This week we finally got the husband’s schedule for the 2019-2020 school year and it contains both good news and bad. The bad news is that, yet again, we do not share the same week off for spring break. The good news is – huzzah! – we both have a two-week Christmas break in 2020. We also have one in 2019, but my experience with school district calendars tells me that these may be the last two-week winter breaks for a long time. (Once the holiday lands on or next to a weekend, all bets are off.)
Naturally, my brain went immediately to that special place: TRAVEL PLANNING. Where could we go? Where should we go? What makes sense with only two weeks? Should we go somewhere we’ve been dying to return to, or try someplace new?
With breathless excitement, I put all these questions to the husband, and the response was predictable: “You’re crazy. It’s two years away. I refuse to even think about this right now.” Knowing where all his buttons are, I started to tempt him with the idea of cycling and hiking Death Valley, with its comfortable wintertime climate, and his ears perked up a bit (and his eyes got a dreamy, faraway look and he started drooling). Then, sensing the trap, he quickly recovered his sensibilities, wiped his chin with his sleeve, repeated that I was a lunatic, and went to work on his bike in the basement.
This fun marital exchange got me wondering if other people plan their travels far into the future, or if I truly am a travel-obsessed wacko. (I can think of worse things to be.) I’m not talking about talking about doing a vacation at some distant point in the future, with noncommittal we shoulds and we ought tos. Heck, we all do that, don’t we? I’m talking about actually starting to research and plan. Maybe not booking flights and accommodations just yet, but definitely starting the planning process, as well as using phrases like “we are going to (insert destination) in (insert date).” At one point, I had five years worth of travel planned out into the future. And guess what – we did all of it. I don’t have that lengthy a list going right now, but here’s what I do have:
Spring Break, 2019:
The husband is going bike packing for the first time, probably out in Utah. I will have to live vicariously through him. (The Utah part, not the cycling part.) (Chance it will happen: 90%)

Summer, 2019:
Quick trip to Leadville, Colorado with the Bobbie. Climb Huron Peak. Do some cycling. (Chance it will happen: 60%)

Summer, 2019:
England/Wales trip. (Chance it will happen: 100%) Everything is booked and ready to go. Has been for months. That’s probably why I’ve needed to plan other trips – I’ve been bored. Makes me a bit nervous actually writing 100%, though. Feels like I’m tempting fate.

Fall, 2019:
20th wedding anniversary four-day weekend. (Chance it will happen: 95%) As of this writing, New Orleans is in the lead among people who’ve offered up an opinion. Lots of people have dissed Miami – not entirely sure why. In researching San Francisco last night I got all excited about Carmel, California, but it’s violating most of the rules I imposed to make the trip less stressful (car rental, long drive from airport), so I’ve reluctantly let it go.
Christmas, 2019:
Laos/Cambodia Multi-Sport Adventure: Asia, here we come!! (Chance it will happen: 85%. The deposit has been paid, the school calendar has cooperated… I just don’t want to jinx our long-awaited first trip to Asia by writing 100%.)

Spring Break, 2020:
Nothing, zero, zilch, nada. Separate spring breaks again. Actually, the silver lining is that I don’t know how many more trips we can fit in and still afford to feed ourselves. It’s good to let the pocketbook recover. I guess. 😦 At least the bunny will be pleased we’re not going anywhere.
Summer, 2020:
Spain/France. (Chance it will happen: 95%. Again, only superstition is keeping me from writing 100%.)

