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Traveling to NYC and Boston With a Toddler

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Recently my husband and I took our 21-month old daughter on a weeklong trip to NYC and Boston, and although we’ve been to NYC a million times, and took our daughter when she was a year old, going with a toddler was a whole different experience. So here’s a trip report from a mom’s perspective.

New York City with a Toddler in Tow

We took our amazing but large UppaBaby Vista, and I can’t tell you how many times that trip I wished I had just given in and bought that umbrella stroller already – because the sidewalks of NYC are small and there are LOTS of people bustling to get around. And the restaurants are tiny, many without highchairs or changing tables (we got to become experts at changing her standing up.) Most of the ones we went to did not have room for a stroller, so we’d have to park our stroller outside on the sidewalk and hope it was still there when we came out (thank you Shake Shack for your indoor stroller parking!)

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Pre-baby, we would walk around, shop, eat, the usual. With toddler in tow it’s all about how do I entertain you all day long. And taking the subway? Forget about it (did I mention how gargantuan and heavy our stroller felt this trip?). We did take the Metro a handful of times, and the best is to just forgo the stroller all together if you can, and wear your child. But that doesn’t work out so hot if you know you’re going to be out and about all day, and aforementioned child is weighing more and more each day. Also, toddlers don’t like to walk forever, eventually they poop out and want mommy to hold them the rest of the 10 blocks, so to us, our stroller was a necessity.

We ended up taking more cabs than we ever have before. And we didn’t often venture super far from our Upper West Side home base. What NYC has going for it  – Central Park. We easily spent almost an entire day here. Little Miss loved the Castle playground, horses, musicians, and all of the other activity surrounding us – and we loved sitting on a bench. We also attempted a trip to the Manhattan Children’s Museum, but be forewarned, on cold days with a lack of options to entertain children with, it appeared every single parent/nanny in the world goes there. There was seriously a line stretching outside and around the block! So we opted to skip that and instead indulge in some delicious Chinese-Peruvian cuisine at Flor de Mayo instead (NOTE: Getting seated by the fish tank to keep the kid entertained is key).

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And one can’t miss the American Museum of Natural History with a kid – although fair warning, attempting to go during Spring Break is the equivalent of going to Disneyland during the holidays. But there are enough dinosaurs, whales and dioramas there to awe both child and parent. After hitting up our fave NYC spots like the Chelsea Market and High Line Park, and getting to try some new eateries (please go and get the pork buns at Momofuku Noodle Bar – to.die.for.), we were ready to bid NYC adieu.

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Staying with Airbnb

Soon after we flew off to Boston for the very first time. We stayed in Cambridge as we were visiting family at Harvard, and it was an ideal location, especially with a tot in tow. Instead of going the hotel route, we chose to use airbnb, which I highly recommend, to rent a 1-bdrm apartment for the duration of our trip. It was perfect. Great location right across from the gorgeous Cambridge Public Library (which has an amazing children’s floor), and having a bedroom with a door that shut was amazing since Little Miss goes to bed earlier than we do and we didn’t want to have to lie there in the dark for hours playing on our cells (who knows what I’m talking about?) There was a full kitchen, which is great for making snacks, etc. It was also less expensive than getting a hotel room. Win-win.

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Exploring Boston

Cambridge itself is super charming. The brick buildings and cobblestone streets made me feel like I was in Harry Potter. It’s lovely to stroll through the gorgeous Harvard campus and peruse Main Street. Of course, Little Miss loved the World’s Only Curious George Store. And another perk is that Boston is just a short Metro ride away, and is small enough to be able to walk everywhere.  We did part of the Freedom Trail while Little Miss napped in her stroller and ate the requisite cannoli at Modern Pastry. Then a short hike over to Faneuil Hall for some decadent lobster rolls and creamy clam chowder. The great day was capped off by a date night (gasp!) at the amazing Giacomo’s followed by “the best ice cream in the world” at Toscanini’s.

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The following day we visited the Boston Children’s Museum which is kiddie heaven. One could easily spend the entire day here, which is good, because admission for 3 was not cheap. And on a particularly icy day, it was the best use of our day. And of course, one does not go to Cambridge without eating at the college-town institution, Mr. Bartley’s Gourmet Burgers where one can order The Viagra, Mindy Kaling, or Conan O’Brian, just to name a few (I went with The Viagra, and it was delicious!)

All in all, it was a memorable and fun trip that we’ll treasure forever. Traveling with kids isn’t the easiest, but so worth it, in my opinion. I already can’t wait for next little family adventure!

Meet the Author | Esther Carlstone


Esther is the mother to a silly 20-month old daughter who hates wearing clothes. Born and raised in Southern California, she attended UCLA where she received her Bachelors Degree in English and continues to live and love Los Angeles many years after. After a decade-long stint as an event planner, she is now a writer/editor for various websites and blogs about all thing lovely at her site, A Lovely State of Mind. She's hates trolling through unorganized sales racks and is obsessed with fashion, food, travel, pop culture, Instagramming, good design, and too many TV shows to count. Oh, and coffee totally counts as a food group (the main one if you have a kid.) You can find Esther on her blog, Twitter, Instagram, and Pinterest.

3 Comments
  • July 8, 2013

    It sounds like you were able to enjoy your trip to Boston, even with a toddler. I have heard that Boston is actually a very family-friendly city to visit.

  • July 9, 2013

    Linda, it was! It was a much baby-friendlier city than NYC in my opinion.

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