I had 3 days in a row off staring into my soul every time I looked at my calendar so I decided that was my sign for another weekend maxing trip. Martha’s Vineyard has been calling to me since a week ago, when I saw a picture of someone eating ice cream there. Also, yes, it is possible to plan this trip a week on advanced.
Day 1- Martha’s Vineyard
This trip started off with no sleep, I arrived in Boston at midnight, picked up my rental and took the 2 hour drive to the steamship parking garage at Palmer Avenue. I don’t know what I was thinking, I ended up falling asleep in the car for 2 hours. At 530am I took the shuttle to the ferry terminal (parking at the terminal is limited and all sources recommend to park offsite). Taking the ferry was pretty straight forward, there are only 2 terminals and at that hour the only way to get to Martha’s Vineyard was to take the ferry into Vineyard Haven.
Since I was arriving at 7am, I decided to have my luggage picked up from the ferry terminal by a local business, Bag and Shag Luggage Service. This was a stroke of genius on my part, it was so nice to not have to worry about dragging my luggage everywhere and it gave me more time to walk around. They were even able to accommodate me after I told them the completely wrong pickup time (7pm instead of 7am…. Whoops).
I started off desperately in need of coffee, so I took a 3 minute walk and ended up at S&S Kitchenette . I loaded up with my usual combo of hot coffee, cold latte and a sweet treat.
S&S Kitchenette
- Hot coffee- no ranking because it was good coffee, the cup was pretty small (probably 6-8 oz) and I didn’t know weather or not I was able to get refills and I was too tired to ask
- Iced Vanilla Latte (half sweetened) (9/10)- perfectly sweet and the coffee flavor was still there
- Lemon loaf (9.5/10)- it had a lot of lemon flavor, the slice was very generous and the frosting was not overly sweet
Edgartown
I decided to take one of the free busses offered by MV to Edgartown- this gave off classic Marthas Vineyard vibes, from small restaurants to cute costal stores there was something for everyone.
The town itself was clean and filled with fresh flowers. I was able to get a walk in and checkout the coast where people were boating and fishing.
After soaking in the views I stopped for another coffee- this time at Toccopuro Coffee. I could tell right off the bat that this was a local favorite, given the number of toccopuro cups I had seen while wandering around. This is a grab and go coffee shop with a specialized coffee menu, they also offer their own coffee brand. One thing I appreciated was the straws offered, they had boba tea straws, as well as a choice of plastic or paper straws. I only had an iced vanilla latte, even though I ordered it half sweet it was still pretty sweet. It had a very strong coffee flavor which is great, but something about it was hard to finish so I ended up discarding it. It was also ready probably 30 seconds after ordering- which always makes me suspicious.
After coffee I hit the shops, along the Main Street and scored a couple cute items.
After shopping I decided to head to Oak Bluffs, the famous site where Jaws was filmed.
Even though my check in time was 4pm, I decided to stop by to see if I could store my backpack while I walked around. To my surprise the room was ready.
Martha’s Vineyard Surfside Hotel
Of note this was a last minute reservation, if I had more time to research I would have stayed in Edgartown but this hotel is centrally located and for the price was a great option for a night on the island. I genuinely believe the value of the hotel far exceeded the cost and I highly recommend it to anyone wanting to stay a night on the island.
My main meal in Oak Bluffs was at Nancys– this was a great place for a seaside lunch and it had a very popular bar. At this point I was near delirium running on 2-3 hours of sleep- so I skipped the alcohol and stuck with Diet Coke and a cheeseburger meal.
Shopping in Oak Bluffs was more tchotchke compared to Edgartown but they had a great Vineyard Vines store.
I finished the day doing the thing that motivated me to book this trip- eating ice cream by the ocean. I stopped by Ben and Bills Chocolate Emporium with every intention of getting candy for my trip back- however my brain was not functioning at that time so I ordered my vanilla ice cream with sprinkles to go. It was fantastic, my main regret is not stopping by more ice cream places but there’s only so much ice cream one can eat.
Day 2- Massachusetts
Staying on Martha’s Vineyard overnight was a top tier decision, I woke up at 530am (unprompted) energized and ready to end my weekend max on a high.
Biscuits (breakfast restaurant- 10/10 this is a repeat for SURE)
I started the morning with breakfast at a local sit down restaurant called Biscuits. It seemed like a very popular restaurant so I wanted to get there as soon as it opened, the place was not packed and I was able to walk in and get a seat. Once I sat down I placed an order for a coffee and the “biscuits breakfast”- the waitress told me they had fresh cinnamon rolls and I am STILL regretting not getting one even if I was going to try a couple bites.
The coffee was perfect, it wasn’t overly roasted or burnt, I’m calling them for the brand of coffee because it was just THAT GOOD. Their namesake, the biscuits breakfast, was a biscuit with gravy, your choice of meat (I went with chicken sausage, for my health) and eggs. It was perfectly seasoned, it was heavy but even though I couldn’t finish it was still the best thing I had all trip (including the ice cream). They even gave me a cup of coffee to take back to my hotel. 10/10.
Shortly after breakfast I decided I was going to try to make the next ferry, which was leaving in 30 minutes. I bypassed the bus and went with Uber to get there on time. Once back the shuttles to the Palmer Avenue parking lot were waiting to take people back to their cars. After paying $50 for 2 days of parking (which honestly is fair because it’s apparently a couple hundred to bring a car to the island) I was on my way.
Plymouth (it’s a town)
I drove 1.5 hours to Plymouth to check out where America started. I stopped by the visitor center, picked up a map and was on my way.
I started with the Mayflower II- it was here I decided to go all in and pick up their Heritage Pass, which was $46 and included entry for the Mayflower exhibit, as well as the Jenney Grist Mill and the Plimoth Patuxet Museum.
The Mayflower II
This exhibit took the least amount of time but it was still fun. You get a chance to board the Mayflower II and see where the pilgrims stayed during their journey to America. If I was a pilgrim I wouldn’t have come here.
Jenney Grist Mill
This was the most fun stop of the 3, but since I own a grain mill I might be biased. The tour took about an hour and walks you through the process of a grain mill, as well as the physics behind how they lifted the corn, directed the water and were able to move the 250 pound stones with minimal effort. After the tour they have a gift shop where you can pick up fresh milled corn and baking mixes as well. Also yes, I got the milled corn. I’m only human.
Plimoth Patuxet Museum
This stop was packed with things to do- honestly I wish I would have started here as it took a lot of mental strength. It included a surprising amount of hiking up hills, getting to talk to members of the Wampanoag tribe, and ended with an immersive experience in a pilgrim settlement, including actors portraying pilgrims. This was highly interactive and it was a lot of fun.
During these experiences I made a couple stops for coffee and snacks.
The Yellow Deli Bakery was a stand out- I ended up getting a sweet cinnamon roll to go, the roll was fresh and there was such a welcoming and warm ambiance it was the perfect rest stop.
Ending the trip I headed to my hotel in Hull, a small town chosen for its close proximity to the airport. If I had to do this again I would have stayed closer to the Boston airport and returned my car early. I stayed at a small bed and breakfast that was cute, but simple. The highlight would definitely be my visit to Doctors Island Brewing Company. They have a couple of their own brews on tap, and some simple bar foods as well.
The evening ended at my hotel and just like that this fever dream of a trip was over. The next day I was back at the Boston Logan Airport, then back to realty. Overall this was a trip I would highly recommend, either for solo travelers or families looking to get away.
Limitless wanderer 
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