Last year, I made a little challenge to average a country a month for the year. While keeping my day job. On allocated leave days. Also, I had been going on a LOT of solo trips and wanted for a change to involve family and friends on adventures.
How I Planned Leave Days
I spent 3-5 days for most of those trips and my most expensive trip was probably to Havana. I was in Montreal for a work trip and it’s a more ideal flight route than through the USA. Singapore had gotten visa-free status recently and it seemed like a good chance to visit.
Instead of maximizing my long weekends by flying first thing Thursday night and returning Monday before daylight, I found it more useful to organize and maximize my time spent on arrival. Different societies have different hustle and bustle times so there might be nothing open on certain days/times. Also if you get in at weird hours, you might end up spending more on getting to town from the airport.
What I did a lot of was to perhaps fly off (or arrive) on Day 2 of any long weekends and take an extra day or two off to get back. This way, it usually ends up being slightly cheaper and there are less crowds to deal with.
I’m personally not big on coming up with detailed checklists of things to do and places to go. My benchmark these days is that if I know I’ll regret not doing/seeing something, I should do it. I hold this philosophy for life too.
Ultimately, I do feel that if you’re doing something for bragging rights, it’s meaningless and personally, I don’t have anything to prove.
Coordination for Travel Buddies
What I usually do is to book trips that I feel has good value and over a time period that I feel good about. The more spontaneous of my trips were to Yangon, Greece, Hanoi, and Japan. Flights happened to be affordable for those places during dates I could travel on.
The most planning that was done were to Kazakhstan – where I joined a unicycle tour, to Montreal (for work), Xi’an for a cousin’s wedding and to Kaohsiung which I had wanted to bring family around to a lesser-known part of Taiwan.
It’s quite straightforward to travel solo since I don’t need to coordinate for leave days. Travelling with company is a little different. An arrangement I’ve found works best for me is to find friends/family who are ok with staggering their arrivals. We’d arrive +/- a day (or two) from each other and this is perfect too since you get some alone time.
Favorites and Fun
On most trips, I’d book a multi-week return flight to a destination and start figuring out where I would go. Short trips make it almost impossible to venture out of cities. I found myself having to commit to staying in one or two cities. A lot of these trips forced me to plan with a strong focus on reducing travel times. I think generally I got to see more of the cities than I usually do.
A common question I do get asked is what my favorite destination is.It’s really difficult to say because you do feel differently about places with time. I think though that this is one of the things that was made most obvious with doing a 12-in-12.
In the moment, I think I really enjoyed Greece in general. The country is perfect for a road trip and travelling solo makes that more inaccessible. I really liked Kaohsiung in Taiwan as well. We visited during their annual lantern light-ups and it was amazing.