Where are you on the spectrum of vacation planning? Detailed to the hour or floating like a leaf in the wind?

Over the years I've done both and I have to say, minimal planning has always been the best. We get a general idea of what we'd like to do and then plan (very) roughly around that. If we decide we want to just relax, we don't sweat any previous plans. If we find someplace interesting and just want to stay., we do that instead. For things that require reservations, we make those in advance and will use those as small anchor points. If we really aren't feeling it, we'll skip those as well.

I guess I'd sum it up by saying that a vacation should be relaxing. Tight and/or rigid schedules are generally not relaxing.

I choose and plan where to sleep and double check if reservations are required for big sights like Alcatraz.

Within that framework I wing it.

To me, it's not a vacation if it's planned to the hour and I'm obligated to do stuff.

I'm going to London in a few weeks for a week and the only thing I really wanted to do was go to Bovington Tank Museum, so I made that known and set that up, which includes renting a car (good luck me, hope I can drive in a different country), an alternate place to stay for a day or two and that's about it.

I want to just exist in a place for awhile, no obligations and just see where things take me. If that means I stay in a 2 block radius because that's what seemed interesting at the time, so be it. You're never going to see or do absolutely every thing you want to in life, there's always going to be something you feel like you missed, but you can't have FOMO because otherwise you end up just running through sights and never really seeing or absorbing anything.

Boy. Sometimes I'm either. I put together a vacation one time, which I haven't gone on yet, called my Austro-Hungarian Empire tour. It's just a trip from Vienna, Budapest, Prague. With train times picked, and a few core sights to see in each location. I had a lot of fun researching and putting together that plan.

But, in my day to day life, I can't really handle lists traditionally. They get me stressed. "If it takes 5 minutes, do it now." and "If you didn't remember, it wasn't important enough".

So, often on vacations, I really appreciate unstructured time. Very little planning. But then, a lightbulb switches and I'm frustrated at having no goal or target. At which point, I need to find something to do. Walk to a specific museum, etc.

I try to think of these things as in balance, and that I don't need to lean too hard towards the organized or the relaxed side. But as I grow older, I realize I do need to make sure I have enough of a core of a plan so as to avoid any big frustrations about "wasted time".

I do both, but allow for unplanned activities. But it's good to never be in a situation where you're in your hotel and just have no idea what to do. I usually have things planned, esp. with regard to things that need to be booked, and have "stretch" goals depending on tiredness. But things that aren't booked I swap around, so I never feel "tied" to a schedule. But I want to be doing something whenever I can.

To be fair, I "vacation" somewhat intensely. Especially if I'm on my own, I usually do 12-16 hours of activities per day. Sometimes even more, like when I went to sleep at 10pm, woke up at 3am for a famous sunrise shot, then hiked for 5-6 more hours, did 3-4 hours of traveling to my next destination, and then did more exploration (it's a city famous for nightlife) until 1am.

True, it's tiring, but I want vacation time to be different, and a daily 9-5 creates little novel memories and is toilsome and tiring in a different way than running around on an "adventure". The feeling of having done a full day of activity and going immediately to sleep after taking a shower is refreshing to me. Two weeks of traveling can feel like 4 months of 9-5 time to me, and that's a success.

By the end of the vacation, I want to feel so physically depleted that I'm ready for a slow 9-5 again. In that way, my travels and daily life feed back into each other.

I was always the freest of spirits on my travels, throwing myself at the world to see what would happen. But since the pandemic, I’ve found that is far less possible. The people who used to kindly help me on my way are much less patient and welcoming now. And there is much less play in the system, with airlines and transportation infrastructure one of the least dependable systems now. On a flight last month from SFO to San Antonio we were rescheduled for the next day and then we spent five hours in the Dallas airport and then three hours on the tarmac and suddenly our vacation was nearly over before it began.

Also, I travel now to get footage of ancient history and archaeology sites and these trips require far more planning and the prioritizing of video capture instead of relaxation or exploration.

The exception to all that is that I can still hike out my front door in San Francisco and walk for several days into nature without any kind of plan. No reservations needed.

Just went on a cross country road trip, (~3600mi, 5800km ) this was my strategy.

1. Decide on primary focus places
2. Create lists of things of interest in those cities
3. Book lodgings where you wanted (we camped for the most part at different places, some hotels, and we actually changed some of those cities halfway through for our return trip).
4. Book activities if needed, but not be forced to do them. This is hard thing to adjust for since I am someone who always wants to 'get their moneys worth'.
5. Once arrived, just kind of decided what we want to do in that moment, I am not going to hold myself to a strict schedule past me made. This includes traveling to and from places, and everything else - we made a lot of discoveries just by driving around and checking out what caught our eye or on the suggestion of the locals.