Christmas, 2020:
?????? That’s the big question. Should it be a destination that has a favorable December climate, such as Death Valley or Australia? Should we finally get back to our favorite place in Jamaica given the dearth of joint spring breaks? If we end up loving the Laos/Cambodia group trip, should we do another one to, say, Thailand or Vietnam? Ugh. So much to think about!!! It’s a wonder I get anything productive done around this house. (The husband would say I don’t.)
So what about you? How far out do you tend to make firm travel plans? What’s your record? Oh, and am I crazy? (If you are going to respond to that last question, there’s only one correct answer. It’s no. Let’s not give the husband the satisfaction of the alternative response.)
Christmas 2020 I would suggest you visit your mother.
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Ha ha! It’ll be the last time we travel over Christmas for several years. I promise.
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I balance good travel deals with planning. Usually I wait till something pops up and then I jump on it. This year is really the first time I’m planning, and it’s mostly because I’m limited on vacation time (so I need to maximize the days I get and plan over long(er) weekends).
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You’re lucky you have the ability to go when the travel deals present themselves. As teachers, we are handcuffed to the school year schedule, which has its pros, but not being able to travel whenever we want is a huge con.
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I’m with you! I have my travel plans laid out for the next five years. Not that they are cast in stone, but I know what I want to aim for. I am a shocker and am planning the next trip before I have completed to the one right in front of me! Off to India next week, but dreaming of walking the Camino Madrid in May! Oh well, there are worse addictions! 🙂 Happy planning, Mel
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I like your travel planning style! Have a great journey in India! And yes, there are much, much worse things to be addicted to.
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We are very similar. My wife’s school calendar recently came out and I got all excited looking at dates. We are planning rural Thailand for spring break, Japan in June, probably Thailand/Laos Christmas 2019. I keep a spreadsheet of all the places in SE Asia I want to see. It is color coded by best times to visit.
To keep some flexibility, until the tickets are bought we always say it is a plan of the day and can be changed! Happy planning, and may the spring break gods line up in future years. Of course, if you both taught at an International School in Thailand you’d have the same breaks each year. Just sayin.
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Ha ha! Duly noted. Maybe after we visit Asia for the first time at Christmas (I’ll keep an eye out for you in Laos), we’ll consider moving there.
Your plans sound great. Japan and Thailand are high up there on the “want to” list. And your color-coded spreadsheet is enough to make any Type A travel planner swoon.
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It’s interesting to read all the different types of planning that go on. You definitely have some great places you’re dreaming about 🙂 We probably plan about 4-6 months in advance? I used to enjoy all the planning before, you know researching, buying the tickets, (I swear by Trip Advisor’s forum), and other pertinent travel plans, but the older I get, it just seems I’m in a fog most of the time as to where and how I start the process. Planning our England/Sweden trip for May, and already I’ve made 2 errors, one of them has cost us 🙂 Just too many components to get it all together.
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Ooh. England/Sweden sounds great. Sorry to hear about that error. I hope it wasn’t too costly. At least you haven’t lost your love for travel – just for the planning of it. I’m sure I’ll get there at some point in the future.
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My folks live in England, and we used to as well. So whenever we visit each year, we try to tag along some other European country and explore it since we’re so close, so Sweden it is this year.
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Awesome post!! Your travel agenda sounds amazing! I can’t wait to hear about these trips – Especially Laos/Cambodia.
As for planning ahead, I am like you and my wife is like your husband. If she wasn’t constantly reigning me in, I would have the next 5 years already planned 😀
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Thanks for the kind words. I can’t wait to go on those trips – especially Laos/Cambodia!
As for the spouses, we just have to persist in the face of their short-sightedness. 🙂 Deep down they know that they are getting the best travel adventures because of us. 🙂
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Indeed!! 😀👍
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Catching up on all your blog posts here! I actually got ahead of myself and said this at the end of one of your other posts (oops!). We plan one year ahead typically. So, we don’t have anything planned beyond this year. Although, we loosely discuss things and try to forecast school schedules, Scout summer camp schedules, and just how much time we can get away with taking off of work!
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Christmas 2020: don’t do Jamaica AGAIN. Instead, go to Domenica, W.I. And stay at Pagua Bay Guesthouse & Cabanas near Marigot. I am rapturously in love with Domenica. It is not mobbed with tourists, the Pagua Bay Proprietors are English-speaking Americans (Alicia is from my adopted home-town in Colorado), and they know all the off-the-beaten-path gems. It was the only time I seriously considered over-staying my VISA. But Domenica is a well-kept secret, so don’t tell anyone about it!
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That sounds lovely. I’ll give it a look. Thanks for the suggestion. (Shhh…)
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I’m good with actual plans through the summer, and with reserved dates through the year (we know we’re going away over Thanksgiving, we haven’t decided where – it’s definitely looking like Central or South America, details tbd).
As for 2020, I have a wishlist, but we haven’t started thinking about it in earnest. I’d say our average lead time is, depending on the complexity of the trip, no more than 9 months out.
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I plan as far ahead as I possibly can. However work schedules get in the way for us. So we go when we can and are waiting on retirement (5 yrs away) to do some really big planning.
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Sounds great!
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I’ve only just saw this post but it seems you decided on New Orleans then? Do I win a prize for suggesting the winning destination 😉 You’re also coming to Asia and not coming to Thailand…😱😱 I’m obviously not doing my job properly haha (but I’m sure Laos and Cambodia are just as nice and I’ll get myself over to them myself soon)
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Actually, the destination has been decided but I’m withholding all details for now. It will be revealed in a future post, so you’ll have to wait to see if you get a prize… 😉
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Haha, you tease 😂
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I don’t think two years out is that far. I usually have firm plans about 9 months out and loose ideas kicking around a year and a half out. So not quite as extreme as you, but you have advantage of knowing your exact holiday schedule (and your travel partner’s!), so I’d probably do the same in your shoes. Early bookers get the best accommodations at the best prices!
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Great post. Having an eye on travel deals closely helps…and seems like you are good at it.
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Thank you!! As far as being good at it… I enjoy planning travel, but good at it? Most of the time I do fine, but I also make mistakes from time to time. Hey! That’s an idea for a future post… thank you! 🙂
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I will wait for it. 🙂
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I came across this old post of yours after writing up my most recent one about my travel wish list. Sounds like we have similar approaches; I’ve planned about 2 years ahead as well. There are just so many places to go and the research process is addictive indeed!
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