Free time is great when traveling alone and less useful when traveling with friends IMHO. Alone I'd pick 1 activity and 1 restaurant per day and have a loose idea of other options.

I've gotten a lot of mileage (pun intended) out of walking from activity to activity. Relatively random walking is a surprisingly high return on investment, but only traveling alone.

Google Maps "Attractions" is surprisingly good. CultureTrip, Reddit (frequently location based subreddits will have a sticky thread about highlights), AtlasObscura, and google were also great for research. "Unique things to do in ..." is a great search term, "unique foods in ..." is also great. There are also several activity websites which are good to page through.

Hostels are pretty great and incredibly easy to manage. Hostelworld is a great app.

Rome2Rio is a fantastic app for route planning.

I try to make a list of things like the best bakery, a top tier restaurant, a trendy restaurant, the best dessert, a trip through a grocery store, a trip through a fruit stand, and things like that.

I think when booking travel hostels are immensely helpful for figuring out what to do. It's most important to pre-plan super popular or limited quantity activities ahead of time, but other than that, often times you can just show up at a hostel with nothing planned and page through the hostels activity book/ask the staff what's cool.

Step 1 - Look at my savings account

Step 2 - Put it off until next year

Repeat indefinitely.

If you do consulting, you can find conferences relevant to your field and tack on some time on either side of the conference.

This is 100% legal. It also reduces the costs of the trip massively.

So I’d look for interesting conferences and build my plan off of that.

Good idea.

Ask your tax preparer about pitfalls if you want to deduct the business part of the trip. Very easy to make good or bad choices that will change the calculus.

I take the opposite approach to what you are doing...

I figure out something that I want to see/eat/experience, and then travel to the required destination.

If I am choosing a destination first, I am probably traveling there for the destination itself, and I don't really plan ahead or care about what is there...I just go and figure it out.

You mentioned flexibility...I think this is key. For me, itineraries or the "need" to have a schedule or do something causes stress, which is what I am trying to get away from when going on vacation.

Geocaching is a good way to find "local knowledge" type of interesting places.

https://www.geocaching.com/

Every year myself and a group of friends go on a long weekend trip to a new place following the letters of the alphabet. There are certain rules (must be a city or town not a country and long haul is ruled out due to cost). But every year we get to go to places that we would have never considered if we didn't have the rigidity of the selection criteria. Quite a lot of fun!

Probably not everyone's cup of tea, but I like concerts, so usually I try to match some interesting band's concert in that place or nearby, then I check if there is zoo, then I do "hidden gems ofplaceiamgoingto reddit" search and criminal levels, that's basically it.

There was a submission today that helps with а task planning using ChatGPT, one of the examples was TravelGPT

https://agentgpt.reworkd.ai/

It depends on what you want from it, but it sounds like you want an adventure.

If I were you in this case, I'd only plan to take cc + cash + passport and some clothes. Don't overthink it.

Try to go to a hostel and stay there with other people. Just follow whatever happens (without doing too much dodgy stuff). Hostel people know how to have fun and find weird things to do. Also, be prepared not to sleep and "relax" though, so maybe only do that for half of the vacation.

Get a train pass and try to move efficiently but staying in places for 2-5 days. Use these 'home base' opportunities as a chance to talk to locals or check sites like Atlas Obscura or WikiVoyage and make day trips or plan your next location. Googling "site:reddit.com $location interesting places" can be helpful too.

I usually travel for several months and hate backpacking so this approach reduces the number of times I have to lug a suitcase around.

My strong preference is to just show up and wait for serendipity to come calling. It works fairly well on day trips. My bride has a stronger preference for planning things out, but we usually have fun with a happy balance.

When we travel to a destination for more than a day trip, we like to pick a base, and venture out from there.

I just tell my spouse. They love to plan.

Putting artificial constraints on part of your trip (say, travel only by canal boat and on foot in NW Europe) can work quite well.

But it depends greatly on your destination. Finding cool stuff in Denali Nat'l Park (Alaskan wilderness) is rather different from NYC, which is rather different from P’yŏngyang, which is...

I make a map of everything interesting, then I just wing it. I leave plenty of stuff unseen, but it's a lot less stressful.

I use Open Street Map to find nice walks and bike rides. I use the local subreddit to find unusual ideas.

LOTS of people on YouTube publishing content about common vacation destinations. If you're going somewhere off the beaten path there still might be content out there of relevance but YouTube is my first stop for research these days.

How can you be sure YouTube isn't telling you where to go?

1) Pick a country I haven't been to and is interesting to me

2) Go to wikivoyage, pick a few highlights that I HAVE to see

3) Book a few youth hostels

4) Go there and walk about the cities while hitting most of what I noted in step 2.

it's a very chill process.

Whether, whether, whether.

You cannot predict it this far out but you can have an idea looking at the closest NOAA/WMO station hisorical data.

Whether what? Whether the weather will be good?

To OP: Last time I went on holiday I winged it and only went to 1 interesting thing which would have been much better booking in advance. I suggest discovering now what you might want to do. Landmarks, events, other cities.

time is precious and better planned. you can always go off plan.. but you can't really go on plan when you're already there

Carving out time for side quests is a good framework!

I wait for someone to drag me along on theirs because there are always deadlines and the idea of asking for time off fills me with dread.