Some folks are able to do this better with friends and some without. You really need to be sure your riding styles and especially your stopping styles mesh well. When you are on the clock there's pressure that little things will eat into. It's not the riding really that gets you but making sure your stops are smooth and efficient. If you've got a friend who has to have a cigarette every stop, or your, ahem, bathroom schedules don't mix, people can get impatient standing around waiting while the clock is ticking. I'm better off on my own.
I learned a few things though doing it. First, I'm not one of those LD guys always looking for the next cert. I think I'd like to do the 50CC cert (50 hours coast to coast across the USA) but that's about it. Second, it does what people call shrinking the map, which at least over here is handy. Where I used to look at the map and think "Wow, that's really far away" now it's "If I start early, I could get there for a late lunch." Here in Texas we have to cover a lot of miles to get to any fun stuff, and being able to have the mindset and the efficiency to cover those miles quickly in large chunks really helps. For instance, recently I was talking to someone about them going to Colorado from Dallas. His plan was to get up and spend his first day riding to Amarillo TX. That's about 400 miles. Then the next day ride into Colorado. He was burning two extra days just getting there and back where I have the confidence to make it to the base of the mountains, about a 700 mile ride, in one day. That gives me two extra days to play in the fun stuff. I can remember when cranking out a 700-800 mile day seemed like a lot, but after doing the SS1K, it all seems very doable.
A couple of tips. First, try to ride a round about route. Out and back usually makes for boring riding coming back, it's better if you are riding and seeing new sights the entire way. Second, try to ride with the sun to your back. If you don't, it's going to be in your face all day, because you'll be riding into it in the morning and into it coming back in the evening. Third, know when to stop. Take a break even if you don't need gas but your body needs it. Don't push yourself unnecessarily just because you are on the clock, that's when it gets dangerous. Also know when to throw in the towel and realize you aren't going to make it. Unforseen things happen and it's better to call it quits than to keep pushing when you know you shouldn't. Fourth, make it a mission of some sort. For me in my RR above, it was about BBQ and my wife's grandmother. It helps to have a mission or something to see rather than just ticking off miles.
Current Bikes:2007 Yamaha FJR1300AE | 2016 Suzuki GSX-S1000 | 1998 KTM 250 EXC | 2001 Suzuki DRZ-400E
Family Bikes: 2006 Honda CRF70F | 2005 Honda CRF230F