My first visit to Martha’s Vineyard was on a day trip from Rhode Island in 2011. My mom was obsessed with the idea of channeling her inner Kennedy, and SVV, my dad, two of their friends and I were all along for the ride.

We took a very rocky passenger ferry over from Providence, and I spent the duration of it paying homage to the porcelain gods (tempestuous seas and my sensitive stomach have never been agreeable companions). It was not the best way to start off the day. Still, we had gloriously sunny weather and I immediately became enamored with the small Massachusetts island, which we toured for the day by bus.

It was charming, it was picturesque, it was not anywhere in a million years I ever thought I’d get the opportunity to visit on an overnight vacation.

Enter: Alex in Wanderland.

It turns out my long-time pal’s mom Kathryn owns a gorgeous Vineyard house right in the center of the Campground at Oak Bluffs, which she lives in part of the year and rents out for six weeks each summer. She was kind enough to let Alex, Angie and me to invade her lovely home for a long weekend—a long weekend that would prove to be not nearly enough time to do all the eating and drinking and seeing we hoped to accomplish.

This time we were already in Massachusetts, however, and the drive out to the ferry spot from Boston, where we’d stayed the night before, was an easy 90 minutes by car.

The first thing you should know about planning a trip to Martha’s Vineyard is that you need to book your ferry quite far out if bringing a car, particularly in the summer months. Friends who have tried to plan similar trips lately were unable to do it because they couldn’t nab a spot on the coveted car ferry. If memory serves me correctly, Kathryn made our June reservation back in March.

The car ferry departs from Woods Hole and was very speedy and smooth, the opposite of our experience traveling over from Rhode Island. We had just enough time to go up top, order a Coke and check out the entry into Oak Bluffs before it was time to climb back into our cars and pull out of the ferry terminal.

The second thing you need to know about planning a trip to Martha’s Vineyard is that many places are cash-only. So if you’re a credit card-heavy traveler like me, stock up on cash at your preferred ATM before you arrive on the island, or else get it in Oak Bluffs before you start your trip. You’ll be glad you took my advice, trust me, as oftentimes the three of us were emptying our wallets trying to scrape up enough bills to pay for our meals.

Alex’s family’s home is located right smack in the historic Martha’s Vineyard Campmeeting Association (MVCMA, aka “the Campground”), just minutes from downtown Oak Bluffs. The tight streets aren’t ideal for driving, so most residents get around by foot. They also all know one another, having been neighbors for years, often decades, and are extremely welcoming of tourists like myself.

You can now book a stay in this Martha’s Vineyard cottage, too

From the moment we pulled up to the 1870 masterpiece, I was bowled over by its beauty. Alex’s mom and her boyfriend had spent the past couple years restoring this old lady to her rightful state; as someone who also is in the midst of renovating a 19th century home, I can doubly appreciate the time and care—and, OK, money—that such a project entails.

Every single room had such character, many remnants of historic memorabilia and so many perfect vignettes that Kathryn pieced together in the most Pinterest-worthy cottage I’ve ever had the pleasure of staying in.

Being plagued with Peter Pan Syndrome—and the fact that I never had twin beds growing up—I immediately claimed what I like to think of as the “kids’ room.” Angie, our matriarch, took the master bedroom while Alex took the remaining queen bed on the other side of my quarters.

It was basically like being at summer camp for a weekend, only my cabin mates weren’t strangers and we were in the Four Seasons of accommodations.

Which brings me to third thing you need to know about planning a trip to Martha’s Vineyard will not come as any surprise now: Skip the idea of a hotel or B&B; you should definitely stay in one of the 300 homes in the Campground of Oak Bluffs, many of which are rented for part of the high season.

Updated in November 2020: Kathryn passed away in 2019 after a 15-month battle with brain cancer. Alex and her sister have resumed care of the house. If you’d consider booking your stay on Martha’s Vineyard with them, you’ll enable them to cover the cost of upkeep for such a special property that meant so much to their mom.

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