Oh, The Places I’ll Go

When I was first thinking about long-term travel, my perfect route hit every continent and focused on hubs of arts and culture. I’d spend a full month in one city, spend the next month making my way to the next stop, later, rinse, and repeat.

Somewhere along the past year, though, I determined that I’d rather leave sooner and do less. Instead of visiting every continent, I’d focus on just three with four months in each. But for quite some time, I’ve been stalled by my own indecisiveness.

Do I trace Africa from Cairo to Cape Town – something I would likely only be able to do during a long-term trip? Or do I take it easier on myself and visit the few European spots that have yet to be ticked off my bucket list?

It’s time to break the rut.

BootsNAll recommends structuring long-term trips around “pillars” – the sights you must see, the places you must go.

My bucket list is about 10 miles long, so it’s taken hours for me to really think critically about what I want to do and where my priorities lie. While I love the idea of selecting one purpose to my travels – like some people want to just volunteer or WWOOF or surf the world’s best breaks – I think this being my first RTW trip, I want a little more variety.

Those key experiences and sights I would never forgive myself for missing out on – if I only have one year, those need to be my focus.


Venice Ponte dei Sospiri

If I hadn’t already been to Venice, it would probably play a significant role in my RTW planning. Luckily I got to visit a few years ago and know I don’t want to spend much more time there.


I’ve ultimately landed on doing four-month tours of Europe, Asia, and South America, which I think will make a good balance of more expensive countries with cheaper ones, and higher stress destinations with more convenient ones, while also hitting many of the items on my bucket list.

That being the scope, my absolute top 12 (one for each month of my trip) would be:

  • Hike the Inca Trail to Machu Picchu
  • Attend a traditional tea ceremony in Japan
  • Watch the sunset on Santorini
  • Swing a hammock on a beach in Bali
  • Zip line through the Monteverde Cloud Forest in Costa Rica
  • Tango in Buenos Aires
  • Explore Angkor Wat in Cambodia
  • Stroll through the villages of Cinque Terre
  • Find my dad’s old house in Bangkok
  • Kayak around the city walls of Dubrovnik
  • Visit the Taj Mahal
  • Tour Iceland’s Golden Circle

As important as flexibility is, at the end of the day, travel is about making choices. Committing to these dozen experiences gets me out of the cycle of indecisiveness and puts me one step closer to what’s really important: being out in the world.


3 thoughts on “Oh, The Places I’ll Go

  1. Pingback: When and Where to Slow Down | WorldSmith

  2. Pingback: Putting the Pieces Together | WorldSmith

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