It's not as benign around here as sailing to Catalina
but, as long as you keep an eye on the wind
and the tide, it's great sailing. The other great thing is that there are so many places to go; if the wind and/or tide aren't working for your initial destination
, there are lots of alternatives.
If you haven't already, download the Dockwa app and register a credit card - you can also use it via a browser. Many of the transient moorings and slips around here can only be reserved through Dockwa and, even if you intend to anchor
out most of the time, it can be really nice to easily reserve a mooring
if the weather
turns against you and you want to duck in somewhere.
made some great boats in that size range but unless you have an exceptionally strong engine
, I would avoid Woods Hole if the tide is running strongly in either direction - I've had to use full power to avoid getting swept onto a buoy.
BTW Edgartown and Vinyard Haven have reasonably priced moorings; Nantucket Moorings are more expensive and have a 2 or 3 night minimum.
Also, take a look at this - I found some useful info here last year. http://www.sailnet.com/forums/us-nor...ay-cruise.html
I've only been in this area a few years but please ask if you have any specific questions.