My wife finally convinced me to take a real vacation this year. We picked Chile because mountains meet ocean there – sounded wild. Started digging into planning and almost quit after seeing how massive that country stretches. Decided to write this because nobody tells you how messy itinerary building gets.
Phase 1: Paper Chaos Mode
Grabbed every guidebook from the library like a lunatic. Spread maps on the kitchen table while eating takeout pizza. Highlighted stuff with neon markers until whole pages looked radioactive red. Realized I had enough sights circled for a 6-month trip. Felt dumb.
Then I did the thing normal people do: Googled “best 2 weeks Chile”. Got twelve thousand different opinions. Wanted to punch my laptop. My dumbass move? Trying to cram both desert north AND glacier south into 14 days. My brain broke calculating 4-hour flights between regions.
Phase 2: Reality Slap
Sat down with my credit card bills mocking me from another tab. Realized we only had about $3000 total. Immediately axed these three things:
- Torres del Paine multi-day trek (crazy expensive park fees)
- Easter Island flight (cost more than our whole airfare to Chile)
- All fancy hotel dreams
Printed a blank calendar for April. Blocked out travel days in red marker – never count these as “vacation days”. Felt depressed seeing how few white squares remained.
Phase 3: Location Tetris
Finally chose: Fly into Santiago, bus to wine valleys, then focus solely on central/south Chile. Hacked the plan like this:
- Santiago: Booked walking tour for DAY ONE (beat jetlag by force)
- Valparaiso: Found Airbnb with killer harbor views
- Chiloe Island: Scheduled two ferry days – heard delays happen
- Pucon Volcano: Left one empty day cause weather screws everything
Biggest win? Not trying to switch towns every damn night. Three nights minimum per spot. Told myself “You’re not 20-year-old backpacker anymore” three times.
Glueing It Together
Took three sticky notes:
- Flight times + confirmation codes
- Bus company phone numbers (Chileans barely use websites)
- Airbnb host names
Made one rule: No pre-booked tours except volcanoes. Freedom to nap matters more than “must-sees”.
Final itinerary looked like a toddler drew it – scribbles everywhere with coffee stains top right corner. But guess what? We actually relaxed in Chile instead of marathon running between selfies.
Would I do it better next time? No chance. Always chaos when humans plan trips.
