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Up north here if you want to extend the season heated wear is the way to go. I have a Gerbings heated jacket liner and the newer G3 gloves and routinely ride upper 20's lower 30's. If I were to be doing an extended ride, similar to yours, I would also invest in their heated overpants and socks. It's a little bit pricey but it works, big time! Also, try to think of the investment as being A LOT MORE than just for the one trip. You'll be amazed at how often you throw the jacket and gloves on. Once you have them you'll be asking yourself why you didn't do it earlier!
If your hands were good you're more than half way there. Thw windscreen will do most of the rest. Add a layer over your upper body. If you have engine guards and don't have lowers try some soft lowers, if no guards add another (thin) layer beneath leathers and pants along with some good wool socks and heavy leather boots (like Red Wings).
I start out in the upper 30s often, leather, layers, and lowers are the key. My biggest problem is always my hands.
+1. The hand are usually the biggest challenge because they are up in the wind. Put the windscreen on and you may save yourself a bunch of money on the electrics. I didn't have a windshield on my Sporty and it makes alot of difference in core temperature. 40+ I just use Draggin' Jeans with thinsulate lined leather chaps and the legs are good. Under 40 I add Under Armour tights. ("Tights" doesn't sound very manly, but they are way warmer, more comfortable and less bulky than long johns.) Same on the top. Under 40 I add an Under Armour mock turtleneck to my fleece and t-shirt under my leather jacket.
How about hauling your bike? Why be uncomfortable to prove something? Riding locally is one thing; a couple thousand miles in freezing temps & possible rain,sleet, or snow does NOT make for a good time when you get there & know you hafta ride back.
IMHO if it ain't fun, I ain't gonna do it. And riding in the cold ain't fun!
With cold weather motorcycle gear (insulated motorcycle over pants, heated gloves, heated jacket liner, 3/4 length touring jacket, & FF helmet) riding down to 32F can be as comfortable as riding in 70F temps even at sustained highway speeds but with jeans/chaps/skid lid your going to be miserable.
Heated gear. Gotta see about warranty for my socks, the wires are all loose now. Didn't wear them last trip from Tn back home. Feet froze. It was 42 degress when I left and 37 when I got home, 700 miles later.
I hate riding when it's under 50, but its under 50 ALL THE FREAKING TIME it seems! (5 or 6 months out of the year anyway)
My hands are the first thing to go, so I would (and plan to) get some 'over glove' types that are insulated and keep the wind from going up your sleeves. I hate fat-*** gloves though!
Windshield is a must, but you still need something to keep the cold off your neck.
If you're just riding for pleasure, though, it leaves pretty damn fast when your teeth are chattering.
For you guys who are heading south from the north east, consider the Auto train. It is really a lot of fun. You board near DC and leave at 4pm. Arrive the next morning at about 9 am in Orlando. Bar car, diner car, good food it's really a fun over night trip. (I get a sleeper cabin, load my iPad w/ movies etc.) They do a great job loading and unloading the bikes too.
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I resisted heated gear for 4 years. But now that I have it - I realized I really wasn't comfortable before.
I rode almost 200 miles each way to my in-laws near Pittsburgh this year for Xmas.
There is a HUGE difference between riding 55mph & interstate speeds. I found I kept inching the heat warmer & warmer and it was only a 4 hour ride.
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