Boston Overnight Trip (With a Baby!)

This summer, John and I were amazingly lucky to have a month off together. We made it a staycation since we are on a budget, and mostly took day trips around Long Island. However, one thing I wanted to do was visit my friend Caren, who lives in the Berkshires. We’ve been chatting every week for a year and a half as part of a mastermind/accountability group and I really wanted to finally meet her! Since we were headed that way, we figured why not make a pitstop in Boston and stay for a night? I’ve been wanting to go back since I spent a few days there during the cold, harsh winter and we figured this would be the perfect time! We did all this with Hailey, who was 10 months old at the time. It was our first overnight trip with her and we were nervous, but overall it went really well!

For those of you looking to take a day trip/overnight trip to Boston, here’s my experience along with what we did while we were there. We did a very condensed version and I’m sure there’s SO much more to see, but we had a timeline we had to stick by.

Where to Stay in Boston:

We stayed at AirBNB in Beacon Hill. It was such a cute area, but it was really hard to find parking and super hard to maneuver a stroller down the narrow streets and steep hills. To make matters worse, we parked at the bottom of a hill, and had to carry pretty much everything in one trip which was hard. Oh yea, did I mention that it was trash day? Because it was, as luck would have it. That meant that the super narrow sidewalks were now even more narrow! We pretty much had to push the stroller in the street. If you’re looking to be in a cute and trendy area, Beacon Hill was really nice and quiet. However, with a baby, we didn’t really get to enjoy going out to eat or anything so for us it wasn’t worth it.

I would have preferred to stay in a hotel with parking or valet service, where they help you to your room with your bags. Baby’s come with a TON of gear, so it would have been nice to take an elevator instead of a narrow winding staircase! 

What to do in Boston:

The next day, we packed up all our stuff and filled up the car. We took a short drive over to the Boston Public Garden and took the first muni-meter spot we found. It was only for an hour, so we decided to grab some breakfast and head back out after to find more long-term parking. 

Coffee and pastries at Tatte

Address: 70 Charles Street, Boston, MA 02114

We happened upon Tatte’s Bakery along the way, and couldn’t resist stopping there for breakfast. It’s super crowded but moves quickly. We had a Pistachio Cherry Tart and a Chocolate Hazelnut Brioche and both were amazing! Everything there looked amazing and I wish I had taken a picture so you can see. Their website is gorgeous and really matches the look and feel of the place, so you’ll get a good idea of what it’s like. We sat outside on their picnic benches and relaxed for a few minutes with our breakfast, then went off on our way. The weather was so nice that day!

Parking near Boston Public Garden

Since there wasn’t any good street parking (especially since the muni-meters were so short) we parked in a private parking lot under the park called the Boston Common Garage. It wasn’t super cheap, however it was super easy to access and there was tons of parking.

Walk through the park

The first part our Boston adventure was taking a walk through the park. We walked by the Make Way For Ducklings statue, we had tons of little kids running around. They were all climbing on them while the parents were taking pictures.

Then we went to the Lagoon where they had swan boats. I was tempted to get on and take a ride, but it was just so sunny that we didn’t want to get burnt. There was also a splash pond in the park, so if you’ve got little kids who like water definitely bring a swimsuit or towel for them! All the kids were loving it so it’s definitely something that your kids will wanna do if they’re slightly older.

Go on the carousel 

During our stroll around the park, we found a carousel and decide to take Hailey on for her first ride. She loved it and it was really cute to see her so happy. It was only $3 too!

Walk down to Quincy Market

Next, we took a walk down to the Quincy Market and Faneuil Hall Marketplace. There’s tons of stores and restaurants over there! You can go shopping at stores like Gap, Old Navy, Home Goods, Marshall’s, Primark, The Flying Tiger, Crocs… there are a ton more, so get your credit card ready! I went to the Primark which has affordable clothes (it’s like H&M meets Forever 21) and The Flying Tiger, which has all the cutest stuff you don’t need but must purchase. Inside the markets themselves were pretty narrow and crowded, especially with a stroller. But, wandering the streets outside was a breeze.

Lunch and drinks at Zuma Tex Mex Grill

There were a ton of restaurants and eateries all around the Quincy market and the shops, but everything seemed really expensive. There wasn’t really anything that appealed to us very much, so we kept looking for something that excited us. At that point, we found a really affordable Mexican restaurant and decided to take a chance on it. The menu was huge and had tons of options, and the kids meal was affordable. The restaurant itself is downstairs and it isn’t necessarily that special looking. However, the food was really good and the service was great. We loved their food and I even had a margarita!

Walk along the Freedom Trail

After lunch and shopping, we took a walk along the Freedom Trail. We saw the first public school and the Old State House, which has a unicorn on it! There were a whole lot more sights on this trail than we actually did, but we wanted to head back since we had a long drive ahead of us.

Making the drive up to Boston is great for an overnight trip is a great idea if you live in the area. It’s got a lot of history and it’s walking-friendly, which is great when you’ve got a stroller! The winters there get COLD so if you’re planning to go at that time, be sure to pack lots of layers and warm clothing! But, during the rest of the year it’s definitely beautiful. There’s something for everyone- great food, lots of shopping, and tons of history. Even Hailey enjoyed it! I’d definitely want to go back with her when she’s older, since I bet there’s a ton more she’d be able to do.