Get into the Shelter Island area. We just finished a wonderful week there. We were coming from Newport
. Our anchorages were -
Mystic CT (we were luck to be able to stay at a friends yacht club pier, but you should head
up the mystic and try to moore up by the museum. Dockage is a little pricey but it does give everyone on board admission to the museum if you choose that route
. Other wise a nice anchorage is off of Mason's Island. It is a long dinghy
ride from there. We also considered staying in Stonington. Also consider West Harbor on Fishers Island)
Coechles Harbor - Beautiful area. It is a little dicey getting in at low tide (dredged to 8') but I assume you don't draw much.
Greenport - This was a touch and go for us to pick up a passenger, but it looked like a good place to pick up provisions. No anchorages though Mitchell Park Marina had dockage for $2/foot overnight and $1/ for the day until 10PM. They also have free pump out at their dock
. We considered trying to rent a car and do the vineyards on the North Shore but time didn't allow that this trip.
West End Harbor - This was too shallow for us with low tide and a SW wind
of 15 blowing is in, but with high tide and not so much breeze we'll try it next time.
Smith's Cove - Stayed here instead of West End Harbor. The next day we went to Sag Harbor and anchored outside. We took the dinghy
in for a few hours and poked around.
Robin's Island - Fine as long as no strong northerly's. If wind
from the north, try Cutchoque Harbor. There are some cute creeks but there is a lot of shoaling at the entrance. We explored the creeks by dinghy.
Block Island RI - We had wind and current
in our favor and made it from Robin's Island to BI via Greenport Island very good time.
During the day the seabreeze often didn't come until 2 or 3 but near the summer solstice we were able to sail late. There was beautiful sailing around Noyack Bay and Little Peconic. Time didn't allow us to get into Great Peconic but it looked lovely too.