Complacent to sailing...
Join the Trailer sailors, (trailersailors.org). Going on a cruise with 30 - 50 other boats including many Macs is a lot of fun. My wife is not crazy about sailing but she loves the social part of group cruising. Highly recommend the cruise in July to the North Channel. It's been rated in Sail magazine as one of the top ten cruising spots in the world.