Vacation planning is awful
December 29, 2023 1:53 AM   Subscribe

I hate vacation planning - reasons inside. This year, I would like to figure out how to make it less terrible for me and my partner.

For context: we are in Europe, so we have a large number of vacation days and quite a large budget - vacation planning should be a breeze, and fun!
But for my partner and me it goes like this:
- Jan - May: we consider several holiday destinations, no concrete planning
- Jun: they propose a location - I find several faults with it - I procrastinate on proposing anything of my own
- Jul: I finally sit down to propose some destinations, they are enthusiastic about them all (which is great! But doesn't help my inability to decide), they buy some vacation guides, which causes me to feel overwhelmed because things are moving too fast
- Aug: we both procrastinate because it has turned into a thing again and we bicker every time we talk about it and nobody has energy for that
- the first weekend of our vacation: we book sth last minute (this is actively painful for me)
- vacation: After the first few days of decompression, the vacation is amazing, we love it and everything is fine.

Please help me save us from what I inflict on us pre-vacation!

I think my main issues are:
- it feels like a big investment with an unknown result - I worry about spending loads of money and having a bad vacation
- it feels so so critical - we really need the relaxation this vacation is meant to provide - and I panic at the thought of continuing the year without it
- it feels like so much work at a time when I'm already very very stressed - and if I want to make sure we don't waste money, and have a relaxing vacation, it is even more work (research on the Internet etc)
- I want conflicting things and cannot seem to prioritize/decide: reasonable cost, location on the coast, lots of nature but a nice town with various restaurants, beautiful hotel rooms and a pool but not a hotel for rich people, exciting new destination but climate friendly, and so on...

Note: I don't think I can outsource it completely to my partner
Note 2: I'm fine with most other decisions, even bigger purchasing decisions.

Do you have similar problems and have found a solution? Or do you have any ideas on different vacation planning tactics? Mental reframing?

Any help greatly appreciated.
And yes, I know we are extremely privileged in this.
posted by any_name_in_a_storm to Travel & Transportation (29 answers total) 14 users marked this as a favorite
 
I don't think I can outsource it completely to my partner

From what you've said, it looks to me like doing exactly that would be a kindness to both of you.

In your shoes I'd much rather cope with the residual guilt from just giving in to this particular personal inadequacy than the horror of the planning.
posted by flabdablet at 2:11 AM on December 29, 2023 [24 favorites]


Maybe you can't outsource it to your partner, but could you show them this question and see if they have suggestions? Are they aware of your mental state at the various stages of the process? They know you better than any of us do and might have great ideas about how to switch it up.

My other suggestion: randomness. This could be introduced at various points. For example, in the Jan-May timeframe, you could write down every location that you consider, ditch ones that are immediately rejected by one of you, and then roll a die to pick. Or in July, partner rolls to decide which one to be enthusiastic about. You get the idea - let your vacation pick you instead of the other way around.
posted by inexorably_forward at 2:45 AM on December 29, 2023 [4 favorites]


Best answer: This sounds like a scarcity mindset at work. The solution is partly to recognize it but also to start making a bit more time when it’s not vacation time, so that your brain isn’t locked into your traveling holiday being your only break from everything. The indicators to me are the mentions that it should be fun to plan, it feels critical, each decision is fraught.

Do you take time to see beautiful things or have a break in your daily lives? Do you relax and enjoy each others company? Do you sometimes do a day trip? Do you have a sense that there will be time in your lives to see and experience the things you want to?
posted by warriorqueen at 4:04 AM on December 29, 2023 [11 favorites]


Best answer: There's an element of risk to vacations in new places. Many hotels and towns will have numerous glowing reviews and also some terrible ones. Even if 80% of previous travelers loved it, your family might not. Or perhaps it was great a few years ago, but is now overrun by tourists and has gone downhill. It's not possible to get certainty about a new destination. That can lead to procrastination.

I deal with this in two ways. First, I choose towns that have interesting history and/or UNESCO heritage sites but aren't the hot craze on Instagram. I would choose Bilbao over Santorini, or Perugia over Venice or Lake Como. This increases the chance that I'll have authentic moments of delight, seeing a gorgeous stained-glass church or a beautiful coastline with few others around. It means I will not be marched with thousands of other tourists like cattle through the Louvre. I'm not trying to find the "perfect" destination, just a pretty place with history and views.

