A Perfect Day On Martha’s Vineyard

Martha’s Vineyard had been on my bucket list for a while- and let me just say, this island did not disappoint. But our day started with a curveball. Or maybe two.

We were trying to catch the Steamship Authority ferry from Woods Hole at 12:00pm, which costs $9.50 per adult each way (totaling $19 round-trip). Sounds easy, right? Well… it would’ve been, if we hadn’t underestimated one thing: the parking situation.

We got there about 20 minutes before the 12:00pm ferry, feeling all relaxed and ahead of the game- until we realized there’s no ferry terminal parking at Woods Hole. Instead, we had to park almost 5 miles away at the Palmer Avenue lot and take a shuttle back to the terminal.

Between parking, waiting for the shuttle, and still needing to grab tickets, there was no way we’d make the 12:00 ferry. It felt like it took forever to park, and the 12:00pm ferry had definitely departed without us, so we booked the 1:15 PM ferry instead.

Pre-Ferry Food Stop: Coffee Obsession

With time to spare, we walked around Woods Hole a bit and stumbled into Coffee Obsession, and I cannot recommend this place enough. I ordered the BLT with turkey and avocado, and it was so good—crispy bacon, fresh avocado, and thick bread that held everything together.

To drink, I got their Leprechaun Matcha, which was a creamy, slightly sweet matcha with hints of mint that gave it a unique twist. If you're ever in Woods Hole waiting for a ferry, definitely pop in here. They’re also super fast, so if you’re trying to get a quick bite before the ferry, this is your place.

All Aboard: The Ferry Experience

We finally boarded the 1:15 ferry, and even though the line looked long, boarding was quick and smooth. We went upstairs and found the perfect spot by a window, complete with our own little couch and table setup. We were able to sip on our drinks while enjoying the gorgeous view.

The ferry ride lasted about 45 minutes, and it was beautiful. Some moments we were so close to shore that you could see homes tucked into the coastline, while other times it looked like we were surrounded by nothing but ocean. The contrast was surreal. I was like a little kid in a candy store looking out that window.

Surprise #2: The Bus Ride

When we arrived in Martha’s Vineyard, we were surrounded by quaint shops and restaurants, but we had our eyes set on Edgartown, a charming historic town on the eastern side of the island. We hopped on one of the Vineyard Transit Authority (VTA) buses and thought we were all set—until I rang the bell and the driver dropped us off… in the middle of nowhere.

Apparently, the VTA doesn't work like most public buses. Instead of dropping you at the next scheduled stop when you ring the bell, they might let you off wherever you're standing, even if that’s on the side of a random road. Definitely a learning moment!

Luckily, we were only an 11-minute walk from Cozy Corner Café, our next stop.

Cozy Corner Café: A Hidden Gem in Edgartown

This café was everything. We got:

• The "Tall, Dark & Handsome" smoothie – made with coffee, cocoa nibs, and blackberries. Super unique and genuinely delicious. It gave me a huge energy boost for the day.

• An acai bowl topped with whipped coconut, peanut butter, and Nutella – this was creamy and flavorful with the perfect texture. Even my boyfriend, who isn’t normally into fruity or “healthy” things, loved it.

• Angelica’s croissant – buttery, flaky, and perfectly stuffed.

• A coffee with mushroom adaptogens- earthy, smooth, and packed with the good stuff. Sounds so different than I’d normally enjoy, but it was great!

Oh- and they even have a massage chair you can sit in while you wait for your food. This spot was chill, welcoming, and honestly one of the best breakfast finds we’ve had.

Exploring Edgartown

Edgartown feels like it’s straight out of a movie. Picture white picket fences, historic churches, and adorable boutiques on every corner. We wandered down by the harbor, explored little alleyways lined with shops, and soaked up the breezy coastal vibes.

I picked up my signature souvenir shot glass—this one had a tiny lobster inside, so obviously it had to come home with me. I also got a postcard (one of our favorite travel rituals) and we stopped for a drink at a waterfront restaurant.

But then came Surprise #3.

Aquinnah Cliffs: Windy, Empty, and Stunning

We wanted to visit the Aquinnah Cliffs, but the bus driver told us his route didn’t go there. Odd, since Google Maps said it did. I walked back to ask again—and just as I approached, the driver pulled away.

The next bus wouldn’t come for another hour, and the trip would take over an hour anyway, so we called an Uber. I did not realize that Martha’s Vineyard is a LOT bigger than I thought. That drive was over 40 minutes long. I truly thought this was the kind of island you could bike around in an hour but I was clearly wrong.

Still, the journey was worth it.

When we arrived, everything was closed and the wind was intense. But wow- the view. The cliffs to the right were layered in beautiful earth tones, literally glowing in the sun. Straight ahead, nothing but endless ocean. It felt so untouched and peaceful. It made it even cooler that we were the only ones there for quite some time.

Back to Oak Bluffs: The Gingerbread Houses

We caught the bus back to Oak Bluffs, and finally got to see the iconic gingerbread houses—and let me tell you, they are even more magical than photos make them look. I expected maybe three houses, but theres actually an entire neighborhood of pastel-colored, fairy-tale cottages.

Each house had its own personality. The first one we saw was surrounded by tulips, looking like it belonged in a storybook. Walking through the area felt like stepping into a little dream world.

Dinner at Dos Mas

Right next to the cottages, we found Dos Mas, a cozy little Mexican spot where we ordered the chimichanga and Mexican pizza. Both were delicious, but that chimichanga hit the spot after a long, chilly day. Warm, crispy, and flavorful—it was exactly what I needed.

The Ferry Back & a Spontaneous Detour

We caught the 8:30 PM ferry back to Woods Hole, and this time, the ride was noticeably more rocky. Once back on the mainland, we made the drive back to Boston, but the night wasn’t over yet.

We ended up at the Encore Boston Harbor casino, where I didn’t gamble but I did enjoy some Shake Shack (always a win). And then came our most unexpected decision yet…

Instead of spending the next day in Boston, we had a spontaneous idea—to catch the earliest flight out to a destination I had never been to the next morning. No plan + no sleep = an amazing trip.

✈️ Want to know where we flew off to next? Stay tuned—my next blog post is going to take you somewhere different... and it was one of the best surprises of the trip!

Other Things to Do in Martha’s Vineyard

If you're planning your own Vineyard adventure, here are a few more ideas worth adding to your list:

• Rent bikes and explore the island on two wheels (just be prepared—it’s bigger than it looks!).

• Visit the East Chop Lighthouse for some of the best sunset views.

• Walk through Mytoi Japanese Garden on Chappaquiddick Island.

• Stop by Back Door Donuts in Oak Bluffs for some of the best donuts (yes, it’s literally a back door).

• Relax at South Beach in Edgartown if you’re visiting in the warmer months.

Martha’s Vineyard is equal parts charming, quirky, and full of surprises, and even though we hit a few snags along the way, it was still an extremely memorable day of our Massachusetts trip. I can't wait to go back (hopefully when it's a bit warmer next time!).

Let me know if you’ve been, or if you have any questions for planning your own trip!