Sailing Conditions
Chappy is an excellent location in the off season. From Memorial day till Labor Day, a local parking permit is required during the day unless you drive a motorcycle. Chappy works well with SW to NW winds. With a strong wind, especially for a few days in a row, there are some nice swells - somewhere in the neighborhood of waist-high to chest-high. There is not much shorebreak to get through, and you get the full brunt of Buzzards Bay 10 feet off shore. There is also good skimboarding at Chappy, and if you're desperate, sometimes can be surfed on a longboard, too.
Kitesurfing
If you are a kiter, when you get to Chappy, park in the public lot, then walk South as far as you can. Walk past the public beach, through the private beach club (walk along the shore and the lifeguards won't bother you - I've never had a problem with it), well past the line of buoys. Set up down there, and please try to keep upwind enough to stay out of the private beach club area. If you are a beginning kiter and can't stay upwind, please don't sail at Chappy, especially in the middle of the day on a weekend. There's nothing wrong with being a beginner, but with a snooty private beach club downwind of the kiting area, it's not the best place to learn. You might consider the marsh area on the other side of the parking lot for learning.
Windsurfers have no trouble setting up right at the public beach in front of the parking lot.