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My Day Spent on Martha's Vineyard

Josie Cataldo | 8/19/2022

Recently, I ventured to the island of Martha's Vineyard for the first time! With only an afternoon to explore this enchanting New England oasis, I had to move quickly to capture as much content as I could. Keep reading to discover some of the highlights of my trip as a Cape Cod girl exploring the Vineyard!

Arriving in Oak Bluffs

After an hour ferry ride from Hyannis, I hopped off the boat in Oak Bluffs and was immediately in awe of the beauty, character, and sense of community. It almost reminded me a little bit of Provincetown with its fishing village feel. Along the sidewalk I saw workers scurrying about trying to complete their opening tasks at various lunch and dinner restaurants. The smell of freshly brewed coffee and buttery baked goods wafted out onto the boardwalk and awoke me from my ferry-induced fog. I walked along the water's edge, explored the trinket shops filled floor-to-ceiling with Martha's Vineyard memorabilia, and photographed the sun-soaked marina before visiting property 27072 to shoot some drone content.

Sheriff's Meadow

Upon arriving at the home of one of our WeNeedaVacation homeowners, I was blown away by the enchantment of his property. Situated on a beautiful dead-end street shaded by lush trees and lined with vibrant rose and hydrangea bushes, the tranquility I felt as I arrived at PID 27072 was undeniable. The backyard features a lightly-tread pathway under a welcoming arch of shade. As I took my first few steps down the trail, I could tell I was nearing closer to the water. The temperature dropped slightly and I could hear the sounds of birds chirping and leaves rustling in the wind. Before I knew it, I was brought to a lookout spot with the most breathtaking view of Sheriff's Meadow. While I knew that PID 27072 overlooked the sanctuary, I wasn't expecting the serenity that I saw before me. As a Cape Cod girl who's used to the roaring waves on the oceanside, the flat calm and crystal clear water was a nice change of pace. After our drone photographer was finished and I photographed Sheriff's Meadow, it was time to say goodbye and explore downtown Edgartown, specifically, Edgartown Harbor Light.


The hydrangea lined streets of Edgartown were bursting with color from pastel pink to royal blue. White clapboard houses adorned with American Flags and nautical door knockers sat side-by-side, taunting passers-by with their picturesque beauty. Antique cars in pristine condition sat in brick driveways, their wood detailing and wind-up windows transporting me back in time. Secret gardens bountiful with lavender, roses, and daisies seemed to be strategically placed in front of sweeping views of the shimmering waterfront. Everywhere I looked, there was a different view to take in, a different perspective to photograph. By the end of my walk along the main streets of Edgartown, my neck was cramping from constantly swiveling my head in an attempt to visually soak up every ounce of beauty.

Edgartown Light

I arrived at Edgartown Harbor Light slightly sweaty, sun-kissed, and sore, but the moment I maneuvered my way through the pathway of overgrown beach grass, I immediately knew the journey had been worth it. While I had seen photos of Edgartown Light, being able to witness its beauty in person was entirely different. Perched at the top of the pathway leading to the lighthouse were numerous painters trying to capture the essence of the landscape, taking time to visually soak in the landscape before putting paintbrush to paper. Every natural detail of the lighthouse and its surroundings is a work-of-art itself. To my right there were dilapidated wooden docks, sailboats breezing by in the wind, and beach-goers sitting by the water’s -edge with their latest beach read. To my left, there was a long stretch of dune grass that ended at the vast ocean's edge. Edgartown Light is an iconic landmark on the Vineyard as it signifies the entrance to Edgartown Harbor and Katama Bay. It's like a sign letting you know you've made it to paradise. I was so glad I was finally able to admire it in person.

Before heading to our next location for content, we stopped at The Seafood Shanty to refuel. Located right on Edgartown Harbor with an outdoor deck, the interior of this seafood restaurant is beautifully bright with natural sunlight streaming in through the seaward-facing windows. The Seafood Shanty is definitely a must if you're looking to enjoy a delicious lunch with a spectacular view. After quickly devouring a blackened Mahi sandwich and taking some much-needed time to hydrate and rest my legs, it was time to head to the destination I'd been waiting to see all day...the Aquinnah Cliffs.

Aquinnah Cliffs

The cliffs of Aquinnah are otherworldly. Rarely am I made speechless by the beauty of a natural landscape after growing up on a place as breathtaking as Cape Cod, but in this case I was. I no longer felt like I was on the island of Martha’s Vineyard, but on the Amalfi Coast, getting ready to cliff jump into the shimmering Tyrrhenian Sea. There will be times on social media where I scout out certain travel destinations to add to my bucket list, but it wasn't until the moment I stepped to the cliff's edge that I realized this was a place on my list. I didn't realize the destination I was pining after was on Martha's Vineyard! The ethereal beauty of the Aquinnah Cliffs is intoxicating. It makes you breathless, giddy, and sentimental all at the same time. I wish I could've stayed for hours because I've been told the sunsets are spectacular. As if the cliffs weren't already the highlight of my day, I looked behind me to see a red-brick lighthouse sitting on the lush green grass. Gay Head Lighthouse occupies one of the most stunning views not only on Martha's Vineyard, but in all of New England. It also happens to be the backdrop for many entertaining events hosted on the island.

My afternoon on the Island of Martha's Vineyard ended with a trip to South Beach, and let me just say that it did not make my leaving the Vineyard any easier. With wispy waves crashing against the shore and sand so soft it makes for the perfect pillow, South Beach is definitely where I'll be going to soak up sun on my next trip back.

My very first trip to Martha's Vineyard absolutely blew any initial expectations I had out of the water. Living on the Outer Cape, it can be kind of tough to find motivation to explore other areas, but wow am I glad I did. I can safely say that my first trip to Martha's Vineyard will definitely not be my last. I left a piece of my Cape and Islands loving heart there.