To Plan It or To Wing It… How Do You Vacation?

To Plan It or To Wing It… How Do You Vacation?

Ivan and I belong to two very different schools of thought when it comes to vacations. I’m very much like my father in the sense that I like to plan. I like to plan the shit out of my vacations. I prefer to get up early, spend the day on the go and see as much as possible. No time for lounging around… there are things to see people and time’s-a-wastin.

Ivan, not so much. Ivan likes to sleep in and see where the day takes him. He says a vacation is supposed to be relaxing. What a crazy thought, right? It can make vacationing together rather difficult. On our last trip to Philadelphia, I tried to reign in my planning. As always, I had a number of things I wanted to do, but tried to let Ivan set the pace. I won’t lie, it was hard for me not to follow a plan, but it made for a pleasant vacation.

Honestly, it was probably one of the better vacations we’ve taken together. We weren’t exhausted from constantly being on the go and we had time to really enjoy ourselves. We still got to see quite a few things, but we did things at a nice, leisurely pace. I can’t promise that I’ll always be able to control my natural vacation nature, but I promise to try.  

My question is, how do you vacation? Are you like me and plan every little detail? Try and cram as much into each day as possible? Or do you like to take things as they come and have a relaxing vacation?


  • i am like you for sure. plan all the things! that being said, i know if i over plan, we get tired and grumpy, end up bailing on things just so we can relax one night. so now i try (*try*) and only half plan. i obviously plan all the big things – flights, hotels, transfers to and from those things. then i plan any tours i want to do because they are not things you can decide on the day, in my opinion. and then.. i stop. sometimes i look into good places to eat near our hotels or try and get an idea of what we might need to do – we have a couple of all day tours in NZ that we will need to pack food for, so i have to know that in advance, you know? but otherwise, i don’t plan every little detail like i used to. i also absolutely allow for relaxing nights. i prefer to go-go-go first thing in the morning, go back to the hotel for some relaxing, pop out for some dinner or wandering, bed kind of early because apparently we are 80. lol. i think there are pros and cons to planning, you have to find the balance.