The Perfect Boston Weekend Trip: A Guide For Your First Visit
Boston is an incredible city, one I never put much thought into visiting as I tend to put more exotic locations at the front of my travel checklist. However the opportunity arose and I took it, next thing I knew I was on a plane and landing somewhere I’ve never been. I’m grateful I made that choice, I had an absolute blast walking the cobblestone streets and living on seafood for the weekend. Boston effortlessly swept me up in it’s charm.
I’ve experienced many short layovers and weekend getaways. You can’t do it all in 48 hours, but that’s plenty of time to get a taste of the history, culture, and character that Boston has to offer. On our Boston Weekend Trip we ate seafood and pastries in the Italian neighborhood, visited the famous and luxurious Omni Parker House, saw where some key events in American history took place along the Freedom Trail, and of course caught a Red Sox game. Whether you’re planning a trip to this awesome city or just there for a layover, I hope these tips help you have the perfect Boston Weekend Trip.
Table of Contents
How to get around on your Boston Weekend Trip?
After landing at the Logan International Airport for our Boston Weekend Trip and departing the terminal, we took the free airport shuttle to Airport Station. Here you can access the “T” Boston’s public transportation train. It is a great method of getting around, super easy and straightforward. You can either buy a reloadable “CharlieCard” or simply use your debit/credit for payment, due to the amount we’d be using this train we opted for the CharlieCard. We took the “T” to “Haymarket” station and got off to walk to the North End, also known as Little Italy.
Boston is one of the most walkable cities in the U.S. and it became our primary way of getting around while staying in Little Italy. Totally worth it as you get to smell all the delicious Italian restaurants and bakeries as you walk by. Aside from walking and taking the “T” Boston has what every other city has Taxis, Ubers, Bike lanes. In my opinion you don’t need to use them, the “T” is dialed in and walking lets you experience so much more.
Protip: Boston also has bicycle rickshaws, more common to see them around Fenway Park and different bars. We did use this unique way of getting around once and it was a blast, he even let us be the DJ. A perfect way to get around after too many Sam Adams (Boston’s famous beer)
Where We Stayed on Our Boston Weekend Trip?
I recommend staying either Downtown, the West End or in the North End. The atmosphere Downtown and in the North End is bit better for tourists than the West End as it has a bit more residential and is a little more quiet. Downtown will have more pricey, upscale hotels than the other two. However any of the three and you’ll be able to walk to many different attractions. As I mentioned we stayed in the North End or Little Italy. Boston’s oldest neighborhood offers incredible food, overflows with history, and buzzes with nightlife.
We arrived at our Airbnb shortly after 7pm, perfect timing for me to crush some Italian food. Our Airbnb was located above a busy Italian restaurant. It was fully booked, which pushed us to go out and explore other local eats. We stumbled on a gem call Nico Ristorante, they gave us a table on a balcony over looking the street. Absolutely f@$king phenomenal food, the entertainment of watching Boston life go by on the street below, my first meal on our Boston Weekend Trip and it set sky high expectations. The city definitely delivered.
Recommendations If You Only Have an Evening?
We only had the evening on Day one of our Boston Weekend Trip however it was a nice way to ease into the city. As mentioned before I recommend grabbing an amazing Italian meal, you really can’t go wrong with any of the restaurants in Little Italy.
After dinner walk off all the pasta by wondering the cobblestone streets of the North End. If you aren’t on Hanover street already make sure you get there and grab a Cannoli from Mike’s Pastry. The lineup will probably stretch around the block, and many people saw it and didn’t bother waiting. However is does move decently quick and in my opinion it’s worth the wait at least once. They also take the time to wrap your cannoli’s in a nice box which I can appreciate
Sweet Treats
We ate our weight in food and had a sweet treat dessert, now it was time to burn off the calories and the best place to do that is at “The Bell in Hand”. Widely cited as the oldest continuous running tavern in America, “The Bell in Hand” is one of the most fun bars I’ve had the pleasure of going to. Located on Union Street Downtown, it’s got a very lively social vibe, great food, and my personal favorite plenty of live music. For some reason live music isn’t popular where I am from but walking down union street and hearing all the different bar bands blast their genres filled me with so much energy, no jetlag on earth could touch me.
We danced and sang at the Bell in Hand until last call, capping off a perfect first day—and we were just getting started.
Day 1 recommendations
- Nico Ristorante (Or any Italian restaurant)
- Mike’s Pastry
- The Bell in Hand
Recommendations if You Have a Full Day?
The Morning
Day two of our Boston Weekend Trip was the big one, we had a lot planned and only a day to do it all. Luckily for me Faye is a superstar when it comes to this kind of thing so we pulled it off and now I will help you do the same. Despite drinking for the better part of a night we started the day in high spirits, walking through Union Street past the bar we were at a few hours before. We visited the gravesite of Benjamin Franklin, stopped into the Omni Parker House Hotel and tried the Boston Cream Pie (they claim to have invented it) and made our way to Boston Common, the oldest public park in America.
