I think the idea is great! just one thing as a user I was kinda lost with the "concept" posts. maybe you should have less of those "concepts" and prioritize user made trips to show on the top? that way it would encourage people to check out real trips and consider them rather than keep creating and flooding the site with no trips actually filled.
Went to Puglia recently with a group of 10 and one of the things we didnt realize in advance was how hard transportation was. Needed multiple vans/drivers to get around.
btw started a convo and then couldnt find it again. ui/ux