This summer, I embarked on an American road trip across the East Coast which included 48 hours in Boston, Massachusetts.
Starting in New York City, then heading to The Hamptons, Providence, Rhode Island, Cape Cod, Boston and Salem, Massachusetts, then onto Portland and Bar Harbour, Maine, before finishing in Burlington, Vermont and New Haven, Connecticut.
If you’d like to watch what we got up to in Boston, rather than reading this itinerary, then you can do so below:
Still to come are videos on our time in Maine and Vermont, so stay tuned and subscribe if you haven’t already!
A little back story before we start the itinerary
This was my second time visiting Boston, the first time being my boyfriend and I’s first ever trip away together when we took a Greyhound Bus from New York to Boston to spend a few days here between Christmas and New Year in 2019.
An older cousin of mine had lived in Boston for around 15 years, so I had heard so much about the city and always wanted to visit. The first time we came here in 2019 was very cold, so we didn’t see too much of the city and we were in the first couple of months of our relationship, so everything was still quite new.
Plus we also ventured out to Harvard University and to Salem during that first trip, so spent around 12 hours in Boston city itself – it was time to fully explore this time around!
I don’t know what it was about this second visit to Boston that made me fall in love with the city so much. I could see why people move here and why a lot of Irish people in particular choose to call Boston home. There was something so comforting about the city that I found I could definitely see myself living here in the future.
Time will tell! Anyway, on to the itinerary and how we spent our short 48 hours in Boston, Massachusetts.
DAY 1: Arriving in Boston
We left Providence, Rhode Island around 11am on a Monday morning, making our way to Provincetown, Cape Cod.
This is only a short drive from Boston, so definitely worth visiting if you’re in the area. You can see what we got up to in Provincetown in my YouTube vlog above.
After filling up on some insanely good clam chowder, we made our way to Boston, arriving to our hotel around 4pm.
While himself worked out the parking situation with the valet, I checked into Aloft Hotel in the Seaport District of the city. We were very kindly upgraded to the top floor of the hotel which had a beautiful view of the city’s skyscrapers.
Once we had freshened up and changed, it was time to head out into the city for dinner.
We thought it would be cute to go back to the restaurant we dined at on our first night in Boston back in 2019, so headed to Boston’s North End to their Little Italy.
We queued outside Giacomo’s along with another 30 or so people who were wanting to sample some of the famous Italian cuisine this restaurant had to offer.
It was definitely worth the wait as we had some of the best food on our whole East Coast Road Trip during this meal – I would highly recommend!
Irish bar hopping
After dinner, we had hoped to sample some famous cannolis from Bova’s but were way too full, so decided to walk into the city centre and have a drink in Roisin Dubh Irish bar which is said to be one of the best in the city.
There was some live music and I actually got to hear one of my favourite Irish songs called Boston Rose, played live in Boston which was a bit of a pinch me moment.
After this, we headed out towards our hotel and went to an Irish dive bar called Croke Park. It’s very much a locals bar where all eyes are on you as soon as you enter through the front door.
There were a few people playing pool and we decided to play some darts at the back of the bar while enjoying a bottle of Magners.
Then it was time to walk back to our hotel and get some rest ahead of our upcoming full day in Boston.
DAY 2: Breakfast at Friendly Toast
I will say, one thing Boston seems to be lacking is good brunch/breakfast options. None of the places we searched were screaming out at us to try, apart from a place called Friendly Toast which we had actually wanted to come to the first time we visited Boston.
Fast forward four years later and it was still coming up as the number one choice for brunch in the city. And since it was a Tuesday morning, we hoped it wouldn’t be too busy and that we could get a table quite quickly.
We did have to wait around fifteen minutes for a table when we got there, but it was better than the two hour wait we were met with back in 2019, so stuck around in the sun outside until a table became available.
I had a sweet portion of French toast with fruit while himself opted for the savoury option of eggs Benedict.
Wandering around the city: Acorn Street & Boston Common
You may already know this, but our favourite way to see a city is to walk all around it. Grabbing a coffee (in this case it was an iced caramel latte from Dunkin’ which also fuelled our whole trip) as we wandered through Commonwealth Avenue (one of my favourite streets in Boston) and then through Boston Common.
After a few stops along the way to sit down and relax from the hot temperatures, we made our way over to Acorn Street and the accompanying Chestnut Street, Cedar Street and Walnut Street.
This area of the city is particularly picturesque with Acorn Street being one of the top photo spots in the city for its cobbled road and New England style housing.
Boston Freedom Trail
After this, we decided to follow the Freedom Trail that you can find throughout the city. Very cleverly, there are red and black bricks laid out in the road and in the pavements that lead you around historic landmarks in the city centre.
Meaning you don’t need a map or a phone to navigate you to the different sights, you can follow the brickwork to the famous locations around Boston.
We also stopped by the Irish Famine Memorial which explains Boston’s aid and involvement and how many millions of people from Ireland immigrated to Boston to survive.
We could sense there was about to be a downpour of rain, so headed to find shelter in Quincy Market.
One of our favourite places to eat in Boston, there are so many vendors in Quincy Market selling an array of food items, but most importantly a lot of fresh fish, lobster and clam chowder which Boston and the surrounding New England areas are famous for.
I had already had my first bite of a lobster roll the previous day in Cape Cod along with my first clam chowder, but I simply couldn’t get enough and ordered a warm bread bowl full of chowder in Quincy Market.
This was the start of many more clam chowders and lobster rolls to come and I’m still having trouble looking lobster in the face three months later.
Red Sox at Fenway Park
After filling up on some very tasty clam chowder, we had to head off to change before making our way to Fenway Park.
It was still pouring down with rain, so we headed back to change into something a little more waterproof and then made our way to see the Red Sox play.
This was definitely a bucket list item for me and it was so cool attending my second baseball game after seeing the New York Yankees back in 2019.
It may have been delayed by two hours due to the rain, but I had a better understanding of the game this time around and really enjoyed the atmosphere. I could definitely see myself getting into baseball if I ever move back to the US again.
DAY THREE: Leaving Boston for Maine
The next morning we checked out of our hotel bright and early and headed to Boston’s North End (Little Italy) to get our hands on some of those famous cannoli’s we had missed out on two nights before.
We stopped off at Bova’s and picked up some fresh cannolis and pastries for the car before heading onto Salem to explore this city again.
After a few hours in Salem, we then made our way onto Portland, Maine to continue the road trip.