From Cobblestone to Coastlines: A Trip Through the Streets of Boston and the Vineyard Breeze
- Chelsea Little
- Jul 19
- 7 min read
Sometimes, a tad bit of exploring mixed with a little bit of seaside wind is exactly what you need in a trip. That’s exactly why I headed to Boston and Martha’s Vineyard for a blend of history, harbor breeze, and an open agenda of wandering the city. From walking the cobblestone streets of Boston’s downtown area to enjoying a 13-mile bike ride across Oak Bluff, I enjoyed every moment of serenity in yet another beautiful city in the United States. If you ever thought about visiting the area, YES, I would recommend it!
My trip to Boston was in August, so the weather was really nice! For this particular trip, I flew with American Airlines, and upon landing, I headed straight to the hotel. I used public transportation a lot for this trip, which was a little different for me, but I learned the ins and outs rather quickly, and it was super cost-efficient. Because at the time, one of the major highways was under construction, the Metro bus was providing free rides to downtown from the airport.
Day 1
I stayed at the Harborside Inn in Downtown Boston, which was central to everything, so a perfect choice. Once I had checked in and dropped off my bags, I was off to explore the city. I started at The Well Coffee House, grabbing something cold to drink. (btw, the weather was perfect-to-warm the entire trip.) I can’t remember the name of the drink I got, but it was one of their summer specials. Blueberry flavored for sure, because that’s always a favorite of mine :). I'm pretty sure it was a blueberry lemonade.
Once I left there, I headed to the African American Museum, which is a registered National Historic Landmark. I did not reserve a ticket online, but you do have that as an option! The price was about $15. I try to visit at least one museum or other national landmark when traveling because how else will you learn about the history of the city?! The museum is located centrally in downtown Beacon Hill.
Fun fact: The African Meeting House is actually the oldest surviving African American Church in the US. They also have a walking trail, the Black Heritage Trail, that gives an account of the African American community in the 19th century.
From there, I headed for a bite to eat! I decided on Luke’s Lobster. Of course, I had the Lobster Roll and Cape Cod Kettle Chips. ( I always love lobster rolls, but my only issue is why are they so small?!)
Because I was already in the downtown area, I decided to just continue walking around to see what was in the area. I did some shopping on the strip, where you can find both chain stores as well as some small businesses.
I ended up walking further and found myself at Quincy Market and Faneuil Hall Market. There were more shops and live music in the courtyard.
Fun fact: Samuel Adams is an original Boston Beer Company brewery. There is a Samuel Adams statue outside Faneuil Hall where he gave his famous speeches on American Independence.
Inside the market, I stopped and sampled some of the food items being sold, but I decided on a cup of Famous Boston Chowder from Boston Chowda! This New England Clam Chowder was “Voted Boston’s Best”, and I can attest to it being very tasty! I’m never afraid to try a city favorite! In my opinion, it is one of the best parts of any trip.
Day 2
The next morning was my day trip to Martha’s Vineyard, and it was a very long day. I booked this trip through Viator, and the cost was $119. This included transportation from the city and the ferry cost. The total trip was scheduled to be about 12 hours, with 6 hours of free time on the island. In my opinion, this is the perfect option if it’s your first trip, you traveled alone, or you choose not to rent a car on your trip. We were picked up between 6am and 7am from our hotels in Downtown Boston. We traveled through Falmouth before arriving at Island Queen to catch the ferry. The Ferry ride was nice and peaceful as we rode into Oak Bluffs. There was an option to purchase an add-on for a 3-hour tour, but I chose to opt out and explore the island for myself!
First things first, I started with breakfast at one of the most recommended spots in Oak Bluffs called Biscuits. I ordered the “Number 2,” which was pretty light and hearty. The food was so fresh and tasted really good. (side note* 'home' fries were really potatoes :)
After breakfast, I went to rent a bike to travel across the island. This was the best idea. Traveling 5 miles across the island along the water was peaceful and serene, making it easy to reach Edgartown. I stopped several times to put my feet into the water and rest along the sand. There were also people out swimming nearby.
