I've begun riding longer rides and have found that I enjoy this type of riding very much. I plan on doing much more bike camping next summer and am starting to mull a cross-country trip next summer as well. I currently have a Street Bob that I have modified to fit me very well. I am super comfortable and can do 300-400 mile rides without any discomfort. My only issue is wind... normally I love the wind in my face, but on these longer rides, I feel like I'm fighting non-stop for hours. It's getting cool here in Upstate NY and while on a 400 mile ride Sunday, I found I was gritting my teeth a lot and flexing my stomach and thigh muscles the whole time trying to lean into the wind (there was a strong headwind for half of the trip). I love the lightness of my Street Bob, but am now seeing the advantage of the Street Glide and it's "bat wing". I just don't know if I can ride with a fairing in front of me... I like seeing the road all the way up to the front of my bike (even though I look well ahead of me while I'm riding). But the fairing would keep me from getting beat up by the wind and allow me to ride longer into the cooler Fall season here. I am also unsure about the added weight of the Street Glide. I love Road Kings (had one a while back), but I can't look through the windshield... it's like watching a hockey game through the glass... I get a headache from the distortion, almost like a sea sickness, so Street Glide would be the bike I would change to. Any advice or experience is appreciated.

 

You can always get a shorter windshield on a road king.

 

Love my SG but you would have to change the windshield to 6.5 or 8" to rid buffeting. As for the weight, it's only 700 lb's and riding with tunes is awesome.

 

I went from a 05 Heritage to my 09 SG.
The ride is totally different, like a VW bug to a Cadillac.
I love the way the SG handles and it is so well balanced.
Maybe you should rent a SG first and see what you think.

Ride Safe

 

I think you will really love the SG. You may want to consider a Klock Wurks 6.5 windshield, as it will be short but efficient. I love my EG Standard and Klock Wurks.

 

+1 on renting a Glide for a weekend...you might very well find you can't stand the fairing in front of you. The Road King with a shorter windscreen is an option (plus, on short trips, you can pop off the screen for the "wind in your face" feeling that you love)
That being said, I love having tunes on the Glide (both on the road as well as at the campsite), and the wind protection on my hands when it really starts getting chilly...

 

If the street bob fits you, and you like it, why not try a windshield on it? I have both the SB and the SG. You can't go wrong with the SG, but that seems like a huge upgrade to block wind. I have a take off shield I can put on my SB that does wonders. And it's height adjustable. I can look over it vs through it.

Maybe visit a dealer and see if they have any shields in stock. They will probably allow you to attach one to the bike to see how you like the height.

If that doesn't work, test the SG as suggested.

 

I have a Fatboy and a Street Glide. Two totally different rides, both nice but for different reasons. I love the power and the cool factor of the FB, but the SG is a much better ride overall. If going more than an hour away, it is my bike of choice every time. Rides better, handles better, tunes, and wind protection. I have a windshield for the fatboy, but still prefer the fairing.

I think that when you test ride a Steet Glide you will see that the fairing is pretty easy to get used to and after a short time you will love having it.

Shakey