This past summer, I was fortunate enough to be accepted into a summer writing program on Martha’s Vineyard. As you may already know, this summer was my first summer after graduating from college and I had just received an offer for a big girl writing job. So naturally, it was an insane summer. Every aspect of my life was changing and I grew more as a person than I have in my whole life. I moved to Kansas City, further away from my family and friends and out of the small town that had been my home for the past 4 years of school. I started my first post-graduation job. And I traveled to and stayed in Martha’s Vineyard… Alone.

Traveling alone isn’t really a big deal, I have done it a few times before and actually enjoyed it. What made this trip so different though was that no one was going to be there to meet me when I arrived. No one would be waiting for me at the airport or when I got off the ferry, I didn’t have someone to call to pick me up and take me back to their home. I arrived in this new place with just myself and my bags.

To say my journey was difficult would be a great understatement. I took a car to the airport in KC, flew to Boston, got on a bus in Boston and rode to Woods Hole, hopped on a ferry at Woods Hole to get to Martha’s Vineyard and then walked from the ferry to the house I had a room at. When I say walked, I mean I drug my luggage about a mile along a dirt road till I finally found the house I would be staying at. I was tired from my trip and good God I hate physical activity, but I was in Martha’s Vineyard and nothing else mattered now.

If you don’t know much about Martha’s Vineyard, that’s okay. All you really need to know is that Martha’s Vineyard is probably the preppiest place in the universe. And I don’t say that lightly. MV is a small island off the coast of Massachusetts that can only be reached by boat or plane. It is a summer playground for the rich, boasting famous visitors such as Reese Witherspoon, Jake Gyllenhaal, and the Kennedy family. It is also the birthplace of preppy brand, Vineyard Vines. And true to the brand’s motto, every day should feel as good as a day on MV.

The island itself is laid back and casual. Everyone is riding bikes, walking, or taking Jeep Wranglers to and from places on the island. The shopping is expensive and the seafood is amazing, but it’s a casual place. Everyone was wearing some casual sandal or boat shoe and shift dresses and cargo shorts were everywhere. Right off the bat, it was my kind of place.

The houses on MV were very typical New England homes, besides the gingerbread like houses littered throughout the island. The gingerbread houses were Victorian styled and painted bright, bold colors. They were beautiful and whimsical and someone was always sitting on the porches, waving to you as you passed by. The house I stayed at wasn’t a gingerbread house, but it was still very New England coastal.

Every morning I was up and out of the house around 8 am, and surprisingly so were a ton of other people. Martha’s Vineyard in the morning was a completely different experience than the rest of the trip. The air was crisp and smelled of salt and everything felt fresh. The atmosphere of the island was groggy and while it was still busy, it remained relatively quiet. I visited a different coffee shop every morning (there isn’t a single Starbucks on the island) and would have to say my favorites are The Black Dog or Beetlebung.

In the morning before my poetry classes, I would grab my coffee and a donut or croissant and plant my butt on a bench by the ocean. Sometimes I would walk along the boat docks, but mostly I just sat and watched the world around me. I think having that alone time in the mornings made me fall more in love with the island than I would have if I had been sharing all of my time with someone else.

During the day, I would attend my poetry classes, which always ended around lunch time. For lunch, my newfound poetry friends and I would try out a different restaurant or go on a new Martha’s Vineyard adventure. We had Mexican at Sharky’s Cantina one day and giant pizza slices near the United States oldest carousel the next! One of the absolute best days on the island, we hopped on the bus to the Aquinnah Lighthouse. On the way to the lighthouse we passed over the “Jaws bridge” that everyone is so keen to jump off of (I didn’t jump… I’m a wuss) and literally watched as people cannon balled into the ocean below.

Once we arrived at the Aquinnah Light house we stopped into the only restaurant on the cliffs to have a beer and literally stare at the ocean. A storm was rolling in and it was amazing to see and feel how quickly the weather changed. The sky became instantly dark, the wind picked up, and the temperature dropped at least 10 degrees. Unluckily for us, we hadn’t come to the cliffs to see the light house and leave, we had come to swim.

The day before, during one of our poetry classes, we had gotten word that there was a nude beach on MV and it was the Aquinnah beach. Naturally, being young poets in a new place, we decided to go and experience it for ourselves. With the storm coming and the serious temperature drop, the beach was pretty much deserted. It was below the cliffs which honestly made it windier than I could have ever imagined. We walked along the rocky shoreline for what seemed like forever until we found a spot with a big enough rock that we could get naked behind. We all quickly stripped and ran through the whipping wind to the icy Atlantic. I would love to say I gently stepped into the water but I was bare bummed and freezing so I thrashed my way through the waves until I was deep enough for it to count as skinny dipping.

All three of us stayed there in the water for a little while, our bodies going basically numb. I tried my best to commit the moment to memory, acknowledging the way the ocean felt, looked, and smelled. On the plane ride back home, I used the experience to finish a poem I had been working on for months.

The rest of my MV trip wasn’t as exciting as that, but I enjoyed every single second of it. I was slightly homesick. I’m not the best at being alone, though this trip really helped me overcome that.

I spent one full day totally alone and it was perfect. I took the bus from Oak Bluffs (where I was staying) to Edgartown to do some shopping. I went to the original Vineyard Vines and to my first ever Lilly Pulitzer store (I had only shopped Lilly online up to that point). Needless to say, I spent a ton of money shopping in Edgartown. Being exhausted from all the shopping, I stopped into a local pub near the water to have a lobster roll and a Coke. This was also my first lobster roll and I can’t say it was the best thing I have ever eaten, but it was pretty good. Maybe I’m not cultured enough for lobster yet.

After lunch, I went to a local bookstore and bought a few books for my ferry/bus/plane ride home and ended the day by visiting the Old Whaling Church and imagining Moby Dick (which took place off the shores of Martha’s Vineyard). The whole day made me fall deeper and deeper in love with the island and every single preppy thing it had to offer. The houses were New England quaint (even the huge ones) and the hydrangea blooms were bigger than my whole head. I am not kidding when I say it is everything I have dreamed of, a preppy place where I could finally fit in perfectly.

When I wasn’t going on big adventures on the island, I spent my days having a beer at the beach, enjoying seafood, and walking around Oak Bluffs. When my time in Martha’s Vineyard did eventually come to an end, I was ready to go home, but so sad to leave. I knew there was no guarantee of me ever making it back to MV, so I made sure to take a really good look at it one last time before I boarded the ferry. Hopefully, I will see it again soon. I surely have found a second home in Martha’s Vineyard.

Always Classy & Confused,





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