Secondly, I choose locally-run hotels that are medium-price and rated more than 4.3 stars on Google Maps. I avoid the lavish highly-marketed hotels that are 3 times the price. Those hotels generate such high expectations that it creates anxiety. By choosing an authentic local experience, it's more likely I'll have a good time with surprises and exploration.
posted by vienna at 4:22 AM on December 29, 2023 [8 favorites]


Best answer: Would it be possible to just say yes to their June proposal? You don’t have to outsource all the planning to them, but the choosing of the destination seems to cause you the biggest part of the anxiety. You always have a great time on the vacation with them once it’s underway. It’s an option to just skip all the hand-wringing in the middle.

I would separately examine whatever is in play about the outsourcing; it may be that they can’t be trusted to stick to the budget/make a thorough enough plan/whatever, which maybe they can work on, but your question feels like it’s at least in part about your anxiety about whether anyone but you can plan it “right”.
posted by hollyholly at 4:28 AM on December 29, 2023 [14 favorites]


Best answer: If you have ten days or a couple of weeks, hedge your bets and plan to go to two places. You can make one of them a place you are somewhat familiar with. Sometimes one or two visits just scratches the surface anyway, and you are aware of things you would still like to do in a place/places to eat or stay that you might want to try the next time. My partner really enjoys a variety of Caribbean adventures, while I could happily just go back to Puerto Rico every time. So we go to one new place and then to Puerto Rico. We have (it sounds like) less money and time than you, so it's possible that in a new place we will wind up at a hotel that's a good deal but turns out to be a bit complicated to stay at. Or the weather happens to be bad or whatever. But then I know we are going someplace that's in my comfort zone and I sort of feel like a regular.
posted by BibiRose at 5:02 AM on December 29, 2023 [2 favorites]


You are in Europe. You are going to go on lots of vacations. They don't have to be perfect. Lower the stakes!

And while you are at it, decrease the amount of planning you require yourself to do. You realistically just need a destination, tickets and a hotel. What actual difference does it make if you don't eat at the most desireable restaurants or get tickets to a museum you didn't even know existed last month?

Maybe try a year of saying Yes. It can include saying yes to whatever destination your partner suggests.
posted by DarlingBri at 5:28 AM on December 29, 2023 [18 favorites]


Can you schedule it out and agree together that you’ll have the destination picked by May 15 or whatever arbitrary date? Imagine it’s a deadline for work or a doctors appointment and cannot be negotiated. Followed by similar hard deadlines for ticket, hotel, etc.

Have you considered using a travel agent? They’re outmoded but I have a friend who works as one part-time currently and does things like plan mystery vacations for people, just give her a budget and preferences.
posted by music for skeletons at 6:16 AM on December 29, 2023 [6 favorites]


If you put a cost limit on the vacation (i.e., take the "big investment" part out of the equation, at least in terms of money), would that help your anxiety?

Or what about just picking one thing to prioritize for (arbitrarily, if necessary)? Like, maybe this year you are prioritizing for climate-friendliness so you rule out any destination that you can't reach via a train journey, but you're "allowed" to splurge on hotels/meals/activities.

I agree with everyone else that you need to lower the stakes! (Or, really, recognize that the stakes are already quite low!) But also sometimes adding guardrails/restrictions (even if you know you've pulled them out of thin air) can help narrow your options a bit.
posted by mskyle at 6:17 AM on December 29, 2023 [5 favorites]


I wonder if you might find your best choice is to give up on 'exciting new destination' in favour of a destination you have already been to that fits all your other criteria.

I know lots of people that love returning to the same place year after year -- it's what the whole time share industry was built on. I'm not suggesting you get a timeshare because those suck but if there's a place you loved that fits your requirement, why not go back there time after time?

Scenery changes seasonally, so maybe you go in August one year and May another. Restaurants will open and close and add dishes to their menu so you can try new ones and revisit favourites. Become such a regular at the little cafe with the amazing breakfast pastry that they are pleased to see you when you return the next year. If you return to a place year after year you are much, much more likely to start to have authentic interactions and to explore the place more like a local than a tourist. You could even work on learning the local language if it is different than yours.
posted by jacquilynne at 6:31 AM on December 29, 2023 [8 favorites]


You have given yourselves far too much opportunity to slosh around and procrastinate. Set closing dates for all of the stages the same way you would with any project. That way you deal with a small amount of pressure on your small deadlines instead of letting it snowball.

