3 Days in Boston

Updated: Oct 21, 2019

Hi there! My name is Ashleen Chappuis (@a.bit.brighter) and I’m thrilled to explore Boston with you!


As the birthplace of the American Revolution, Boston is known for its history, but with a thriving job market and new cruise ship terminal, this rapidly growing city is hard at work on its modern reputation.


Boston is a very walkable city that’s great for a long weekend or as a home base for a larger trip around New England. The city is spilt into over 20 neighborhoods and across the Charles River from another city, Cambridge, so there are plenty of options for visitors looking to spend a longer time in the are as well.


The best time to visit Boston is June through September, though May and October can be beautiful if you’re lucky! Late spring here is on the cooler side, think 50’s to 70’s, but the streets are busting with color. Flowers are blooming in every window box on Beacon Hill, the trees in the Commons are coming back to life, and the locals are excited to shed their winter coats for some time in the sun. Don’t be surprised if the whole city seems to be out in shorts on the first really nice day of the year!


The summers are warmer, generally in the 70’s and 80’s, and with the warm weather comes rooftop patios, outdoor seating, and open windows all around town. Touristy areas tend to fill up around this time as the number of cruise ships picks up and more out of town visitors decide to take advantage of the nice weather to see the city. However, if you go a little ways off the beaten path, you’ll find a relatively calm city waiting for you to explore.


The early fall sinks back down to between the 50’s and 70’s as the leaves start to turn. You’ll find leaf peepers and locals wearing flannels and boots while enjoying the crisp fall air and all things apple. This is the best time of year to take a trip up north to Vermont or New Hampshire to see the mountains covered in shades of orange and red.


Late fall to early spring is cold, and Boston is a bit bleak so the city has 2 public outdoor ice rinks to try and brighten the mood. Visitors at this time tend to be going north for skiing or snowboarding or just in town for the holidays. A couple of Christmas markets pop-up around the city, and Boston puts up a big tree in Faneuil Hall that is well worth checking out!


Regardless of when you visit, Boston has a lot to offer. In this itinerary, we’ll visit some classics, a few local favorites, and a couple of hidden gems. Ready to get going?


Boston Day 1

The very first place to start in Boston is the Commons and the Garden. These two neighboring parks are situated downtown and create a patch of peace in all the hustle and bustle. The Commons is the larger park where a lot of Boson’s outdoor festivals are held. The Garden, on the other hand, is a bit more picturesque with flowerbeds, statues, and a small pond. It’s the setting of Robert McCloskey’s children’s book, Make Way for Ducklings, (you can visit a statue of Mama with all her ducklings in the Public Garden) and home to Boston’s swan boats, which take you around the pond and the little island made just for ducks.


Once you’ve gotten a chance to look around, head over to the information desk near Park Street Station in the Commons to start the Freedom Trail. If you want to hear about the local history from someone wearing colonial garb, stop inside the booth to buy tickets. As a big fan of walking tours (and people wearing costumes outside of Halloween), I’d recommend getting tickets. However, if you’d rather do it yourself, the Freedom Trail is free! Just follow the red line painted on the street. Keep a close eye on it because as you move, the line will switch between being red paint on tar, red brinks lined with silver stones, red bricks in cobble stones, and just red bricks going in a different direction than the other bricks making up the sidewalk.