Boston with a 2-Month-Old: Our First Trip with a Newborn (and What We’d Do Differently)

Flying with a 2-Month-Old (Thank You, Delta)

We flew Delta, and two little things made the flight so much easier:

• Fidget spinners with suction. These were absolutely great. They stick to the tray table, so we weren’t constantly dropping them on the airplane floor and wiping them off. Finley was almost four months old when I first wrote this post and still loved them, so they’ve gotten plenty of use since.
• Noise-cancelling baby ear muffs. Finley wore them during takeoff and landing while drinking a bottle or using a pacifier, and he didn’t mind them at all. He didn’t wear them the whole flight, because they made it harder for him to sleep, but they were perfect for the loudest parts.

Our biggest advice: don’t introduce anything brand new for the first time on the plane. We practiced wearing the ear muffs around the house before the trip, so they weren’t a surprise. Test everything at home first, so you already know what your baby will tolerate.

A few more things that are good to know before you fly with a newborn:

• Lap infants usually fly free. On U.S. domestic flights, babies under 2 can typically ride on your lap at no cost.
• Breast milk and formula get a pass at security. They aren’t limited to the usual 3.4 ounces. Tell the TSA officer, and they’ll screen them separately.
• Pack a copy of the birth certificate. Airlines can ask for proof of age for lap infants. For two-mom families, having it on hand is extra peace of mind.

Getting Around Boston with a Baby (We Skipped the Car Seat)

We used public transportation for most of the trip, and honestly, it was one of the best decisions we made. It got us around the city fast, with zero parking stress.

• Get a CharlieCard, or just use your phone. We paid $25 each for the weekend. You can also tap your phone wallet instead, so you don’t need to make a special stop for a card.
• The baby rides free. Little kids ride free with a paying adult, so Finley didn’t cost a thing.

Why we chose the subway

We did not want to haul Finley’s car seat all over the city. We had debated bringing our Nuna car seat everywhere and hoping it survived the weekend. Instead, we checked it at the gate for the flight and didn’t drag it around the city.

We also brought our Nuna TRIV stroller and LYTL bassinet, because Finley liked the bassinet way more than his car seat. We checked the bassinet at the gate too and hoped for the best. And honestly? It came back completely fine. Thank you, Delta Airlines. 😂

Leaving the car seat behind made Boston so much easier. We could hop on the subway, walk everywhere, and keep Finley comfy in the stroller and bassinet.

Where we stayed

We stayed four days at a hotel near Quincy Market, the Bostonian. It put us within walking distance of the market, the North End, and the Sam Adams taproom, with subway stops close by for everything else.

Where to Eat in Boston with a Baby

One of our favorite parts of traveling is obviously the food, so having a baby was not going to stop us. The trick is picking places with a little flexibility: room for a stroller, outdoor seating, or a corner where you can feed or soothe without stress.

• Saltie Girl (Back Bay, 279 Dartmouth St). They have both outdoor and indoor seating, which is so nice when you’re traveling with a baby and want options. And obviously, if you’re in Boston, you need the lobster roll. The sticky bun also deserves its own fan club. Come hungry.
• Tatte Bakery & Cafe (Beacon Hill, 70 Charles St). If you want to eat here, get there early. It was packed when we went. The breakfast menu is huge, with a whole lineup of sweets, coffee, and tea, and it’s the kind of place where you can take your time before heading out for the day.
• Ciao Roma (North End, 5 North Square). Full disclosure: we didn’t actually get to eat here! It was full when we walked by, so if it’s on your list, plan ahead.

Boston was gorgeous in the fall, and it was so nice to be outside with Finley. Our rule for this trip: pick a few things we really wanted to see, and leave plenty of room around them for feedings, changes, and naps. These spots were perfect for that, because you can wander at your own pace and leave whenever the baby is done.

