Oct 17, 2015

Short term travel for the vagabonder wannabe

Traveling is best when there is an open ended expanse of time. But what if that's what you don't have? For the last decade, my wife and I have longed to head out on that open-ended wanderlusting journey, but career ambitions have gotten the better of us. Thus, we’ve been crafting the art of short term ( 1-3 weeks) international travel. What follows is an outline of the mindset and approach needed to make the most of your limited time. Before you read on, I assume that you:

  • like to experience a trip instead of ‘checking-out’
  • you’ll have more to spend (particularly on logistics) than the long-term vagabonder
  • you see the value in a flexible itinerary
  • you’d like to avoid the traditional tourist line when you can
If that’s not your cup of tea, you may find the suggestions in here not fitting to you. If you typically book cruises, close this browser immediately.


First and foremost, be researched, but not regimented. There are young travelers and newbs who need to have an itinerary, but a flexible plan is better. What if the weather sucks? What if you want to stay longer or shorter? How do you stay flexible? It’s so much easier now that’s it used to be. Our trip to Italy, 10 years ago, we’d start calling down the list of Lonely Planet’s accommodation section the day before, but more often the morning of, our intended arrival. Now, Airbnb, cheap international data plans, and a few handy smartphone apps make flexible travel much easier.

What does it mean to be researched? Logistics, areas of interest, and knowing what needs to be planned. Let's start with areas of interest. I'm assuming you know where you want to go. But let’s be more specific. What is there to do in a region? What are the highlights? Food, adventure, sights, culture... Use TripAdvisor and Google to get a lay of the land. Read travel blogs to find compelling experiences. You are looking for depth here not the postcard stuff, but what's underneath. Time of year, touristy rating, cost, time commitment... That's the depth you are looking for. Be judicious in determining whether your content was paid by an interest other than traveling (like a hotel chain sponsoring a blogger, a country promoted post). Not that sponsored content is useless, but the intentions of the author can be misleading and often outright deceptive. This scathing review of a TripAdvisor post is just the tip of the iceberg.


Now if you have strung together a few places of interest, start flushing out logistics. How do people get around: train, bus, car, motorhome, walking, scooter, bike...Travel forums and travel blogs are great at digging this stuff out. Renting a car buys you the ultimate freedom, but knowing the bus/ferry/train schedules can work well too. Don't be intimidated, but read up on other's impressions of those transportation modes respective to your frame of reference. For instance, do you drive on the other side of the road? Do trains tend to run late? Is English common? For instance, in Croatia, the ferry schedule changes with the season. Finding accurate info online can be a challenge. This is why I created a search engine based on narrative travel blogs.

Commit at the last responsible moment

What needs to be planned and what can wait? Do you need to book that tour in advance because it sells out? Obviously you need plane tickets there and back. What about inter-region flights? Only a few places to stay at a particular area? Book it. The more you can widdle this down the better. Here is the key: there are lots of things to do in a region and reserving your commitments to the last possible instant increases your chance of finding that key piece of information that might totally change your mind. For instance, we did a zip line tour that we booked hours earlier. Most people book, weeks or months in advance. For us, it turns out the tour was on the way between cities we were traveling to. Lots of people recommended we visit Plitvice Lakes in Croatia because of the expansive beauty and unique landscapes. Well the weather was crap when we would pass by this area, and another less busy park, was convenient for our itinerary and the weather was great. You could also go swimming there and its was less crowded. We decided to go there the morning of. It’s these last minute plans that seem to have the best effect on perceived travel experience. Serendipity, can bring a lot of joy to a trip. Working to find serendipity is a bit like hammering water to make it flow, but you can create the conditions that improve the chance of making it happen.

Sample Itineraries

You need to put it all together by knowing where to start. What direction to head? Sample itineraries? What-if scenarios on that itinerary. There are some sample itinerary websites out there. You can get a sense from ’trip blogs’ of where to head. Q&A travel sites can also help with itinerary generation. I posted this on Trippy and got 3 pretty decent answers. In the end, we didn't pick any of these specifically, but the information provided was helpful.

On-the-ground planning

Lastly, I relish the experience of piecing things together on the ground. You can pick up information from locals or other travelers. Once you are on the ground use Google Maps, TripAdvisor, saved information from your travel investigations, travel books, and importantly Airbnb. Lots of times the host will provide you some key information in making the most of you time. On the ground intel, adjusting, re-routing, last-minute decisions...helps to seed those moments of serendipity.