It's a mix of planning, I know my interests and excitement levels change, so I'm not going to be beholden to anything I initially wanted to do, so I kind of make a list of things I would like to potentially do, and then decide throughout the day/time I am there. Takes a lot of pressure off my shoulders, even on things I have to book, I will just eat the cost if I decided to move on to something else. I consider that part of the vacation expenses. Just reduces stress and increases interest because I'm not forcing myself to do anything specifically.

Note: a road trip is not a vacation, do not expect relaxation, but it does give you an exhilarating euphoria once you've done it all.

What we often do is plan around restaurants we want to visit, which gives us locations to be in at specific times. Then we can sort out travel and accommodation as required (ie, in Japan we booked trains and hotels but in Germany I'd wing it a bit more and just turn up and find somewhere to stay)

I like to have a list of a few non-food things to see in each location which is then used or ignored as we feel on the day. If there is something in particular that we really want to do or see that might sell out, then we tend to book that thing. Sometimes I don't want to think and just picking something off a list is nice. But it's just as likely we'll get distracted by some weird museum or pretty park or whatever.

My parents recently went on a fully organised holiday tour in India, where every day had a fully managed itinerary from breakfast until tea and they said it was weird but kind of fun and also they never wanted to do it again.

Used to be a plan the whole trip out day by day, live like the locals, cram in as much as possible type of guy. But a few years ago we tried out a resort, and to be honest it was really relaxing to do 0 planning beyond booking the resort, then sit down with concierge when we arrived and book trips for the week. Especially now with a kid, I need as easy as possible.

My partner and I have two types of vacation: city and beach. A city vacation, say Rome or New York City, is more well-planned, while a beach vacation is very loose. They each serve their purpose, and they have some things in common, probably due to the type of people we are.

Either way, we will have some flags on an offline Google Map. In the city, these will be predominantly restaurants, but also points of interest, a grocery, and our accommodations. On the beach it'll be our spot, some beaches nearby, some restaurants, and a grocery.

Few of these things will be obligations, although we'll have some "must see" items and tickets/reservations for them, if possible. In Tokyo, for example, we made it to Team Labs - highly recommended! - but missed out on the Miyazaki Museum - couldn't get tickets :(.

We use some apps to keep track of things (Tripit, Kayak) and we book flights and accommodations as far ahead as we can (usually 6-12 weeks). I feel like these two pieces are the most organized we are.

We've done some long-term travel (10+ months) , as well, so we're very much in sync with each other about most things.

If I don't know anything about a place, I'll chatgpt some suggestions to get me started. It's a good aggregator!

We're somewhere in the middle. My wife and I both research things that we might want to do before we go so that we're not sitting around trying to figure it out when we get there. But we always leave room for flexibility and spontaneity. There are also times where we plan something, but something better comes up when we get there, so we'll change plans. Flexibility is key to relaxing travel, IMO. It's kinda like planning a wedding - if you try to force it to be a certain way down to the minute, you'll likely wind up stressed and disappointed.

I do a lot of 'planning' in making a custom google map of places that look interesting in the area I'm visiting, but I do very minimal planning on when to go to each place. I don't plan exactly which places we'll visit each day (there is usually too many places on the map to go to them all anyways) and just go by whatever sounds good in the moment. I usually buy the hotel room in advance -after making the map so I can see what area seems convenient to get a hotel. I like my approach because I can decide to go to a place I want to go, and after I'm done with that place I have a lot of flexibility while still having a list of worthwhile places to go to so I don't feel like I'm missing out.

I usually book hotels one to several days out on road trips so I can make changes of plan. I hate showing up in town and not knowing where to stay (if you are unlucky you can wind up searching a few places) so this is a good compromise.

If I am travelling solo or maybe one other person I am likely to try transit-based tourism, which is mainly about adding enough slack in your schedule.

My wife and I took a vacation to Oslo for Christmas this year, one which had very little planning. She kept commenting positively about how I didn't insist on occupying every second of the trip with activities, like her father always did on trips. Sometimes we went back to the hotel and relaxed because we needed some downtime, and that's fine. We're definitely on the low-energy end of travelers.

When it comes to activities, I like having one or two things planned per day MAX. Some days might have zero things -- wandering around and trying stuff out can be fun! And it's good to have some flexibility so that if something changes (rain on a day when you wanted to be outside, something being closed on the day you planned to visit) it doesn't ruin an exact timetable and can more easily just swap it with something else you wanted to do. Someone else mentioned planning around food and I also like that strategy -- but I'm also a very food-motivated traveler lol

I've always loved my family's approach to this: one day planned, one day completely free, alternating. You make sure that you get to do the 2 or 3 major activities that you want to go there for, but you also leave the overall vacation a lot more relaxing overall.

