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.
Photo is Ginza in Tokyo. Japan is one of my favorite places to show people around.
I would have forgotten about my promise to post this in November if it wasn't for, well, everyone else very tactfully reminding me that I said I'd do it. The timing works, though. My bag is packed for a two month trip that will bring me to thirteen countries by plane, train, car, ship, and even bicycle. I'll be traveling with friends and solo, and will be staying with friends, in hotels, and in AirBnbs. Weather will range from warm and sunny to snowy. In other words-- I'm packed for everything.
Despite being ready for whatever, my bag is extremely light. I keep flirting with my arbitrary ten pound goal, but never quite make it. Last time I checked I was at ten pounds and four ounces. Having such a small and light bag is what enables me to move quickly with minimal preparation. It's critical that I can comfortably carry everything with me in any situation. Even if I have a full day in a city with no hotel, I shouldn't be limited in activity.
If you're new to my gear post, every year I post a full inventory of the items I carry on the road. I've been doing this consistently for eight years and have influenced most other nomads who post gear posts. I'm always trying to strike the perfect balance between agility, preparedness, and adaptability. It's not enough to have everything and to be able to carry it, my gear must be able to span short trips, long trips, formal trips, casual trips, cold trips, and warm trips.
This year I am going to talk a little bit more about how I make gear decisions and provide some alternate choices where they make sense. As I've traveled more and seen investments in expensive gear pay off, I'm more willing to spend lots of money on gear I know will last. However, if you're on a budget or just don't travel as much, you might not get as much utility from the gear as I do. I'm also making an effort to use gear than anyone can buy (unlike the mythical Versace Wool Jeans of years past that are impossible to find). I believe that there is only one item this year that is impossible to get, and one more that requires a trip to Japan.
One of the perks of being a stay at home parent is that you get to take off and do things at off peak times. We've been fortunate enough to do with this big trips like our October 2012 Disney trip where the crowds were considerably light and weekly trips to the grocery store which is s a different place Monday through Thursday.
This time we planned on taking a two day, one night trip to Cincinnati with our kids and before any jokes are made or eyes rolled about Cincinnati as a vacation place let me say, it was great. Our daughters - ages 3 and 5 - had a wonderful time and even though the stuff for my wife and I to do was somewhat limited we both loved seeing them have fun.
If we had so much fun then why did I keep track of every dollar we spent for this trip? Part of being an Epic Dad means making good financial choices for your family and that means using dollars efficiently, in this trip we did that. The other reason is to give other families that read this an idea about what it costs. If cost was no option you and I would fly business class to go ranching in Jackson Hole one weekend and then fishing in the gulf the next. Cost matters.
Based on the weather, cooler on day one and warmer on day two we decided to first go to the Newport Aquarium. The drive took us about 2.5 hours and like all our road trips I made some PBNB sandwiches (peanut butter, Nutella, and banana).