Terra

It's going to depend so much on how and where you plan to use the stroller, and whether you want something that can eventually be used for a second baby. I don't drive and we knew we wanted 2 kids, so I needed strollers that really worked well and had okay storage capacity. I went through a few different strollers to accommodate different activities and different life stages. All of them were used in conjunction with babywearing because sometimes in the city a stroller just doesn't work at all. I got a City Select first because I wanted something I could convert when we had a second, and the versatility was nice, but all the front to back strollers are so unwieldy to push. Having a tiny baby facing me (preferably not in a car seat) was important to me, and it was a good choice for that, but once both kids were bigger I sold it. I also had a not-quite-umbrella stroller, the Zoe that isn't the super tiny travel size, for those days I wanted to keep it light and only needed it for one kid, but they're really only well suited to smooth floors, like museums, so I only used it if I really needed something small and easy to fold. My second set of strollers, once I knew we weren't gonna have anymore newborns, were a City Mini GT and a Mountain Buggy Duet. The GT is a really solid choice as long as your kid is old enough that you feel comfortable not having eyes on them at all times. Sturdy, handles well, basket is not amazing but it's good enough, folds quickly, and they're popular enough that it's easy to find one used - I think mine was $20 on craigslist and all I had to do was stuff a little piece of cardboard into a spot where the front wheel liked to stick. The Mountain Buggy Duet is relatively unknown but my absolute favorite for when I needed both kids in a stroller. Rugged as hell, smooth to push even with one hand, amazingly shockingly astoundingly narrow for a side by side - I think there's less than an inch difference between it and the City Select single. You can fit this thing on a CTA bus without folding it or blocking the aisle (I did avoid crowded buses with strollers but I surprised a lot of people when they saw it squeeze in). You can take one seat off and attach a shopping basket if you've got one in preschool all day and the other at home with you running errands then put the second seat back in for a weekend zoo trip. It was a pain to fold but I rarely needed to fold it. It's not the best stroller for big kids since it's so narrow, but my oldest was a shrimpy toddler. God, I miss that stroller. If I knew then what I know now I probably would have gotten it and just used it with the basket when my first was born. I also borrowed a Bob double to get the kids to and from school when we were avoiding the bus during covid and it snowed and snowed and snowed and snowed one winter. It did well in the snow but it's so so big, I couldn't even get it in my garage without folding it. If you plan to do a lot of trail walking off road kinds of stuff, a single Bob would be a great choice once baby is big enough, but I wouldn't bother for just city walking.

If you’re looking into different brands, I have LOVED our Zoe strollers. I don’t think there is anywhere to test them out, but I’ve had the single, the double, and the jogger and I have loved them all. They’re awesome for travel too. 

If you’re looking into different brands, I have LOVED our Zoe strollers. I don’t think there is anywhere to test them out, but I’ve had the single, the double, and the jogger and I have loved them all. They’re awesome for travel too. 

Our twins are 3.5 years old, plus we have a 6.5 year old. We have an Uppababy Vista with double seats, plus a piggyback board. That’s our go to for the farmers market, or any local place that will be busy. We have a Wonderfold W4. That is for the zoo, walks to daycare or other local spots that we need to cart a lot of stuff, plus the kids. We have a Zoe Twin. That is for travel or just throwing in quick if we think we might want wheels but aren’t sure. We have two Zoe singles. This is our current favorite configuration for trips- the twins fight when side by side and two singles fit in rental cars better than the double. Plus our 6 year old can still ride when she occasionally needs a break. They collapse at the jet bridge super easily. Flying with the Vista sucked.

ZOE single stroller, make sure you get the right model. It is literally one hand fold by pulling up the seat and it will collapse easily so you can carry the child one hand and carry the stroller another without too much trouble for stairs or getting into the cab.

We had so many different strollers for different purpose. Our fav is ZOE, it is truly a one hand fold esp you have to hold your child one hand while the other hand folding the stroller. A lot of it depends on how crowded the bus is, if it is not too busy then prob no need to fold but it is packed, prob a good idea to fold it up while you sit and hold the child.

I have a 4 year old and a 9 month old! It was so stressful finding a double that made sense with the age gap. If you’re not ready to make a big buy before your trip, I’d rent a double Bob to try it out. We’d have gotten one when baby was born if it were newborn compatible- we love our single Bob and our older will still be comfy in it for a few years. If I were on the market for a double now with my 9 month old, I’d be scoping Bobs out. We bought a secondhand uppababy and immediately sold it to someone else on Marketplace- it was just too small for the wide age gap. My average-sized older daughter’s legs were dangling comically out of the toddler seat. Other moms I know with an age gap wider than 2 years also ditched their uppababy. We’ve loved our Zoe single for our older and will probably get a double eventually when we need it for travel. If you’re flying in, it’s a great, lightweight travel stroller! Only issue is storage, but we hack our way around it with big carabiners and side saddle storage attachments. I ended up purchasing the Austlen Entourage for our big family stroller during a Prime Day. The sit/stand option, the ability to shorten it with one hand if big sister isn’t using it, and the storage are what sold me. It has a bassinet mode for newborns, which I also wanted in case we have a 3rd. Let me know if you have questions about this one! It’s not the easiest to handle as an inline double, but it fits right through every door!

We love our Zoe! My only gripe is that the storage is limited compared to a legit double stroller (common with many travel strollers), but we do well with their side saddle mesh bags and a big carabiner on the handle for jackets and lighter bags.

For reference we love our Zoe for travel if you're looking at it, but it doesn't fit all of your criteria. We've upped the storage capacity with a carabiner on the handle and purchased the side mesh bag attachments for it. We also looked at the Baby Trend Sit n Stand and the Joovy Caboose for compact double options.

We have the single and it fits easily overhead. The twin isn't advertised to fit overhead and I'm not sure it would.

We’ve loved ours for years! I don’t think you’d regret it. Zips around the parks great and couldn’t be easier to fold down at the airport gate.