Anyone looking for a long weekend getaway? I’ve got just the town for you…Boston! We went there last year in the fall after we spent a few days in Bar Harbor, Maine and it was the best city I’ve been to in a while. And that led to this Boston Travel Guide.
I’m a city person. I live in a city and like vacationing in a city. I love the hustle and bustle and the options of restaurants and activities a city offers. Boston is a city that combines New York and Chicago and marries them perfectly. Big city feels with Midwest friendly people, makes for a great Boston vacation.
Anytime I go on a trip I do a ton of research on what to do, where to eat and what to see. I’m my own worst enemy sometimes though. I schedule out every minute and over think everything. Sometimes I forget to schedule downtime.
However, I’ve learned from my mistakes and now build in extra time to just wander. I use this time if something catches my eye or if I get a good recommendation while on the trip. The best things are recommended by locals.
Here is my top ten list of things to do in my Boston Travel Guide. Some of these were planned ahead of time and some I stumbled across along the way. All will make for a memorable Boston vacation.
Freedom Trail
If you are going to Boston you are walking the Freedom Trail. The 8th grade geek inside of me was super excited for this educational activity. Start at the beginning and follow it all the way through. I wouldn’t recommend going into every stop along the way, but for sure take a minute in the Granary Burying Grounds. It’s hauntingly beautiful.
Boston Common
I LOVED spending time in Boston Common. It’s a mini central park and it’s gorgeous. There are plenty of benches or spots on the grass to sit on and take in the day. Every tree in the park is absolutely gorgeous, like the tree above. I highly recommend grabbing some street food inside the park. I love hot dogs and they taste even better from a street vendor.
Where Everybody Knows Your Name – Cheers
If you go to Boston you have to visit the iconic Cheers bar. Grab a picture outside and reminisce about the show you probably shouldn’t have watched when you were little, but did.
Little Italy
Out of all the Little Italy’s I’ve been to this is my favorite. Every restaurant is packed and serving the most delicious food. Head there early to grab a table as most places do not take reservations. Stay late for the wine and genuine old school neighborhood feel. One of my favorite places to grab dinner is Bencotto in the North End.
Mike’s Pastry
You haven’t had a cannoli until you have had one from Mike’s Pastry. The bakery is a zoo at all hours and there are people everywhere. It’s been a staple in the North End since 1946 and once you taste their cannoli you will know why. Figure out where the line is and yell your order when it’s your turn. I suggest ordering two; a classic cannoli and a unique one. You will thank me later that you got two!
Boston Public Library
This is a classic library complete with the old school green desk lamps. Stop by the courtyard and take in the fountain in the center. It’s a great spot to relax and read a book. Afterwards, head over to the main hall to take the most old fashion Instagram photo ever. Be quiet though because it’s still an actual library.
Newbury Street
Located in the Back Bay neighborhood, Newbury Street is a full day destination. Head there to shop boutiques and major retailers, like Tiffany’s, M.M. LaFleur, Longchamp and so many more. After you work up an appetite grab brunch at one of the adorable restaurants on the street. My favorite is Stephanie’s on Newbury Street they have a build your own bloody mary that is to die for!
Boston Public Market
One of the biggest year round indoor public market that has 35 local vendors. In the summer months the market expands outside and fills the streets with fresh fruits and vegetables. Everything is locally sourced from Massachusetts and New England. You can find just about everything there from fresh produce to dairy and seafood. You can also pick up baked goods as well as fresh breakfast, lunch, and dinner.
Door Tour
Boston has some of the cutest houses with the best door fronts. I swear decorating the front door is a sport in this town. Pick a residential street and walk down it looking at every brownstone, you won’t be disappointed. If you wander down to Newbury Street you can head back to the city center on a residential seat and then through Boston Common. It’s the perfect day!
Quincy Market
The market has been serving the people of Boston since 1826. While a lot has changed since then the grounds are rich with history. Today is has about one hundred shops including retail and food vendors. All the structures are original and you can find period performances outside the market doors.
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