Fun Fact: Oak Bluffs is one of the six towns on Martha’s Vineyard and is known for being a place for the African-American elite, but there is a history of segregation and classism throughout Martha’s Vineyard. Most of the racism took place behind closed doors and wasn’t typically displayed publicly. More recently, it has been called “The Black Hamptons” due to its growing popularity among upper-class African Americans. Oak Bluffs was once one of the only vacation destinations where Black families could buy property and gather freely.
The most beautiful part of the island was seeing the colorful “Gingerbread” cottages and the famous lighthouse.
After plenty of sightseeing and a lot of bike-riding, I stopped for lunch at Martha’s Vineyard Chowder. The service was great, and I settled for another lobster Roll (I’m in the North, what else would I have?! lol)
The day was long, and I continued to venture on the island until it was time to meet the group for the boat ride back to the other side.
Once we returned, I headed to the hotel to shower and change clothes. I headed back out to grab some dinner. I headed to the Rooftop at the Envoy. It was such a beautiful night out to be on a rooftop. I believe there was a party happening, but I just enjoyed my solo area.
I ended the night with a movie on the lawn, which I just happened to stumble across. This ended the perfect summer night!
Day 3
My last day in Boston was very eventful! I slept in a little, then got dressed for my last day in the city. I couldn’t leave Boston without visiting the famous Acorn Street in Beacon Hill. It is one of the most photographed streets in the US! The cobblestone lane and the 19th-Century Row Homes show off a classic New England scene. It's beautiful and definitely makes you feel as if you are in an old movie!
Leaving Acorn Street, I walked through Boston Public, which is right next to the Boston Common. It’s actually the first botanical garden in the US. This is the perfect place for a slow stroll and a peaceful break from the city. There are swan boats available to take a ride across the lagoon.
I travelled from there to Parish Café in Back Bay for brunch. From the long line waiting, I could tell it was going to be great! Each sandwich is named after the chef who created it, among some of Boston’s famous chefs. I honestly don't remember what I ordered, but it was delicious and filling!
From there, I walked to the Boston Public Library, central. This library was the first US Library to let people borrow books and take them home, hence its “Free to All” motto. The library was so beautiful, and Bates Hall is even better in person than in the pictures. I loved that they have a large room for the teenagers full of games and activities for any teen!
I decided to head to Newberry Street for some shopping! On the way, I passed through a street market full of vendors and got a nice, freshly squeezed lemonade!
Some people refer to Newberry Street as “Rodeo Drive of the East,” because it's full of cute boutiques, picturesque cafes, and beautiful brownstones. They had some high-end designers mixed in with some small street vendors and businesses.
Fun fact: The street was once underwater, which was then filled in during an expansion project!
Walking through Boston Common, I then headed to South Station to get to the other side of town. I took the subway and headed to Cambridge for a trip to Harvard! ( I went to “Harvard of the Midwest,” so of course I had to visit the original Harvard, IYKYK :) I walked around the campus, went into the bookstore, and grabbed a souvenir!
Once my time was up, I headed back to the other side of town to grab my suitcase and head to the airport. I enjoyed lunch at the Black Rose Café, an Irish pub located near the hotel, and then left for the airport, where my flight was delayed. And delayed again. But that's another story!
Overall, my trip to Boston was amazing! I loved everything about the city. Being able to see so much history in one trip is always amazing. Enjoying such beautiful weather, nice people, and such scenic views was such a breath of fresh air! I can’t wait to get back up Northeast to see more beautiful cities! From walking on the cobblestone streets to stumbling upon movie nights on the lawn, every moment felt like both a charm and an adventure. With a mix of history and modern energy, the city felt timeless and innovative!
I’ll see you soon, Boston!
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