How To

How to…See the World

A number of friends and readers have asked me how I travel so much or how I am able to plan such trips. I have been fortunate to have jobs with decent time off, but the real trick is how I go about trip planning. If you find yourself stuck, try the following steps and you too will be traveling in no time!

  1. Identify where you want to go
  2. Figure out whom you want to travel with you
  3. Determine when you can travel

This may sound simplistic, but it just takes a little bit of work upfront to set each of these lists up.

1.) Identify where you want to go

A travel list helps you figure out your priorities. If you haven’t done so, even something as simple as a Google Sheet or an Excel spreadsheet with the following columns can be an easy way to prioritize which places are on the top of your list:

City Country What to See/Do/Eat Risks Must Do
Kingston Jamaica Beach, Swimming Hot, sand Find that beach from that one movie…you know the one
Paris France Croissant, Cafes Don’t speak French Eiffel Tower, The Louvre

2.) Figure out whom you want to travel with you

Some people love traveling alone. I’ve been to Seoul, Puerto Rico, and Panama by myself and while I’ve had awesome trips in each place, I prefer traveling with 1-3 other people. It makes transportation, lodging, and activities cheaper and frankly it’s more fun to try a variety of food and events when you have friends along. If group travel appeals to you, here are some questions you might want to consider before inviting people to join you:

  • Where do my friends want to go?
  • Where do I have friends, family, and other contacts?
    • Knowing someone in country can make a place seem more attractive or easier to get around and do things.
  • Who speaks a language or has experience with a particular country?
    • This is far more important in less developed countries or places where your native tongue is not spoken!
  • What are my travel styles and how do they match with my friends?
    • Are you a high maintenance traveler (nice hotels, business/first class, organized tours, etc.) or do you prefer the adventures and laidback trips (flying by the seat of your pants, no formal agenda, wander from town to town)?
  • What do I want to see/do on this trip?
  • Will this person (that you are inviting) commit to our plans or be a habitual flake?
    • Probably the single hardest and most important question that I ask!

3.) Determine when you can travel

Literally print out a calendar or use your phone/computer and identify weeks or weekends during which you’d like to travel. This way when you’re scanning a deal site like Kayak or and you come across a great deal, you’re ready to pull the trigger.

Be organized - just enough to figure out when you can go!

Be organized – just enough to figure out when you can go!

If you’re thinking about integrating all of this information, you can easily set up a Google Sheet and then send it to your friends. Start by adding columns for your friends’ names, the top places you or they might want to go, and then figure out when you want to go – either weeks, weekends, or even months:

Name Paris Lima Beijing Aspen 6/5/16 6/12/16 6/19/16 6/26/16
Jason Yes No No Yes   Free Busy Free Free
Lisa Yes Yes Yes Yes   Busy Busy Free Free
Kristen No No No Yes   Busy Busy Busy Free

So it looks like everyone wants to go to Aspen and can go the week of June 26, 2016. Hopefully that works for you too. 🙂 This kind of organization might seem a bit over the top for some, but for those of you who want or need a little structure, I hope you find this helpful. Until the next trip!


Categories: How To

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