I did a search and didn't find anything, but this may be a well-worn subject by now.

Last year, I went to Japan for the month of September. With my mild OCD and the fact that I knew it would be easier to organise everything from this end as much as I could, I started planning in mid-March, booked everything by the end of May, then spent a few months fretting about various hotel choices, rearranging days, etc. Then I went to Japan and thoroughly enjoyed myself.

This year, my holiday is a little closer to home, and although it's not til August, I've already got a loose list of places I want to go, things I want to see, aswell as 2 hotels booked (okay, so one is in Edinburgh which is always busy during August). I think 1 more month of organising and I'll have it sorted. I do enjoy the planning, poring over google maps, etc, and frankly for the Japan trip, the organising was definitely half the fun, but it does mean that I'll probably never enjoy the delights of laterooms.com or lastminute.com

I'm just wondering if my planning ahead is freakish, or does anyone else spend 3-6 months planning and arranging a 2-3 week trip?

You're not the only one. Our reasons may be different, but to us planning a trip is part of the fun. Right now we're starting on Scandinavia for June/July.

(OTOH, I'm going to London in the middle of next month, and haven't booked anything yet. Fortunately, the FT Presidents' Day Do will take care of much of the agenda.)

I'm more in the last-minute camp but there are plenty of people on these boards who plan much further in advance than you do, especially vacations. Many premium award tickets are released ca. 11 months out in miniscule numbers so you can bet folks are planning those junkets way ahead of time.

Plus, as you've discovered, advance planning lets you enjoy the anticipation phase of the trip.

Arranging a trip six months in advance hardly qualifies as OCD, especially on this board.

I've organized trans-pacific vacations using FF front-cabin awards 10 or 11 months in advance, easily. The last one led to a running master itin / trip note that was 10 pages long by the time I printed it off and we packed our bags.

I tend to do more extensive and long-range planning for places I haven't been before.

As an example, we went to Paris (my first time!) over Christmas 2008. I started to plan the trip in the spring, and spent countless hours over the subsequent several months reviewing and organizing names of restaurants, getting hours for museums, and developing itineraries to try to coordinate our museum plans with restaurants in the area, etc.

We're going back to Paris next week. I have had the plane and apartment squared away for a while, but have done very little other planning. I took a quick look at my old itinerary with a thought to updating it for this trip, but have decided to basically wing it.

I think my wife enjoys looking forward to trips more than the trips themselves.

For my Alaska trips, I plan them 1-2 years in advance. It is much cheaper that way. Car rentals booked 10-11 months in advance for Anchorage can be $95/week but booked 5-6 months in advance can be $250/week or more.

Booking cabins in highly-prized locations requires advance planning, as does campgrounds in places like Katmai National Park. Many cabins are booked exactly 6 months to the day in advance of arrival.

I am already sketching out an Alaska itinerary for 2011 so that I will have it pretty firm 11 months in advance, when I can seek frequent flyer seats then start looking at rental cars, etc.

As was mentioned above, the planning is almost half the fun.

For many other trips, I don't plan them nearly as far in advance.