Comment by mikesabat

My current 'favorite idea I probably won't build' is an sms chat bot that does exactly this for guys in their 30s & 40s. The hard part is actually organizing the group of friends to pick a weekend and location. So a bot that can help with all of that first, is really compelling for me.

OP, let me know if you want to do a user group trying to help us organize a trip.