Hey Andrew, I think anywhere you go there is going to be the potential of you being on the older side of the customers, it's just the nature of our sport. However, depending on what part of the country you are looking
http://www.otownwatersports.com is a great place to go for an older person. You are close to downtown and a host of other things are within walking distance(restaurants, movies, shopping). The accommodations are nice and the clientele, in my opinion, skews older.