Re: Best months for coastal hop up East Coast
chef2sail has a point about motoring, especially later in the day and at night when the winds typically die down. Your best bet is to plan on motoring from Cape May to Block Island and hope you can get some sailing in.
jimrafford also has a point about the water being cold in May and June. Actually, the ocean temperature doesn't peak until somewhere around the end of August. We usually launch our boat in mid June, but rarely do more than a day sail until July, when the air and water are more comfortable.
If you take the inside route through Long Island Sound, you'll want to pay attention to the currents and plan your sailing around them. We use Eldridge's tide tables, but there are other sources, including some chartplotters. If you continue through Fishers Island Sound, make sure you know where the rocks are, particularly the "clumps" and the line of reefs between Fishers Island and Watch Hill.