Hitomi's already planned out most of our vacation for the end of the year.
I know it seems early, seeing how it's just May. However, given the busy travel season and rapid disappearance of airplane seats at the end of the year, it's not too soon. One tour we wanted to go on, a cycling tour in Vietnam with the same company as the one we had in Thailand, already sold out seats. Many tour places are reserving spots for end of 2008.
Going back to my Orcas Island tour, I'm thinking either just post Highschool graduation or one year after or before, really I thought the correct way to travel was like my parents always did it. Travel to an interesting place, stay at inexpensive places, do what you like. There was nothing formal about it, and my Orcas trip didn't really require too many reservations and didn't have much planning, besides being dropped off and picked up at the Anacortes ferry terminal.
There was one difficulty when we didn't plan adequately ahead. Arriving in Friday Harbor in the afternoon, there weren't any close public parks reachable in time, and as it grew dark, we had to settle for what was on the main road out of town. The commercial camp wasn't in any particularly scenic spot, but had a volleyball net, and a social atmosphere.
Last year, paddling from Tofino to Hot Spring's Cove, most of our progress was determined by the weather. For instance, we spent an extra day waiting for the wind to die down, and spent our last day of the trip in Vancouver, B.C. enjoying a night on the town. Sure, we had to scramble for a hotel room, but it was better than camping one more night where we were.
Perhaps I'm lazy, but I have never really determined out trips very well in advance. What I found was any sort of rigorous planning sort of kills the spirit of adventure. Kevin, my friend, is like this as well. Almost, for any overnight hike, he comes up with a couple of places to go. (We usually just choose one spot. One time we went on two fairly difficult hikes in a day, the latter in deep, plunging snow. This was a little more work than we wanted.)
For travel planning, Hitomi's very meticulous. Our trip to Japan and Thailand was outlined in great detail. She's loves to (or feels compelled to?) stay up late into the night researching things to do. ("It's 4am, go to bed" — "I'm not a kid…") And since I handle the outdoor trips completely, including most packing, I let her work out everything for these oversees sorts of trips. Still, I got thoroughly chewed out in Tokyo for not contributing to her plans or coming out with things I wanted to do. Admittedly, I didn't really contribute anything, but I didn't see any reason to. When somebody's that into making plans, it's usually better to stay out of their way.
Additionally, I get chewed out for my plans. Every hiking trip I come up with is responded to with a concern it will be or is too difficult. Certainly, there have been some torturous trips, but such is the nature with hiking big granite things. And trail conditions vary from steep hard (rocky, exposed, hot, not well maintained) to steep easy (forested, wide, cool), so it's difficult to judge based on distance and elevation alone. Her overnight pack also weighs as much as many people's day packs, but still half the time she refuses an overnight. Personally, I'd rather spend the night someplace, rather than drive 2-3 hours out that evening. (Hitomi usually gets to sleep in the car on the way out.)
The trip plan is much like the Thai/Japan trip, we're doing two countries in one vacation. The trip to Vietnam is pretty much buttoned up. But our trip to Taiwan is still unplanned so far. I'll probably end up putting my two cents in for Taiwan — I bought a book on cycling there — but Hitomi outrightly refuses to go on any non-guided trip. Which I can kind of understand in Vietnam, but not in a place like Taiwan. I ordered a book, and a map. The east coast is fairly unpopulated and scenic. We'll see what comes of my plans.