The Million Dollar Question: to Plan or Not to Plan your Trip?

If you read my guide to saving money before traveling, then you know that I'm an advocate for planning in advance when it comes to affording your travels. However, does the same planning apply to the creation of your itinerary? The answer is it depends. When traveling through Thailand, Bali, and Japan I tried both-- building my itinerary as I went along and having one laid out weeks in advance-- and found that there are pros and cons to both winging your trip and having it planned to the T. It really comes down to what kind of person you are and what type of experience you want. Here's a look at the two so you can determine whether you'd enjoy a planned trip or more of a spontaneous one. 

The Pros of Planning Your Travels

  • I planned the first two weeks of my trip to Thailand a month in advance, which meant having all of our hotels and ferries booked. I didn't have a day-to-day itinerary where I scheduled daily activities, but we did know exactly where we would be on a certain date. The advantages of this approach is that you put all the work into planning your trip in advance so that when it comes time to travel you can relax and simply follow the itinerary you made for yourself.

  • It also gives you a sense of purpose and direction knowing where you're going. Traveling is a chaotic upheaval of your day-to-day routine and so implementing some order into that can be a relief to some.

  • You will have your pick of hotels and Air BnB's to choose from if you book them way in advance, especially if you're planning on going somewhere during high season. Conversely, if you go on TripAdvisor a couple of days prior or even the day of you'll find that some of the more popular hotels are booked.

  • When it comes to airfare, you will often save money by booking far in advance. However, this often isn't as dramatic as you'd think. I sometimes found airfare that was cheaper by booking a couple of days in advance or only just slightly raised.

The Con of Planning Your Travels

  • You really can only guess the experiences you'll have at each place you travel to, especially if you've never been there before. What if you find Phuket to be crowded and overwhelming, but meet new friends in Koh Phangan that you want to hang out with for a few more days? If you book your hotel and transportation in advance you get stuck following an itinerary that you planned before knowing how you would feel about the area, the vibes, and the people there.

The Pros of Not Planning Your Travels

  • Some people get stuck over the fact that they need to plan a trip months in advance to have a good time while abroad, when the truth is that it is very do-able to plan as you go and book hotels a night before or even the day of. For those who have an extremely busy work and home life, you can take comfort in the knowledge that you don't need to plan meticulously. Instead, they can pick up and leave, plan their trip as they go and have no problem doing so.

  • You won't lose money by booking hotels a few nights in advance. It's a common misconception that booking a hotel months in advance saves you money. The truth is that hotels determine their prices based on the season and so if you book a hotel room months in advance for the high season, you'll still have to pay a much higher price then booking a hotel room the day before during low or shoulder season.

  • If you're more of a "go with the flow" type of personality you'll likely find this type of traveling refreshing. Figuring out your day as you go along gives you a sense of adventure and excitement that you really couldn't get in your regular life.

Cons of Not Planning Your Travels

  • Being spontaneous isn't for everyone, and you may feel a bit stressed at the aspect of having to figure out where you're going next the night beforehand.

  • There are some things you may miss out on if you don't plan them far enough in advance. As stated earlier the most popular hotel rooms may be booked and their may be some guided tours, boat rides, etc that will be booked unless you plan them in advance.

  • You may end up spending a bit more money on airfare, then you would if you booked in advance.

My Experience

Like I said, I planned the first two weeks of our trip to Thailand a month in advance, but simply because I ran out of time, I had nothing planned after that. Having those two weeks planned out was nice in the sense that it gave us some order when we were first getting used to traveling in Thailand. However, there were plenty of times that we wished we could have stayed longer in certain areas that we absolutely loved, but had to move on due to prior bookings.

The first night that we didn't have anything planned was definitely a bit of a shock. I was worried that the best part of our trip had come to an end and now we were going to just be aimlessly wandering around trying to figure out where to go next. That only lasted a night though, as the next day we made the decision to book a flight to Ko Samui and check out that part of Thailand. Just like that we had a plan

Not having anything booked made it so that we had to make decisions of whether we'd stay another night or go somewhere else every day, but some of my best memories of Thailand were made because we were able to stay extra nights in the areas we loved.


At the end of the day, both strategies work when traveling and that is all that matters.

My Recommendation: For those who like order and organization, planning your trip in advance by booking hotels and transportation can eliminate the stress factor of being in a new, foreign place. However, I think having a daily activity itinerary is a bit much as you can't predict the days you feel tired and just want the chill, the days you feel like adventuring, etc. Instead, if you want to plan your travel activities create a list of the things you want to do in each area and then when you are there you can choose the ones you want to do. Note: for boat activities, guided tours, etc. you should book in advance during high season as they will often fill up. 

On the other hand, for those who are more laid back, you'll be better off having a loose schedule around your trip so that you can stay a few extra nights in the places you love and leave early for the ones you're not feeling. 

Note: You can also try having a happy medium by finding hotels that have a free cancellation policy. However, keep in mind that many do not offer this so you'll be limited in what hotels you can book.