Strollers...

You may not NEED it on the ship, but if it's a comfy familiar place for kiddo, it might be nice to have. I saw a fair number of mom's strolling their napping kids around the ship on our TA last year.

I'd personally rather be annoyed by having a stroller and not needing it than needing one and not having it.

And if you do get a new stroller I'd try to get him used to it before you go so it is a familiar, comfy place for him.
Unfortunately for us, he tolerates a stroller when we are adamant he ride in it but doesn't love it. He actually rarely sits in it - just stands in the seat so he can see everything. And, never slept a single moment in a stroller since he was born :rolleyes2 The FOMO is strong with this one.

By the end of a Disney day, he will voluntarily climb in more often so I know his legs will need it off ship and would definitely be annoyed if we skipped it and he decided we needed to carry him.

I went through a good deal of Barcelona after the transatlantic of 2022. The only sidewalk that I found normal to walk on was around the Basilica. Most of the port stop’s have the rock paths and will launch your 3 yr old and leave him singing “all I want for Christmas, is my 2 front teeth.”
I had a stroller until my daughter was 5 years old for those 15 hour days with the ability to nap.
If you absolutely must bring a stroller, and I understand why, I would bring one with medium to large, pneumatic tires. You will be able to walk every where with pneumatic tires of the stroller. You will want/have to carry the small and medium plastic wheeled stroller or child at some point in Barcelona without those.
Look up Italian stroller, see what they sell there. I didn’t see many strollers, but I did see people struggling. Very few wheelchairs except usually locals in a restaurant. I remember thinking as I passed a family that I was so glad I didn’t have to walk around with a stroller on this vacation.

Plan B invest in a hiking style backpack, one that straps on onto the waist to defer weight from the back and shoulders. They make a 50# kid seem like 20#. Search for a toddler carrier or Tula Baby Carrier. I can’t say enough about how shifting some of that weight to your hip bones make a huge difference. I’m sure you will find other places where you will say “let’s go _____, we can bring x with the backpack” See if you can find a few to try. Some are okay, one you will love, one your partner will love. Some are built for women’s bodies some are built for men’s bodies.

This is very helpful, thank you! I think we may give some serious thought to the backpack - he's tall but really don't weight much. I think he'd still "fit" in my Lillebaby carrier but not comfortably. With 3 adults, we might be able to share the load.

The best stroller for uneven terrain are jogging strollers. I would find the smallest jogging stroller that your child can comfortably fit in. I would also just bring it on with you. The less that other people handle it the better.

We have a jogging stroller (we only use it for jogging and hiking) but that thing does not fold down hardly at all! Maybe I can find a used jogging one that folds down better - I can't remember what brand we have.

We used a City Mini on the Magic in the Med; our son was 3 as well. If you have a City Mini, you know how easy they are to fold. We didn't hold up any lines and didn't feel like giant awkward Americans (which we have before when we traveled internationally with a double jogging stroller). Florence and Rome were definitely more difficult to manage d/t the ancient streets but we were so thankful we didn't opt for a cheap umbrella stroller. We saw others struggling. Since that was our normal stroller, he was super comfortable and just napped when he was tired. When we did Pompeii, I put him in a Deuter backpack I bought used. Yes, he was big, but it was one of my better parenting decisions. Plus I burned a ton of calories that day.
We have an Uppababy and while it folds fairly well, I hate to drag something that big and expensive. I'm going to look into the backpack option!
 

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