It’s an obvious thing I know, but Project Planning exists for a reason.
posted by Tell Me No Lies at 6:48 AM on December 29, 2023 [2 favorites]


Best answer: Hello, me! I mean not me, but, I really sympathize with this. Some of what works for me:

* My goal at all times is to eliminate the risk of failure. Not to maximize it! I never, ever attempt to have "the best vacation ever." What I want to make sure is that we stick our budget and have a good time - the best? Who cares, you can never be sure of that. What this means is that I give myself permission to "settle" for a good trip I'm very confident I'd enjoy, vs obsessing about whether some other option might be a little better.
* I do in fact outsource a lot of the planning to my partner, shamelessly. In relationships very often one person is just better at a thing than others; we don't want to reflexively 'make' one person do all of the work but it's also ok to acknowledge this truth.
* Our system is heavily based on the following system: My partner selects possible options (they actually hate making decisions) and I make the actual call. For example: "For our next trip, we're going to either do a very urban trip to Paris, a driving tour of northern Italy, or we'll hang out on a beach in the Caribbean." I do not attempt to fine-tune beyond this most of the time; for example I don't say 'driving sounds fun but how about Spain instead." This continues down the line for any major decisions. Again, I am not fine-tuning, I'm "just" picking the best option that's presented to me.

My goal is not to have the best vacation possible. My goal is to make decisions and have a good vacation lined up far in advance, and then enjoy it. I spend my entire workday maximizing and fine-tuning systems; by focusing on "doesn't suck" I give myself permission to make the decisions early and often and then move on with the rest of my life and look forward to the trip.
posted by Tomorrowful at 6:51 AM on December 29, 2023 [9 favorites]


It sounds like the biggest stall point in your process is choosing the destination, and the issue is that you and your partner can't agree on a destination. My proposal: take turns picking destinations. If you aren't that into the destination your partner chooses, you get unilateral choice over the next one, so it's all good. (If you want to hedge your bets a little, you could each have a list of, let's say, 5 places that you absolutely won't go to.)

I actively enjoy researching trips, so take my advice with a grain of salt, but one thing that cuts down on a ton of time is outsourcing my research to blogs. I've had the best results by looking up the name of the place you're going + amount of time you're going to spend there + itinerary so e.g. Prague 5 day itinerary. Most bloggers recommend accommodations too.
posted by capricorn at 6:59 AM on December 29, 2023 [8 favorites]


Go the same place you went last year.
posted by amtho at 7:00 AM on December 29, 2023 [1 favorite]


My partner and I are making lower-stakes decisions for shorter-term trips, but we kind of split things up. Something I want to do is often driving the choice of general destination. He has more opinions about places to stay, so he picks options he likes for me to choose from. We figure out actual things we want to while we're there together.

Would it work for you and your partner to split things up and make choices on firmer and earlier deadlines? Maybe they give you a few options for destination by March (for example) for you to make a final decision (or vice versa), then you have a month to pick a few hotels for them to choose from, and then you can start sorting out any on-location plans you want to make.
posted by EvaDestruction at 7:08 AM on December 29, 2023


In the U.S. there's a travel agency that solves this problem by sending you on a surprise trip. You tell them your budget, they book everything, you just go. Maybe they could tell you if anyone in Europe does something similar?
posted by shadygrove at 7:40 AM on December 29, 2023 [1 favorite]


Planning a vacation (for me anyway) is more stressful when I can feel the clock ticking (only two budget rooms left at the hotel I want! flights should be purchased in the next week! etc.)

In January, pick a destination and don't worry if it's the best choice. If it seems enjoyable, with opportunities for fun and relaxation, that's enough. I like the idea above of you both alternating who picks the destination. Or if that really won't work for you, in January you each research 2-3 places and make mock itineraries for them, and then you do ranked choice voting and go with whichever option wins.

In any case, settle on a destination early so you can book items (like accommodation) that tend to get limited (and more expensive!) the longer you wait. That alone will take out a lot of the stress of planning and cost.

