Short on time? Follow this link to a Google Maps version of our Boston itinerary with all of our favorite spots labeled! You can “follow” the guide, and the saved locations will automatically transfer to your own Google Maps account.
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Exploring Massachusetts’ North Shore
We had a fabulous 3 days in Boston running around its brick-lined streets. Boston might be our favorite city in the U.S. now. We are obsessed.
Boston was the last leg of our New England road trip that we did last month, following a stint in Southern Vermont and a sleepy stay on Plum Island near Newburyport. We walked almost twenty miles in the three days we had to explore Boston, and we loved every minute of it.
We’ve compiled our best recommendations in this 3 day Boston itinerary. Prepare to walk a lot, and come with an empty stomach.
Stay in Beacon Hill
Prepare yourself for a steep credit card hit for your lodging in Boston. We went the Airbnb route and still spent more than we were expecting to. We won’t recommend the specific listing because we didn’t have the best experience, but the bottom line is that you should expect an expensive price tag to accompany your choice.
However, we DO recommend staying in Beacon Hill. I always pictured Boston covered in bricks, cobblestones, and dimly lit coffee shops with flowers out front. Turns out I “pictured” it that way because of all of the Instagrams I’ve seen of Beacon Hill.
We loved staying in Beacon Hill because it is tucked away from the hustle and bustle of the city but also close enough to walk to almost anywhere we wanted to go. It’s also just so cute and picturesque. Make sure to stop by Acorn Street, a teeny-tiny cobblestoned residential lane that’s also known as the single most photographed street in the U.S.
Grab breakfast and coffee from Tatte Bakery in Beacon Hill (no questions, just go). We loved this spot.
Pretend to be a genius at Harvard
Take the T over to Cambridge and spend a morning walking around Harvard. The campus is beautiful, but I have to say I was a little thrown off by all the tourists (Tyler is rolling his eyes at me, and yes, I know I’m ridiculous). Take a walking tour led by a Harvard student, buy a mug at one of the many gift shops, and do your best to schmooze your way into the students-only section of the library (I think we all know how that played out for me).
On your way out, swing by Crema Cafe around the corner from the campus. If you’re hungry, try the quiche du jour.
Investigate an art heist
We did a lot of recon for this trip to Boston on social media and with friends. We wanted to make sure we didn’t miss anything crucial. A couple of spots turned up time and time again in our research, and the Isabella Stewart Gardner Museum was one of them. EVERYONE was so worked up about how we just HAD to come here.
The Venetian Renaissance-styled museum houses a collection of art curated by Isabella Stewart Gardner, an extravagant and colorful Boston socialite, in the late 19th century. Gardner and her husband voraciously gathered a wide range of world class art with which Gardner eventually filled her museum. (Read more about Gardner’s fascinating life and personality here).
In 1990, two thieves dressed as polices officers managed to make off with thirteen works of art (including pieces by Rembrandt, Vermeer, Manet, and Degas). This heist is still unsolved and known as the single-largest property theft in history. (Learn more about the heist here).
We definitely recommend blocking a couple of hours to explore this museum. Admission is waived for anyone named Isabella and discounted to visitors wearing Red Sox gear, both provisions outlined in Isabella’s will.
Date night at the ballpark
A trip to Boston cannot be complete without a visit to Fenway Park. If the timing lines up, definitely buy tickets to a Red Sox game. Tyler and I naturally bought the cheapest tickets available. Upon arriving at our seats, popcorn and beers in hand, we found them positioned directly behind a huge pole. The seats behind us and in front us were all empty, as we were the only fools who didn’t read the fine print on the tickets. So in order to avoid having to lean to the right or left for the entirety of the game, don’t make that mistake.
Grab a pregame dinner at Sweet Cheeks, an amazing barbecue joint down the street.
And–this is important–at some point in the night, make your way over to Bleacher Bar, a lively bar situated behind the wall of the outfield. The huge field-level windows provide an awesome spot from which to watch the action.
A visit to the iconic Fenway Park is still worth it even if your trip to Boston does not land during baseball season.
Walk the footsteps of the founding fathers
Plan to spend a few hours retracing the steps of our nation’s founding fathers on the Freedom Trail. This pathway threads together all of Boston’s most historic landmarks. Take a guided tour, or do what we did and follow this guide as you make your way past each historic site (made right on Google maps and incredibly helpful).
The trail begins at the Boston Common and ends at the Bunker Hill Monument. Fuel up at Thinking Cup, across the street from the Boston Common. We also popped around the corner to check out Brattle Bookshop and definitely recommend the stop to my fellow bookworms.
Cruise the Esplanade
Schedule some time in your itinerary to walk the Esplanade, a wide pathway that runs right along the water. This is a beautiful way to see the city and get some extra steps in, and we loved watching the sailboats and rowing teams roll by. Walking this path before sunset was one of my favorite parts of our time in Boston, in spite of the few near-catastrophic cyclist encounters.
Carb-load in the North End
We sadly were unable to get a reservation at any of the restaurants we had starred in the North End (Carmelina was at the top of our list), but we still made our way over one afternoon on a dessert pilgrimage.
I mentioned earlier that a few things kept coming up in our research about Boston for this trip, and “GET A CANNOLI” was something that seemed to be absolutely crucial. There are two world famous cannoli shops in the North End: Mike’s and Modern. Tyler had already visited Mike’s on his last trip to Boston, so he wanted to test out Modern. Tyler is borderline embarrassing when he tries food that he loves, especially dessert, and he did not hold back after waiting in line for 30 minutes at Modern. I’m talking a full breakdown on the sidewalk here.
Window shop (or real shop) on Newbury Street
I obviously prioritized Newbury Street on our agenda. A picturesque brick street full of all my favorite stores? No brainer. I let Tyler have the Red Sox game, so I didn’t feel bad for spending a little time meandering through this adorable area.
Need to feed your shopping buddy? Try a taco at Lolita or a sticky bun at Flour Bakery. I was a little skeptical (I mean what even is a sticky bun anyway?) but this pastry was SO good.
Have a beer for us at Harpoon Brewery
Tons of friends suggested a visit to Harpoon Brewery, We wanted to go SO badly, but it was closed for their Oktoberfest celebration when we were there. It’s at the top of our list for the next time we visit Boston, so we decided to include it on this guide even though we weren’t able to go.
And last but not least, dinner and drinks
As with any big city, the dinner/drinks scene was a little overwhelming to us at first. We ended up finding some amazing spots, though. I just love a good dinner.
Try the Salty Pig for charcuterie and a fun wine and beer list or The Beehive for live jazz, chandeliers, and fancy cocktails. We loved the pizza and house-made ice cream at Picco and swooned over the sandwiches, each designed by a different Bostonian chef, at Parish Cafe. We also recommend a pit stop at Drink, a menu-less speakeasy whose mixologists will craft a cocktail based on your preferences.
Boston is such an incredible, walkable city, full of great restaurants, coffee shops, and history at every turn. We had a blast exploring for 3 days in Boston and were so sad to fly home. Let us know what you thought of our list and if we missed anything!
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