Three generation travel has become a once or twice yearly event for us. My folks, my sister, and my nuclear family have now done a handful of trips together. Paris and Osaka were the first two, followed after a long hiatus due to Covid by trips around Korea, Taiwan, Ishigaki, and back to Osaka.

What makes these trips fun for all.
A foundation of strong planning, and freedom for everyone to do something they like.

What does this mean.
Right now, with an unpredictable toddler in the mix, this means minimizing room for surprises. I book direct flights only these days, which is greatly aided by my home airports being SFO/SJC and ICN/GMP — massive hubs for international and domestic flights both. I always select seats in advance. I request meals for the kids when I can.

I book the most comfortable hotel with connecting rooms and suites possible at my destination (I could write many pages about this sub-topic), and I generally splurge on the hotel-provided transportation. I want them tracking my flight and ready to go when I land, and I want them to call ahead and usher us in the door when we arrive.

Those two things are usually more than 70 percent of the expense, and they tend to be 90 percent of the possible headaches.

What else do I do to prep.
Make a Google Maps List of the area around the hotel, with lots of pre-vetted dots for everyone to explore.

I click virtually every single business around a many block radius around the hotel, and I add the good ones to my List. I share the List with all the adults who are on the trip, with some notes for what each place might offer of interest.

I’m trying to create safe and high probability conditions for serendipity. I’m trying to let everyone discover on their own, but provide helpful guidance. Especially if they’re minding one of the kiddos.

What else.
I try to make a lunch reservation at a very yummy place.

This is for me, since I like to try good restaurants, and also for the group to break bread all together at least once per trip. It’s hard to get coordinated for each and every meal to be shared. It’s nice to do, but everyone being hungry at the same time is a low odds event. Plus large groups at restaurants are hard for everyone.

For breakfast, I either opt the early risers into the hotel breakfast offering so they can go on their own, or if there are better offerings around the hotel, I recommend them on my Google Maps List.

One thing I try to do upon arrival at the hotel is take the first meal as room service, with the whole family present. It serves as sort of a kickoff meal — orientation if you will.

What about stuff other than food and lodging.
I leave that almost entirely open.

What is drawing us to a place? If it’s a beach, then I make sure we are staying right on that beach. If it’s a vibe, then I make sure we are staying in the middle of or with direct access to that vibe. If it’s a museum, then I check the access to that museum and whether I need advance tickets. And so forth.

Most of my foreseeable problems I try to solve with my choice of lodging. As described in my First Blog Post:

How do I move the odds (of serendipity) in my favor.
1. I pick a neighborhood where serendipity is likely.
2. I look for quiet side streets off main drags.
3. I use Google Maps Street View to ‘drive around’ the neighborhood for visual cues of charm.
4. I pick a hotel or B&B next to a cute cafe. (I don’t care about stars; I do care about ratings.)
5. I don’t set a strict itinerary. I pick a handful of things I’d like to do, then let the days unfold.

This is not easy to do with a multigenerational trip, given that the whole fun of a big family trip is shared and separate space, and that connecting rooms/suites and large comfortable Airbnbs are not easy to come by.

So, you just have to start planning well in advance. I’d say three months plus.