Our Top 10 Tips for Traveling in Boston

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What to do in Boston

Insider’s Guide to the city

Looking to head to the home of stunning cityscapes, championship sports games, the Boston Marathon, and of course clam chowder? Our list of favorite things to do in Boston is complete. From what you should definitely do to what you shouldn’t do while in the city, here is our insider’s guide to Boston. 

1. Stop searching for happy hours in Boston—they don’t exist

In November 1984, Massachusetts became the first state in the nation to implement a happy hour ban. Currently, there are eight states with similar laws, including Rhode Island and Vermont. 

2. Newbury Street: great for shopping, average for eating

304 Newbury Street by Thatch, Boston – Updated 2023 Prices

Everybody flocks to Newbury for the shops, but we recommend heading elsewhere in the city for better food, less crowds, and a more local experience.

If you’re determined to eat something on Newbury, make sure it’s a lobster roll at Saltie Girl!

3. Take “the T”

how to get around boston subway

The train that gets you around Boston is called “the T”, not the subway or the metro.

4. Opt to not drive 

If you’re going into the city, we suggest walking, taking the T, or grabbing an Uber. Parking is a nightmare, and the city of Boston is extremely happy to dole out parking tickets.

5. Boston Common: America’s oldest public park!

Boston Common - Visit the Oldest City Park in the United States – Go Guides

And, it happens to be our favorite place to hang out on a summer day. Grab a blanket and some snacks and set up a picnic with friends.

6. Forget the accent

Don’t walk around testing out your Boston accent or asking somebody local to say, “Park your car in Harvard Yard.” Cars aren’t even allowed there.

7. What not to call Boston

Only tourists refer to Boston as “Beantown”, so we’d advise leaving that one at the airport. You’d be accurate to call it “City of Champions”... but best not to parade around saying that aloud. 

8. Want to get out on the water? 

Paddle Boston - Charles River Canoe & Kayak :: Sales, Rentals, Trips,  Instruction, and Gear in Boston > Rentals

Head to the Charles River and rent kayaks and paddle boards for epic views of Boston and Cambridge.

Rent from Community Boating for our favorite experience on the river.

9. What to skip

You aren’t missing anything if you skip the Cheers bar or don’t snap a photo on Acorn Street. A spot we'd recommend stopping instead: Sandwiches at Sam LaGrassa's.

10. Do hit Fenway Park

fenway park

Don’t skip Fenway Park just because you aren’t a Red Sox “fan”. It’s fun, easy to get to, and the perfect place to get a good sense of Boston locals. Beware: Bostonians take their sports very seriously, so we suggest root, root, rooting for the home team when you’re at Fenway.

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