• Boston Public Library (Copley Square, 700 Boylston St). It’s gorgeous, and the architecture alone makes it worth the stop. There’s a beautiful courtyard where you can sit or stroll, and people are actually in there studying, which made us feel like we’d accidentally walked onto a movie set. 😂 Easy to add to any day without spending the whole day there.
• Harvard (Cambridge). We took the subway over and walked around campus. Obviously, I had to have my Elle Woods moment. You don’t need a plan here: just explore, take pictures, and go at your own pace.
• The North End. It honestly feels like a little Italy right in Boston, packed with restaurants and bakeries. It was one of our favorite areas to wander, because you’re not rushing from one attraction to the next. We walked right past Ciao Roma, but it was full.
• Quincy Market (206 S Market St). There’s a ton happening around the market, with food, shopping, and plenty to see as you walk. The Sam Adams taproom is right nearby, too. Since our hotel was close, we could pop over, stroll, and keep moving when Finley was ready.
• Salem (day trip). We also spent a day in Salem, just north of Boston. Fair warning: we didn’t pack for rain and got stuck there in the rain. Learn from us and bring rain gear for everyone, stroller included.

Good to know: the library and Quincy Market are easy with a stroller. Beacon Hill’s brick sidewalks are bumpier, so a carrier helps there.

Map of Our Baby-Friendly Boston Spots

Every place from this post, in one spot. Tap a place to see it on the map and get directions straight there.

Fun Paid Activities

• Boston Freedom Trail Walking Tour. You can walk around with your kids and learn some history while burning some energy.
• WHALE WATCHING. This one is super fun and you can see large whales, which every kid is usually so excited on the tour.
• Boston Tea Party Museum. We found this one to be so much fun. Kids can learn and throw some tea into the harbor.
• New England Aquarium. Prepared to be amazed at this aquarium. This is great to escape the cold or rain, and you will all love it.

What We Packed for Traveling with a 2-Month-Old

Having the right gear made a huge difference. These are the things we were so glad we brought:

• Nuna TRIV stroller and LYTL bassinet. This bassinet stroller worked perfectly. Finley liked the bassinet way more than his car seat, and it came back from gate check just fine.
• Noise-cancelling baby ear muffs for takeoff, landing, and loud places.
• Fidget spinners with suction that stick to the tray table, so nothing ends up on the airplane floor.
• Bottles, for feeding during takeoff and landing.
• Snacks for you, because the baby isn’t the only one who gets hungry on the go.
• An extra outfit for the baby and for you. Trust us.

What we wish we’d packed: rain gear. A stroller rain cover and rain jackets would have saved our day in Salem. Pack them even if the forecast looks clear.

What We Learned Traveling with a Two-Month-Old

The biggest thing we learned: having a baby doesn’t mean you have to stop traveling. It does mean changing your expectations.

Before Finley, we probably would have planned every hour of the trip. With a two-month-old, that just wasn’t happening. Sometimes we needed to stop and feed him. Sometimes we needed to change him. Sometimes he needed to sleep. And sometimes we were ready to leave somewhere because the baby was done, even though we weren’t.

And that’s okay.

What worked for us was planning a few things we really wanted to see and leaving lots of flexibility around them. The right gear helped a ton, but the most important thing was simply being willing to adjust.

What we’d do differently

Pack for rain. We didn’t, and of course we ended up stuck in Salem in the rain with a two-month-old. A stroller rain cover and a couple of rain jackets take up almost no room, so bring them no matter what the forecast says.

Would we take a baby to Boston again?

Absolutely. Was it different from traveling before baby? 100%. Was it more work? Definitely. Was it worth it? Every second.

Finley came with us, we explored Boston, ate some really good food, and made memories as a family of three. That’s all we wanted from the trip.

You don’t have to wait until your kids are older to travel, and you don’t have to wait until the world feels perfect for families like yours either. You just have to slow down, pack a little more, and let the itinerary change.

Watch our Boston Trip

We also filmed our trip to Boston with Finley, so if you want to see what traveling with a two-month-old actually looked like, check out our video below.

Boston with a Baby: FAQ

You Can Do This

Your first trip with a baby won’t look like your trips before, and that’s the best part. Go slow, pack the snacks, and soak it in. Whatever your family looks like, you belong out there too.

Looking for more LGBTQ+ friendly getaways? Read about our fall weekend in Saugatuck. Planning ahead for your little one in other ways? Here’s how we started a 529 plan the week our son was born.

Got questions about traveling with a baby? Drop them in the comments or send us a message on Instagram. And pin this post for your first family trip!

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