Building a Travel Itinerary That Survives Real Travel Days

Almost all self-booked itineraries suffer from being overplanned. This type of traveler books out every minute of his or her time with up to 5 activities per day and does not include any morning’s without activities. In between his or her trips, he or she has no time for recovery either. A flight lands 90 minutes later than planned, a museum is closed for a private function or a trip to a local market takes a bit longer than anticipated. By day 2, the initially so well-planned itinerary has already come undone a number of times and the traveler is grumbling already.

I recommend following a framework which can save you 80% of trip stress related to your itinerary. This is the framework that I’ve personally used over the last decade for planning trips for myself and for my friends and family, and it always seems to work really well.

The 70/30 ratio

70% planned, 30% free. The free time will fill up with everything that you had not anticipated. Like that small café you walked past on the first day and wanted to return to. A small museum that a complete stranger recommended. A half day of recovery from jet lag. The storm in the afternoon that causes a re-rout.

When your itinerary is completely full then every disruption (and there will be some) will feel like a failure and every item that you fail to complete will be a source of regret. Don’t make life this hard for yourself. True every time.

Fixed items versus floating items

Sort everything on your itinerary into two buckets:

Fixed items – F: flights, trains, prepaid tickets with a fixed date for entry, restaurant reservations, hotel check-in at the hotel, organized tours with a fixed itinerary – nothing can be changed here. Floating items or activities that you can fit around your fixed schedule of bookings (beyond the flights as described above): Museum visits; Exploring entire neighborhoods; Going to the beach or pool for the day; Visiting local markets or going on extensive shopping trips; Casual restaurants rather than a booking at a high-end eating establishment.

On the other hand, most travel itineraries are comprised of Floating Items which could easily be moved to a different day by a number of hours. As I mentioned in the first strategy, museums and galleries are perfect examples of Floating Items which can be scheduled for a given time but have to be treated as Flexible Items in actuality in case other opportunities present themselves. Thus, when adding a planned activity to your itinerary, clearly label whether or not it is a Fixed or Floating Item, so you know what to do in the event something unexpected comes up along the way.

When going through your Itinerary and making out your reservation confirm each item with an upper case F or a lower case f. Remember that upper case F is for Fixed Items that can not change such as flights and or pre-paid tickets and or other events of a fixed nature whereas a lower case f is for the Floating Items that can move about. Fixed Items such as flights and hotel bookings are best to confirm the day before as opposed to the morning of travel. I can personally attest that to arriving a day early on two occasions would have meant a Missed Connection had I not.

The morning question

Every morning I ask myself: ‘What is the one thing today that, if I do nothing else, would still make today a good day?’

That thing is often not the thing that you planned. You planned to go to the morning opening of an art museum. But instead you spent the morning having a long coffee at a cafe near your hotel, so that you could feel refreshed and have energy for your travels. That was the one good thing that you did that day, and that was enough to make the day good. The rest could have been forgotten.

How many cities, how many nights

2 nights = 1 full time in a city, 1 day to ‘sort out’ in a city (1 night). e.g. one night in a new city arriving = next day start to get into the swing of the city, 2nd night same, and 3rd = start to feel at home. Long trips: 3 nights = 4 full days. 14 days = 3-4 cities. 14 days in 7 cities is far too many & will be totally exhausting & be nearly all forgotten.

As a general rule for very long trips, 3-4 days in a city is better than 2. The 4th day is when a city stops being a destination and becomes a place. You recognize shops. Waiters recognize you. You have a good sense of direction without needing to refer to your phone constantly.

One generally has 3-4 full days per city to get a good grasp of a place, and see its various spots. For example, a 14-day trip to 3-4 cities would be excellent, however a 14-day trip to 7 cities would be tiring and quickly become forgotten.

Buffer days between transits

Add a buffer day to the start of your trip before any flights that you could miss. If your international flight leaves on a Sunday then your last day of activities should finish by Friday night. Use Saturday for last minute packing, laundry, rest etc. Travelers who book a Saturday evening dinner booking prior to a Sunday morning flight are at risk of missing their flight.

I have learned that the cost of one activity day is less than the cost of a missed flight and subsequent booking losses (hundreds to thousands of dollars). So I like to arrive a day early (which happened to save me twice in the past when my connecting flights were late).

What to do when the plan breaks

Things go wrong. The flight is cancelled. The museum is closed. You arrive at the hotel to discover that they have booked you for only one night instead of two. What do you do? The plan has gone wrong but that is not a failure – it is your trip telling you something. The real question is how you respond to it.

My rule of thumb is to have one cup of coffee before taking any action when plans are foiled. This one small cup of coffee, whether black or white or with sugar or without, is the space between the failure of plans and my successful working around that failure. It is my one ritual and it is small, but it makes all the difference. And if I am traveling with someone else then we can have one cup of coffee together too!

For serious disruptions to your plans such as a flight being cancelled, your bag being stolen, or a border being closed then ring your emergency contacts. Home or local is irrelevant – they will immediately calm you down and help formulate the first course of action.

Document everything in one place

One document not five apps. The document should contain all the necessary information to handle any eventuality, and it must be offline accessible. The following are the sections that need to be included, in the given order:

Flight times and confirmation numbers. Accommodation addresses and check-in details. Emergency contacts, both local and home. Daily plan, with F/f markings. Restaurant reservations. List of phrases or words in the local language. Random notes from your research.

I keep all my information organized in a single Google Doc for the trip. I save it offline before I leave and add all the relevant information. If something then breaks during the trip, I have the information for the whole trip at my fingertips in one document. This one document has saved me more trips than all the travel insurance in the world put together.