Originally Posted by Minnewaska
You must arrive by 2 or 3 in many anchorages around here to either get the choice spots or any available mooring. Although, we have many places to bail to, if it doesn't work out well. Then again, some of our anchorages are inconceivable they will actually fill.
IMO, if one really wants to SAIL
in a cruising ground as popular as southern New England, keep the size of the boat modest, and her draft minimal... There's good reason why keel/centerboarders have long been a great choice for such an area, they often allow you to anchor on the periphery of an otherwise 'filled' anchorage, such as a place like Cuttyhunk so often is...
This is the big conundrum of summer cruising in such an area, if you want to score a mooring in so many places, you need to arrive early... That time is often before the afternoon sea breeze kicks in, so those who might actually prefer to SAIL to their destination are generally gonna 'lose out' to those who will depart early in the day, and motor all the way there...
Sometimes, the best thing you can do is put away the cruising guide, and simply pull out a chart
... You might be surprised what you might find, a perfectly suitable spot that has yet to be 'Active Captain Certified'... (grin)
Nantucket's Head of the Harbor is one of my favorites... It's tricky getting up there, not every boat can make it... But if you do, it's like having Great Salt Pond all to yourself, I've yet to ever see another cruising boat when I've been up there...