15+ Best Things to do in Boston, Massachussetts

Looking for the best things to do in Boston, Massachusetts? You’re in luck, travel enthusiast, you’ve stumbled upon the perfect post!

Growing up on the East Coast (NYC to be exact), I’m ashamed to say I haven’t made my way up north to Boston enough as I should.  Being only a few hours away, Boston makes a wonderful weekend trip from NYC, and I wish I had taken advantage of it’s close proximity before moving to California.  Since I’ve only explored a few times (and not thoroughly enough!), I’ve asked my friend Cassie from Wandering with Coffee to give us the low down on her favorite things to do in Boston.

If you end up in this New England city, promise you’ll bring me back a cannoli from the North End. xx

Pre-Travel Guide to Boston

How to get around

Public transportation is going to be key here. I highly suggest NOT renting a car because it will be a waste of money. The MBTA (referred to as the “T” by locals) is relatively easy to use. “Inbound” is towards downtown boston, and “outbound” is towards the suburbs like Allston, Brighton, Roxbury, etc. At every station there is a map of the stops, and if you want to get somewhere but don’t know what stop to get off at, use google maps and click transit, ta-da!, it’ll tell you what line  to take (they are organized by color) and what stop to get off at! It’s really that easy, I promise!

If public transportation is not your thing–uber/lyft is a great option! If you use the “pool” option you can get across the city for about $5. And of course Boston is the walking city, so get a good pair of shoes and follow the freedom trail to find everything you could ever want to see!

Important things to pack

• Walking shoes will be necessary whether you intend on taking public transportation or not. You will be walking, it only makes sense.
• Rain jacket (NOT umbrella) – Since Boston is simply way too windy to use an umbrella, I highly suggest a rain jacket with a hood [Editor’s Note: I live in this one]. Also, Boston is notorious for having crazy changes in weather so even if it looks like it will be a nice day, pack one anyways.
• Sunglasses-so people don’t see you cry when you realize you’re on the wrong subway line, or when the glare from the skyscrapers hits you right in the eye.  😛
• Headphones-if you’re travelling alone to Boston, headphones will be your best friend. Locals always plug in before they step out the door, whether walking to get a coffee, or getting on the T. You’ll feel weird in the silence if you don’t have earbuds.

Where to stay in Boston

Honestly, hotels in Boston are heavily overpriced because there are so many popular attractions around. If you have to stay in a hotel I recommend staying a little further away in a suburb like Cambridge (right across the Charles River).

If you have extra money to spend, check out the Fairmont Copley Plaza which is gorgeous and super convenient, or the Westin Boston Waterfront which is right on the harbor and has the best views! [Editor’s Note: We stayed at the Hyatt Regency Boston and loved its location and fantastic on-site restaurant.]

AirBNB is not technically legal in the city but there are still a ton of great listings that could save you hundreds! It’s just a little more on the DL (down-low).

When to go

Before moving to Boston I did a ton of research, and most web sites stated that summer is the best time to visit. However, I disagree. While it is true that summer in Boston is quieter because most the college kids have left, it’s also hot AF.

And if you’re planning on walking around the city like most people do, you will hate yourself. If you’re planning on filling your itinerary with things to do in Boston during the summer, it may be hard to accomplish them all because of the harsh heat conditions.

I suggest visiting during fall for a few reasons! First, the Boston Common will be colorful and pretty! Second, you will not die of heat if you walk around, you may even get to wear a sweater! And Third, you get to deal with more locals, and less tourists, aka more professionals to ask directions from and less fools trying to escort thier eight children onto the T. Boston is absolutely beautiful in Autumn, you’ll see.

Important phrases / Local Lingo

• Bostonians are harsh people, so they won’t mess around with you pronouncing something wrong. The main one to know is Copely Square (pronounced like COPley, not COPEly).
• A popular slang is that the subway aka the MBTA is exclusively called the “T” like I said earlier. If you go asking around about the subway, you will get side-eyed and ignored.
• Dunkin Donuts is super popular for unknown reasons because I personally hate their coffee. However I did get yelled at by the customer behind me when I tried to order “incorrectly” so heed my warning: if you want a coffee with cream and sugar, order a medium “REGULAR”, and you will fit right in.

15+ Best Things to Do in Boston

1. Eat Pizza in the North End

The North End is the Italian neighborhood of Boston and I personally believe it has the absolute best food anywhere in the city. I suggest wandering around the old buildings, grabbing fresh made gelato on street corners, and getting classic cheese pizza from my favorite place, Umbertos.

