Planned Itinerary or Go With the Flow? How to Choose Your Travel Style // 130

Are you a spreadsheet traveler…
or a go-with-the-flow adventurer?

The way you live your everyday life often shows up in how you travel.

In this episode, Cheryl breaks down the real pros and cons of planning every detail versus leaving room for spontaneity — especially for solo travelers.

Because there’s no “right” way.
There’s only what helps you feel confident.

What’s Inside This Episode:

• The real pros of planning your trip
• Where over-planning creates stress
• The freedom (and risks) of spontaneous travel
• How to choose the right balance for you

Cheryl’s Recommendation

If you’re a first-time solo traveler → lean more toward planning.
If you’re traveling in high season or popular destinations → plan more.
If you’ve traveled solo before → try a hybrid approach.

Book your flight.
Secure your first night.
Anchor a few key experiences.
Leave breathing room for discovery.

Travel isn’t about doing it perfectly.
It’s about doing it in a way that builds confidence.

If you're planning your first solo trip and want structure without overwhelm:

👉 Download the free First Solo Trip Framework at cherylbeckesch.com

Transcript

Travel Styles: Planned vs Spontaneous

Speaker 1 0:00

In your day-to-day life. Are you one that loves spreadsheets and planning every little detail of your day? You have a routine that you do every day and you don't deviate from it. Or, if you did, you kind of feel a little off kilter. Or maybe you just like to go through life and just kind of winging it, letting maybe some other people kind of dictate what you do, where you go. Maybe you just don't like making decisions.

Pros of Planned Travel Itineraries

Speaker 1 0:30

Think about that and what type of in the realm of, what type of traveler you are, because often, how we are in our day to day is going to carry over into how we approach travel. So I'm going to talk today about the pros and cons to a planned itinerary of travel versus spontaneous travel, and ask yourself which one are you? Welcome to Solo Travel Adventures. I'm Cheryl Esch, and I probably would say I'm somewhere in the middle of that graph. I do like some planning, but I also like to allow some space and time for my trip to have some spontaneity to it. Well, let's dig deeper, though, and talk about there are pros and cons. Now. One way is not better than the other. There's no wrong or right way as far as how you approach how you travel, but I just want to share. There are pros and cons for both, so not that either way is right or wrong. Some of it depends on your personality. What type of person are you? So, with a planned itinerary, something that you take care of, whether you do it yourself or you use a travel agent, or even maybe a tour group, everything is planned out for you for the most part. This number one positive thing about doing it that way is that there is no stress or no worries about what you're doing, where you're going, and in most people, they feel safer this way, in knowing where they're going to be when they're going to be doing something, and it just gives them a peace of mind, you know. So if that's you, you know planning, go for it. This is probably your style of travel.

Speaker 1 2:28

Now there's also number two planning your trip ensures that you get tickets or entrances to some famous sites. Often, if we just show up and there's only a lot amount of tickets or entrance for a certain thing, we're going to miss out on that opportunity. But if you plan ahead, you're going to ensure that you get entrance or you get the ability to see these things. You know there are, of course, certain activities that you really have to think ahead of. So my example for me is I'm going to Iceland very soon and I wanted to kind of wing it, but as I was planning, I realized, for example, if I really wanted to get a chance to go to the Blue Lagoon, which is very popular place, that I was going to need to schedule that and get an entrance ticket way in advance, which I have secured, because many of them were actually already sold out, even though I did this about two weeks ago. So there are definitely that's definitely a positive thing to be thinking about right.

Speaker 1 3:39

Number three another potential pro is that you potentially get good deals. You get better deals if you don't wait. Sometimes, as we know, last minute planning or last minute decisions can cost us more money, especially in airlines. But that also could translate to some other things, such as accommodations, because when accommodations start to get scarce, typically that price goes up all right or you miss out on you know everybody's already purchased something in that good deal or budget range of things. So that's a positive in your planning. And number four it gives you that peace of mind again that you could actually share with a family or friend, exactly where you will be. They'll know where you're going to be, especially if you're traveling internationally. It kind of gives us a peace of mind that someone knows where we are and by having that planned out it's easy for you to just maybe share your itinerary and they will know day to day where you're going to be.

