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Late May on the Chesapeake is generally nice weather. However, it could be fu ll summer with hot & sticky weather. Or it could be more spring-like. Every now and then one of the last cold fronts sneaks in around Memorial Day, or a low off the Delmarva peninsula will bring in some raw weather off the Atlantic. So you do have to bring a range of attire, or get a good forecast just before packing your bag so you know which way it's trending.
I would tentatively plan for warm weather, but bring a light fleece layer in case. Rain/foul weather gear would be smart, as we get quite a few summer storms this time of year.
While maybe not "the best", I would probably go with your kayaking pfd. The neoprene zip jetski pfd will likely be too hot/sticky and restrictive. The water will be warm enough for swimming, so for now your type III is okay. If you enjoy your lessons and decide to really get into sailing, eventually you might want to consider investing in a more sailing-specific vest. But what you've got is fine for now.
You'll want sunscreen, spf lip-balm, sunhat, and sunglasses too.
Some folks like to wear sailing gloves, especially if your hands are on the tender side.
As far as other clothing, SPF-rated quick-dry materials generally work well. Non-marking shoes too. And try not to bring too much aboard - sailboats are always tight on space.
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT
Last edited by JohnRPollard; 04-16-2010 at 12:51 PM.