Caboose RS Sit & Stand Double Stroller

4 in total, with two children. I don't drive and we walk daily, in all weather. I had a Graco Comfy Cruiser as my daily driver. Less than $200 and it was an absolute workhorse. I used it for over 6 years, between the two kids. Huge basket was perfect for grocery shopping. We also had a Joovy Caboose, for the short period of time when my older child was not a reliable distance walker, and needed a place to rest. And then two running strollers - a Chariot Cougar 1 and Cougar 2 (single and double versions of the same stroller). My youngest is 4 and we are still using the Cougar 1 for runs together.

In-line is so much easier.

Depends on how old your first is. I have a joovy sit and stand that’s good if your oldest will be 2.5-3+ when baby is born. Younger, I’d get a full double. Or, just be a cool mom and get a wagon. Wagons are the same size (usually) as a double stroller front to back but way more useable space. I have a larktale caravan for my two and it’s amazing. It even has a car seat adaptor for newborn days.

Having maneuvered both, trust me that the in-line strollers are worse. The number of ankles that would be clipped because it is so hard to gauge depth… Side by side is wide but much easier to control your footprint.

My older kid had one really good tantrum when she realized she had to walk and then she was fine after that. We ended up getting a secondhand Joovy Caboose that we really like for neighborhood walks, but otherwise my older kid just walks.

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.

I took a Joovy Caboose when we went to DisneyWorld and it worked amazingly. It’s technically a double stroller with a spot to sit or stand plus the reclining seat in the front. It was perfect to hook a diaper bag to, is easy peasy to fold up, and overall is just a great stroller. I’m going to Disneyland in a few months and that’s one of my top things I’m hauling with us!

The side by side strollers are a pain to navigate around the crowds….I wholeheartedly suggest the joovy caboose! It was a dream in Disney World and I’ll be buying one secondhand solely for our Disneyland trip in the Spring.