Umbertos is on the main street- Hanover, and is only open daily from 11-3 (or until they run out of pizza, and they will!) so get there early. I promise it’s worth it. Eating pizza in Boston’s North End will almost make you feel like you’ve stumbled into Italy! It’s that drool worthy.

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2. Have Drinks at Top of the Hub

I actually used to serve at Top of the Hub, and I promise you- the food is not worth it. The view, however, is. And grabbing an over-poured $15 drink at the bar here is going to be way cheaper than stopping at the Skywalk two floors down.  So grab your friends, go up to the 52nd level and have a alcoholic Pumpkin Iced Coffee with a view (perfect for your Autumn visit)!

3. Shop on Newbury St.

Of all the things to do in Boston, Newbury Street is one of my favorite places. The street itself is cobblestone and has beautiful trees that have christmas lights wrapped around them in winter! Newbury St is also the hub for anything you need. High fashion mixes with hipster coffee shops and a CVS. You could spend an entire day on these seven blocks shopping, and eating. My favorite places include Madewell Clothing, Pavement Coffee, and Jennifer’s Nails!

4. Brunch at Trident Booksellers & Cafe

In addition to all my favorites listed above for Newbury St, Trident is my number one. This bookstore and restaurant is located right next to the Green Line Hynes stop so it’s super convenient. It’s also the coolest place I’ve ever seen.

Trident is located in a brownstone building and is two stories. Half the store is a bookstore that has everything from magazines to bibles (and a lot of cookbooks!), the other half is a restaurant that serves the BEST brunch food including stuffed french toast, and delicious breakfast sandwiches.

Also their TVs behind the bars are always playing movies, not sports for once!!

5. Picnic on the Public Garden

First let me start by saying this is not really common, however it is super fun. My friends and I packed sandwiches, chips, and bottles of Absolut and lemonade and sat out on the garden for a perfect afternoon. Something to note is that most of the grass in the Public Garden is off limits as they are trying to preserve it, but there are also plenty of places to lay out a blanket.

Picnics are more common on the Boston Common (right across from the garden) but the Common is notoriously dirty and is the hangout for a lot of the homeless. So trading the Common for the Garden is highly suggested. The garden is super popular because it’s full of bright flowers and is famous for the “swan boats” that float in the pond.

6. Faneuil Hall in Winter

Faneuil Hall is really popular due to Quincy Market which has been turned into a food market. Of the things to do in Boston, it personally isn’t my favorite place because it is swarmed with tourists and has really bad cobblestone that I almost always sprain an ankle on.

However, Faneuil Hall during the winter season is a must see, this is because it is covered in lights and is host to Boston’s Nova Scotian Christmas tree that is gifted from Canada every year- and it is HUGE.

7. Drink wine by the Charles River

If you’re looking to relax for a bit, I highly suggest bringing a bottle of wine to the docks on the Charles River. On a sunny day you can catch sailing and rowing practice for all of the different schools, and at night it’s a great place to catch the sunset.

You can find these docks located just off the Charles River Walk which is a great place to bike as well, but my favorite (quieter) dock is the one that is located behind the Boston University Campus.

8. Check out Brattle Bookshop

If you like magical things, of the things to do in Boston, this bookshop is for you. It looks like it’s straight out of Harry Potter and is a hidden secret even from some locals. This bookshop is cool because it’s outdoors in an alleyway, and has a ton of different books that are CHEAP, like $1-$5.

It also has some modern art decorating the ally. Perfect hipster spot to check out if you’re in the market for some books-or even if you don’t like books, because it’s that cool.

9. Go to a Red Sox Game

This is super popular but I have to put it on here, cause I honestly believe (even if you hate baseball), this should be on your Boston to-do list. Fenway Park is the oldest ball park in America and it’s also really cool looking. The John Hancock sign lights up during night games and the skyline of Boston is perfect in the background.

Fenway is however expensive and has limited options for food since it’s so old, so unless you’re planning on going for a classic dogI suggest eating and pre-gaming on alcohol before the game.

Also the old seats are super small so if you’re curvy at all I suggest picking a ticket in the newer seat area or getting a standing ticket. If you really hate baseball, Fenway offers tours every day!

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10. Isabella Stewart Gardner Museum

This is my favorite museum in all of Boston! First it’s in a mansion that actually belonged to Isabella Stewart and it is gorgeous. The courtyard has a bunch of greenery, and art. The other rooms are filled with artwork that she collected herself.