I really appreciated an exercise we did when I was in a training course for work. We took, I believe, the 16personalities test the day before and we were comparing how well people fit into their assigned categories. For one of the categories, there were only two of us labeled "perceivers" and the rest were "judgers." The instructor had us decide on a hypothetical trip we'd take as a group and then split us by personality type and told us to plan the trip (we were going to go to a big NASCAR race).

The two of us who were perceivers went off and came up with our own plan. The basic plan was that Friday, after class, we'd all meet in the parking lot, head to the store for food and alcohol, then drive down to the track. Because we were going to a NASCAR race, we didn't plan much more than that. Maybe we figured out a little more, but that was the main thrust of the plan.

When it was time to come back together with the rest of the class, we found that they hadn't even finished planning their Friday evening. They needed every single detail figured out ahead of time (exactly when to meet in the parking lot, which grocery store we'd go to, what time we'd arrive, etc).

That's when I figured out why I felt like I didn't really fit in with my coworkers and when I first found out that there may be some value in personality tests.

We usually plan a few "big things" as anchor points around which a trip is structured. For example, last year me and my SO went on a trip to NYC for our anniversary. We had our anniversary dinner planned out, as well as tickets for two shows we saw while there. Everything else we did, like visiting the Guggenheim, was played entirely by ear. It gives us the flexibility to relax, sleep in, and try things we didn't know about beforehand.

We also always make sure to have at least a day or two where nothing is planned ahead of time.

I have to plan it down to the MINUTE (okay, hour). Otherwise... I'm not actually going to get anything accomplished.

Basically, there's always a lot to do- specifically if I"m visiting one of the Big Cities- and never enough time to do it all. But really, the worst offender for me is planning meals. I have a horrible habit of "eh, I'll eat whenever I get hungry and whatever's close". Well, this usually becomes "ok, I'm hungry, and I have no idea where to eat... Let's check Google maps... Wait, the nearest place to eat is either rather pricey or several miles away? Crap."

Or to phrase it another way: if I try to be spontaneous, I get overwhelmed and become very disorganized, ultimately accomplishing very little of my original intentions

I get decision paralysis pretty hard if I have too many options. Therefore my vacation planning comes out to planning a few large scale things, and filling the rest of my time unplanned. As an example, I travelled throughout Europe last summer. We spent 3.5 days in Paris. Why 3.5? Because I wanted to buy train tickets super early, and those dates seemed fine. Then I started to scaffold those days with stuff to do. We only had a handful of “must see” things (like your feelings on Alcatraz). I think it was a guided bus tour, the Eiffel Tower, and a walking tour guided by a local (called Paris Greeters, and highly recommended). We roughly planned one for each day, although the bus tour was pretty flexible to fill other spare time. Those appointments gave me the structure I needed to limit my options. From there, I can go into random museums or other attractions that seem appealing without being hit with decision paralysis. Also, since some events are planned ahead of time, I am never stuck unfulfilled, like your Iowa trip.

Detailed.

It goes against my disposition, but when I have not planned things out I've missed out on things.

Researching things in the area gives me more of an appreciate when I am there, particularly places with a history.

I tend to think of vacations as a set of goals. Some of those goals need forethought and preparation, some don't.

For example, I went to Austin for the eclipse. Seeing the eclipse was the primary goal of that trip, I showed up with eclipse glasses and filters for my binoculars. I booked a room in the totality that was walking distance from several parks so traffic wouldn't be an issue. There was a chance I wouldn't be able to see it because of the weather, so I also had some other goals that were a little easier to come by, like eating great BBQ. I try to keep these things kind of non specific (lots of restaurants and they don't take reservations) because new information about them comes up when you're actually at the location. Many of the BBQ plants had a 2+ hour wait standing in the sun, which is not my idea of fun. Concierges are great for info on fun places to go and a resource that I think a lot of people don't realize is offered along with the room at many hotels.

I do handle hotels and car rental when it's needed ahead of time if there's a plane involved. For a road trip, as long as you're willing to keep driving you don't really need to set up the hotels ahead of time, you can book the room from the parking lot. Once driving up the Pacific Coast we found a town that had all the rooms completely booked, but the owners of a fancy resort let us stay in an attic room they don't normally rent out. It ended up costing us about what you'd expect to stay in a city hotel instead of their usually very high pricing.

The one thing I want to avoid is getting stressed out because I'm falling behind on my list of planned activities. I'd rather be sitting in my hotel room than worried because activity a ran late, so now I might miss out on activity b, which I've already paid for and really wanted to do.

Leaf on the wind, for the most part. I prefer to explore and take my time when visiting other places. I can't relax and have fun on a schedule or planning a billion places to visit. The idea of skipping a place because it's not on the list or rushing a visit because you're behind schedule, just sounds terribly wrong. There are so many gems out there you'll never see online or in the "top places to visit in ___".

