Itinerary-Free Travel: Pros & Cons

When I first started traveling by myself (or with peers) at age 16, my trips were pretty well planned in advance. I would have all of my flights and hotels/hostels booked. I knew the route number and departure time of every train I wanted to take. I usually even had a good idea of what sights or activities I would do each day.
This is how most beginner travelers start out. Having a solidly planned out itinerary helps you deal with the multitude of new and unknown things that travel inevitably throws at you. The more I traveled, however, the less structured my trips began to be. I would still book flights and accommodation for the entire trip ahead of time, but not worry about transportation that had multiple options per day or what exactly I would do and see.

Now, the majority of my trips entail buying a one-way plane ticket a few weeks in advance and maybe booking an Airbnb for my first night. I might have a vague idea of where I want to go and how long I will stay but generally, I just wing it!

This itinerary-free travel style is not for everyone. It has its perks and pitfalls. Whether it’s right for you depends a lot on what kind of person you are. I’m going to go through some of the pros and cons so you can decide if spontaneous adventure is up your alley.




Unexpected Destinations

One of the best parts about not having a pre-planned itinerary is that you can go wherever you want. So many times I’ve had other travelers or locals I met along the way mention a super cool place to visit that I had never heard of. Itinerary-free travel gives you the flexibility to change things up and check out these surprise destinations.

In one major example, my cousin suggested that instead of my vague plan to travel south after visiting her in Sweden, I go north and catch a boat from Stockholm to Helsinki. I had never even considered the ferry to Finland. From there, she continued, I could also get a boat to Estonia and travel down through the Balkan countries. This was a region I had never been to before where my budget would stretch farther than in the west. Sounded great to me!

So, at the drop of a hat, I completely threw out my original plan and ended up spending the next two months heading all the way through the Balkans down to Romania and Croatia. I explored some absolutely amazing places I never thought I would when I bought that original one-way ticket to Sweden. That adventure would never have happened if I had planned everything in advance.




Besides changing up where you go, itinerary-free travel allows you to be spontaneous on a daily basis. I’ve often gotten chatting with fellow travelers in a hostel and ended up joining in with their amazing plans for the next day or deciding some sight I hadn’t thought about is worth a visit after hearing about their experience there. It gives you the freedom to do what you feel like in the moment without disrupting your entire trip.

When I was hitchhiking around Iceland, my ride dropped me off in a small town about an hour from where I was trying to get to for the night. I was pretty tired, so when I spotted a campground just up the road, I decided to stay there that night instead of waiting for another lift. Like many Icelandic towns, this one had a local thermal bath. I spent the evening soaking away the road surrounded by small-town locals, a very traditional experience I never would have had if I hadn’t spontaneously changed my plans. Because I didn’t have pre-booked transport or accommodation, I was free to do just that without losing money.


Guided by Experiences


Let’s say you roll into a city and plan to spend three days there. On the first day, you wander around and check out a few things and just aren’t impressed. Or it strikes you the wrong way and you don’t like the feel of the place. This is a legit reaction! But you still have to spend another two miserable days there 🙁 Not so with itinerary-free travel! Not impressed? Move on.

On the flip side, you may roll in and absolutely fall in love with the place. It’s so gorgeous! There’s so much to do! You don’t want to rush your experience just to stick to your itinerary. If you don’t have a set plan of travel, you can take your time and stay longer. This is what I mean by being guided by your experiences. You don’t know what you’re going to like until you get there.

Work Around the Weather


Weather is something you cannot plan. And you can’t even get a really accurate prediction until a few days in advance. Say you’ve planned a beach day in the middle of your carefully crafted itinerary but when it arrives, the weather is cold and rainy. No fun… If instead you vaguely want to hit the beach sometime on your trip, you can take advantage of sunny days as they come without being locked into a schedule that may or not be favorable weather-wise.

Take Advantage of Deals


Being more flexible with your itinerary allows you to take advantage of deals. I love me a low-fare calendar when booking plane tickets. By checking the price for the same route on multiple days and booking the cheapest day has saved me thousands over the years. Sometimes museums or attractions that normally have an entrance fee are free one day per week or month. With no itinerary, you are more likely to be able to take advantage of these kinds of deals and save money.

Quality Over Quantity


While my early adventures with strict itineraries were amazing and fun, they were very jam-packed. I was trying to fit so much into a tight schedule. I only had a certain amount of time in each place and that was that. I found myself skimming through attractions so that I could see everything I had planned.

Without a strict itinerary, it’s easier to spend more quality time in a destination or attraction you’re enjoying. You don’t feel that pressure that you’re going to miss something amazing because you won’t have time. Even those with limited vacation time can make the most of it not by seeing as much as possible but by experiencing what they like more deeply.






I’m someone who’s prone to anxiety. I know, why do I put myself in a situation likely to exacerbate this by traveling without a plan? I ask myself this very question at least once every time I travel. It can be extremely stressful not knowing where you’re going to sleep the next night or how you’re going to get to your next destination.

This pressure and potential panic is not fun. But it can be instructive. I’ve learned to rely on my abilities and instincts and to get creative. Now I’m used to it as a low point that’s part of the experience. If you don’t deal with anxiety well or thrive under pressure, however, this can be a deal-breaker to itinerary-free travel.

Last Minute Rates & Availability


I already exalted the amazing deals you can find when you have the freedom to be flexible, which is entirely true. The opposite is also sometimes true. If you don’t have things booked in advance, there’s always the possibility that accommodations or transport options will be full, attractions closed or unavailable, or that the price will have risen with demand. At the last minute, there may be no other choice and you have to pay more or move on. I know I’ve somtimes had to book a room that cost more or was not in my ideal location because the ones I had scoped out before got booked up by the time I actually finalized my plans.


Planning/Booking Takes Away from Travel Time


Speaking of planning – when you don’t do it all in advance, you have to do it on the go. That Balkan adventure I mentioned earlier? I spent an hour or two almost every evening of that journey researching ways to get where I wanted to go, things to do there, and booking accommodation for the next day or two. This is time I could have spent further exploring whatever exotic locale I found myself in or relaxing and enjoying just being there. One thing planning in advance does allow you is to be present in the moment on your trip and not worry about the logistics along the way.

Packing Appropriately


If you don’t know exactly where you want to go and what you want to do, packing appropriately can be tough. Even within one region, like Europe, temperatures can vary quite a bit. Summer in Sweden is very different from summer in Croatia, for example. Besides the climate, there are activities. Maybe you pack for a beach trip and then change it up and decide to go hiking in the high mountains. The gear you need for these activities is wildly different. You can always pick up things you need along the way, of course. It’s just an added hassle.

The pros of itinerary-free travel outweigh the cons for me. This might not be the case for everyone. I hope this breakdown will help you decide how much you want to plan your next trip in advance or how much room you want to leave for spontaneity 🙂


*This post includes one or more affiliate links. I earn a small commission (at no extra cost to you!) if you purchase a product or service through one of these links. Find out more here.*

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