How Much to Book in Advance vs Improvise: A Practical Guide

Deciding between to book in advance or to travel by ear can be tricky for many travelers. For most trips there will be some bookings that should be made in advance and some that are better to leave open. I detail a framework for planning based on my experiences traveling both ways on many trips.

What to always book in advance

Yes, book some things well in advance and try to lock in the bones of your trip (the international flight, the first three nights or so of your arrival city and any necessary bookings for things like restaurants, museum tickets, or Inca Trail permits). This is a hard habit to get into for many long-term travelers, however, for real value, lock in the international flights as far in advance as you can (90-120+ days), for the best rates on hotels book the first 2-3 nights of your arrival city and have all of the required reservations for things that sell out well in advance.

What to never book far in advance

However, for other parts of your trip the opposite is true. For trips with a flexible itinerary that include many trips for internal travel (trains, buses, short flights) wait until closer to the date to book as these are often found to cost the same or less when booked near the time of travel. For accommodations after the first 3 nights of your trip you never know where you’ll end up so it’s best to wait until close to the time of your stay to book as well. Activities that are dependent on weather or your level of energy are best to book the day of as you’ll be able to tell what the conditions will be like and how you’ll be feeling.

The peak-season exception

Note: this is also reversed for off-season. Peak travel, for example European summer, Japanese cherry blossom time or a Caribbean Christmas, is best booked well in advance, as supply may be restricted in order to guarantee a decent return for travel providers. For example the most popular places to stay may well book up 3-6 months in advance for peak season travel, but the cheapest places to stay will generally be the first to book up for peak season, after which winging it for a cost effective place to stay will only bring stress.

In my last trip I put the advanced booker and the wing it person to the test. Here is what I have come to understand regarding reservation planning for your next big adventure.

The cost of getting it wrong

The cost of getting it wrong is more than the savings from getting it right. If you book non-refundable accommodations and your plans change, you will lose money. If you don’t book and a room for which you are looking becomes unavailable, you could end up paying twice the price for a room or a lower quality room. The key is to calculate the cost of potential failure for your specific needs and then compare that to the potential savings from booking something refundable for the first change in your plans. That is the rule that I have found to hold true for me in the past.

What I do in practice

For the traveler though, after much time on the road, I find that I lock in the bones of a trip before I even book my flight, reserving international flights and the first-week’s worth of accommodations for arrivals as well as must-book reservations (for restaurants, museums, etc.). On the road, the 30-40% of nights of your trip that you leave open to whatever happens as you’re on the road are almost as cost-effective as booking those ahead of time for you (in terms of value, not price). And that’s to say that I book most of my reservations on refundable terms – even at higher rates – for that extra protection as well. This way, I get the greatest amount of value for my time planning, and the greatest amount of flexibility on the road.

Plan your trip(s) effectively for your next travel(s)

Plan your trip with a hard date and a budget in mind. These are the constraints of your trip and will shape your trip more so than your wishes for places to visit. Write out a plan for the structure of your trip on paper with a map before you start to book anything. Routing out a trip on a paper map as opposed to searching for flights and hotels on a booking site for travel reveals mistakes that can cost you days on the road as opposed to dollars. Add a contingency line to your plan from the start. This means one buffer day per week, booking flights and hotels with a 100% refundable cancellation policy (even if it costs a bit more), and keeping a small reserve in your budget for contingency purposes. As with most things, contingency planned for in advance is far, far cheaper than the same contingency found and booked while on the road for your trip.

Closing perspective from years on the road

I want to emphasize that this is what works for the majority of travelers, the large majority of the time. If you’re traveling, it’s only a matter of time before you start to develop your own insights. The articles that you read, conversations that you have with fellow travelers and what ultimately helps you is when you go on the road and put all of that into practice. We recommend that you read a lot, have a lot of conversations with your fellow travelers but when you develop a practice, that practice needs to be something that is going to translate into your own way of doing things and help you to improve your travels as a result. I always say that there is only one way to learn how to do something and that is to do it and so that’s what you need to do with all of this as well. Just trust your own instincts and with time and experience develop a practice that is going to help you have the trips of a lifetime.

Tara Singh reviewed this for me. It was also cross-checked against my own experiences.