But just generally....try to have a less maximalist view of travel. I have traveled quite a bit, and while some of my favorite memories are based on my tendency to plan, others occurred spontaneously. Travel never goes entirely according to plan, but that can be some of the fun if you learn to enjoy unpredictability - I mean, it's relatively rare in our regular lives, so think of it as an interesting novelty. There is no one "perfect trip" out there, despite what any travel-influencer or blogger might claim. There are a lot of places where it's hard to have a truly bad time, given their natural beauty or food or arts/cultural resources - just aim to have a good time, not a perfect time.
posted by coffeecat at 8:22 AM on December 29, 2023


How about making the planning less stressful by making it more routine?

Spouse and I meet at least quarterly to plan upcoming trips. For our most recent we did the following:
- sketched out when we want to travel in the next year based on current and anticipated commitments
- looked at possibilities for travel in the next couple months
- booked a trip for next month (short city trip to see a performer we like)
- set a date for planning our big summer trip within the next couple months
- talked about a few destinations we would like to visit this year and the types of trips we liked in the last year

We've been doing it this way for a few years and now have a good idea of what we like and don't like. We use a travel agent when we are going somewhere new and don't want to do the research. We have also established some no-brainer sort of trips where we know exactly the type of transportation we will take to get there, the types of activities we will do there, and the hotel we will stay at -- these are favorite destinations both close-by and further away. We're not perfect -- our vacations aren't always insta-worth, and we each get grumpy at times -- but we have fun and if something tanks in one way or another we frame it as a learning experience.

The frequent conversations about travelling make each trip less a TRIP OF A LIFETIME, so reduces the stress. Also, from the spending money side, working through Ramit Sethi's Rich Life Journal really helped align us both on what we value on trips, making it easier to make suggestions and decisions.
posted by chiefthe at 8:39 AM on December 29, 2023


To add- I have found Reddit to be a great source for travel planning. There you'll find trip reports written by ordinary people who aren't trying to hype anything, but will give honest descriptions of their experience. There is still plenty of information there, but it's less overwhelming vast than a guide book (to me, anyway).
posted by coffeecat at 8:40 AM on December 29, 2023 [1 favorite]


I'm terrible at going on vacation, so this is "do as I say not as I do" but...

- I want conflicting things and cannot seem to prioritize/decide: reasonable cost, location on the coast, lots of nature but a nice town with various restaurants, beautiful hotel rooms and a pool but not a hotel for rich people, exciting new destination but climate friendly, and so on...

Pick one or two per vacation! You can have several vacations!

"A historic city near mountains we can get to by train." "An all-inclusive hotel with a pool somewhere sunny." "A house in a French village". Etc. These still require decisions but you need to narrow the possibilities, knowing that you will have other holidays in this and/or following years in which you can do the other great, different things. As others said, lower the stakes.

And/or try using a travel agent - they still exist! Tell them "We want to stay in a historic city in Central Europe we can get to by train. We have x days total and y budget" or whatever. Have them suggest things and pick one and book it.
posted by fabius at 9:21 AM on December 29, 2023 [1 favorite]


Get out of the scarcity mindset. And...chill out some.

90% of what makes a vacation "good" or "bad" is the people taking it. And most of what makes up that remaining 10% is entirely situational and has nothing to do with WHERE the vacation is: weather, illness, travel industry disruption, some kind of massive fuckup. You clearly already know that, it is okay to skip the parts of your old process that suck and just pick something.

Just freakin' throw a dart at a map, book the bare bones of the vacation near that spot within 48 hours of the dart throw, and decide to have a good time. Aside from generalities of weather and culture, WHERE is actually pretty unimportant in the grand scheme of things.

I mean, make it easier on yourself by choosing somewhere near the dart that has known-good tourist infrastructure, don't pick a hut in a forest down a dirt road because y'all are not ready for that kind of vacation yet. And before you book accommodations, TRY to come to an agreement with your partner what the 3 top priorities are since that will dictate the nature of that accommodation. Like, we prefer some kind of kitchenette where we have the ability to make and store basic food rather than eating out every meal (but might make an exception for something with easy on-premise options or being right on a main drag with markets and restaurants), we like having a separate sleeping and living area, and we don't mind being a little bit away from the main busy areas we're going to visit to but too far and we'll get lazy and never go out.

