We spent a long weekend in Boston last weekend (thanks to the amazing Delta flight deals for only $100!) and realized December was the perfect time to visit! We lucked out with great weather in the 40’s and 50’s and loved the festive holiday decorations all around the city. We received so many fun recommendations of things to do in Boston from friends and did a lot of research on our own, so keep scrolling for our highlights!
Day 1
Freedom Trail
We got off the plane in Boston and stepped right onto the Freedom Trail! It was our first time to the city so we had to see all the historic sites. We spent about 4.5 hours walking the 2.5 mile trail, but stopped for some snacks and drinks between stops. My favorites were the Granary Burying Grounds to see Paul Revere and John Hancock’s graves, Faneuil Hall, Paul Revere’s house, and the USS Constitution. Definitely take a tour of the Paul Revere’s house ($5) and the USS Constitution and museum (free!).
Faneuil Hall Marketplace
Take a stop on the Freedom Trail to visit one of the markets! We explored Faneuil Hall Marketplace which first started as a market in 1826. And we had to get some clam chowder from Boston Chowder Co.
The Bell in Hand Tavern
After our chowder, we needed some brews to wash it down so we headed to the oldest tavern in the US, built in 1795, The Bell in Hand Tavern! You’re definitely in the middle of tourist haven in this area, but the streets are so cute.
Winsor Dim Sum Cafe
Make sure to check out Boston’s Chinatown – and get some dim sum! We ate at Winsor Dim Sum Cafe (all made to order) and ordered the potstickers, mini pork buns, and fried egg roles. Yum!
Beerworks Brewing Co
Later in the night we stopped at Beerworks where we had the best beer of our trip! If you want a fun spot with good beer right downtown, this is the spot for you! And fun fact, this craft brewery started in 1992 – way before the craft beer craze!
Day 2
Tatte Bakery and Cafe
We stopped for coffee in the back bay at Tatte which has to most unique pastries! We ordered the blueberry hazelnut muffin and the Pistachio cranberry croissant. The perfect way to start the day!
Boston Public Library
If you’re a fan of architecture, photography, history, or just pretty buildings, make sure to check out the Boston Public Library. It’s an iconic spot in the back bay and has a beautiful courtyard that can’t be missed!
Cheers
It might be one of the ultimate touristy things to do in Boston, but we had a great time at Cheers! There’s 3 bars in the building, one in front, one in back, and one upstairs. The upstairs bar is the set bar, so try to get a spot there if you can!
Shopping in Beacon Hill
I fell in love with the Beacon Hill area of Boston! It’s especially cute in December all decked out for the holidays. We shopped around for Christmas gifts and some things for ourselves 🙂 My favorite stores are The Flat of the Hill, December Thieves, and Rugg Road Paper Company. Be sure to check them out and to also walk down the adorable cobblestone side streets.
Harvard
We couldn’t go to Boston and not visit Harvard, so we took a 15 minute Uber into Cambridge. We walked around campus, stopped in the bookstore, and had a beer (or two) around town. I also couldn’t resist buying a Harvard sweatshirt so I looked like the ultimate tourist!
Bowl Haven
One of the most unique things to do in Boston is to go candlepin bowling! This kind of bowling uses really skinny pins and much smaller bowling balls than normal. Bowl Haven is located in Somerville, near Harvard, and is the ultimate retro spot! Bowling costs $30 per hour and there’s also an awesome pizza spot on site. Make sure to try it out – it was one of our trip highlights!
Day 3
Boston Cream Pie
Get some Boston Cream Pie at the place it originated – the Omni Parker House! This Boston hotel is beautiful. We decided to get the Boston Cream Pie for breakfast (because why not?) and enjoyed it with coffee. The pie is on the menu all day for $10, but be sure to plan for more time than you think – it took us about 15 minutes to get seated when the restaurant wasn’t full.
Trillium
Trillium has a few locations in the Boston area, but we stopped in at the Fort Point location in south Boston. We had some of the best beer of our trip here and loved the lively atmosphere!
The Barking Crab
We NEEDED more seafood before we left Boston, so walked the quick distance over to The Barking Crab after our time at Trillium. We met a friend for lunch and ordered the grilled lobster which was absolutely amazing! This little seaside seafood shack was just what we needed.
Modern Pastry vs. Mike’s Pastry
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The two most popular pastry shops in Boston’s Little Italy – Modern Pastry and Mike’s Pastry – are a must visit! It’s seriously like you’ve died and gone to cannoli heaven. We ordered a cannoli at each spot and did a taste test to see which one we liked best. In the end, I liked Mike’s better and Cole liked Modern better. If you’re going for variety of cannolis, head to Mike’s. If you’re going for atmosphere, head to Modern!
We LOVED our weekend in Boston and will be back for more, no doubt. Leave a comment of your favorite things to do in Boston that we should check out next time!
Where did you stay in Boston? What neighborhoods would you recommend to stay in for a walkable trip?
Thanks for explaining that you need to stop and get some authentic Boston cream pie. My husband and I are going to Boston in June for a work conference, so we’re turning it into a trip. I’d love to find some fun activities we can do together while he’s not at work.