First we start with where we are going.
Every year it is the same for us now to visit family, but before, we used to travel everywhere so this was very exciting.
Then we choose what dates / when / what season we are going.
This is also kind of tricky because we both work full-time, we don’t want to go when there’s nothing to see or do in the city itself, AND / OR when it is SUPER BUSY because it’s tourist season because you’ll pay a lot of $$$$$$$$$$$$$$. We’d rather go off-peak but not so off the reserve that we end up being bored.
After those two main things are nailed down, we make a list of everything we HAVE to do based on Where / When to get an idea of the priorities we need to cover.
1. MAIN PEOPLE TO VISIT (IF ANY)
So for instance, if we are going to Paris for 2 weeks during summer, the main thing is to see his family, so that becomes #1 on the list.
We normally stay with them, but since there are so many we can choose from, we usually plan to stay one week with one relative, and another week with another.
That solves accommodations, but if we didn’t have relatives to stay with, then we would choose the People To Visit, and then note where we would have to stay based on proximity to them.
2. MAIN THINGS TO EAT
No trip is complete without things to eat.
We list out any special things or restaurants we want to eat, like let’s say Berthillon ice cream on Ile-St-Louis. That goes on the list too, and we usually try and figure out if we can merge a visit with a friend with an outing for ice-cream so that we kill two birds with one stone.
3. ACTIVITIES TO COMPLETE
Sometimes, depending on the city, if we don’t know it (or even if we do), we make a note of what we want to do as well, other than visit people and eat. In Hong Kong for instance, I like to ride the tram (which we would do a lot of anyway), but I also like The Peak for the view, so we’d make a note to go to The Peak.
I also very much enjoyed visiting the Chi Lin Nunnery in Hong Kong, so that would go back on my list as places to visit.
4. ROUGH MAP OF WHEN / WHERE / WHO
After we have all of that, then we map out a rough schedule. Day One – Visit X, Eat Y, and so on. We don’t plan more than 2 activities in a day because we know that visits go on longer than expected, etc.
We always schedule in family / friends first.
They take up all the priorities in our schedule, and we confirm with them if they are taking days off, going on vacation, won’t be there, etc so that we can maximize who we see.
Then with the holes in our schedule, we choose what we want to do and eat (if they don’t happen to join up with a family / friend outing), and schedule to the opening times of places — some places are closed for holidays (we sometimes visit during holidays), so we need to know if it’s a waste of time to visit the Chi Lin Nunnery if they won’t be open!
5. CONFIRM ACCOMMODATIONS & TRAVEL
After all that is done, we survey the schedule, adjust it to make sure we leave enough time for taking public transit, delays in flight times, and have time to eat or in this case, have a quiet place for Little Bun to nap, and make sure we aren’t overbooked.
Once that is done, if we haven’t already worked out accommodations, we pick an area that is central to what we want to do that is within our budget (think 3-star, 4-star if we feel fancy), and search for good deals in that area, multiplied out by how many days we are staying.
We also work out that the hotel has to be near public transit (nobody wants to limp back to a hotel room, and the closer it is the better), and we also plan the scheduling of travel if need be, like taking a bus to another city to visit a friend, means that we need to schedule in time to get ready for this bus, make sure we know when this bus leaves, get to the station 1/2 an hour early, plan for when to return on the bus back, etc.
We also consider taking a bus versus a train (I MUCH prefer a train) to get to another city, or to go from the airport to the city, etc. We don’t cab anywhere because it’s too fancy for us so this adds an extra layer of complexity.
From there, it’s then just booking everything and making sure the schedule makes sense with ample time for delays in visits or impulse changes / insistence of friends that we stay the night & not return to the hotel in another city.
Roughly, that’s what we do.