Just make a handshake agreement both of you will make a good-faith effort to have a good time wherever you go. And please remember: you are not being forced to take the same vacation year after year, this is at best a 1-year commitment. If you start to regret your choice for non-serious reasons like "what if we hate it" I guess ask yourself how many things you hate, really? Like, how many entire regions do you seriously loathe so much you couldn't possibly make the best of it?

Other things you can do to get out of this awful mindset:
- Stay within 3 hours' travel from home so you can just go home if it's that awful
- Ask a friend who generally has good vacations to pick one of their past vacations for you to copy
- On New Year's Day this year, each of you pick a location (either of you can do the dart-throw for your choice) and you flip a coin and that's where the damned vacation is going to be this year. You can't change your mind, sorry, Lyn says you have to make that one work unless something terrible happens there and tourists should stay away, in which case Lyn says you have to go to the other option.

Or, you want me to pick? Okay, go to Edinburgh. Coast, city, restaurants, things to do, beautiful, interesting, tons of day-trip options, long daylight and mild weather in Aug-Sept which sounds like your desired travel window. Fringe is August, so either go to that or avoid it, and book early.

If you are in Scotland already, then go to...(throwing a virtual dart)...Sofia. Shitload of stuff to do in Sofia and it's gorgeous. You'll find plenty to do. (r/travel seems to recommend Plovdiv as a better base)

Also, all you absolutely HAVE TO secure in advance is travel and lodging. And for us (and we are very good travelers and have a good time wherever we go) we like to lock that in so we know the exact dates, and then pick one or maybe two 'anchor' activities to book ahead. For us this is often some kind of performance and one tour of some sort - walking ghost or history tour, food tour, an excursion or otherwise visiting one of those places you have to book in advance.

Everything beyond that is just ideas dumped in a google doc - here's a cool museum, I just saw this restaurant mentioned in a youtube video, did you know they have a Pickle Parade happening while we're there?, ooh it's an aquarium where you can feed the piranha, this place invented pie, this botanical garden's corpse plant might bloom while we're there. A couple weeks before vacation (or anytime you're bored and feel like daydreaming about vacation) start rearranging those suggestions into parts of town and operating hours, working around your 'anchor' plans, and a suggested itinerary will fall into place. Maybe the Pickle Parade wasn't a super-high choice but there's a cool museum and also an interesting restaurant in that neighborhood so hey, let's check it all out on parade day.

And if you don't have a good time this year, it should at least give you some direction about what you want to do next year.
posted by Lyn Never at 9:27 AM on December 29, 2023 [5 favorites]


Best answer: Here's my solution to this dilemma, which may or may not work for you:

Go to a place where
- Plenty of local people live all year round
- There's good cheap public transport going to other interesting places
- There's different kinds of geography nearby e.g. the coast versus the mountains, or the old historic town versus the walks in the hills
- It's only a couple of hours flight

Go in the off season so it won't be completely clogged with tourists. Get an apartment with a view (and maybe balcony). Bring a book, maybe a couple of small form factor games, earplugs, and any random little thing you might be upset not to find in the apartment (like decent tea bags).

This process works for me, to ensure that there's a zillion things to do and if any of those things turn out to not be perfect, there's a different option for the next day. If I can't find a restaurant I like, I can grab interesting groceries at the market. If the weather is terrible I can sit and play games and look at the view. If the town is boring I can get on the train and go exploring. If the beach is terrible, I can go hiking in the hills. If the tea is terrible, I've got my own. If it's really ALL TERRIBLE then it was pretty cheap so, better luck next time! (It's never been even a little bit terrible).

The Mediterranean coast has a whole bunch of places like this.
posted by quacks like a duck at 11:09 AM on December 29, 2023 [1 favorite]


I am perhaps the wrong person to ask because I LOVE PLANNING VACATIONS!! In fact, anticipation is the best part in many ways. I do have a suggestion: why not choose one weekend to plan a trip together from start to finish? Go out to dinner on Friday night and brainstorm locations, then choose Saturday morning and do research. On Sunday you can book the tickets and then relax!!
posted by smorgasbord at 8:43 PM on December 29, 2023 [1 favorite]


Best answer: One thing my partner advised me to consider, when ch helped a bit, was that the more time I spent planning the thing the more of an emotional investment I had in getting it right. So I actively to cut short the time I spend planning particularly if I'm go in by somewhere where I know, realistically, that I can't afford to get all the things i like.

