Hi Jess, I feel you on the OOT bag dilemma. For a while I was torn on getting them because our group was filled with veteran travelers so a lot of them would know what to bring already. I made a very very simple OOT bag maybe two weeks before we left. I did one bag per couple and all the singles received their own bag. I included a beach mat, an electronic fan, bottle of sunblock, welcome note, and our magnet favor. I was worried about not having enough in them, but found that simple was the way too go since most people didn't expect to get anything at all. EAch guest received one at check-in. I got rave reviews for them despite the small selection of items included. We thought about giving them out before leaving but it wasn't really feasible considering I did them only two weeks before leaving. Plus, not everyone was local and we wanted everyone to enjoy the surprise of getting a treat when checking in. We fortunate though, because we didn't have too many to carry since we only had 25 guests. We were able to put all of them in suitcase.