I see this question alot amongst people planning trips across the state or across the world. I rode USA and central with numerous different friends, and then South America solo. Do not be mistaken, riding solo and with friends is a COMPLETELY different experience. Your daily routine, your daily decisions and even your budget can be affected.
So what about the bike security?
Some people that when they are riding solo they can´t leave their bike alone. I believe leaving the bike is not a concern, it is to a degree but its not your biggest. At borders you can park a bike outside the window to keep an eye on it, or in a worst case, find one of the many guards with shotguns and park it next to him. If you do end up needing to go inside a large supermarket (most likely only in the USA) you can take your tank bag inside. Your bike should be lockable except for the tank bag. Bike security is a huge concern everywhere in Latin American countries. Parking lots and supermarket lots usually have a guard posted to watch customers vehicles. Give a salute to the security guard so he know who you are and whose bike it is.
My only chain snapped in Colombia when I was solo. I left my bike with a 40yr old women who was shorter than the bike and lived with her chickens and palm tree farm for 40 years. I hitched into town and got a chain. I gave her 1 or 2 bucks which she appreciated greatly. Bike security is always an easy situation to handle.
So what about the solo experience?
Riding for days and days solo will be a test of your personality. You might enjoy checking in to the hotel and being by yourself, or you might get a little bored walking around by yourself. I found it more fun with friends, but when I was solo I learned to enjoy things that I hadn´t tried, and I found myself in conversations I would never have been with if I had been with a friend. I was getting into conversations with shopkeepers and people on the street who wanted to know who I was and where I was from. If you like a beer after a day of riding, it is a great opportunity to go and find a bar, and interact with the locals.
If you do choose to go with a friend, the most important part is finding a friend you are compatible with, and you can keep communication levels good in stressful situations. Some people have found motorcycle headset systems like the scala rider G4 as a great way to stay in touch. Adventure motorcycling isn´t always peachy and if you are going to be getting on each other´s nerves than you should really rethink your trip plans. An alternative is just going with your friend and trying anyway, if it doesn´t work, you can take different routes for a week and reunite down the road and see how it goes. Nothing is set in stone. Riding solo does give you a sense of independence you won´t get riding in a group.
