Riding suits from companies like Aerostitch, Belstaff and Firstgear are very popular. They are quite waterproof, but not very warm. Expect to need additional layers below about 55°. These suits do not pack very easily - if you're going to be somewhere with temperatures above about 90° you might have a problem finding space to put them.
I cannot speak highly enough of electric vests. They pack very small, and they add fifteen degrees to your riding temperatures. The only problem with them is that if you give one to a woman, ten minutes later she'll love the vest more than she loves you.
I have a Kilimanjaro which I rather like, but it's not as useful as my Columbia ski jacket: the Kilimanjaro is not nearly as warm in cold conditions, the liner is almost worthless when worn as a separate jacket, and the Kilimanjaro is nearly impossible to pack away if I don't want to wear it. All told, the Columbia is a better choice for two-up riding. Note: I've now had my Kilimanjaro liner custom modified with a lot more insulation, and it's a real jacket now.
Saddlebags are for clothes and my bathroom kit. It's worth it to go to a backpacking store and get a nice kit bag that unfolds and hangs up. I pack a toothbrush with a bristle protector, toothpaste, shampoo, conditioner, razors, shaving cream, pumice stone, comb, hair brush, scissors, nail clippers, deodorant, q-tips. If you're bringing a passenger who's unfamiliar with motorcycle travelling, it's worth it to pack a similar travel pouch for her which also includes hand lotion, baby oil, and baby powder. You can buy all these in travel sizes at any supermarket or Wal-Mart. If you don't pack for this hypothetical unfamiliar passenger, she'll bring all these things but in full size and use up half a saddlebag.
For clothes, no matter how hot you think it's going to be, always pack a sweatshirt. In the summer, always pack a swim suit. If it's cool, I often ride in denim pants. However, I do this knowing that if I fall down, I'll get a worse burn from the denim than I would from bare skin on the road. If you're terrified of road burn, pack no Levis.
Winter clothes are a necessity if you're travelling in the northern US in the spring or fall, or any time if you're going to the Rocky mountains or Canada. I don't care what the temperature is in Las Vegas, it will be cold at 13,000 feet. To the right is a picture taken in Edmonton, Alberta, Canada, on July 12th, 2004 - that's snow, enough that it closed the freeway for 12 hours. The right hand side is the 'before', the roof of the submerged red Honda is circled. The left hand side is four hours later when the water had drained off. I pack a jacket with removable liner, snow pants with attached bib, electric vest, and gauntlet gloves, times two if I'm carrying a passenger. A very good jacket is worth the price - you can always get it on sale at ski shops in the spring, and you'll wear it for several years. I use a Columbia with a zip-out down liner that can also be used as a jacket all by itself, available at Campmor, or I wear a Firstgear Kilimanjaro. On cool evenings May-September, I wear the Columbia jacket (without the liner it's basically a windbreaker) and give the liner to my passenger. Jackets must seal at your throat and have a flap over the zipper, or they're worthless on a motorcycle. Leather looks very nice, but it's very hot in the summer and not very warm in the winter. A big hint: you never see people ski or snowmobile in leather. Snow pants are about $20 at a spring sale at your local sporting goods store.
You should have no problem packing for a two week trip on a stock ST. There's a lot of room in the glove boxes and saddlebags, and you can strap camping gear and cold weather gear on the passenger seat and luggage rack.
Two up, if you're going out for more than one or two nights, I think a trunk is a necessity. If you're going out for more than a week, it's useful to have a rack for the top of your trunk so that you can strap a carry-on bag on top. If you have a bag on top of your trunk, your cold weather gear goes in the bag.
Tank bags are not always thought to be the most attractive of accessories, but nearly everyone who goes out riding for more than a couple days has one. They hold water, snacks, chapstick, maps, sweatshirt, spare bungees, and little thingies you buy along the way. I think it's good to get an expandable tank bag. This lets you stuff things somewhere until the evening, when you'll have time to repack properly.
Some very helpful things include:
Try to organize things so that you can get to what you need in the middle of the day quickly without unpacking half the bike. This means the last things to pack, that is the things on top, are: maps, road atlas, jackets, gloves, ski pants, electric vests, lunch kit, radios, cds.
If you mean to camp out, you need a decent sleeping bag, a Therma-rest, and a tarp for ground cover. This is enough in California, Oregon, Nevada, Arizona, Utah, New Mexico, and western Texas. If you'll be camping anywhere that has bugs, that is anywhere else, you need a tent. This is no joke up north: there are mosquito swarms in Alaska and northern Canada that can kill a 2500 pound moose from loss of blood. I prefer the $20 two-man tents you get on sale at K-Mart or Wal-Mart which have tarps for floors. I prefer the 6' x 5' models, as they pack smaller, but some people prefer the 7' x 7' models. These tents last several years, they pack small and light, and if you wreck it somehow, no big deal. I own expensive tents, but I think it's foolish to pack them on a motorcycle. Good camping gear at a good discount is available on-line at Campmor.
