11 Things I Learned on Our First Family Trip: The Good, The Bad, and the Ugly

When my husband told me he wanted us to go to New York City in February with our then-3-month old and 23-month-old sons, I thought he was crazy. How on earth were we going to do that? Sure, it’s something we would’ve just picked up and gone to do before kids – but how were we going to do that now? How would we fit 2 cribs in a small NYC hotel room? How would we carry multiple car seats? How would nap times work?

Despite my concerns, we decided to bite the bullet and go. Before adopting the boys, we had stated that we didn’t intend for our lives and adventurous spirit to be snuffed out. And this, this is when the rubber was about to meet the road.

Heading to the Big Apple

I really don’t love planning for trips, and funny enough, neither does my husband. We love to leave room for fun to just happen. We love for local experiences to jump out at us and restaurants to invite us in with too-good-to-ignore happy hour deals. So, here’s what we had planned: 

• Take a direct flight to NYC departing at 7:00 AM
• Stay at the Hampton Inn Manhattan/Times Square Central for 3 nights. They could “most likely” get us 2 cribs in our room, so we went on that assumption.
• Bring an umbrella stroller for our toddler and no carseat (public transit only)
• Bring a Doona stroller-carseat combo for our baby
• Take a direct flight back departing at 9:00 PM

Seriously, that is ALL we had planned. The rest, we figured, would come to us as it always had on trips!

Getting Schooled: Lessons Learned

I will say that overall, the trip was really fun and enjoyable. We really want our kids to see the world while they’re young – even if they won’t remember it. That being said, we learned a lot about planning, flying, sleeping, and more.

The Good

• Probably the best move we did was our stroller/carseat decision. Having one stroller per kid – scratch that, one lightweight stroller per kid – was the only way we could accomplish this. As much as I admire the Uppababy Vistas around the city (especially the Upper East Side), bringing our heavy stroller would’ve been a mess. Using only public transit, navigating the streets with these puppies was hard enough. Many subway stations didn’t have elevators in easy-to-find places – or elevators at all. 
• Our hotel, Hampton Inn Manhattan/Times Square Central, was also awesome. At less than $200/night (February though), we were right in the middle of the action. It was clean, safe, and did give us two cribs. Did I mention they also had free breakfast?
• Summit One Vanderbilt’s new observation deck was one of the things we got into. It was seriously so great for all ages. Our son skipped through the balloons while we admired the views. It was well worth the price.
• Even a cold visit to Battery Park Playscape was still very fun! The slides and playscape were beautiful and fun for all ages (just ask my husband).
• We bought Cozyphones for the flight and for on-the-go toddler naps. Paired with his usual lullaby playlist, this worked wonders!
• For a long weekend trip, bringing diapers and formula was the way to go I felt!

The Bad & The Downright Ugly

• Probably the rookie-st mistake we made was with the hotel. While nice, we were trapped in a dark room with our two kids at their bedtime (7 p.m.). Though pricier, a suite or Airbnb might’ve helped us enjoy and unwind a bit more together
• I said it before, but I’ll say it again: not all of NYC is wheelchair/stroller friendly! We had to carry the kids a few times and let me just say, I was tired by the end. Bulk up, ‘cause carrying kids is a reality in NYC.
• Flying late at night was rough on the way back. Our older son was so energized from seeing everything that he was wildly overtired at the airport. It wasn’t pretty!
• We forgot any rain gear… and it rained! I mean, seriously, it poured. If you’re going to be walking around the city, just pack an umbrella!
• In the future, I would put a few “wish list” spots on a list and hope to hit a few of them. With kids, it’s critical to be flexible, but if you’re too flexible, you might find that you don’t end up doing anything.

Would I Recommend to a Friend?

I’d rate this one an 8/10, would recommend to some friends. A trip to NYC with littles is not for the faint of heart – and it is not for those who hope to be doing a lot of little-kid-focused stuff. However, for those looking for an adventure (dare I say, challenge?), this is a fun trip that you’ll remember forever. Be prepared to be tired and be prepared to work – but be prepared also to show your children one of the most magical, bustling cities in the entire world!