Talking to twenty people, and talking to two
Group size changes this job more than the weather, the season, or the route. It changes it more than the subject does. And you find out which job you are doing about ninety seconds before you start.
What twenty people need
A large group is an audience, and an audience has physics.
You have to be heard, which means the quiet observations go first. You have to keep a shape, or the back of the group ends up two crossings behind the front. You have to build in pauses for people to catch up, and those pauses have to look deliberate rather than like waiting.
Most of all, a large group has to be carried. Twenty strangers do not ask questions early. They wait to see whether questions are allowed, and by the time they have decided, you are three stops in. So you perform a little. You project. You make the first ten minutes work harder than they should have to.
None of that is dishonest, but it is a different skill from the one that makes the material good. It is closer to stagecraft.
What two people need
A small group is not a smaller audience. It is a conversation, and if you try to perform at two people they will feel it immediately, the way you feel someone reciting at you across a dinner table.
With two, everything inverts. You stop projecting. You can say the quiet thing first, because there is no back of the group. You can stand still for a long time in front of one facade, because nobody is drifting. And you get asked things constantly, which means the route stops being a sequence and becomes a set of doors you can go through in any order.
You also cannot hide. In a group of twenty there is always someone laughing, always some ambient energy that carries a flat patch. With two people, if a stop is not working, it is silent, and the silence belongs to you.
The thing I got wrong
For a while I thought of the small tours as the bad days. Fewer people, a thinner morning, the arithmetic obviously worse.
Then I read my reviews properly.
The tours guests describe most warmly are not the big ones. They are the small ones, and they say so explicitly. One review says there were only three of them, and that this made it "very intimate and interesting." Another simply notes the group was small and that it was very nice. One pair found themselves on a tour with only two guests, and the review they left afterwards is one of the most detailed I have.
So the mornings I experienced as failures are, from the other side, the best version of the thing I sell. That was an uncomfortable discovery and it changed how I run the small ones. They are no longer the tour I would have given to twenty people, delivered to three. They are their own thing, and I now open them differently.
What actually transfers
Almost nothing about the delivery. Nearly everything about the preparation.
The reading is identical. The photographs and old maps I carry are identical. The decisions about what to leave out are identical, because those are decisions about the city rather than about the audience.
What changes is the order, the pace, and how much of the two hours belongs to me. In front of twenty people I am talking for most of it. In front of two, if I am talking for most of it, I am doing it wrong.
Which one is better
The honest answer is that they are different products and I would not want only one of them.
The large tour is the one where I am proudest of the material, because material has to be genuinely good to hold twenty strangers on a cold morning. The small tour is the one where people actually understand things, because understanding happens in the follow-up question and a big group rarely gets to ask it.
If you want the second experience, you can just book a private walk and have it deliberately. Same reading behind it, same route knowledge, and two hours that are structured around what you keep asking rather than around what twenty people can be kept together for.
Tell me who is coming and what you are curious about, and I will build the walk around it.
The reviews quoted here are on my FreeTour listing, where you can read all of them, including the critical ones.
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