Booking to Boarding
A planning timeline for making travel feel smoother before you ever leave home.
This page exists for two reasons. First, I was a dummy and messed up an entire trip to Australia because I failed to read the details of their visa. I got stranded in San Francisco and had to create a whole new trip to go back.
Second, I got stuck in the Louvre on my only sunny day in Paris. That mistake came from overplanning and not leaving room for the trip to develop.
So through those experiences, I have built a timeline that actually works.
Start Now
Dream Destinations
You are not planning the trip yet. You are giving the trip a reason to exist.
Before flights, hotels, travel documents, or a complete wardrobe overhaul, decide where you actually want to go. Travel is about fulfilling something, whether that is a desire, a passion, or a curiosity.
Whether it is the Super Bowl, Wimbledon, lying on an exotic beach, or seeing your favorite artist at Red Rocks, it is your list to create. Start simple, but expect the list to grow as you see more of the world.
Need some inspiration? Check out where I am currently dreaming of.
As Early As Possible
Visa & Travel Requirements
Bad planning shows up at the airport.
It is never too early to check travel requirements. A U.S. passport opens a lot of doors, but some countries still require visas, additional forms, vaccinations, or extra planning.
I check entry requirements when I start considering a destination and again when I book the flight. The U.S. State Department is usually the best starting point.
9 to 13 Months Out
Flights
The dream list becomes useful the second a deal appears.
Flight schedules usually open around 9 to 13 months out, depending on the airline. If you are using points, earlier is usually better, especially for partner redemptions.
This is why having a dream list matters. When a good route or redemption appears, you can move quickly instead of starting from scratch.
When You Book Flights
Hotels & Ticket Research
Flexibility is a feature, not a flaw.
I usually book some form of accommodation when I book flights, but I avoid prepaid rates unless I am completely locked in. Flexibility is valuable, especially on a first-time trip.
Plans change. Trips evolve. Keeping hotel options flexible lets you adjust the trip once the details become clearer.
The other thing I do here is research ticket requirements for the sites I want to visit and plan accordingly. Some sites sell out early or have very specific purchase windows. The Last Supper is the one that always comes to mind. Others can be purchased in the week before. Knowing the requirements ahead of time will save you from missing out.
Check out my City Guides to see if your destination is on my list and jump start your research.
2 Months Out
Plans & Ground Travel
You are not planning every minute. You are setting the trip up to work.
This is when I start turning the idea of the trip into an actual plan. I do not need a minute-by-minute agenda, but I do want a clear list of things to see, eat, photograph, and experience.
Do not overplan. Some things are better left flexible for weather, energy, or mood. For anything that requires a reservation, look for flexibility where possible.
Once the plan starts to take shape, figure out ground transportation. Some cities need a rental car. Others are better with public transit or rideshare. If you are renting in Europe and cannot drive manual, book an automatic early.
1 Week Out
Packing
Future you is not packing calmly at midnight.
Open the weather app on your phone and start building the packing plan. Think through outfits, adapters, chargers, cameras, batteries, and any other essentials before the night before your flight.
Do not wear the outfit you want pictures in at the Eiffel Tower to work. Put it in your suitcase ahead of time.
3 Days Out
Aircraft & Flight Setup
Control what you can before the airport controls you.
Now it gets real. Check the aircraft and plan around it. One airline’s economy class can be completely different from another’s, and even the same airline can vary by route because of differences in aircraft.
- Can I charge my devices?
- Will WiFi work for the whole flight?
- Do I have lounge access?
- Is there food I actually want?
- Is there in-seat entertainment?
- What is my delay or cancellation backup plan?
If you are going to be stuck without WiFi, download movies or books to occupy your time. Having the right accessories in your bag ensures your phone does not die before you land.
24 Hours Out
Final Adjustments
At this point, you are not planning. You are executing.
Confirm reservations, check the weather, decide which days make sense for the items on your list, and make any final bookings.
Decide what time you need to get to the airport. Schedule your transportation. Triple check your luggage.
You have done the work. Now the goal is to leave calmly and enjoy the trip.
Part of Traveling Well
Plan early enough to create options, not constraints. Know what you want to experience, but leave enough room for the trip to breathe and become something memorable.