Cons of Over-Planning Your Trips

Speaker 1 4:45

Now there are some downsides to planning everything, especially planning everything to a T, meaning every single day, maybe even every single block of time, hour or whatever is planned with an activity. Now, by doing that, it kind of does create some stress in a certain way, in that you feel maybe rushed in the process of your travels and feeling like you have to kind of get to that next place. Oh, we only have this amount of time, and so it really locks you in and it kind of gives you limited or no flexibility in your travel. So you can kind of feel a stress component when you, um, when you do plan and you plan actually maybe too much, right. And number two, you might miss out on a hidden or local place of interest. Often when we're just, you know, focused or geared to just going here and here and here next, we miss out on seeing some other potential. You know gems that are around us. Maybe you see a local cafe or restaurant that looks really intriguing, but you've already planned something else, so you have to miss out on that. And number two you might also just miss out in general having a serendipitous meeting with somebody or have an unexpected encounter or experience. We don't allow that space for that to happen. We often will walk right by it. We won't even know that that lovely sort of encounter was right in front of our eyes the whole time. So that's the pros and cons to actually planning a really set itinerary for your travels.

Benefits of Spontaneous Travel

Speaker 1 6:38

Let's talk about if you were to go just spontaneously, outside of, of course, maybe planning your flight right. We probably want to get those flights, but once you get to your destination, you're just going to wing it. Number one you do. The pros of that is that you have that freedom and you can even change your mind. You can change your plans as you go along and as you see fit. Maybe you want to spend a little extra time in this city that you really enjoyed instead of moving on so quickly, because you have this set plan and you have to follow that plan right. Number two spontaneous can, in a sense, be less stressful. Having, you know, that whole idea of having to be somewhere exactly at a certain time or place right, and that's, you know, gives you that freedom, as I mentioned before, to just do what you want. And number three, you might have more opportunities, with a spontaneous kind of approach to your travel, for chance encounters or again discovering some of the local hidden gems.

Downsides of Winging Your Trip

Speaker 1 7:47

Now, there are some downsides, of course, to just being spontaneous and kind of winging it when you get there. One is that you can definitely miss out on deals. So you know, a lot of times, as I mentioned earlier, uh, sometimes accommodations are limited. If you wait too long, like once you get there, maybe you run into where you've come upon a city that is having maybe a huge festival and you didn't plan on that, you didn't realize that, and when you got there there were no accommodations left, or what you did find were like these really pricey hotels that really are just not in your budget, or you weren't planning on spending right, but you need a place to stay. So that is a downfall, unfortunately. Number two, as I mentioned, your's, uh your choices uh may be limited, uh, for just a lot of things, not just accommodations, but also like tickets to something special, tickets to, maybe, the Louvre, some. Some of these things have to be purchased ahead of time, right? So you definitely would miss out on some of that, right, so you definitely would miss out on some of that.

Speaker 1 9:04

And then, um, another kind of downfall of not planning. You know, without a plan, often I find that, um, people meander, um and don't really have a focus, and sometimes this is good, but sometimes it can be a waste of time, possibly, if you, um, maybe have missed an iconic spot just because you were busy that day Not that it's not a good thing to walk around a city unplanned but maybe, after you've done that, you realize oh, I walked by this, but I didn't realize it right, so, because you hadn't really done any research or planning, you might miss some of those opportunities, which is better. Well, there's no right or wrong way. And again, going back to, maybe, what your personality is and what you sort of kind of feel, you know, this is how I operate, this is what I need is going to be the approach to your travel that you're going to take. Need is going to be the approach to your travel that you're going to take. Now I make a suggestion, a couple suggestions here.

