Where you travel to is a big question and there’s thousands of right answers.  A few things that you may want as criteria:

  • Affordability- living somewhere for months is a lot different than getting a hotel room for a few days.  This can touch on everything from travel costs, to accommodations, to the exchange rate and general cost of living.  Going to Dubai for a month costs a lot more than going to Mexico for a month.
  • Cell coverage – ideally compatible with your current phone and carrier
  • Internet – you may not need blazing fast speeds, but you’ll likely need a broadband connection and a stable one that doesn’t drop out on you every 10 minutes
  • Security – everyone has different comfort levels when it comes to feeling safe and secure.  A small economically depressed town has a very different vibe than a four star resort in the same country.
  • Healthcare- how important is it to you that you have first class medical facilities near by?
  • Communication – Do you speak the language?  Will the people there speak your language?
  • Timezone – if you need to collaborate and coordinate with your team, or your clients, its good to not have the daily 3 PM status call taking place at 3 AM in your new location.
  • Relaxation or Adventure – when you aren’t working do you want to lounge on the beach and work on your tan or do you want to hike through the jungles to see ancient temples?  Or would you prefer exploring Berlin’s nightclubs or shopping at Harrods?
  • Difference Quotient – do you want to be somewhere that feels largely familiar?  Are you okay with being unable to drink the water or eat vegetables that you haven’t soaked in bleach for 20 minutes?  Are you okay with eating with your hands?   How about the bathroom facilities?  The world is a vast place and it can be more different than you can imagine – in both good and bad ways.
  • Accessibility – getting off the beaten path can be great, but having 30 hours of travel each way can be exhausting and stressful.  Also think about this in terms of healthcare.  If something serious happens to you, how long would it take for you to get transported to a hospital you would trust?