AI-powered multi-city flight planning assistant

Stop drowning in flight options and plan your multi-city trip with confidence.

The Multi-City Flight Planner helps you work out what to search, what to compare, what to ignore, and when to stop researching — without a million tabs, screenshots, and spreadsheets taking over your life.

Get The Planner for $27 →

$27 one-time payment · Instant access · Future updates included

Built for multi-city trips Route strategy first No endless searching Works with your priorities
You: I have 11 flight options and I genuinely cannot decide.
Planner: Three weeks is a long time to be in research mode. Before we go through all 11 — what matters most on this trip?
You: Mostly cost, but not a horrible travel time.
Planner: Good. Share your three cheapest options and the one with the best travel time. We do not need all eleven.
Laptop showing a screenshot of multi-city flight planner gpt
Secure checkout via Gumroad
Instant planner access
Quick-start guide included
Future updates included
This is the bit that makes people spiral

You do not have a “finding flights” problem.

You have a too many possible decisions problem.

You can open Google Flights. You can search Perth to Tokyo, Tokyo to Seoul, Seoul to Taipei, Taipei home. Then you can reverse it. Then you can try a different airport. Then you can test one day either side. Then you can add an open-jaw option. Then suddenly it is 11pm and you have made precisely zero booking decisions.

“I’m sick of having a million flight options bouncing around in my head and I have no idea how to work out which route to take or how to find the best flights. I’m so overwhelmed.”
The real problem

Every search creates three more searches.

Multi-city flight planning gets messy fast because you are not just comparing flights. You are comparing routes, dates, airports, layovers, airlines, baggage, risk, convenience, and whether the “cheaper” option is actually worth the extra faff.

1

You do not know where to start

Return flight? Multi-city search? Open jaw? Different destination order? The first search feels like a guess.

2

You keep collecting options

Tabs, screenshots, handwritten notes, spreadsheets — and somehow the more you collect, the less clear it feels.

3

You are scared of missing something better

What if there is a smarter route? What if tomorrow is cheaper? What if you book and then realise you picked the wrong entry city?

Meet the planner

The Multi-City Flight Planner gives you a thinking process, not another pile of options.

Most flight tools give you more results. This planner helps you make sense of the results you already have — or work out which search to run first if you are starting from scratch.

Route strategy first

Before you compare flights, the planner helps you think through destination order, open-jaw options, date flexibility, and airport choices.

One step at a time

It does not dump a giant research list on you. It asks the next useful question and keeps you moving.

Booking confidence

When options are close enough, it tells you. No more researching forever because you are scared of choosing.

What is inside

What you get when you buy

This is a simple, focused product built to help you plan flights without turning the whole trip into a second job.

The Multi-City Flight Planner

An AI-powered planning assistant trained on a practical flight planning framework for complex trips, multi-destination routing, open-jaw decisions, and option comparison.

Quick-start guide

A short guide showing you how to use the planner, what information to bring, and how to get useful recommendations faster.

Future updates

As the planner improves, you receive access to updates so the tool keeps getting sharper over time.

See it in action

This is what makes it different from regular AI chat.

It has been trained to reduce overwhelm, not create more of it. That means fewer vague lists, fewer “you could consider…” rabbit holes, and more practical decision support.

When you have too many options

You: I have a spreadsheet with 11 flight options and cannot decide.

Planner: Share your three cheapest options and the one with the best travel time. We do not need all eleven.

When a cheaper fare may not really be cheaper

You: The budget flight is $180 cheaper per person.

Planner: Before assuming that is the better option, what luggage are you bringing and are baggage fees included?

When you need permission to stop

You: Should I keep looking?

Planner: No. The differences are too small to matter. Based on your priorities, this is the option I would book.

Before using the planner

  • You have too many tabs open.
  • You are not sure which route to search first.
  • You keep wondering if a better option exists.
  • Your spreadsheet is getting bigger, not clearer.
  • You feel stuck between “keep researching” and “just book something.”

After using the planner

  • You know which route structure to test first.
  • You understand which trade-offs actually matter.
  • You can compare options through your real priorities.
  • You know when another search is worthwhile — and when it is not.
  • You can book with far more confidence.
Who this is for

Built for travellers planning trips with moving parts.

If you are visiting more than one city and every decision seems to affect the next one, this is exactly the kind of trip the planner was built for.

This is a great fit if…

  • You are planning a multi-city or multi-country trip.
  • You are trying to make the most of limited travel time.
  • You are comparing different entry and exit airports.
  • You want help narrowing choices, not more tabs to open.
  • You want a practical second brain for route decisions.

This is not for you if…

  • You want someone to book the flights for you.
  • You need visa, immigration, or health advice.
  • You are looking for hotel, restaurant, or itinerary planning.
  • You only want the absolute cheapest fare, no matter the trade-off.
  • You do not want to provide any trip details for the planner to work with.
Meet Gayle

Why I built this

I have spent more than 20 years planning multi-city trips and trying to squeeze as much as possible into limited travel time.

Most of those trips involved the same challenges: multiple destinations, different arrival and departure airports, school holiday constraints, and far too many flight combinations to compare.

Over time, I developed my own flight planning framework to help me work through route options logically, compare trade-offs, and stop drowning in browser tabs, screenshots, and spreadsheets.

That framework became the foundation of Snowflakes & City Lights, where I share practical travel advice based on real trips throughout Japan, Singapore, Hong Kong, Macau, Vietnam, Taiwan, and beyond.

The Multi-City Flight Planner is simply that same framework turned into an AI-powered planning assistant.

Instant access

Get The Multi-City Flight Planner

Start turning flight chaos into a clear search strategy today.

$27

$27 USD · One-time payment · Future updates included

Get The Planner →
FAQ

Questions before you book your seat?

No. You will still use flight search tools like Google Flights, Skyscanner, or airline websites. The planner helps you decide what to search, how to compare options, and when you have enough information to book.

No. It does not book flights or take payment for flights. It helps you make a clearer, more confident booking decision.

No. It is useful for anyone planning a multi-city trip. It was built from real family travel experience, so it is especially good at handling constraints like school holidays, limited leave, luggage, timing, and destination trade-offs.

No. This is intentionally focused on flights and flight-related decisions. It does not provide hotel, restaurant, attraction, visa, immigration, or health advice.

You can start from scratch or bring options you have already found. The planner will ask for the information it needs one step at a time, such as your starting city, destinations, rough dates, trip length, and what matters most to you.

Regular AI often gives you more ideas, more options, and more things to research. This planner has been trained on a specific flight planning framework that prioritises route strategy, decision-making, trade-off evaluation, and knowing when to stop researching.

Yes. Future updates are included with your purchase.

Checkout is handled securely through Gumroad.