Finding Your Travel Planning Balance

Speaker 1 10:12

If you are a new solo traveler and or even just a novice and you're going maybe on your first solo trip, I do highly suggest you plan as much as you can. Suggest you plan as much as you can. Many people even choose to do a tour. Yes, I know there's some debate out there as to whether, if going on tour group is considered solo travel. I'm not going to debate that here. I recommend it because it's kind of a safe place to go, in that you are going by yourself but you are with other people, um, and the trip, in almost all respects except for probably your airfare has already been planned for you and some tour groups do allow a little, um, kind of your own time. So just look into that if that's something you're interested in. I also suggest leaning more on the planning side if you're going to a very popular destination Because again, you're going to run into a lack of accommodations, you're going to run into just not having those opportunities to see some of those iconic things and also consider what time of year you're going Because, for example, you know Italy. I'll just use Italy for an example. It is a very popular. Especially in the summers it gets super busy. I would highly recommend you do as much planning if you plan to go in the summer Now, if you plan to go in the off season, possibly even those winter months, you can probably be a little more free and have that less planning approach to allow yourself, you know, that opportunity to.

Speaker 1 11:52

You know, see if you come across anything that kind of catches your eye, that are just exploring with some freedom. Now again, ask yourself, which one am I? I personally am somewhere in between and I feel like in encountering many other solo travelers that have done they have a few solo trips under their belt, I find that those people tend to also be somewhere in the middle where they have certain things planned, but they're going to allow some space, allow that freedom to maybe walk around, maybe even a day or two extra. I'm going to not be stressed about moving on so quickly and maybe, oh, maybe, I'm going to stay here a little longer versus oh, maybe I don't like that place and so I'd rather spend more time in X, y or Z, I will have to say. Going back to the idea of planning with in mind this kind of a popular place. So I have come across.

Speaker 1 13:01

I do tend to sometimes lean slightly more to spontaneous. I always always, of course I book my flight. I always book my first night and usually my last night, because I usually want to stay maybe near the airport. So I always have those, but I leave usually the rest to determine once I get there. However, I am finding in my planning of my trip to Iceland and again because it is a popular place, for example, I missed out on I had had a suggestion from somebody to stay at this wonderful guest house and it was down near the Blue Lagoon, but a little southeast of it, which is the direction I'm headed after I hit the Blue Lagoon. Staying at the Blue Lagoon is super expensive, so I wasn't staying there. I found this great guest house by someone recommending it to me, but I didn't book it right away and when I went back about a week or so ago, there were no spaces left right, so I missed out on that.

Speaker 1 14:06

So I'm finding that, uh, particularly in Iceland and there may be other countries you encounter and you may want to if you're not sure if the country you're going to is, um, you know, popular and that maybe you should do more planning and less spontaneous. Um, you can ask other people that have been there what their experience was, but also consider the time of year. Obviously, what we call high season is definitely a time when you probably want to plan, versus the shoulder or off season. You might have more flexibility there. So think about it. Are you a type personality where you like to have everything planned to a T and you take your spreadsheet with you on your trips? You have everything printed out or saved somewhere, maybe in an app or in your notes, or do you just like to go with the flow in your travels? Go with the flow in your travels. Either way is great, because you want to travel the way that makes you feel the least stressed, the most confident and probably the most safe. Right Now.

Listener Reviews and Closing Thoughts

Speaker 1 15:22

I want to give a shout out to two wonderful ladies recently gave me some reviews this month, in March, and I want to just thank you. I love them. I love hearing from people. A shout out to Sammy B 0, 5 0, 7 0 7. And to novice adventure Thank you for your review. I'm actually going to share those.

Speaker 1 15:48

Um. Sammy B says I love Cheryl's encouraging and useful information for solo travel. Also, she has a great voice for podcasting. Thank you so much for that, um, and I'll be honest, uh, many years ago I actually didn't like my voice, but many people tell me that I used to teach yoga, so like there's that calmingness that does tend to come out, and so thank you for that review.

Speaker 1 16:15

And then from Novice Adventure it says Cheryl is such a natural at sharing her adventures, wisdom and encouragement. Her calm and soothing, easy to listen to voice and helpful tips Pack every podcast with so much inspiration that I look at travel in a whole new, exciting way. She's helping me dream again. Oh, I love to hear that and I bet she will for you too. So, yes, I hope you are dreaming of your next place and you too can join these ladies that left these beautiful reviews. It does help out the podcast, so you can go on to Apple podcast and leave a review if you've enjoyed this episode or any episode in the past. And sisters, get out there and have that adventure.