I'm American and my best travel friend is Belgian. We discuss this all of the time. We both work in the hotel industry.
I can't tell you how many times a European traveler shows up during an event or festival when there are no available rooms in the entire city including surburbs.
My friend finally had a "bad experience" in Wales and realized that she wasted so much time just to find a room. When she planned our 2 weeks in Germany and Austria, she had all but 2 nights reserved. I know she did it to make sure I was happy.
The only reservations I make are plane and hotel. My travel guide/tourist info center/hotel front desk helps me with everything else.
I love to travel and this forum is fun to read. There is some great advice too.

Thank you all for your replies.

BTilke - I'm not looking down on anyone, I was just curious at the different approach.

I hadn't considered that 2 weeks was a maximum holiday.

Valtor - you can answer as well, I didn't mean to leave you out.

So basically the main reason for planning is because you enjoy it. Thank you, question answered.

I get 5 weeks vacation. I usually book my flights quite far in advance, sometimes 6 months or so, if I'm using ff miles. But another reason for booking so far in advance is work related. I'm an IT consultant, and I usually work on projects. If I get approval in advance and I'm assigned to a new project, I can tell the project manager that I'm going to be away and they can usually will work around my plans, and if they can't, well, too bad. Too many of my co-workers say that they can't ever find the time to take a holiday. I can see how that happens if you don't plan in advance. There's usually more work than people to do the work.

In terms of accommodation, we tend to book ahead more now than we did in the past. But depending on where we're going, we may not book every night in advance. When we were in Greece a few years ago, we ended up in Turkey for a week, with nothing planned.

I rarely plan the actual days in advance. I love doing my research and I have an idea of what I want to do, but I rarely make a decision until I actually get somewhere.

Back in the late 70's I visited Paris on my own. I don't know if I even had a guidebook with me. I know I didn't have any rooms booked. I spent last week in Paris - 28 years between trips - and I was much better prepared. I know I enjoyed both trips!

Just realized that it was a question for Americans, not Canadians!

>>"Just realized that it was a question for Americans, not Canadians!"<<

Actually, Canadians are American in the broader sense of the word, but that's another thread.

<i>3) Buy plane tickets.
4) Ask for vacation time.

...

and bardo1 writes: &quot;Did you perhaps switch steps 3 and 4?!&quot;</i>

Ah ha! So someone discovered my sordid little habit!

Really, I often do book my plane tickets before I ask for the vacation time. While I'm not a top manager, I work in a &quot;we need you all the time&quot; kind of office -- You can't take more than about 10 days because if you stay longer, you can start to FEEL the office politics start swirling around your irresponsibilty. Yep, it's that kind of place.

Anyway, I've never had my vacation request turned down when I say &quot;I checked the vacation and project schedule and it looks clear for (these 8 days in March), so I'm going to (Ireland, Germany Italy, whatever.)&quot; It HAS happened when I say &quot;What would you think if I took 8 days in March?&quot;

But I do this 4-6 months out.

Really, it's just a defense mechanism against the knee-jerk &quot;but we NEED you!&quot; response. Really, I'm not indispensible. SHHHH!