How to Have a Fun Weekend in Boston

History, good food, cool walking tours and cannoli... what's not to like about Boston? Here's how we spent a fun weekend in Beantown (with a baby in tow!).

I NEVER USED TO SAY NO TO A COOL TRAVEL OPPORTUNITY.

But when my husband asked if I wanted to meet up with him on a work trip to Boston, I hesitated. It meant flying by myself with a 5 month old baby, and then traveling with said baby. How much would that change the dynamic of our trip? Would it be so stressful and exhausting that I’d wish we’d just stayed home?

Ultimately, I decided to go.

I figured Boston would be a great place to travel with a baby. It’s compact, walkable, plus people seem to be really family-oriented based on what I’ve seem of Bostonians in the movies. ALWAYS a good way to judge people and places, right? I mean, Mark Wahlburg is from Boston, and he’s all about “saying hi to your mother for me.”

We ended up having a great time, and are so lucky to have a flexible baby. We even enjoyed two nice dinners out while the baby slept in an Ergo carrier. I know these days are numbered, so we’re enjoying it while we can.

HERE’S HOW WE SPENT OUR WINTER WEEKEND IN BOSTON.

Where We Stayed:

We dropped out bags at the Chandler Studios in Boston’s South End. Boston is one million years old, and when it comes to hotels, we all know that means teeny-tiny rooms. Chandler Studios offered nicely appointed, standard-sized rooms (unlike the Chandler Inn across the street, which had shoebox-sized rooms according to my husband who’d checked out both); clean, modern and featuring a kitchenette– perfect for storing breastmilk and washing bottles. Or keeping your beer cold. Whatever.

This wasn’t a luxury hotel experience, but it was absolutely perfect for what we needed. Not too expensive, right across the street from a drug store, in a more residential neighborhood full of cool shops and restaurants, yet close enough to walk to Boston Common and downtown.

What we did:

Since we had just over 36 hours in town, we needed to narrow down our activities substantially.

We’re into eating/hiking/seeing historic things when we travel, so we opted to walk the Freedom Trail. This 2.5-mile, red-lined route leads you to 16 historically significant sites — like the Massachusetts State House, old churches, and cemeteries.

History, good food, cool walking tours and cannoli... what's not to like about Boston? Here's how we spent a fun weekend in Beantown (with a baby in tow!).

It was actually the perfect thing to do with a baby in December. We bundled up, got a little exercise and some fresh air, then dipped into a historic church, landmark or restaurant every 20-30 minutes to warm up. At 32 degrees and breezy, Bostonians kept commenting that the weather was unseasonably cold. As a Minnesotan, I didn’t think it was too bad.

You can sign up for a guided Freedom Trail tour, led by actors in 18th Century garb. While I love having someone who can answer all my questions, I find the costume thing to be terribly embarrassing. Instead, we downloaded the free Freedom Trail Walking Tour App, which included maps, GPS, lots of info at every site and allowed us to set our own pace. Recommended!

History, good food, cool walking tours and cannoli... what's not to like about Boston? Here's how we spent a fun weekend in Beantown (with a baby in tow!).

The Trail started about 1.5 miles from our hotel and we opted to walk, stopping for breakfast (more on that next) on the way. King’s Church, Quincy Market (which was totally awesome on the outside and a totally lame tourist trap on the inside), and the Paul Revere house made for great pit stops. King’s Church accepts donations, and the Revere house costs $3.50 to tour. It’s old AF as far as American history goes (1680!) and well-preserved as far as I could tell.

Where We Ate:

Sure, Boston. You’re full of history and stuff… but when we travel, everything is planned around food. Here’s where we ate.

BREAKFAST

I’m obsessed with breakfast, and Flour Bakery + Cafe does one of the best in town.

History, good food, cool walking tours and cannoli... what's not to like about Boston? Here's how we spent a fun weekend in Beantown (with a baby in tow!).

Owned and operated by Chef Joanne Chang, this order at the counter spot does incredible baked goods, coffee, salads and sandwiches. It’s also SUPER busy on weekends, but the line moves fast, so relax. They make the most incredible breakfast sandwich. The eggs are beaten (with lots of cream), then baked, rendering a souffle-like egg, then topped with cheese, roasted tomato, bacon and dijonnaise. And PS I just found this video for how to make it at home! Thank you, internet!

