mev

From the Cycle America web site, it looks like they also sell one-week segments in addition to the entire nine-week trip. If you can't go the entire distance at once, this might give you a chance to try it for a week and get an idea of company and riding. If the company is good, they should be able to give you referrals of people who have done trip before and their experiences. They may be able to answer the age question more directly [though my two cents is less individual age and things you know about general health and family history].

There are trade offs between doing your own trip vs. a supported company - and some it is a matter of preference. A group like this will have a mostly fixed schedule and each day you either ride or catch the SAG vehicle for some of the time. They will carry your gear and so your role is to show up and ride.

Your own trip should be less expensive and you get more options on how you structure things. You can adjust distances a little easier for weather, mechanical issues or your own pace. You'll end up carrying more but also be able to adjust things as you work things out.

Even before such a ride, you can also experiment with your own shorter trips - both looking for local rides or on web like National Tour Directors site: http://www.bicycletournetwork.com/. You can also do some of your own mini-trips over weekends and the like to get your own preferences.

I have done a little bit of both. I've done some organized supported rides like Ride the Rockies or this summer will be Bicycle Tour of Colorado. I've also done a fair amount of my own touring including two trips across the US and once along each coast. There is a time and preference for both types of rides.