How to Plan a Group Trip With Friends

I love planning trips for my friends. I think that it’s a great way to do a service to my friends, to spend time with them, and to foster new connections between them. I believe that if all of my friends are good friends with each other, that makes my friend circle very strong.

The biggest trips I’ve planned for friends are two one-week train trips around Japan where I planned an entire secret itinerary. I’ve also planned lots of cruises where I organize the port stops as we go. Countless friends and groups of family have come through Budapest and I’ve taken them around.

People always thank me for organizing these trips, but it’s totally unnecessary. I benefit just as much as they do, and it’s a lot easier than people expect.

The hardest part is just picking some dates and making the trip happen. The best way to do this is choose a few “anchor” people and work with their schedules to find good dates. You book your flights and then start inviting other people. You will never get everyone to go at once, but if you have a few people locked in early, you know that you’ll at least have a good small trip and it will build momentum.

Plan one activity and two meals per day. I have experimented with planning a lot more, but I realized that large groups of people are just much less efficient than small groups, and that bathroom breaks, snacks, people getting lost, taking pictures, etc. cuts into time. People don’t like it when I’m rushing them along to the next thing.

Your two meals and one activity will often fill the day. When it doesn’t, you can always add another optional activity in later. Or you can let someone else suggest something. If it’s a good group of people, you’ll probably have a fun time even if you’re just walking around a new city. At first I would worry about filling up every minute, but now my goal is to just make sure there was a focal point of each day and that we didn’t have to have the low-value discussion of where to eat.

There’s often the misconception that leading is about wielding power. Actually it’s mostly about making good decisions for a group so that they don’t have to exercise that responsibility. It’s a service.

Before a trip I write down all of the things I’d like to take people to do and all of the restaurants I’d like to go to. Then I write a list of the days we’ll be there and start filling it in. I try to choose restaurants that are near the activities, and also try to vary the activities. If something requires a lot of walking one day, I’ll follow it up with something more relaxing the next day.

If I have too many activities, I’ll sometimes put them as bonuses on the days in which they’d best fit. I don’t stress about it if we don’t have the chance to do them, though. You can’t always do everything on one trip.

This method is extremely easy and low stress, both for you and for your guests. Consider doing a friend trip to a place you really like visiting, or even hosting people in your own city. It’s a very satisfying way to provide some value to your friends and to strengthen relationships.

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Photo is Ginza in Tokyo. Japan is one of my favorite places to show people around.

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