I'd love to do a padded roadtrip with a group of ABDLs, so that I could wear at a variety of destinations in one go. I've gotten close to doing this on a few occasions, but every time something fell through.
Obviously, attending an ageplay convention and wearing for the duration would be amazing. Unfortunately, most of them are either inconvenient timing wise (Capcon) or have gotten pretty subpar reviews from friends who attended (WCJG), but I may try to go for Teddycon at some point in the next few years or look for a smaller one somewhere.
As a huge theme park enthusiast, I'd also love to do a padded visit to Disney World. However, this would also need to be a group thing with other littles who all fully agree that the trip would be more about engaging the little side than getting the most out of the parks themselves, as I've found doing a full day diapered at a theme park is actually more trouble than it's worth (that said, padded half days to my local parks in the cooler months are amazing).