How to Spend 2 Days in Boston

North America, Ultimate Travel Guides

As a history geek, pastry addict, and whale enthusiast, I loved Boston. There’s something about the city and what it offers that makes traveling there a unique experience. I’m somewhat low-key jealous of people who live there. Must be nice.

Jealousy aside, here’s how to spend 2 days in Boston!

Introduction to Boston

USA

Official Language(s): none at federal level, English is considered the national language

Currency: U.S. Dollar

Emergency phone number: 911

When to Go to Boston

September – October

Go in early September if you plan on catching a game at Fenway Park. But if baseball isn’t your top priority, try to aim for the leaves changing. Fall in Boston is so, so pretty. The weather is crisp and cool. Or it’s pouring buckets. There’s really no in between. Bring an umbrella.

Where to Stay in Boston

HI Boston Hostel

Boston doesn’t have too many hostels, so unfortunately there isn’t too much to choose from in the way of cheap accomodations. Luckily the HI hostel chain has a location here within walking distance to the Boston Public Garden.

How to Get Around in Boston

MBTA Pass

Much of Boston is pretty walkable, although the city does have pretty good (and surprisingly cheap!) transportation options. Worst case scenario, you can always get an Uber.

Where to Eat in Boston

Mike’s Pastry

My Uber driver’s parting words to me as he dropped me off in Little Italy were, “Make sure you check out Mike’s Pastry, best cannolis ever.” Strong words, Uber man. I had a cannoli in Florence that knocked my socks off, so there’d be a lot to live up to.

The line was long, and halfway through I wondered if I should just call it quits. I’m so glad I didn’t. Uber man was right, the cannoli brought me right back to Italy.

Trattoria Il Panino

There are so many great dining options in Little Italy, that it’s hard to just pick one. Trattoria Il Panino stuck out because of the classy atmosphere and killer delicious homemade pasta. I’m so glad they believe in portions by the truckload. It makes for fabulous leftovers.

Neptune Oyster

Boston has, to my best estimate, six million places to get seafood. Probably. Everywhere I looked, I saw some form of a seafood joint. It was awesome.

I’m not really an oyster person (it’s the consistency, not the taste) but the casually crowded Neptune Oyster is a classic stop. Really, it’s hard to wrong here.

Espresso Love

I wouldn’t be me if I didn’t try coffee from every nearby establishment. I joke, but only kinda. Espresso Love won me over. First of all, the staff are a delight. So nice and so accommodating (I was traveling with a friend who has Celiac’s and they were super helpful in making sure she got what she wanted.)

The coffee and made-to-order pastries were so good. Apparently this an offshoot of the one in Martha’s Vineyard. So… I better go to that one too.

Day 1 of 2 Days in Boston

Museum of Fine Arts

Every day at 10:30 a.m., the Museum of Fine Arts has an hour-long Highlights of the Museum Collections tour. It’s free, and a great way to see the coolest displays. If you’re short on time, you’ll hit just about everything. If you’ve got plenty of time to spare, make mental notes of exhibits to come back to.

My personal favorite was the Impressionist Collection (of course). They even have a Monet room. I about died of happiness.

Isabella Stewart Gardner Museum

I waited outside in the rain without an umbrella for an hour to get into the Isabella Stewart Gardner Museum.

It was 100% worth it, but buy a ticket in advance. My point is, this is possibly my most favorite museum ever, and I feel like I’ve seen 12,000. Isabella Stewart Gardner wanted the museum to be an experience. She hit the nail on the head. I felt completely immersed in the artwork, like every piece was meant to be there.

Fenway Park

There are a couple of ways to see Fenway Park. First is the old fashioned way; buy a ticket and watch a game. But some of us don’t have the time/can’t be bothered with the sport. That’s okay, Fenway offers tours of the famous space that take roughly an hour.

Harvard Square

Harvard Square has been a gathering spot for ages. You can start here, then poke around Harvard’s campus. It’s a beautiful campus with museums open to the public. Not to mention, it’s just fun to walk around.

Day 2 of 2 Days in Boston

Copley Square

Copley Square is the hub of Boston. There’s always something taking place there, from farmer’s markets to a demonstration. And there are some gorgeous, iconic buildings for your visiting enjoyment.

Trinity Church

Let’s start with Trinity Church. It blew me away, it was so beautiful. Built in 1877, it’s been wonderfully preserved. The man who designed the interior, John La Farge wanted to create “the feeling that you are walking into a painting.”

He succeeded.

Boston Public Library

You’ve definitely seen the Boston Public Library in a movie or show. The green lamps are instantly recognizable. But beyond that room is a gorgeous library that I could spend hours in. I might even study.

Boston Public Gardens

If there’s one thing I love about giant cities, it’s the effort they put into creating a massive greenspace. Boston Public Gardens is stunning, and there’s so much to see.

My childhood reemerged when I saw the Make Way for Ducklings statue. How great was that book?

Freedom Trail

The Public Gardens are right by Boston Common, where you can start the Freedom Trail, either by yourself or with a tour group. If you’re a history nerd, you’ll love it. Every building and area that had some role in the lead up to the Revolution is highlighted.

Whale Watch at Long Wharf

This will take a bit of fanageling to fit in, but a whale watch in Boston was one of my favorite experiences. A ship will take you far out into the ocean, and you’ll get to see whales in the wild. It was breathtaking.

I don’t really have any pics cause, uh… whales move pretty fast. But you’re guaranteed a whale sighting. If not, they’ll send you a rain check for a future watch.

Cost Calculator

Know Before You Go

Driving here is an exercise in frustration. Roads are old, windy and narrow. Getting in and out the city takes patience and time. I hardly know how Bostonians do it. So if you’re planning a road trip or wanna take an Uber, keep that in mind.

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Safe travels!

-Maggie

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