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Oh, I'm a planner all right, I plan everything.
I travel every day but one layover day, and I plan long days at each end of a trip (but like you, a short exit day at the end), and short days here and there to allow for fishing or whatever, and a change of pace. I consider a "plan B" for in case I can't make the plan A.
I guess I'm one of those "Russians" that the old fogeys were unable to understand from the other thread - I have goals for my trips - to see some new country each time, maybe to revisit some favorite spots, and to travel fast and light and hard, to challenge my limits - part of what I want out of a trip is the workout. I don't like to sit around camp and relax all day, or fish all day for days in a row - I'd be bored stiff - I do have slow time built in, and fishing time, but mainly I like to paddle and explore, so I do.
To do the trips I like to set up, I need to know time and distances between here and there, and more or less be "on schedule", or I won't make the loop in time to get back to work when I need to. So I have a campsite in mind for every night, and a plan B if I don't get there, because I've been hammered by headwinds for the last 3 days in a row (and some shortcuts figured out if I need them). I break down a day's travel into increments - canoe 3 miles = 1 hr; portage to lake X, 80 rods = 30 min etc, and I add up those increments to make a 10 hour day (typical) or 12 hr day, or 6 hour day if I want a short day. Its easy to just wing it for a short day, no big deal if you start late or finish late, but for a 12 hour day I need to be more precise in my planning.
I like to go light weight, cause I'm getting to be an old fogey myself, and things hurt, or don't work as well as they used to. So I've been buying new gear over the past few years to cut ounces - to do that you have to weigh everything you have, and select for the lightest, and maybe for what to leave behind. That's all part of the planning I do.
I even plan for a change of entry date, if I can get to Atikokan early enough to make the change to a day earlier. This year, I have an entry reservation for the 25th, but am going to try and get there in time to switch to the 24th and get an extra day on the water. Planning for that, I have the extra day's food packed - if I can't make it in time, I just pull that one day's food out - it would take about half a minute to make that change.
Part of my planning, for traveling light, is to be real precise in what food I bring, so I don't bring anything extra, except for a ziplock sandwich bag's worth of extras. Each day's food is packed into one bread bag (I can do that even if I pack for two people, though I'm going on a solo trip this year), and the bread bags are numbered and packed into my food bag so each new day's food is on top when I get to it - a lot more efficient than digging around in a pack, trying to decide if I want this, or that or the other for dinner today, especially if I'm hittin gcamp at 7 or 7:30 - I really hate to cook in the dark. For just me, for this year's trip - 12 days food weighs just 15 lbs, 2.3 ounces - about 20 ounces a day. Can't get that light without a lot of planning, and I've been perfecting my food packing for years to get it down that low - more planning.
The result of all that planning, is I have my trip set up the way i like it - 160 miles, 60 portages, and I know that I will carry 92 lbs across the portage from Nym to Batch, inlcuding a qt of water, on day 1 of 12, and I know I will be back in time for the 1300 mile drive home when I need to be.
Not a system that appeals to everybody, but it suits me. I do the same planning if its just me, or me and my bro. Have done the same for a group of 4 on a couple of trips. I would not trip in a larger group, too much trouble trying to get more than four people to agree to anything, so you tend to sink to the lowest common denominator. For a large group like you are taking, 8 people, I think everybody has to plan their own food. I plan a slightly easier trip if my brother goes, and for a group of 4, a much easier trip - the more people involved, the harder it is to match likes and dislikes about food, pace, and even where to camp. For a group of 8, I'd think that a base camp trip would work best.
So laugh at me if you want to, but I enjoy the planning as a part of the trip, and the challenge of keeping to a light load. The more ambitious the trip, the more planning you have to do to make it.
I'd guess that for people who are more or less "local" to BWCA, planning isn't as important - they can get there several times a year and do some eays trips and some hard trips, focus some on fishing, or more on a relaxed pace - but for me, if I'm lucky enough to get up there once a year, well, I do a lot of planning - part of the anticipation.
Now on the other hand, I do a lot less planning for local paddling trips, overnighters or 3 day trips, and I'm not so weight conscious - don't need to be for river trips with no portages. But I still don't cook much - I hate to do dishes when I'm out having fun.
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