Summer Bicycle Touring

In the past, I have mentioned that I would very much like to do a short bicycle tour. While I'm not one to take off for weeks or months at a time to engage in a bicycle trek, I really would love to go for a few days and simply take in scenery and see how a shorter adventure would go. At the moment, I'm trying to work my mental state up to the idea of going on a short tour early next summer, possibly travelling from San Diego to the central coast of California. Why Cali? Well, I'm somewhat familiar with the state having grown up there, but I also know that there's so much I haven't seen. Additionally, the weather tends to stay more moderate, so I wouldn't have to worry as much about extreme heat and cool (at least in the summer). I also have relatives up and down the coast, so if all hell broke loose, I know there would be someone to rescue me. Sam, whether he likes it or not, will likely be suckered into this adventure with me (though I am fairly certain he would want to come along regardless), so that will allow a partner on the roads to help keep me moving along. I have also had the opportunity to take the scenic Hwy 1 route from Oregon down through northern California and it was quite beautiful (though not by bike as it was many years ago), so I thought perhaps trying out a southern route by bicycle could be a great option.

A bicycle tour likely wouldn't include a lot of this... but it might be a great time!

While this is the area that is currently in my head to do a short tour, I am open to other locations, and thought perhaps others might have suggestions on a good route to try out for a 2-5 day bicycle tour.   I'm also concerned about the southern Hwy 1 route in California. From the quick reads I have done online, it looks as though that route goes either back inland significantly (which I would prefer to avoid), or it travels through some rather iffy terrain with few directional signs (it seems more than one individual has become lost on this route).

web survey

Another option to get some experience and not be gone for days would be to try out a quick over night locally - basically traveling as far as I can in a day, camping, and coming home. This option is probably the most sensible in the immediate future, and while I'm open to the idea of starting such a trip before summer ends, I still think I'd like to have a slightly longer one at some point in the future. What do you think? If you were going to do such a trip, would you want to try out a shorter time period close to home first, or would you just go for a longer round first so you don't talk yourself out of it? I think I'm somewhere on the fence with this, so thoughts are certainly welcomed.