Trip planning: why I’m looking more than a year ahead

Basically conversations with Chris lately have gone something like this:

“So I’m thinking we should go to (place name) over Columbus Day weekend.”

“We’re going to Oktoberfest right before that and Venice after, it is too much.”

“Huh? No, I’m talking about the next Columbus Day. 2018!”

” … seriously?”

So yeah, I’m trying to map out our travel destinations for all of 2018, basically. Yes, Chris (and uhh a few other people I’ve mentioned this to) think I’m crazy.* But listen, I have my reasons (beyond being obsessed.)

  1. Making sure we are being strategic about what weekends we plan travel.* Chris’ work schedule means that he gets every other Friday off (he works nine hour days). This year, I didn’t really look ahead well enough at the combination of RDO days and federal holidays, and missed some opportunities where we could have timed trips differently to use less leave. Next year, I’m planning our longer trips in ways so that we can end up with, say, 10-day trips that use only four days of Chris’ vacation time.*Originally ony of my goals was to avoid having trips super close together (our two big trips, France and Ireland, were less than a month apart) but it kind of seems like they are going to end up being close together anyway because of when holidays fall. Ha! 
  2. Planning for when visitors come. If we get a schedule set for when we’ll be out of Sicily, the various friends and family members who are talking about visiting next year can use that to plan their own trips to see us! (Which we are so excited for, guys!!)
  3. Being strategic with our credit card points. As I mentioned in this post, I have some hotel points stockpiled in a few different currencies. Knowing when we want to go where helps me a) decide at which property I’d like to use them, and b) actually make this happen. Award space can fill quickly at highly desirable places and times of year, so booking early is often a must. Knowing that we want to go to the Hilton Malta on X weekend also allows me to check to see how many more points I need to make it happen, and thus make an informed decision about what credit card I want to be using to rack up points.
  4. Top pick of AirBnBs (and hotels). In the summer months here, the best AirBnBs at desirable tourists destinations (like San Vito Lo Capo or Tropea, for example) can book up quickly. Knowing where we want to go when means I can be looking ahead and get the best selection when time comes to actally book. I actually already booked one place a few weeks ago for summer 2018. It is a cool treehouse on Lake Bled in Slovenia that Chris saw last year and wanted to visit, but there was no availability even months ahead of when we wanted to go. This year, I was on top of it!  Added bonus: they honored the 2017 prices even though I found out they intended raise them by 20 euro per night in 2018 (we communicated via e-mail because rooms weren’t even available to be booked online yet).
    Looks nice, but does it have AC? Because AC is a deal breaker. (Chateau d’Usse)
  5. Getting the best price for flights. Trying to time it right when buying a plane ticket is a frustrating business. Booking too early could mean missing out if prices become cheaper down the line, but waiting too long could mean your preferred flight sells out. Planning ahead means I can set up price alerts for flights and, combined with looking at options compulsively periodically, I at least have a general idea of what pricing has been doing for a specific place. For instance, if I saw a flight for Rome to Lisbon for 100 euro it might seem good, except that I know a few weeks ago I saw one for 75 euro. See? 

*This post is in no way intended to lay out the case to my husband for why I’m not crazy. Well, “in no way” is probably a bit strong. I should probably say it is mostly not aimed at Christopher. Love you hon!

3 Responses

  1. MA Douglas

    Thank you for this blog! It is so refreshing and educational. This is the only way in which I will ever experience such a wonderful place. Hope you & Chris & Kiddos are having a good time – it appears as if that is true.

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