If you buy a sleeping bag, you'll likely hear and read a lot of opinions on the heat retention properties of various fill materials. It's all nonsense. The heat properties of a sleeping bag are determined only by its loft (that is, thickness), nothing else. Laws of physics. The various different fill materials have different properties when wet, and they have very different weights and stuff to different sizes. This is a big deal if you're backpacking, but not such a big deal on a motorcycle. If you carry a passenger and ever mean to camp out, make sure your two bags can zip together.
A Therma-rest serves two important purposes: if you're over 30, it means when you wake up your back still works. And, it provides most of your insulation from the cold ground. You lose most of your heat to the ground. If you have a small two man tent, you don't need the therma-rest gizmo for holding two together, the tent will take care of that. A 3/4 length is fine, you don't need anything under your feet. However, I recommend you get one that's 1½" or 2" thick when inflated.
You can get compressible camping pillows - I own several. I never bring them on rides. I put my jacket and pants into my sleeping bag stuff sack and use that for a pillow.
Some motorcyclists pack cooking gear, etc. I don't, so I don't know anything about this stuff. I only stop to sleep or sight see. I do carry (see above) a couple spoons, a backpacking can opener, and a nice pocket knife.
West of the Rockies, you can camp pretty much anywhere away from the cities, except for the beach. It's illegal in most of The People's Republic of California for The People to sleep on the beach. To camp elsewhere, just find a dirt road, ride down it a mile or two, park, and sleep. It's better than even odds you're on government land, and no one cares anyway. You needn't worry about critters - they're worried about you. You do need to be careful about temperatures. It gets very cold at night in the desert from November through April. You can very easily have 85° weather during the day, and 25° weather at night. Of course, if you're over about 6,000 feet (2,000m), you also need to be careful about temperatures. At 12,000 feet (4,000m) it's always cold and windy at night. I won't camp at over 6,000 feet unless I have a truck and a lot of gear.
East of the Rockies someone owns everywhere, so you need to find a campground.
Weather is an important part of motorcycle travelling. In my opinion, if there's heavy rain or thunderstorms ahead, either go around or sit planted for a day. If you want to know tomorrow's weather, check the weather maps at this site, or the travel forecasts at AccuWeather.com, or the travel forecasts at Weather.com, or watch the radar maps on the 10 o'clock news in your motel room. Don't listen to the weatherman, and ignore the National Weather Comedians. And remember, the newspaper you just bought this evening was printed last night and typeset yesterday.
If you're east of the Mississippi and it starts to rain, pull over at the nearest cover. It will pass in half an hour. If you're west of the Rockies and it starts to rain, you have a big problem: it's going to rain for the next five days. If you're in Ohio, you will get rained on. If you're in Wyoming or Montana, watch out for snow. Maybe in July and August you can slack off just a little. Not in June or September though. If you're going to cross Texas, bring a book, lock your throttle, and lock your handlebars. You only need to look up at the highway about once an hour. If you're in Nebraska and the wind stops or you see a tree, pull over immediately and take a nap. You're having road hallucinations.
Buy some bread, fruit, cheese at a supermarket, and picnic in some of the beautiful scenery you're driving through. It's healthier, cheaper, faster, more romantic, and more scenic than any restaurant you'll find. Other than that, I guess it has little to commend it. Try local foods - strange cheeses and breads in Quebec, seafood bought at small kiosks on the coasts, local fruits and vegetables. Any jam with a local label is pretty much guaranteed to be excellent, especially if it's made from a berry you've never heard of. As far as I'm concerned, if you're on a long trip and eat at any restaurant chain, you have failed yourself and your passenger in a most heinous fashion. I bring an insulated nylon lunch box. This lets me keep fruits, chocolates (important if you're riding with a passenger) or whatever. I dump in a bunch of ice from a gas station drink, and that keeps things cool all day.
Generally, you don't need motel reservations. I never stay in large cities, so I don't know anything about getting a room in New York or Chicago. In small cities, there's always something available. There are a few exceptions: if you're looking for a room in Vermont, New Hampshire, or Maine in the summer on a Friday or Saturday night, you'd better have a reservation. Apparently the entire population of Boston drives up north every weekend. Similarly on the north-west coast of Michigan. This is easier to understand: if you lived in Detroit, wouldn't you want to leave at every opportunity? Same thing at Lake Tahoe, but you can always find a room in Reno unless it's Hot August Nights. These are the only places in North America where I've ever had any problem finding a room.
Don't over plan your trip. You can get software like MicroSoft Streets or Rand McNally Route Planner and plan your trip down to the mile and minute. Remember, you're on vacation. It's good to have a general plan and some basic maps, but being on a tight schedule while on vacation just sucks. Check out side roads - the thin wiggly roads on the map that go from nowhere to nowhere are the best roads in the country. Get lost - it's a lot of fun, actually, and you almost always see some really neat stuff. Whatever else you do, avoid interstates at all costs, especially if they charge a toll. I'd rather stay home and watch re-runs of Gilligan's Island than ride on any toll road I know of. Oh, and be very careful in Pittsburgh - even the locals get quite thoroughly lost if they take a wrong turn. It's hopeless for us: you'll be able to see exactly where you want to go, but it will be on the other side of an unpronounceable river, and the nearest bridge will be six miles away. One day the Steelers will win a game because some west coast team couldn't find the way to the stadium in time.
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