Best method for me is to have something in mind and goof off on the way there and after. The most planning for me is where I'll be staying and maybe transportation. If there's something specific, like going to Alcatraz, I look it up ahead of time just in case. I've noticed the more people there are, the more we actually have to plan a few things in advance. 😭

The fast pace of schedules and the need to see everything even if you only took a minute to do it reminds me of those people who never take their eyes from their cameras, they can check off that they were there but more often than not miss out on actually being there. You might as well watch VR videos & 360 images of the same places, it's a similar experience without all the hassle. We should, as a society, say it's ok to say you were there if you just went there in VR. Maybe then those spots won't be quite so crowded.

Echoing the thoughts of many in this thread, I’d say somewhere in the middle. I like to plan out the general idea, like where we’re going and how we’re getting there. Then I try to get an idea of who or what we want to visit while we’re there. If there’s a LOT of interesting things to see we’re both interested in, I might even make a list and try to keep track of when things are available. But ultimately, it’s all non-committal and nothing is planned down to the hour. It’s more like “hey it would be really cool if we have the time to see this”.

I prefer this, because I feel like it motivates us to actually get off our butts and do something, rather than sit around in the hotel room. Both of our families plan their vacations very differently, but I’ve noticed both of them suffer from this problem. My parents plan out their departure to the dot but never know what to do once they actually arrive. My SOs parents are more leaf on the wind, but still suffer from the problem of not knowing what to do if say the weather turns or someone cancels on them. So for us, having a vague action plan has kind of worked as the best of both worlds because it gives us an idea of what to do, but also flexibility.

The only things I plan, for the most part, is accommodations. Sometimes I will want to go somewhere more exclusive that will require reservations like a fancy restaurant or a show.

My husband is the complete opposite. He spends days worth of time researching the destinations we will go to and come up with a complete itinerary. It drives me a bit crazy.

I find a few things I'd like to do where I'm going, and plan ahead for those (buy tickets as needed), but that's about it. I aim for one "major" activity a day to give myself time both to enjoy it and to do other things as well. I travel to the same places often to visit friends so I have ongoing lists of places to visit there, but I don't pressure myself to go to as many of them as possible. I travel mostly to go to concerts, but while I'm away I also really enjoy museum and art gallery visits, so I always plan for a couple of those too. Too much planning stresses me out though, so that's why I stick to one planned activity per day.

As an example, my trip to London last year looked like this on paper:

Day 1: Nothing major planned that day in case of flight delays making us arrive late
Day 2: Meeting with two friends living in London that I usually only see every couple of years when we all get together at an industrial music festival in the US
Day 3: Meeting with two friends from the Netherlands who were going to be visiting London at the same time as us
Day 4: Trip outside the city to Royston because my partner wanted to visit Royston Cave
Day 4: Natural History Museum visit because I really wanted to see the Titanosaur exhibit
Day 5: Peter Gabriel show
Day 6: Tate Modern and Sky Gardens
Day 7: Nothing planned that day, we'd figure it out later

...but in reality we did a lot more than just those things - those were just what we needed to plan ahead since we had to get tickets and arrange meetup times/spots with other people. We spent most of the second day wandering around record stores (which started after I found out Third Man Records opened a London location since my last visit), found a great little Georgian restaurant down the street from the Natural History Museum after our visit, and ended up using the last day of the trip to do a bit of extra shopping and go back to an amazing Indian restaurant we found on our first day there.
I kind of learned my lesson on day 6 though, as I figured both visits were planned far enough apart to manage both (Tate was booked for 10 AM-ish for a special exhibit to start the visit with, and Sky Gardens was booked for 9 PM), but we spent so long at Tate Modern that we had to rush a bit to make it to Sky Gardens on time.

The last time I went to Montréal I only got through about half the list I'd made of places to see and things to do, but at the same time it gives me more reasons to go again and see what I missed. I also bookmark places I really enjoyed (good restaurants and etc.) to return to on future visits.

For the most part, living in England with a family and not having lots of funds, it's a package holiday with the likes of Jet2 to somewhere hot in Europe.

Last year was the first time we did a week all inclusive to Tenerife and it was wonderful. No extras to spend out on. Just a week of sitting around a pool, eating in a glutinous manner, drinking all day and vegetating. Having 3 teens and a 3 year old makes for not doing big adventures out.

We did a spontaneous water park, that was it.

So the planning is mostly searching for package holidays. I'm hoping to do a decent adventure in a few years time though, something like New Zealand or Japan, and plan it all myself.

Both... Kinda.
I over research the place I'm going and save everything on Google Maps, but go with pretty loose plans. I have a list of ideas so I'm not left with unwanted downtime, but my days are flexible enough to change plans if I hear about something cool.
I get back each night with enough time to make a schedule for the next day or decide on to see where the day takes me. But during my wandering, I still have all those places saved on Google so I can easily see what's around if I need to.