Deciding where you want to travel is all well and good, but once you’ve got your destination sorted out there are still plenty of practical details to work out. As much as we like to picture these trips as some sort of magical teleportation to an incredible location with nary a concern to trouble this new and wonderful state of relaxation and bliss, well, sometimes it doesn’t exactly go down that way. When it comes to the logistics of physically moving from place to unfamiliar place there are often more decisions to make than most people realize.

Stay in one place or spread your time among several locations? The main consideration here is how much time you have. If you are hoping for any relaxation at all you will need at least two weeks before even considering multiple stops. If you decide you will have enough time to move around, however, I generally allow three or four nights for cities, and closer to a week for beaches or hiking destinations. Unless your favourite thing in the world is riding cramped Central American buses on rough, neglected roads, then eleven Guatemalan cities in nine nights seems reasonable.

High or Low Season? Often this will be dictated by your job or family or other personal considerations but, if you have a choice, these two options can offer surprisingly different experiences of the exact same place. High season usually has the best weather and/or the most popular festivals, but will be more expensive, more crowded, and you will probably need to book most things ahead. Low season allows for more spontaneity and means fewer tourists. Although, in some places, much of the tourist infrastructure will close in the off-season, and now and then a pesky monsoon could encroach on your fun.

Tour or Independent? If you’ve ever considered scrapping an entire trip simply because you hate the planning side of things, or become debilitated with fear when eating mystery empanadas without knowing the exact location of the nearest flush toilet, then maybe the comfort of an organized tour is just what you are looking for. On the other hand, if you’d prefer to avoid being part of a large group herded to and fro by a single pink umbrella, then you might be better off running your own show.

Carry-On or Checked? These days going carry-on can save you a little bit of money, but your main consideration should be how disastrous it would be if your luggage took an unplanned detour for a few days. On brief trips you can theoretically pack lighter and go carry-on, especially since you don’t want to waste any of your precious days shopping for replacement toothbrushes and dolphin-themed shorts. But if waiting a couple days for your foreign exchange calculator and favourite straw cowboy hat isn’t of paramount importance, you can make your travel day much more comfortable by checking your luggage, allowing you to browse the airport magazines unencumbered and get in an extra fifteen minutes of reading while all those people with large cabin bags nervously queue up to make sure they get on before the overhead bins are full.

Backpack or Suitcase? For me, it comes down to one simple question. Will you ever have to transport your luggage over terrain that isn’t conducive to wheels? That beautiful, powdery beach loses some of its lustre when you are sweatily dragging your wheeled suitcase along it for half an hour. On the other hand, if you are expecting to be met at the airport by a cheerful attendant offering door-to-door service and a welcome cocktail, you will be hard-pressed to notice the benefits of a backpack.

Public transport or car rental? There are parts of the world, such as Egypt and India, where a foreigner renting a car is a decision on par with butt-slapping an armed security guard or drinking a tall glass of diphtheria. But there are also many places where driving yourself is actually quite reasonable, and allows you the freedom to travel on your own schedule and make changes on the fly. Just be aware that no matter how inclusive your credit card rental coverage seemed based on the three lines of terms and conditions you read before getting bored, there is always some stress involved with driving someone else’s vehicle, and knowing they will be practically euphoric to have you pay for even the slightest hint of damage.

What should I read on the plane? Well, funny you should ask, because it just so happens that my newest travel book is now available online! “Roam: The 9 Greatest Trips on Earth” is a detailed account of the very best trips we have ever done. Stories and anecdotes, details and advice, poor hygiene and ugly hats. Find out more at routinelynomadic.com, or go directly to Amazon, iBooks or Kobo online.