
Joolz
Aer+
Travel-friendly, city-nimble, but tiny storage and struggles off-pavement.

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My son was still a baby himself when my daughter was born (11 months difference) and wasn’t yet walking. Baby wearing was not an option because I could not effectively pick him up and carry him whilst also wearing my newborn. So double stroller was a must. As soon as he was walking confidently and my daughter was sitting well, we switched over to a joovie caboose ultralight… it is perfect for a small age gap, the eldest can be secured properly or get in and out or stand and the youngest can be seated comfortably with a tray. It folds out easily. If you get any pram, don’t get one with loads of parts that need clipping together and instead look for simple one move fold out types.
The perfect option is the Joovie Caboose Ultralight, it’s amazing. The older can be fully secured on a seat they can get in and out of themselves and also stand if they wanted instead… the youngest can be in the front with a tray and a more proper seat. Fold in and out in one click. Wide as a normal pram. Love mine. Not for newborns though so stick it out for a few months then get one, you won’t be disappointed!! Picture of it below. 
I have a similar age gap and love the Joovy Caboose Ultralight sit and stand. It navigates like a normal stroller and my only complaint is that the bottom basket is on the small side. It can be really heavy to push up hills but I just ask my older kid to get out and walk!
Yes! And I should have clarified it's heavy because we have two kids in it, the stroller itself is pretty lightweight.
We switched from our Vista 2 stroller, now that our babies moved up to convertible car seats. Now we have the Joovy Caboose Ultralight. It's a tandem style stroller, folds up well, and weighs 25-ish lbs. We didn't like the basket underneath, it's hard to get to and it's small. We bought it used for $120.
I ordered 3 different stroller and chose this one: [https://www.amazon.com/dp/B01N15BCSV](https://www.amazon.com/dp/B01N15BCSV) It worked well for our 5 and 3 year old. We took it to Mexico and used it all through out the airport. My 5 year old did not sit in it for a long time but it was a LIFE SAVER when going through lines and walking through the airport to our terminal. I just needed something to contain them while we did the logistical things. My 2 year old napped well in it too. It collapses pretty small so you can give it to them at the gate. Highly recommend! I would suggest whatever you buy, test it out with the kids to make sure everyone fits comfortably.
Stroller recommendation: if you're planning to have another child some time in the future, I recommend getting this Joovy stroller - [Joovy Caboose Ultralight Sit Stand Double Stroller](https://www.target.com/p/joovy-caboose-ultralight-sit-stand-double-stroller/-/A-50915415?preselect=50838795#lnk=sametab) It allows an older sibling to sit or stand in the back, has a big storage area underneath, and you can add an adapter that lets you attach baby car seat carriers. I got this stroller along with the baby carrier adapter and later the compatible rain cover (once past carrier age) and LOVED it. I used it with the Chico KeyFit 30 car seat/carrier. I actually never ended up having a 2nd child, but this stroller was still fantastic, especially when my baby turned into a more independent toddler who didn't always want to be strapped into the front seat. Unrelated, but I also super recommend Dr. Brown's Milestones Cheers 360 Spoutless Transition Cups. Annoyingly long name but AMAZING sippy cups and significantly better than other 360 ones. Comes in a couple different colors and sizes, with handles on the smaller size. I was on 7 months of bed rest during my pregnancy, then COVID happened towards the end of it and the world basically shut down, so I tested out nothing. Instead I did certifiably insane amounts of online research.
My kids are a simular age gap and we got a tandum double stroller and still use it now (my kids are 5.5 and 3). Its the joovy caboose ultralight and bought a rear seat so my older can sit and nap when needed. Definitely my favorite for taking the kids around, fairly easy push and fold is simple but its pretty long when folded and doesn't stand on its own when folded. But we've taken it to other countries, farmers markets, pumpkins patches, museums, malls. But yes we do have a bunch of strollers 🤣 a nuna, bombi gear single, the joovy, and we just recently got a radio flyer wagon. Bombi gears makes a double stroller (side by side) which folds really nicely. I love our single one by them. I haven't really found any stroller or wagon great in sand but I don't really go to the beach with one often. I did read of people adding little snow sleds under the wagon wheels to drag it easier through the sand but haven't tried it personally. Good luck!

Joolz
Aer+
Travel-friendly, city-nimble, but tiny storage and struggles off-pavement.

Bugaboo
Butterfly Series
Durable, compact for city travel, good storage, but expensive.

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UPPAbaby
Minu V3 Stroller
Compact travel, decent storage, but pricey, seat not upright.

UPPAbaby
Cruz V3
Durable, massive storage, great service, but heavy and bulky.

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