited car access on and off the island, some Vineyard regulars book their reservations a year in advance, before even securing a rental house! Now that we’re on and off as often as we are, it won’t be long before the Steamship Authority employees are greeting us by name — especially my mom.

Late Thursday night we finally made it onto the island, greeted by a wall of drizzling rain. We took shelter at Red Cat Kitchen, one of my new favorite Oak Bluffs finds. In spite of the amount of time I’ve spent on Martha’s Vineyard over the years I don’t have much of a pulse on the restaurant scene, as my parents tend to prefer eating at home to eating out. Now that I’m going back as an adult with a full fledged aversion to cooking, I’m enjoying sussing out new favorites around the island.

Friday morning we woke up to beautiful blue skies surrounding The Campground. We grabbed Tucker — who we made an honorary member of our girlfriend getaway, despite the gender issue — and I took the girls for a stroll through Oak Bluffs and down to nearby Inkwell Beach.

Inspired by the unseasonably warm weather, we decided to try to really make a beach day out of it. After loading up the car with all the necessities — when did going to the beach become such a mission? — we trudged all the way to the opposite side of the island to South Beach, only to find it completely abandoned. And for good reason. It was so windy, we sat shivering wrapped in our towels for all of ten minutes before deciding to call it quits.

It wasn’t a total waste of a trip though — we had the biggest laugh of the weekend as we observed Tucker conquer his fear of the clearly-evil, possibly-possessed, washed-up piece of driftwood in the surf. That dog gives me so much joy.

After a lazy afternoon around the house and bopping around Oak Bluffs, we made our way out to uber-charming Edgartown for sundowners at The Shanty. The island was still in that blissful pre-season lull and we had no trouble snapping up parking on the street or seats at the bar — two feats that will be small miracles come August.

And we toasted to a beautiful weekend.

When it got to chilly to sit outside, we sought warmth in Sharky’s Cantina. Now, I’ve occasionally had to defend Sharky’s Cantina’s honor a few times before when skeptical friends wondered how a place that looks suspiciously like a Jaws-themed Margaritaville could possibly be one of my favorite island haunts. But Sharky’s hasn’t won Best of the Vineyard four years in a row for nothin’! This place serves up some mean Mexican, and I’ve never convinced anyone to eat here who didn’t walk out a believer.

Plus, they serve tasty (and strong) cocktails with names like Just When You Thought It Was Safe To Go Back In The Mason Jar.

Now, here’s where things got really wild, guys. We went back to the house, cracked open a bottle of vino, and played Cards Against Humanity. Yup. Pretty much flippin’ things upside down with our wild ways. What can I say? Martha’s Vineyard isn’t really a party town.

Or so I thought. Having polished off the wine, we decided to take a midnight stroll to Circuit Avenue to see if any of the bars were buzzing. And that’s when we found The Lampost (that I’d later find out is nicknamed, crudely but not inaccurately, The Trampost). Walking in, we were ID’d by two large bouncers whose uniforms read “NO DOGS AND NO UNDERAGE.” Good thing Tucker stayed behind to guard the house. And when we climbed the stairs to the attic, we were met with a full on raging Myrtle Beach-style dance party. Not exactly what we expected to find on the quaint island that the president vacations on. But we turned to each other, shrugged, and tore the dance floor up until the lights turned on at 1am.

Saturday afternoon, we were joined by mom and my sister, who was fresh out of her first year of teaching and in need of a serious summer vacation. Though I’m not doing a full blown house update this year (next summer, I swear!) things are very much still in flux and so we spent a good part of the day hauling in furniture my mom brought down from Albany, debating which rugs needed to be returned, and discussing floor sealant. The joys of new old home ownership!

Olivia was having a good time, I swear!

But of course we couldn’t let a day go by without a trip to the beach. We found that State Beach, just a ten minute drive from my house, was the perfect destination. Calm and sheltered from the wind, it was more than hot enough to lounge around in our swim suits, even if we didn’t venture into the water much.

Tucker, however, made big progress! He cracked me up all weekend at the beach — eating sand, playing with seaweed and shells, and digging himself holes when it got too warm. At one point he must have really been overheating, because my water-shy pup went for a full doggy-paddling swim! I had never seen him (willingly) do such a thing before and it cracked me up to watch him very soberly paddling in a small circle before flopping back on the beach with a huge sigh. That dog is nothing if not dramatic.

That evening, I took the girls for the full Up Island experience — journeying out to the Aquinnah cliffs followed by a seafood sunset in Menemsha.

Olivia might kill me, but I just have to show you the below photo. The one above is what we aim for, right? Everyone looking decently cool and collected, and we manage to achieve that probably a full 3% of the time. But let’s face it — real life is mostly the below before shot. Ah, sisters.

lighthouse selfie!

After hemming and hawing about whether or not we should take the late reservation at acclaimed restaurant State Road, which I’m dying to get to someday, we decided to keep it simple with a beach picnic. After rejoicing at rolling into a beach-front parking spot an hour before sunset, we set out for provisions. I’m not sure what obsessing over parking availability is a symptom of, but I certainly don’t think it’s hipness.

Menemsha is famed for its seafood, and while local favorite The Bite closed an hour before sunset (Really, The Bite, really? That seems like a poor business decision…) the girls grabbed lobster rolls at Larsen’s and we spread out with our cooler of wine on the sand.

world’s cutest gas station

Having joined in for the cheer at the final slice of sunlight dipping below the horizon, we made our way back to Oak Bluffs. There, we celebrated suger-free mom’s birthday with a big ol’ heaping of fruit cake, an idea I swiped off Instagram.

But before the rest of us sugar lovers could turn in for the day, we made what was quickly becoming our daily pilgrimage to Circuit Ave for ice cream. As Olivia would say, “An ice cream a day keeps the skinnies away!” Wisdom.

Sunday morning my mom treated us all to breakfast at Biscuits, her favorite local haunt. Though the family and I were staying on for the rest of the week, it was Kristin and Michelle’s last day on the island, and they just couldn’t resist the urge to twin one last time. They claim they didn’t plan any of this.

I can’t tell you how happy this trip made me. While it was incredibly stressful to plan due to both the ferry schedules and the growing pains of my family learning how to share a family house (thank you for the beautiful weekend, mama!), our three days there were so blissfully chilled out. I remember laying on the beach with my favorite dog and my favorite girls on one of my favorite islands and realizing I couldn’t remember the last time I’d been so relaxed. I hope it will become a new tradition for our trio.

After just a week on the island, I was off to Philadelphia for a reunion of another kind. Stay tuned!