If you want to avoid crowds check out Westport MA and Menemsha in Martha's Vineyard. Both beautiful. You can anchor off the Menemsha beach in any wind that has an S in it, but otherwise if it has an N seek better shelter. Lake Tashmoo is a natural hurricane hole in MV.

When you go to Block Island make it a weekday. Holding is poor and so are many people's anchoring skills, so if t-storms are in the forecast try to get a mooring (call harbormaster if you can't find a green or orange ball in the S end of the pond). In fair weather you can anchor in the east. Check out the dinghy beach on the east end of the pond, land the dinghy and walk across the road and dunes to Crescent Beach. Fantastic. Walk south on Crescent Beach into town. Land the dinghy at The Oar and get free water or buy ice and other stuff at the convenience store, or get a cab (or walk) to town where there are many restaurants and a supermarket.

On the way to LIS you should stop in Stonington CT and Mystic (lots to see/do there, and some great restaurants), then head south to the Eastern LI forks. Nice shopping in downtown Mystic near the drawbridge, and make sure you try Mystic Mud ice cream at the drawbridge. It's world-class ice cream.

Do not miss Gardeners Bay in Eastern LI. It's ringed with great harbors about 2-hours apart and has clear water and great day sailing almost all the time with sheltered water and 10-20 knots winds. The best is Sag Harbor for provisioning and restaurants -- very boater friendly (call harbormaster for town moorings) or anchor outside the breakwater. Second best and much lower-key (no super-yachts) is Greenport (town moorings or private marinas). All the other harbors are very quiet and might be good destinations for holiday weekends. (Skip Montauk Harbor -- it's ALL about sport fishing and the gold-chain crowd is the dominant species).

LIS in August in settled weather is usually SW 0-5k in the morning and SW 5-10k in the afternoon. Very lazy, often hazy-hot-humid. September it picks up 5-10 in the morning and 10-15 afternoon. September-Nov you get a front coming through every 5-10 days with clocking winds with rain, more rain and gale force (northeasters). Jerry's concerns about an hurricane are a little overstated because they usually miss us but you do need to keep alert and watch the projected tracks daily, and they influence the weather even when they miss.