Planning Short Trips and Thoughts on Spontaneity

There are a lot of great things about working and traveling. Figuring out how to make the things you want to prioritize in your life work together is an important and universally applicable lesson. On the surface, it may seem counterintuitive to attempt multiple trips a year while holding down a full-time job… and I won’t say it’s always easy. But I will say that if I’m making it work, you can too.

One of the most important aspects of balancing work with travel, in my opinion, is that you have to drop all your preconceived notions. And in planning my most recent trip abroad with two of my friends, I realized that one of these notions that needs to be dropped is the idea that you can only truly experience a new place in the world if you experience it spontaneously.

Let’s Talk About Spontaneity

If you are a natural Type-A planner, then the whole idea of wanting to organically and spontaneously discover things to do and sights to see after you are already in a foreign country makes you hyperventilate a bit. But if you are like most travelers I’ve met, you have some level of natural flexibility… and if you’ve traveled quite a bit, you are well aware that some of the best finds are located off the beaten path. Time in a new place to be spontaneous - to discover a corner cafe, or an alley pub, or a forgotten park, or a tiny art gallery - is some of the best time you can spend in a new place.

So how do you build in time for those spontaneous finds when your time is extremely limited?

Planning Smart

As anyone who has traveled abroad (or even to a neighboring city) knows, things don’t always go as planned while traveling. Generally, planning an itinerary listing every activity for each day with a timeline of when each activity is supposed to start is a waste of your time, because things will happen every day to throw off that plan. That being said, it’s much more difficult to just buy a round trip plane ticket and try to figure out everything (accommodation, transportation, what you want to see, what cities and countries you want to visit, etc.) when you only have a limited amount of days off work.

For a short trip (like a 10 day trip from work), you need to try to be somewhere in between no plan whatsoever and every day planned down to the minute.

You need an outline.

Plan A Trip Outline

The beauty of planning a trip outline is that you are addressing the big ticket items ahead of time, but you are leaving time for spontaneity within the country or city. Before each trip using vacation days from work, I have my flight purchased. I also know where I’m sleeping each night - the city and the hostel. Last but not least, I know how I’m getting from city/country to city/country (trains? buses? connecting flights? etc.)

And... that is about all I know.

On my most recent trip abroad, I realized that my travel buddies wanted to add a bit more to the outline, like the sights that they wanted to target seeing each day. I don’t think this was necessarily bad, but I also want to be honest about the fact that I’m not sure we hit our daily list of sights exactly as planned on any of the 10 days of the trip.

As long as you know where you’re staying, each city/country you are visiting and how you are getting from place to place, you can relax a bit. Talk to the people at your hostel front desk, other travelers you meet and locals about the best things to see and do in the city. It’s good to have an idea of some of the things you don’t want to miss, but it’s also great to be able to take a local’s recommendation on an off-the-beaten-path find.

You may not be able to be quite as spontaneous as a long-term traveler due to time constraints, but you can find a balance between planning and spontaneity even on a short trip.

How do you balance taking advantage of limited time in a new city with organically experiencing the city? I’d love to hear your thoughts and advice in the comments!