Business 101

No bookings = no tour.

Unless, you base a tour solely around a destination you desire exploring. 🏆  

It all depends on the pillow princess & her motives. Many will need 3+ solid bookings to even consider touring a city. Some cities are not eligible to tour, do that’s a fly me to you arrangement. I myself don’t leave the house without a 50% deposit.

Follow the money!

I go anywhere that makes financial sense! And living abroad makes it a much more deliberate decision than hopping a domestic flight, train, bus or driving myself around the country.  
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Sometimes, it's a FMTY (dinner date minimum, plus travel expenses) that sparks the decision, but usually, it's just a guaranteed dinner or sleepover with the timing of left to my discretion. A FMTY is obviously set for a particular date/location, so I look to expand my time in that city based on the other fun I can arrange on moderately (for me) short notice. My preference is to have a location/time frame set 6wks in advance but the FMTY can sometimes be a 10-14 days notice.  
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If it's the sponsor scenario, then I throw some lines in the water in area and once I've amassed sufficient sincere interest, I work to coordinate schedules. If all the duckies look as if they'll line up just so, then I secure them in their preferred spot and announce the tour looking to fill in any gaps. Between the sponsor and duckies, I know it's an adequately profitable trip and if the gaps get filled then it's a great trip! Occasionally, short of that, if there’s a critical mass of ‘quickies’ (2-4hr inquiries) and if everyone’s schedules align so it makes sense, then that’s the trigger... but that's A LOT more cat herding😵‍💫 and less frequent.
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So collecting serious inquiries (understand/agree to screening/deposit protocol, often even volunteering everything in the first few exchanges without a specific time frame in mind) from various places is super helpful! A particular frozen midwest city with a giant shiny public art installation seems to be popping up lately so who knows, that may be the next fun spot in the spring!

This is a great question! And I actually love questions like this because the business side of this world is really interesting once you slow down and look at it. A lot of things that seem mysterious from the outside make way more sense when you realize this really is a business… just one with a very human layer to it. I digress.

 
I’m glad you asked. For most providers, it’s usually a mix of things, not one single factor. One thing that helps is separating "Touring" and "Sponsored Tours" from "Fly Me To You", because they’re structured differently.

 
Touring (Traditional):
This is when a provider commits to being in a city for set dates and opens availability to multiple clients during that window.  The trip is justified by projected demand: past bookings (if they've been there before), inquiries, pre-bookings, or strong historical performance. No single client is responsible for making the trip happen, and the provider is spreading risk across the schedule.

 
Sponsored tour (how I structure it):
A sponsored tour sits between touring and Fly Me To You. One client anchors the trip with a longer booking (for me, a minimum of four hours), which makes the travel financially viable. That booking gets priority in my schedule, but the trip itself isn’t exclusive. If I arrive early or extend my stay, I may see other clients around that anchor date. At this point, over half of my "touring" falls into this category.

 
Fly Me To You (FMTY/my operation)):
This is fully exclusive. When I fly in for this, you are the reason I’m there and first, and often only, client I see (my preference). My time and energy are reserved for you, and that day is blocked off regardless of the session length, even if it's the minimum. However, anything I choose to do *after* that is entirely my decision and on my dime. It’s designed to feel focused, private, and uninterrupted.

 
As far as how a city actually gets chosen, I’ll use DC as an example because it’s a pretty typical arc and a major touring spot for almost all providers. I started getting a steady stream of emails asking if I ever came out to DC; mostly from social media. I didn’t announce anything right away. I then posted an ad in the area just to see what the response looked like.
When people didn’t read the ad thoroughly (which happens), I didn’t get annoyed, I just explained where things stood. Once there was enough consistent interest to feel solid, I scheduled the trip. What started as a market I visited maybe twice a year is now closer to four, simply because the demand is there and it makes sense logistically. That’s usually how it works at its healthiest: interest first, structure second, travel last.

 
Social media has made this easier too. It lets people get a feel for who you are before you ever land. Shared interests matter more than people think. I’ve had tours happen because of love for college football, books, anime, "shit posting" Twitter takes… all of it counts.

 
Different providers do this differently, but the strongest trips usually aren’t speculative. They’re built around real interest that’s already there.

-- Modified on 12/23/2025 1:58:44 PM

New cities

I was thinking the same—thank you for posting! ☺️ I’m definitely open to adding new cities. I receive many requests about visiting new locations, but at the same time it can feel like a gamble. Ultimately, everyone’s goal is to stay busy and make the trip worthwhile.

I keep a little list of cities from which people have reached out asking if I would come, or where clients live, who have seen me while visiting my town and expressed interest in seeing me in the future.

If it’s a city that I would enjoy visiting anyway, it takes a few were interested potential clients for me to consider scheduling a visit.

Before choosing dates, I reach out to those clients to try to schedule appointments.

It’s too expensive to tour to lose money.