A First Timer’s Guide to a Long Weekend in Boston, Massachusetts

The first stop on our Maine Honeymoon was a side-trip to Boston. Boston is a major destination, a big city with a small footprint, and we were only able to allot a couple of days to exploring it. We knew we had to have this stop buttoned up to get the most out of it, and now I’m sharing these secrets with you!

Brookline, MA

I like to fondly refer to our hotel in Brookline as the “shittiest hotel in the nicest neighborhood.”  Frankly, that’s where we always look to stay.  We look for the nicest, safest, cleanest, most top rated neighborhoods in a metropolitan area, and then we find the cheapest hotel that area will allow.  In Boston, even the worst hotels didn’t come cheap.

JFK National Historic Site

We landed in Boston in the early afternoon, and took a Lyft to our hotel.  We immediately dropped everything in our room and ran out the door to our first stop.  As avid National Park visitors, we pulled out our National Park Passport and ran to the JFK National Historic Site in Brookline, just a short walk away from our hotel.  We knew we would be too late for a guided tour, but the last hour of the day is set aside for self-guided tours.  They have an introductory video (which I highly recommend), a listening device with Rose Kennedy narrating life for the Kennedy’s in this home, and a ranger stationed on each floor to answer questions and tell additional stories.

John Fitzgerald Kennedy National Historic Site
The John Fitzgerald Kennedy National Historic Site in Brookline, Massachusetts. This is where John F. Kennedy was born and spent the early years of his life.

At the information desk, they had a stack of maps of the Brookline area with suggested places for dinner.  We grabbed our map and headed to our next spot, a small place for a bite of pizza.

OTTO Pizza

Unbeknownst to us, we found ourselves at a place that actually originated in Portland, ME, one of our future stops for this trip.   There was a wait for a table, but the bar had full service and had plenty of seats open.  We grabbed a couple of slices of pizza — they mostly had New York style pizza (or maybe BOSTON style pizza, depending on who you ask) and one Detroit style pizza — we had a few beers, and continued down the road for dessert.

J.P. Licks

I’ll be honest, the name of this eatery piqued my interest.  J.P. Licks is an ice cream shop that had probably 40 different kinds of ice cream, and just as many toppings, creating a completely customizable experience.  We stuck with the standard flavors and skipped the toppings, but highly recommend this spot.  The ice cream was delicious and the service was even better.  We really felt welcome here.  Seating was limited this fall, I can only imagine what it looks like in the summer, but it is absolutely work the stop.

After dessert, we did two things that we always do on trips like these.  We bought a Metro Pass (in Boston, they call it a “Charlie Card”) and we bought some groceries.

Where to Buy a Metro Pass (Charlie Card)

Finding a Charlie Card proved more difficult that we originally thought.  Buying a one-time use pass was easy.  Nearly every stop along the route sold one of those.  But we needed a 24-hour pass so we could get around all day the next day.  Be careful, your Charlie Card day pass is good for 24-hours.  Don’t use yours to get back to your hotel for the night and then sleep off 8-hours of use.  Instead, buy a one-time ticket to get home and use your pass the next day so you have plenty of time to get where you need to go!

We used THIS LINK to help us locate a spot that sold a Charlie Card.  We ended up at a small liquor store a few blocks away from the main part of town.

Trader Joe’s

Next stop was a Trader Joe’s on Beacon Street.  We grabbed some essentials for the remainder of our trip (bread, lunch meat, cheeses, breakfast muffins, yogurt, fruit leather, granola bars) We bought things we could use for quick and cheap snacks throughout the trip to tide us over.  This way we would be able to eat a quick breakfast in the morning (our hotel did not provide a free breakfast) then explore a bit, eat a lunch that we packed, and then splurge on dinner and treats along the way.

Boston, MA

That night, we took a trip into Boston to grab some dinner and drinks at a brewery near Boston Commons.

Democracy Brewing Company

We were ready for a low-key evening, and that’s exactly what Democracy Brewing was able to provide.  We settled into a corner booth, had a beer flight and a few appetizers to go with it, and enjoyed some time side by side with some locals (who were just getting their night started instead of just ending it.)

We roamed around the area after dinner, and found ourselves walking through Boston Commons in the dark (an experience that felt incredibly safe.  Tons of people were walking around this area still.) They had a carousel running and we just sat in the grass and watched the lights spin around for a while. It was such a wonderful way to end our evening.

A Carousel on a dark night in Boston Common
Carousel in Boston Common

Fenway Park

Fenway Park, empty, on a tour of Fenway, taken from the top of Green Monster
A view of Fenway Park from the top of the Green Monster

The next morning, we took the tram back into Boston for a tour of Fenway. We took the 9am tour, planning to spend the rest of our day on the Freedom Trail.  I cannot recommend the Fenway Tour enough.  Not only for baseball fans, but for anyone interested in learning a little bit more about the history of Boston.  Baseball is such an integral part of this city, and our tour guide was so passionate about the history of Boston Baseball.  He told so many great stories, and we got to see the park from every angle imaginable.  Sitting on top of the green monster, sitting in the oldest seats in all of baseball, sitting in the press box, you can see almost every inch of Fenway on the basic tour, or upgrade to a tour that gets you on the field and inside the Green Monster.  You can buy tickets here.

The Freedom Trail

I’ve got a whole post, my ULTIMATE Guide to the Freedom Trail (going live in a couple days!)  Click here to read everything you need to know about walking the Freedom Trail from start, at Boston Common, to the finish at Bunker Hill Monument.

I was a little bit skeptical about doing something so touristy on a weekend, but I am so glad we took the time and fought the crowds to learn more about our country’s history.  I love incorporating history into travel, and Boston was the jackpot for that!

After a full day of walking, climbing, and standing in lines.  We were absolutely exhausted by the time the sun went down.  We settled back into our hotel (after dealing with a maintenance call…I told you, shittiest hotel in the nicest neighborhood…), got into some comfy clothes, and ate pastries in bed.  Where did the pastries come from, you ask?  You’re just going to have to check out my post on the Freedom Trail to learn more!

The next morning, I walked to pick up our rental car while Jason packed up our room and got us checked out.  Once we had everything taken care of, we drove down south to the Sam Adams Brewery and Tap Room (a bit of a long haul if you would try to do this via public transportation.  I’d recommend driving here or taking a Lyft.)

Ula Cafe

We arrived a little early, so we grabbed coffee and a scone at Ula Cafe.  There were tons of people already busy working here when we arrived.  We found a table in the back and waited for the brewery to open.

Sam Adams Brewery and Tap Room

Unfortunately, the tours were cancelled for the day, but the Tap Room was open and they walked everyone through the tasting process and gave everyone a free beer for stopping by.  We grabbed a flight here, hung out for a while, and then left Boston.

Beer Flight at the Sam Adam's Tap Room
Beer Flight at the Sam Adam’s Tap Room

Boston is such a fun city and it’s so easy to spend a weekend of non-stop moving here.  Know what you want to do before you go, and hit the ground running.

Do you have any favorite spots in Boston for my next visit?  Leave them in the comments below and let me know where to go next!

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