Travel Insider: Advance Booking vs Going with the Flow

Travel is the ultimate expression of freedom. You've escaped the normal boring duties and routines of your everyday life so you can experience new people and places. The last thing you want is to be too restricted by a tightly planned itinerary or, conversely, to be stranded with no place to sleep because of a lack of planning.

So how do you balance booking your plans in advance while still keeping your options on the road open to some famous traveler serendipity? First you have to weigh the pros and cons of each approach. Different personalities need different planning strategies to feel comfortable leaving home and to have fun on a trip. 

Pros of Advance Booking:

  • The peace of mind of always having a bed to sleep in and a ticket onward
  • Never scrambling last minute to find out how to pick or get to your next destination
  • Establishing and sticking to a pre-planned budget
  • Being able to book tickets to local events before you arrive

Cons of Advance Booking:

  • Losing the freedom to jump in on some last minute activities on the road
  • Being stuck for days in a place you're not particularly fond of
  • Having to leave a place you really love sooner than you want to 

Pros of Going with the Flow: 

  • Being able to go anywhere you want on the turn of a dime
  • Having the freedom at any point of the trip to stay longer in a destination
  • Being able to tag along with friends you meet on the road on their plans

Cons of Going with the Flow: 

  • Bus, plane, or train tickets being sold out or sold at sky high last minute prices
  • Not being able to coordinate transit to your next destination
  • Not finding a place (or at least an affordable place) to sleep
  • Not being able to keep to a budget as easily 

Ideally, you will want your trip planning to have a mix of both these strategies --but it's an imperfect science. I've done month long trips before where I've pre-booked all my lodging and buses between destinations and they went really well. But there were definitely some moments where I wished I could have stayed in a certain place for longer or shorter. I also attempted a trip where I planned literally nothing in advance and found it really difficult to find affordable lodging or even transport that would go where I needed it to. 

Your best bet is to do some preliminary planning to make sure there are bus or train routes between cities you think you would like to visit and sketch out non-binding route. Then, when you look into lodging for each destination, you can gauge which places will most likely always have an open bed and which sell out fast and need to be booked earlier. Using this method will allow you to nail down some definite destinations while still having the option to do spontaneous things in between. 

And don't ever be too too worried about not having somewhere to sleep. Airbnb usually turns up a good amount of options in areas scant on hostels and the generosity of the folks on couchsurfing should never be underestimated. 

(Brought to you by Ally Thibault)