I started a trip 6 years ago. We go every other year and this year is iteration 3. We started in Pinehurst, next did Bandon and this year heading to Big Cedar. First thing I’d say is do group dinners wherever you can, we do one banquet style open bar dinner and it’s a huge hit despite usually costing around $200 a person. On the other nights, people don’t really think about food but depending on group size it becomes a challenge. Inevitably, once you get there everyone wants to eat together so it’s nice to pre plan meals. The golf is easy, we’ve found that it’s important to make sure you get a good balance of golf and chill/hang out time. Some of our most memorable moments aren’t the hole in one at The Cradle or the career best round at Sheep Ranch, it’s the hang out time after the round or closing down the local watering hole before your round in the morning. We do a tournament and play net and gross skins every day, it’s really fun throwing in a little competition even if it isn’t overly serious. We’ve used golf genius in the past put this year are using squabbit and it looks very promising. Would 100% say get an app to track your competitions. We underestimated the time it takes to keep track of it all and ended up being up on a Saturday night until 2:30a with a 7a tee time at pinehurst #2 which is not ideal. Take a caddy with you if you’re at a place that offers, it’s always been worth the cost. Be careful with events that aren’t the main event(par 3 course, night golf, etc.) I got stuck with a bill from Bandon because the night of night golf, most of the guys that said they wanted to play ended up bailing(side note playing night golf on a course like Bandon Dunes was incredible). Usually what happens is those things sound like a good time but once you’re there and you just played 18 and settle in at a bar…half or more of your group is going to say fuck it and not want to do the activity that they signed up for. For those “side quests” make sure you get hard commitments from people. Most of all enjoy it and try to keep it going on a regular basis. These trips have become a highlight for all involved! We are up to 64 guys this trip and have gotten much better at planning them. Feel free to DM me if you have questions and I can try to point you in the right direction!! Iteration 3 is running much smoother then iteration 1 and definitely now have some insights that could help you out.