I think I may be the lone tandem stroller lady, but we've travelled in June with a number of combinations of kids from infants to 6 year olds (3 of them the last 2 trips). We didn't use the front tray so the older one could hop in and out no problem, and the little one could lay all the way back. The front seat did recline a bit and our 2.5, 3 or 4 year old (depending on the year) slept no problem when she needed to--believe me, when they're tired there, they can nod off almost anywhere! Plus, with the sunshades on you can create almost total shade for the baby in the back with a light blanket. (You didn't mention when you were going, or maybe I missed it?) The tandems (to us) were much easier to maneuver through crowds, sidewalks and main street shops, although I will say they are not super lightweight from a lifting standpoint. But then again, we were usually folding maybe twice a day, depending on which park we were at. (We stayed at BC and BWV so two of the parks are walkable if you want.) Friends who were with us had an almost 4 and baby in I think one of those Cosco dark green double umbrellas and they were struggling a little with the weight difference, crowds, and going over grooves and bumps. Just my .02, but probably you won't go wrong with whatever you choose because it's really whatever you are most comfortable with. Good luck and enjoy your trip!