Question: How do you plan your trips? I want to have a great time on my next trip to wherever but I am not sure what factors to take into consideration when planning.

Answer: 90% of my trip planning is usually process of elimination and based on a combination of time of the year, language, main objective & cost. Other factors like security, live events, touristy v non-touristy usually end up falling into one of those larger categories. 

For example, my last trip to Spain & Portugal were because: 

  • Time of the year: it’s summer in most of the northern hemisphere but summer-winter in San Francisco. So I wanted a place with heat, sun & beaches. (Goodbye Southern Hemisphere & far north countries)
  • Main objective: My goal was leisure. So that also eliminated any places with dubious security, huge crowds/massive events or vastly different customs/cultures that I would need to study up on. (Goodbye costal Africa, Asia-Pacific, Mexico)
  • Language: I wasn’t in the mood to adapt to any new languages or customs. Not struggle too much with language. So that eliminated any non-English, Spanish or Portuguese countries as well. 
  • Cost: the bulk of costs is usually airfare, unless you’re well connected or have mad miles. So I always run a few searches at least a month before to see what the cheapest destinations are (direct where possible) from my current location. San Francisco happens to be super far from almost everywhere, so this is usually a pretty big factor for me since I only just started working in the miles game. 

So in the end, my options were Spain, Portugal, well-frequented Mediterranean countries like Greece, the English/Spanish/Portuguese-speaking Caribbean like Aruba or Curação and Australia/New Zealand. In the end, I found a dope 1 way ticket to Barcelona for $600, bought it instantly & went from there. Europe tix from SFO are usually $800+ so I didn’t want to let that chance go!

Also as a general rule, I try to force myself to go to new places, even though there are places I’d love to just go to again & again…I can do that when I’m old & less adventurous. 

Handy Links 

  • Kayak Explore – Visualize the cheapest destinations from your current city 
  • Skyscanner – Leave the ‘To’ box empty to search all prices from your destination to anywhere in the world 
  • – Use my referral to get $20 off your next hotel/hostel/apartment booking & plan based on where you can get the most insane hotel/apartment!

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