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I book my cruises as far as 18 months in advance - it's the only way to be assured of getting the stateroom I want.

Then the shore excursions, air and pre/post-cruise hotels are booked 3-6 months in advance of departure...

I wish I had the luxury of time to just wander, but as long as my vacations are precious commodities, I will be planning some things. I always keep an open mind, though, and certainly don't follow a strict itinerary.
Part of the fun of travel to me is the research I do to educate myself about a place and make the most of my time, so planning is fun to me also.

It depends on where I'm going - if it's somewhere I think there might be some great places like NYC that I don't want to miss, then I do a list. If it's just going to some wilderness spot or small town, I let fate rule the day.

My greatest fear on a trip is to spend most of the evening wandering, with luggage, and trying to find a place to spend the night.

I'll book the flights AND the hotel, then grab the pack, camera and guidebooks. But I'm not going anywhere unless I am satisfied with the first 2.

I used to be a hardcore planner, but now I'm in between. The awakening happened in London this past March. My wife and I had the absolute best day ever without planning nary a minute. It was serendipitous over and over again and what made it better was that I didn't have to stress about it for weeks to make sure it was just right. Everything just happened. Now, I try to be a hybrid planner....I bring some maps and an internet connected device for emergency surfing, but for the most part, we just kinda go and see what happens.

Planning is half the fun!

total planner. i have to know where i'm staying and what i'm doing (not a day to day itinerary, just a general idea). my friend is going to indonesia for three weeks and just has her flight planned. no hotels, nothing. kinda freaks me out! lol. but good for her. :)

I always make a list of where I'd like to go, and end up putting dots on a laminated map of the place I'm visiting. I pick where I'm going to start my day--but then just end up wandering to what's nearby on my map. No worries if I don't get to everything on my list, but I don't spend a lot of time wandering around somewhere I'm not interested in. If I could get more than a few weeks a year to take vacations, I'd probably plan less.

Trust me, it's a lot more relaxed than it sounds--especially when compared with the regimented vacations my family took as a child. My mother stopped letting my father wear watches at one point because things just got ridiculous.

It depends on what I need more: escapism or a less to do. If I am looking forward to my vacation as an escape from a miserable situation, I will do a lot of planning as a form of escapism and anticipation. If I am just overwhelmed with the number of things in need of doing, then I avoid planning since it is just another source of stress.

i do a ton of research before i go- it actually gets me all excited about my trip. i book the flight and hotel and print out lots of stuff to do- and check the local independent paper. that way once i'm on vacation i've got a pile of options- i'll pick a neighborhood or place to start the day and then i've generally got lots of options in the area. this worked perfectly in portland recently. i had the address of #1 a Mr T themed art show, #2 a map of independent record stores, #3 a list of great parks and restaurants. its was the best.
i've also tried the other way and its resulted in nice suprises like hauling my pack all over ilha granda brazil with a stomach bug in the heat trying to find a place to stay. if i'd planned ahead i would have been on the beach instead of stressed out.

I love doing lots of research before and then picking and choosing when I'm actually in a place. The only things I book in advance are my flight and perhaps a couple night of lodging. I only travel with carry-on so it's not like I have to spend time packing. It helps that I try not to vacation for less then three weeks at a time.

The thought of going on a big cruise ship for a vacation sounds like punishment, now being a small sailboat in the med for a couple of weeks is great.