It has officially been three months since my Martha’s Vineyard trip, two months since my Boston Travel Diary was posted, and one month since I created the draft of this blog post. In other words, it’s time for this blog to go live and it’s time that I post more often. After almost a year of blogging, I’m still struggling with balancing adult life and blogging so much so that I’ve decided that one of my next pieces will be about my blogging struggles. Let’s save that for another time and focus on Martha’s Vineyard.
As many of you know, my boyfriend and I took our first big trip together to Boston and Martha’s Vineyard about three months ago and we had an absolute blast. We had such a great time that we just booked our third big trip together to New York City in about two and a half months (let’s hope I have a blog post up before then). If you want to learn about how we spent our day in Boston, you can read all about it in the blog post Travel Diaries: Boston. This post is solely about Martha’s Vineyard and the adventures that one can embark on!

We started our day in Boston (EARLY – around 6am, Dunkin was necessary to wake us up). We packed up our things, got ready, and got on the road to catch one of the early ferries over to the Vineyard. The drive from Boston to Martha’s Vineyard is around 2 hours without traffic, which makes MV a perfect location for a day trip. Martha’s Vineyard is also small enough that you are able to easily do it in one day.
Before we even got to the Vineyard, we made sure to find a spot for coffee to get our second caffeine fix of the day. We found some thanks to the Steamship Authority cafe. The ferry ride was about 45 minutes and our first stop was Oak Bluffs. OB is a very small, very quaint part of the Vineyard. The town is FULL of cute houses with the most unique architecture and color schemes. For me, the best part of Oak Bluffs was the stores. Our first stop was the Black Dog, where my boyfriend treated himself to such a nice long sleeve shirt (I saved my money for our next stop).
Our next stop was none other than the ORIGINAL Vineyard Vines. To say I was excited to go in would be an understatement. Y’all know I have a minor shopping problem so going into one of my favorite stores was a risky move. I was able to control myself because I wanted to see what else the Vineyard had to offer. I was able to walk out of Vineyard Vines with only a new hat (which is so good for me). And the hat was perfect because it was a very windy day on the Vineyard.
We hit the beach before heading to quintessential Martha’s Vineyard, Edgartown. The beach along the coast of Oak Bluffs was quiet, calm, and peaceful. Despite all that Oak Bluffs had to offer, I was ready to begin our trek to the other side of the island. The first stop we made once we got to Edgartown was FOOD! We ate lunch at the Seafood Shanty, it was right on the water and the perfect place for our midday break.
By this time, our day had quickly gotten away from us, our bodies were starting to realize how tired we were, and we had to start thinking about heading back to the mainland to begin our journey home. BUT we weren’t letting that stop us from getting one last stop in. Our last stop on our Martha’s Vineyard tour was a BEAUTIFUL lighthouse. This lighthouse was obviously a tourist trap but, honestly, I was not complaining whatsoever because it was stunning.
The lighthouse was a little bit off the beaten path. The lighthouse was right in front of a beautiful inn, that must be fancy because as we had our picture taken a Senator (I couldn’t tell you who but my political science loving boyfriend geeked out over it – it was so cute) walked out of the doors to get into his car. After we stopped being “starstruck” we headed down the dirt path to see the lighthouse up close.
The closer we got to the lighthouse, the more my preppy heart started to soar. It was smaller than I thought, but the perfect size for the quaint nature of Martha’s Vineyard.
The base of the lighthouse was a compass, as I think most lighthouse bases are (not entirely sure because this was my first lighthouse visit). I was drawn to the East point of the lighthouse compass as the point was marked with a simple “E” and I have an affinity for “E’s”.
We finished ooo-ing and awe-ing and headed down to the beach to take a “dip”, more like dip our toes in the water because it was still a little too chilly to get all the way in; which is why white denim shorts and a lightweight sweater was PERFECT for an early summer day at the Vineyard. We said our goodbyes to the Vineyard to headed back past the most adorable Edgartown cottages and onto the ferry.
It was hard to stop myself from taking pictures of all the cottages we passed because I fell in love with each and every one of them. Here are a few of my favorites that we found!
Our next stops were pretty boring compared to the rest of our trip: 45-minute ferry ride back to mainland Massachusetts, gas station to fill up and get snacks, and then 9-hour drive back home to reality.
My weekend in New England was absolutely incredible and I’m already trying to find an excuse to go back and visit SOON!
Until Next Time,
Emily Jane