One of the most important and stress-inducing aspects of any major trip is accommodations, or where to sleep on the road. It can be argued that, after setting up your route, this is the most important part of the planning process, because wherever you are, the sun will eventually set and when it does, you’ll want somewhere to lay your head. But should you book your travel accommodations while you’re still at home or once you’ve hit the road?

Pros and Cons of Pre-booking

Pre-booking has its advantages and disadvantages. Arriving with your reservation in hand is a huge convenience. It’s nice to arrive at a new destination without having to worry about where you’re staying. This method really reduces arrival anxiety – you can simply land, pick up your luggage and head directly to your hotel or hostel for a nap.

The downside of pre-booking is having to cancel your room reservation and potentially lose your investment when inevitably, your plans change. Or what if your room looks nothing like the one you booked, but you’re paid up for a week. It may be hard to get out of your reservation with a full refund.
If you know you want to pre-book, here are some tips

• Don’t book on unfamiliar hotel booking sites. If you do, call the hotel (no matter where it is) to make sure the reservation sticks, and write down the name of the person you spoke (and the date you spoke to them) to so you can reference them to the person that checks you in. Confirmations can mysteriously “disappear” and whole hotels can suddenly be booked solid whether or not they said they had a room for you.
• Read reviews on sites like Trip Advisor or Expedia before booking to get a feel for other people’s experiences. But be sure to take their opinions with a grain of salt– even the nicest places have the occasional bad review and everyone’s standards are different.
• Travel services are another way to book rooms abroad. You may pay a little more to use them but they can be extremely helpful in navigating the minefield. Most of them have direct relationships with the properties they sell and will know a lot about them. You also will have recourse if something goes wrong with the reservation. Or if you need to change it, they can do the legwork.
• Hostelworld.com is a good site to make hostel reservations in many countries around the world. Call ahead to confirm just in case.

Pros and Cons of Booking from the Road

The obvious benefit of getting your accommodations as you go is the flexibility it allows. You don’t have to rush to your next overland destination on your trip because you already have a room booked, and you can choose your bed based on first-hand observations rather than online research.
Of course, this comes with a serious downside: having to find a place to sleep when you arrive. There are three main ways to book from the road:

1. Walk up and book

This method can pay-off but there’s a serious risk of being shut out or paying way too much. Rack rates (the walk-in price) at hotels and hostels can be discouragingly high. The payoff is a spot at a place that’s exactly where you want it and as it appears without having wasted any time booking a room before got there.

2. Phone ahead

A somewhat more fail-safe method is to call the hotel, just before you arrive. This will remove the dreaded turn-away in the lobby. You do run risks of limited availability so if you’re going with this method, it’s a good idea to call in and reserve as soon as you know you’re going to a certain place. Because if there’s an event going on a room can be close to impossible to get. Get a local sim card for your phone or travel with a good international plan.

3. Book online

This is by far the most convenient option. Just make sure you’re making your reservations from a respectable internet connection: a hotel business center, corporate franchise (like FedEx) or a friend’s house. Random internet cafés, while handy, are often highly susceptible to identity theft. Rick Steves has a great article on how to keep your information safe while using the internet abroad. The key points for internet cafes: make sure to delete your history and any cookies (personal info the browser saves automatically) and sign out of every sensitive site you log into.

So how should you book your rooms for a long-term or RTW trip?

We think it’s best to book your accommodation for the first 2 or 3 nights in each destination so you can rest easy and acclimate to the new city and then move to a spot in a better location at a lower price after you’ve settled in.