The really cool thing about this museum though, is the story; this museum was actually robbed on March 18, 1990 and the painting have never been recovered to this day. The frames still hang from where the paintings are supposed to be.

11. Sip Coffee in the Boston Public Library Courtyard

This may sound like a boring idea for what to do in such an interesting city like Boston, but I promise that this will not disappoint. First the public library is one of the first in the country, and the inside is beautiful-lined with marble and gold. It’s also free so that’s a plus.

The main thing to see here in my opinion however, is the courtyard. It is open air courtyard with a beautiful fountain, columns, and tables to sit and read at. It is the perfect place to relax for a bit, and a plus is that there is a coffee shop right inside the library for you to grab a cup of jo at.

12. Dinner at Lincoln Tavern in South Boston

This is not even on tourists radar yet, cause it is a bit out of the downtown. However, this is my absolute favorite place to grab dinner at. I suggest taking an uber here. The drinks are different and delicious, and the food is unbelieveable. If you catch this place on a weekend they also have live music!

I recommend getting a reservation just to ensure you don’t have a wait-cause locals always crowd this place it’s too good. I would recommend a dish but the menu changes frequently to showcase new dishes. If you can’t make time for his one night, I highly highly suggest their brunch and alcoholic iced coffees Fri-Sun.

13. Take a Picture on Acorn Street

This one is simple, go to Beacon Hill (next to the Boston Common) and find Acorn St. It is the most photographed street in the country, and for a good reason! No wonder it’s one of the best things to do in Boston, it’s quaint and colonial and picturesque! Luckily the locals that live on this street know they’re lucky and won’t be bothered by another person taking a picture of their home.

14. Eat at a Food Truck in the Boston Common

Stop by the fountain right near the green line Park Street stop, that has a perfect view of the State House, and grab food from one of the food trucks parked there! It varies daily but my favorite is the Clover truck! There are tables you can sit and eat at or you can grab a spot on the grass. You’re just like a local!

15. Harbor Cruise

This is for sure touristy but oh so worth it, and one of the most popular things to do in Boston for visitors.  If you go to the harbor by the NE Aquarium there is a booth for tickets to many different cruises that you can take!

My favorite is the history cruise that takes you around the harbor and talks about all the history of Boston, did you know most of the land Boston sits on is hand made?! There are also romance cruises, adventure cruises, and more. I highly suggest doing it once! They usually only last an hour or two.

Other Things to do in Boston if You’ve Got More Time:

1. Boston Duck Tour: Climb aboard a unique amphibious vehicle and discover Boston from a different perspective. The World War II-style “Duck” travels on land and water and takes you along historic streets and into the Charles River on an 80-minute tour of the city.
2. Harvard Tour: Enjoy a 70-minute tour of America’s oldest university. On the Hahvahd Tour you’ll embark on an entertaining journey through Harvard Yard with a current student. Enjoy tales of Harvard’s history and culture as you see famous landmarks and monuments.
3. Whale Watching Cruise from Boston: Join this 3-hour cruise for the opportunity to spot whales off the coast of Boston. See these magnificent creatures close-up from the deck of your ship. Spot Humpback and Finback whales and see White Sided Dolphins frolicking in the waters.
4. Old Town Trolley Tour: A Hop-on, Hop-off tour with a twist! Climb aboard a trolley and experience a combination of transportation and on-board entertainment. With your full-day ticket you can hop off at 20 stops throughout Boston close to more than 100 points of interest!
5. Day Trip to Martha’s Vineyard: Explore quaint Martha’s Vineyard island and discover beautiful beaches, nature preserves, historic villages and gingerbread houses, to name a few of the delights that await. Cruise across Vineyard Sound and take part in optional adventures.
6. Historic Sightseeing Cruise: Discover the historic and contemporary milestones of Boston’s inner and outer harbors during this fun, informative, fully narrated 90-minute tour.
7. Boston Sunset Cruise: End your day on a perfect note on this 90-minute sunset cruise which provides spectacular views of the sunset and the Boston skyline.
8. Freedom Trail Walking Tour: Walk through history along the Boston Freedom Trail’s famous red line to experience some of the most seminal landmarks of America’s revolutionary founding. Walk in the footsteps of the founding fathers from Boston Harbor to Boston Common.

Have you been to this New England city before? What are your favorite things to do in Boston?