The ultimate sandwich of Chef Joanne Chang of Flour in Boston is their famous breakfast sandwich with a delicious, unique souffle-like egg. Subscribe for more sandwiches: http://goo.gl/Z7lbS Watch more My Ultimate Sandwich: http://bit.ly/WZOWot Flour’s famous egg and cheese sandwich is brought to life by Joanne Chang as she walks you through each step of this delectable breakfast bite.

We also visited Mike’s City Diner— a beloved South End neighborhood breakfast spot. It’s got that 1950s diner vibe, with big portions and friendly service. They weren’t even annoyed when we rolled in with a stroller– they folded it up and put it in a back room for us.

LUNCH

We were only in town for one lunch, and opted to eat in Boston’s North End. Famous for its Italian food, there are lots of great restaurants to choose from– notably, Regina Pizza and Neptune Oyster. We tried to go to the latter, but it’s literally the smallest restaurant I’ve ever seen, doesn’t take reservations and had two-hour wait for a table. If it had just been Josh and I, we for sure would’ve put our name on the list.

History, good food, cool walking tours and cannoli... what's not to like about Boston? Here's how we spent a fun weekend in Beantown (with a baby in tow!).

We did not eat at Neptune Oyster, but you should.

Instead, we went down the street to Antico Forno, a Neapolitan pizza place with ample space. The pizza was nothing special, but it suited our immediate food needs. Plus, even mediocre pizza is still pizza.

If we’d had more time, I would’ve checked out Santarpio’s. Established in 1903 and still family run, the place is legendary. I mean, just go to their website and look at the guy who’s pictured in the header. Seem like someone who knows their stuff. Oh well, next time.

COFFEE:

Mid-afternoon, we stopped at Modern Pastry for a coffee, pastry and general warm-up. Open for over 70 years, this ain’t your hipster, pour-over coffee bar and that’s precisely what I like about it. One of our Uber drivers recommended it over Mike’s (the North End pastry shop everyone talks about). I didn’t think I liked cannoli, but I tried a bite and it turns out they’re delicious.

History, good food, cool walking tours and cannoli... what's not to like about Boston? Here's how we spent a fun weekend in Beantown (with a baby in tow!).

DINNER:

We ate two dinners in town, both within walking distance our hotel. Coppa, Chef Jamie Bissonnette’s intimate and casual Italian restaurant specializing in charcuterie, plus pizza and shareable pastas/proteins. It’s small, candle-lit and dare I say a little romantic… even if you are trying not to spill food on your sleeping baby’s head. Bissonnette, along with business partner Chef Ken Oringer, operate a few restaurants in town (Toro = Spanish food; Little Donkey = “global” cuisine). They’re all excellent choices.

History, good food, cool walking tours and cannoli... what's not to like about Boston? Here's how we spent a fun weekend in Beantown (with a baby in tow!).

My husband is all about Italian food, but I’m all about the Asian cuisine. On night two, we visited Myers + Chang— Joanne Chang’s (remember her from breakfast?) full-fledged restaurant. Inspired by Taiwanese soul food and Southeast Asian street food, it’s big/bright Asian flavors with loads of modern style.

History, good food, cool walking tours and cannoli... what's not to like about Boston? Here's how we spent a fun weekend in Beantown (with a baby in tow!).

Sweet &amp; Sour Brussels Sprouts &nbsp;| &nbsp;Myers + Chang – Boston</p>”>We ordered a lot of things to share, notably the smoked spare ribs, sweet and sour Brussles sprouts, braised pork belly buns, and dan dan noodles. Each item was better than the next, and even my Italian-loving husband was like “this stuff is delicious.”

Of course, no trip to Boston is complete without some clam chowder. Unfortunately, we didn’t have time to eat any in town. BUT! Our flight was delayed, and there are a bunch of Legal Seafood outposts at Logan Airport. Josh and I each ordered a cup and you know what? It was delicious and the perfect send-off to a successful Beantown trip.

What are some of your favorite spots in Boston? Share in the comments– I’m sure we’ll be back!

History, good food, cool walking tours and cannoli... what's not to like about Boston? Here's how we spent a fun weekend in Beantown (with a baby in tow!).

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