How to Plan a Trip, Step by Step
Most planning stress comes from doing things in the wrong order, usually by booking accommodation before deciding the shape of the trip. Here is the sequence we use for every route on this site.
8 min read
1. Dates and season first
Decide the window before the destination, because the season rules out and rules in whole categories of trip. Andalusia in August and the Dolomites in November are both technically possible and neither is advisable.
Check local holidays and festivals at this stage, not later. Ferragosto in Italy, Semana Santa in Spain, Golden Week in Japan and August closures across southern Europe all change availability and price dramatically.
2. Style, then destination
Answer the honest questions: how many hours a day do you want to be out, how often will you pack, where does your money do the most work, and who is coming.
Only then choose the country. This ordering is the single biggest improvement most people can make to their planning.
3. Shape the route in nights
Write the trip as a list of nights, not days. Four nights here, three there, two at the end. If the list has more than three entries for a ten day trip, cut one.
Put the most demanding place first and the most restful last.
4. Transport between bases
Check the actual connections before booking any accommodation. Ferry frequencies, train times and the difference between a two hour and a five hour transfer will change the plan.
Book long distance trains and internal flights as soon as the shape is fixed, since these are the tickets that get more expensive with time.
5. Accommodation
Book refundable where possible and judge by walking time to the station and to the eating district. Confirm lifts, air conditioning and check-in arrangements.
For anything over four nights, prefer an apartment. For anything under three, prefer a hotel.
6. The short booking list
Every trip has two to four things that genuinely need advance tickets. The Alhambra, the Borghese, the Vatican, the Uffizi, a specific restaurant, a cooking class, a guided hike. Write them down and book them together in one sitting.
Everything else can be decided on the day, and should be.
- Book ahead: timed-entry museums, intercity trains, one special meal, any guided activity
- Decide on the day: most meals, city transport, which park, which church, whether to nap
7. One page, offline
Put addresses, confirmation numbers, transfer times and emergency contacts on a single page and save it offline. Screenshots of tickets too, since station wifi is not to be trusted.
Share that page with someone at home. It takes two minutes and solves the only real problem with losing a phone.
8. Leave a third of it empty
If every afternoon is spoken for, the trip becomes a schedule to execute. Aim for one planned block per day and let the rest happen.
The best afternoons on almost every trip are unplanned ones, and you cannot book those.
9. Stop planning
At some point more research produces worse decisions. When you have the nights, the transport, the rooms and the short booking list, you are finished.
Read one book about where you are going instead. It will improve the trip more than another twenty reviews.
