Three decisions first
Most bad trips are planned backward, starting from a photograph of somewhere and working toward the money. Settle three things before you pick a place: what you can spend in total, which dates you can really take, and how you like to travel, whether that is lying still or covering ground. Those three narrow the map quickly. Then look at season. The shoulder season, the few weeks on either side of a destination's peak, usually offers most of the weather at noticeably lower prices and with half the crowds. For much of Europe that means May and late September.
Book in this order
- Check your passport first, because many countries want six months of validity beyond your stay, and renewal takes weeks. Look up the entry requirements at the same time.
- Book the flights, which set the true dates and are the price most likely to move against you.
- Book the first and last nights, so that you land with an address and leave from somewhere near the airport or station.
- Reserve anything with limited capacity, such as timed museum entries, popular trails with permits, a long-distance train or one special dinner.
- Fill in the remaining nights, on rates you can cancel, as the route firms up.
For an international trip, start three to six months out. A domestic long weekend needs three or four weeks.
Pacing the days
Count nights, not days. Every change of base costs most of a day in packing, checking out, transit and finding the new door, so allow at least three nights per stop, and hold a one-week trip to two bases. Give each day one anchor, such as a museum, a hike or a market, and group everything else by neighborhood around it. Check the closing days before you fix the order, since many museums shut on Mondays or Tuesdays, and look up public holidays and festivals, which close some things and raise the price of others.
One folder
Put every confirmation, ticket and address in one folder on your phone that works offline, and send a copy to someone at home. Add the address of each lodging, the check-in times and how you are getting from each arrival point to each bed. A plan that lives in six different email threads fails at the first airport without signal.
Tip Plan the arrival day and the day after it as light days. Almost nobody does their best sightseeing on four hours of sleep, and a slow first day makes the rest of the trip better.
