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I think you'll be happy with either stroller, it's more of a question of what will stress you out more.

Personally, I would feel most comfortable wearing the baby and using the smaller stroller when required. I would definitely bring baby's carseat for the cab ride - it's a long ride from LaGuardia.

This time of year midtown is SO CROWDED that the bigger stroller might stress you out. But the joovy caboose looks smaller than my citi mini, and if you'd rather walk than ride the subway, the 7 year old might want to ride (idk how much of a walker DD7 is)

Another thing to consider is stroller wheel size. If it's supposed to snow, it might get slushy and you might want whichever stroller has bigger wheels. As for the bigger basket, I wouldn't leave much in your basket when you're in touristy, holiday crowds. Too easy for pick-pockets to take advantage.

It's also worth investigating whether any museums you want to visit allow strollers. I think most do, but I'd look into it.

Have fun! It's such great time to be in the city! I grew up outside of NYC and now live in Texas and I miss it so much this time of year!

I would not bring a car seat; Legends car service is fantastic for trips to and from the airport and has rear facing or forward facing car seats; they prob have boosters too (lo1 is still forward facing so I haven’t checked!). They’ll bring whatever combination of seats you need and you can book ahead of time online.

For trips around the city, there are Uber’s that haVe immi go seats. Not ideal but better than nothing

Otherwise public transport is key. For the strollers, think about whether the subway stations near your hotel and destinations have elevators. On the uws, the 1/2/3 has elevators at 59, 66, 72, and 96. B/c doesn’t have elevators except at 59. We only take our big stroller if we’re using those stations, otherwise umbrella stroller or carrier.

@lindseykaye: hey! a couple of things---a brand new CAMP store just opened in the Hudson Yards. There's also a Dylan's Candy bar there (there's one near the first CAMP location, too).

But more importantly, your hotel is super close to the best cookie place in the world, Levain. You HAVE to go get a cookie from there. You are also really close to Central Park and could go to Wollman rink for some ice skating or just go to the playgrounds.

If you want some fun places to eat with kids (I'd try slightly off hours, like an earlier lunch or an early dinner), you can try Black Tap or Sugar Factory). CityKitchen is good for a family if you are near Times Square, or Empanada Mama is a favorite of my kids if we meet my husband when he gets off work.

@lindseykaye: hey! a couple of things---a brand new CAMP store just opened in the Hudson Yards. There's also a Dylan's Candy bar there (there's one near the first CAMP location, too).

But more importantly, your hotel is super close to the best cookie place in the world, Levain. You HAVE to go get a cookie from there. You are also really close to Central Park and could go to Wollman rink for some ice skating or just go to the playgrounds.

If you want some fun places to eat with kids (I'd try slightly off hours, like an earlier lunch or an early dinner), you can try Black Tap or Sugar Factory). CityKitchen is good for a family if you are near Times Square, or Empanada Mama is a favorite of my kids if we meet my husband when he gets off work. Crowds are super insane right now in front of the Christmas windows at the department stores, so if you can ever go during off hours, it's more fun. Don't Miss the Saks 5th Avenue Frozen 2 themed Windows. They have a little Frozen 2 walkthrough inside Saks too, but it may be sold out now (only $5 ea).