Well, dur, right? If it’s possible to not invite The Needy Friend, The Drama-making Friend, or The Prone To Sulking Friend – don’t invite them. The best co-travelers are good-natured, adventurous, self-entertaining, and compromising. Even if they’re none-of-the-above, they should be independent so if you want to do something they’re not interested in, they’ll happily do something else on their own.
In my experience, it’s easiest if one or two people are in charge for the big purchases. After the trip, you can post the final charges on your private Facebook page and your friends can Paypal you the money. For our trip, I booked the hotel and the two friends who contributed their vehicles for driving bought all the gas.
I’m a firm believer in the open-ended travel plan – enough planning that you won’t miss the important stuff, not so much planning that you feel smothered or can’t change things up. We planned when we’d see The Important Stuff and researched a barbecue place, but we left plenty of space for alone time and poking around.
You know what makes people unpleasant to be around? Being hungry or tired. It sounds mom-like, but bring snacks and water to share and make sure you have plenty of down time. Walking around a new city in the sun is oddly exhausting.
You know what else makes people unpleasant? Being in a group for 16 hours (or maybe that’s just me?). Make sure you all have time to spend however you’d like and don’t hesitate to opt out of stuff if you just want to read in the park by yourself.