
Joolz
Aer+
Travel-friendly, city-nimble, but tiny storage and struggles off-pavement.
Running these analyses costs money. Buy through my links to help keep lights on! I may get a small commission.
Tandem for the win (I have the gazelle and it is the workhorse). Side by side doesn't really work in an urban city. It is more like a FU to pedestrians on the sidewalk as you literally block it. I also have a Thule chariot and veer which takes up as much space as a side by side. Maybe the wagon XL is a tiny bit more narrower. It is unwieldy to navigate and good luck if you go to small shops because you can't navigate through the aisles.
Tandem for the win (I have the gazelle and it is the workhorse). Side by side doesn't really work in an urban city. It is more like a FU to pedestrians on the sidewalk as you literally block it. I also have a Thule chariot and veer which takes up as much space as a side by side. Maybe the wagon XL is a tiny bit more narrower. It is unwieldy to navigate and good luck if you go to small shops because you can't navigate through the aisles.
If you live in a dense city then I would recommend a tandem. We use the Cybex Giselle. Side by side isn't practical. It takes up the space on sidewalks (I called it the blocker), barely fits in elevators, and you can't navigate the shopping isles of many downtown stores or even fit through the single entrance door. At our daycare, we have someone that has a side by side stroller and I cringe all the time as the monstrosity comes in and everyone has to shuffle around this beast. I also have the Veer Wagon (quad) and only use it for going out on adventures like the zoo, amusement park, etc. My preference is the stroller in the city (and we have 3 under 3).
We love our all terrain Veer wagon. We have the toddler insert and extra basket. We also used our car seat and bassinet with it until baby could sit with the harness. Both kids love it and it was easy to take on a road trip (took up less space in the car than the stroller). We have a 5yo and 8mo.
A veer 4 seater. I have one and it washes with a hose. I love mine so much lol
17 month gap here. We got the Veer XL with the infant carrier attachment. We love it. Our firstborn is completely over the stroller already so no way were we doing a double.
It’s a bit heavy but doable. I think like 35 pound without any attachments. And it folds down nicely for storage or the car. It has a push and pull option, both of which are very smooth.
If you want the most amazing wagon ever made, that your kid can nap in, get a Veer. They make 2 and 4 seaters, I would just get the 4 regardless. Not worried about napping on the go and want great quality for slightly less get a BOB. I’ve had both and can’t recommend them enough.
I got a mockingbird single to double and I loved it as a single but hated it as a double. And everyone is going to bla bla bla about how more expensive ones are better--and they are for sure better--but I just really dont like the tandem seating. The only single-to-double I would ever consider the bugaboo donkey. I think your younger child will grow out of being okay sitting in the seat with the bad view. I now own a bombi twin *side by side double* and veer cruiser XL (4 seater wagon, but smaller than most). Both of those are more expensive than the mockingbird(when i bought it anyway). I just think as a FTM its so hard to know what youre going to want even for your first kid, let alone future kids. So in conclusion, i generally think single to double strollers are not great, with the only exception being the donkey, something I wasny going to invest in by the time my second arrived.

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.

UPPAbaby
Cruz V2 Stroller
Durable workhorse with massive storage, but heavy and bulky.

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.

Ranked #1
Joolz - Aer+

Ranked #1
UPPAbaby - Vista V2

Ranked #1
Thule - Urban Glide 3 Series

Ranked #1
Bumbleride - Era

Ranked #1
Joolz - Aer+

Ranked #1
Thule - Urban Glide 3 Series