How do I plan and book a trip?
Start With Context, Not Flights
Before opening Google Flights or seats.aero, you need to understand the shape of the trip. I ask myself the following questions:
Who’s going on this trip? - A solo trip and a family trip are completely different problems. Award availability, cancellation flexibility, and seat counts matter far more when you’re booking multiple people.
Who are you in charge of paying for? - If you only need to cover yourself, you can ball out. If you need to coordinate with friends on flights and are trying to travel together, you will likely need to choose between spending points and being alone or cash and being with your friends.
How much time do you actually have? - Are you locked into exact dates, or do you have a range? Even a one or two day buffer can completely change what’s possible.
What are you willing to pay - in cash and points? - Points aren’t free, and oftentimes depending on how long you’ve been doing this it can be immeasurable based on the levels you’re willing to go. Sometimes the best move is mixing cash, points, and positioning flights. Decide early what' ‘worth it’ means to you. Is this a bucket list trip? Is this a destination wedding you want to extend?
The goal here isn’t to limit yourself - it’s to avoid chasing flights and hotels that never fit your real constraints.
Think in Routes Before You Think in Awards
Once you know the boundaries of the trip, zoom out. Start with general routing, not specific flights. Are you traveling from the US to Europe? Or are you traveling from Seattle to Maui? This matters in the flexibility that is available. With general routing, you learn that routes are more common than others, and are often cheaper / offer more availability.
Where are you going, and how many destinations are you trying to visit? If more than one, you can now schedule flights in various orders to see all the places you wanted to see, but sometimes find better awards flying into one city over the other. For example, if you want to see Italy, Switzerland, and France, US -> France might be cheaper than US -> Switzerland and France -> US might magically be cheaper.
Now that you have a general understanding of the general routing, you can dive a little deeper. Take a look at flightconnections. You can enter the spot you want to fly to (for instance CDG) it will show you all the routes that fly there. Most likely you will find a US connection, which might pose a good opportunity to find award flights through there. Let’s imagine you want to visit Crete, they do have some international routes, however its much more likely you will find availability into Athens, then a small hop onto Crete.
Once you understand the map, everything else gets easier.
Ground Yourself With Cash Prices
Before diving into award charts, always check cash prices. Cash prices give you leverage:
You know when an award is actually good value. For instance, if a business class flight cost $5,000, but 50k miles, that is 10 cents per point and exceptional value.
You know when to stop forcing points. If you are finding cheap cash tickets, why waste points when CPP is likely around 1 CPP?
You can spot routes that tend to get discounted close to departure
I’ve seen this play out personally. On a recent trip from Tokyo to Honolulu, I checked flights two days before departure and found that a new business class ticket was cheaper than what economy had cost earlier. That kind of opportunity only exists if you’re still checking — and not emotionally locked into what you already booked.
Cash prices keep you honest.
Then Zoom Into Award Possibilities
Once you understand the routes and have a sense of what the flights cost in cash, that’s when awards start to make sense. At this point, you should already know which airlines operate the routes you’re considering and which programs are capable of booking them. Frequency matters too — routes that operate multiple times per day or week tend to offer more opportunities for saver space than those with limited service.
This is where tools like seats.aero become useful, not because they magically surface perfect redemptions, but because they let you observe patterns. You start to see which programs release saver awards regularly, which routes are consistently overpriced, and where flexibility actually pays off. That context is far more valuable than any single result.
Instead of asking “What’s the best award I can book?” ask better questions. Are there alternate routings that price lower? Would shifting your dates by a day or two open up saver availability? Are there current transfer bonuses that meaningfully change the math? You’re not hunting for perfection here — you’re narrowing the field to options that make sense for your trip.
Book Opportunistically, Not All at Once
One of the biggest mindset shifts is realizing that a trip doesn’t need to be booked in one shot. If you find a segment that offers strong value and comes with cheap or free cancellation, it’s often worth locking it in. That gives you upside without committing the entire plan.
From there, let the rest of the trip evolve. Set alerts for other legs and allow better options to surface over time instead of refreshing searches every day. Trips change, availability opens, and pricing moves — your bookings should be flexible enough to move with them.
Re-Evaluate as the Trip Gets Closer
As departure approaches, your focus naturally shifts from optimization to execution. This is the point where small details matter more than squeezing out extra value.
Confirm logistics with your hotels. Make sure they know who’s checking in, whether they offer airport transportation, and if there’s anything you can handle ahead of time to make arrival smoother. Check whether you need visas or online entry forms and complete them early if possible.
It’s also the right moment to think through how you’ll move within each country. Trains, public transit, and rideshare apps are easier to understand before you land, and downloading what you need ahead of time saves stress later. When researching activities, zoom in geographically. Looking at specific neighborhoods rather than entire cities makes planning feel grounded and manageable.
The Real Skill Is How You Think
Eventually, trip planning stops being about award charts and tools. Those will always change. What doesn’t change is the way you approach the problem.
Start with context. Understand the map. Ground yourself in cash prices. Book flexibly. Stay curious all the way up to departure.
You don’t need to plan perfectly. You just need to think clearly. Open Google Flights, sketch a route, price it in cash, and then see where points can do better. The first trip is always the hardest. After that, you’re no longer guessing — you’re building a system you can reuse every time.
Start planning your next trip. The clarity comes faster than you think.