I just got back from a trip. It got me thinking about how to take better holidays—here are my reflections.
1) Travel around passions, not destinations
There are two ways to travel:
- Destination-driven (e.g. visiting popular countries and ticking off attractions)
- Passion-driven (e.g. building a trip around hiking, skiing, or diving)
Destination-based travel can feel like a checklist—something you do because you “should,” not because you’re thrilled to.
Passion-based travel is extremely rewarding. There’s nothing like doing what you love or satiating your curiosity.
2) You can’t control the weather
If your plans hinge on weather (think hiking, scenic views, or skiing), be ready to pivot when it doesn’t cooperate.
For weather-dependent trips, book hotels and activities last-minute based on the forecast. Pre-booking a scenic hotel risks a fogged-out view you can’t enjoy.
3) Spontaneous beats planned
Expectations shape your experience—and over-planning tends to inflate them.
My most memorable experiences are spontaneous ones. So leave space and time for spontaneity to happen. For example, instead of reading reviews of all the restaurants, ask a local’s recommendation on where they normally eat.
The flexibility to stay a day longer at a place or leave earlier is extremely underrated. You never know how much you like or hate a place until you’re actually there.
That said, being too spontaneous and doing no planning can lead to wasted time and money.
So find a sweet spot.
4) Rent a car if possible
Cars give you the freedom to go where you want, whenever you want to.
You don’t have to worry about catching the next bus and let it limit how long you stay at a place. This freedom is often underrated. In places where you don’t feel comfortable driving, consider hiring a driver instead.
So far, the freedom of renting a car or driver has outweighed the cost.
Tip: When driving on the opposite side of the road, a helpful rule of thumb is to keep the driver’s side closer to the center line or barrier during turns.
5) Go far out, fast
When you first arrive to a country, immediately go to the furthest place you intend to travel to on your trip. Don’t spend a day in the city or rest near the airport.
Once you reach your furtherest point, slowly travel your way back to the big city.
Do this as most cities are more similar than different. You’ll waste days feeling like nothing much has changed if you stay near the city.
If you travel remote first, you’re immediately transported to a different world. You’ll perk up and you take it slower. And when you eventually go back to the city before you depart, you’ll probably see the city in a different light
6) Aim for 10-12 days of travel
14 days can drag on too long.
8 days often feels rushed.
12 days hits the sweet spot: 10 full days to soak in the experience, plus 2 for travel.
7) Embrace hiccups
Screw-ups are the stories you’ll tell later. Even if it sucks right then, you’ll look back and smile.
8) Fewer Places, More Depth
Ironically, I enjoy spending more time in a few places rather than checking off all the attractions in the area.
Less time in transit means a richer trip.
Three nights in one hotel feels comfortable. Changing hotels every two nights gets exhausting.
9) People make or break the trip
Don’t travel with someone who complains. The most memorable moments will be the ones where you connect with new people.
Conversely, having a bad experience with people ruins the trip.
Corollary: don’t aim to check off places. Instead, aim to connect with as many people as possible.
10) Explore vs exploit tradeoff
We all balance exploring new places with revisiting favorites. A good balance is 70% exploration, 30% sticking to what I know I love.