The Freedom Trail starts in Boston Common, marked by a Red line on the sidewalk it guides visitors to various landmarks telling the story of the lead up to the American revolution. We didn’t have time to fit the entire 2.5km trail while appreciating all the stops in our itinerary, however we did make a point of seeing a few such as Park St. Church, Faneuil Hall and Paul Revere’s House. You can complete the walking tour in half a day, and I recommend it to anyone interested in North American history.
The Afternoon
After wondering around Boston Common in the morning we went North toward Beacon Hill in the afternoon. Beacon Hill is a historic neighborhood full of brick houses, cobblestone streets, and gas lit street lanterns. Walking through this neighborhood actually feels like you’ve stepped back in time. It is much more quiet and slower paced than the lively downtown area, perfect to soak in it’s historic charm. One of the attractions in the area is Acorn Street, one of the most famous streets in Boston and one of the most photographed streets in the United States. The aesthetic here is unmatched, when the sun hits the brick houses at the right angle in creates the picturesque imagine the photographers are chasing.
It was a cool place, however people actually live on this road and hence have to deal with the constant crowds. While I didn’t see it happen I heard that occasionally homeowners will come outside and yell at tourists. Fair enough, the constant crowds right outside my front door would get to me too. I suppose that’s what you sign up for living on a street like Acorn Street. After dodging angry homeowners we headed south back toward Boston Common then West to visit Faneuil Hall, an important gathering place on the Freedom Trail that colonists used to debate and protest British rule leading up to the war. And right next to the hall sits Quincy Market, an area full of artisan shops, street performers, and delicious food stalls. I had the best lobster roll of our Boston Weekend Trip here and probably best of my life.
The Evening
After a quick bite and people watching at Faneuil Hall we went back to our Airbnb to get ready for the main event of our Boston Weekend Trip, a Red Sox game. Faye loves the Red Sox and I love watching live baseball so it was a no brainer to do. We had to take the “T” from the North End to Kenmore Station. From there we walked to Fenway Park, Americas oldest active ballpark in the MLB. While I enjoy watching baseball I can’t say I’m the biggest sports fan in general. However walking in Fenway is something an avid sports fan should experience. The feeling was hard to describe but it has a certain charm I haven’t felt in any other stadium, plus it reeks of beer and hotdogs which I love.
There isn’t much to say here other then you’ll want to get your tickets early depending how which team the Red Sox are playing and how they are doing in the MLB standings. Red Sox vs Yankees is a notoriously hard and expensive ticket to get because of the rivalry. We saw the Tampa Bay Rays, much more manageable. Once you find your seats have a cold Sam Adams or 5 and soak it all in, a cool experience I hope to do again someday. Ideally next time the Red Sox will win though.
Repeating the nights
After the game we had a few drinks in the bars around Fenway Park, eventually we hopped back on the “T” and got back to Union Street. I stand by that “The Bell in Hand” is a must do and we almost went back but figured we should try something new. We chose an Irish Pub called Hennessy’s, and another night of drinks and live music commenced.
Day 2 recommendations
- Walk the complete Freedom Trail (if time is scarce visit a few of the sights)
- Try Boston Cream Pie at the Omni Parker House
- Walk through Boston Common
- Wonder around Beacon Hill and visit Acorn Street
- Eat a lobster roll and browse what Faneuil Hall and Quincy Market have to offer
- Catch a Red Sox game at America’s oldest active ballpark
- Hennessy’s (if “The Bell in Hand” is full)
What to do Differently With More Time?
The morning after our Red Sox game and partying at Hennessy’s we didn’t have time to do much aside from grabbing a coffee from Dunkin Donuts and head to the airport. Including travel time our trip was about 48 hours, that left roughly 36 hours for our Boston Weekend Trip. A taste but not long enough to fully experience it. I still had a Phenomenal trip and will return someday, this is what I recommend you do if you go with more time than I had.
As mentioned before I would walk the entire Freedom Trail and really soak in the history of each stop. I would love to visit Harvard Yard and see parts of the prestigious school. Visit one of the many museums in Boston, the Isabella Stewart Gardner Museum has an art heist story I want to see. As well as the interactive Boston Tea Party Museum. I would love to do a day trip out to Salem, especially around Halloween. The whole town dives in Halloween headfirst, it would be fun to be apart of. As well as learning about the witch trials that the town is famous for.
These are some of the things I will definitely do next time
- The full Freedom Trail
- Visit Harvard
- Visit the USS Constitution
- Visit the Isabella Stewart Gardner Museum
- Day trip to Salem
Final Thoughts on Our Boston Weekend Trip?
I absolutely loved our Boston Weekend Trip, while there is plenty left for me to experience there I feel that I got a perfect welcome to the city. I think people put things off for too long because it wont be a “perfect” trip. Or you worry that traveling to certain destinations wastes money because you’ll have to pay to visit them again someday. I don’t believe the micro trips like this one are a waste. I made plenty of memories and experienced things I would not have otherwise. My desire to return to Boston is stronger than my desire to visit for the first time, I can’t wait to get back. My advice? Do the weekend trip away, you won’t regret it.