The other thing is to read about optimisers and satisfisers, if you haven't already. Understanding these tendencies has helped me be more chill in the way that everyone absolutely ve is suggesting you do (which is a great idea but very hard to achieve).
posted by jojobobo at 9:29 PM on December 29, 2023


It seems like your partner is really trying to help, bless their heart! I think you realize this based on your post, but as others have said, you’ve now put yourself in this position of being the gatekeeper for this Big Decision of where to go. Your partner sounds agreeable to any place, and you even recognize that you always enjoy yourselves regardless of where you end up!

I love planning vacations so take my advice with a grain of salt: What I do is figure out what I need from a vacation THIS year. Do I need to rest? If so, I prioritize luxury and comfort and (for me) affordable lodging within walking distance of a beach. Do I want to see and do lots of cool things? Look for places with great restaurants and museums and shopping. Maybe it has elements of other great things too, but pick 1-2 things to prioritize based on your gut reaction to how you want to FEEL on vacation. This year. There will be many other years and vacations to come!

Then, I would recommend all the advice about adding some element of randomization to take the pressure off The Big Decision. I saw a fun couple’s game on tv once where they had these categories; I think theirs were 1. Domestic Destinations and 2. Foreign Destinations (maybe they picked 3 each?) and they would write them down and draw them out of a hat one by one. The last one left is where they went. You could decide on 2-3 categories based on things you both agree are must-haves for this year’s vacation (e.g. warm, budget friendly, etc).

Finally, as others have said, all you have to do then is book the flight/train and you’re locked in and aren’t allowed to second guess yourself. If you have a few days flexibility you can save some money looking at price calendars. Then set a budget for lodging and have fun looking at all the cool places to stay in your price range and pick the place that best suits the “2025 Vibe” or whatever. If you can afford it, do all of this immediately following your next vacation or as early as possible before your stressful season. Or even ON vacation! It will be cheaper and there will be plenty of lodging options no matter where you go, so you can have fun picking a place and researching things to do there in the interim.

I think the reason I enjoy vacation planning is the fantasy of it all. It seems like you’re missing out on one of the crucial functions of a vacation, which is looking forward to it in times when you really need a break! It sounds like you have enough vacation time and budget to either have fun with it OR outsource it if that would take the pressure off. Vacations are a chance to treat yourself and your partner to a wonderful thing, and that includes the planning process itself—you both deserve the vacation AND to not have to stress about the vacation!
posted by a.steele at 1:40 AM on December 30, 2023


I agree that it sounds like your major challenge is choosing a destination. This is actually a good thing given that it sounds like you already have previously tossed around a selection of places you would like to vacation.

I recommend making a big list or spreadsheet with all the places you have ever thought you might want to go. Then either alphabetize them and take vacations to all of them over time in alphabetical order, or number them and use a random number generator to pick the next destination. This way the decision is made for you and you know you have already preapproved the destination since it is on the major list. As a bonus, this takes care of multiple years of vacation destination planning.
posted by donut_princess at 6:26 AM on December 30, 2023


So step back on all the planning. If you manage to enjoy your last minute ventures you’ll enjoy most anything.

Your options are

- travel agents, some still do exist
- small group tours, you only have to get to the departure point, the tour guide figures out all other things. If you want to add a few days to decompress pre departure that is easy enough to accommodate
- any package trip or cruise

What all these things have in common is that most of the planning is done by someone else.

All you two have to agree on is a country to travel to or even just a climate.
posted by koahiatamadl at 8:21 AM on December 30, 2023


If you go the same place as last year, you don't have to do any more research except to make sure your favorite things (place to stay, etc.) are still there. You *might* lose out on some novelty, but your goal here is relaxation, which you can definitely achieve.

Or, if you preferred the place before that, or one before that, go there.
posted by amtho at 9:31 AM on December 30, 2023


Response by poster: Thank you all for the answers!
posted by any_name_in_a_storm at 3:12 PM on December 30, 2023


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