If you are going inside Long Island
, your biggest schedule issue is waiting in Manhattan for a weather
window along New Jersey
. Early May is prone to gales and this piece of the coast is a terrible place to be caught in bad weather as there is very little refuge for a deep draft
sailboat. A friend was caught in a spring gale a few years ago that saw gusts past 60 knots. Worse, Cape May is a very, very dangerous piece of coast in a bad sea. The shallow water can set up a steep sided 10ft sea that is far worse than what you would find 50 miles offshore
Even if you don't get wind
, it can also still be very cold in May. A hundred mile beat into a stiff southerly in 40-50 degree temperatures is no fun.
Again, if you allow time to pick your weather it should be a pleasant, safe and easy sail.