We'll be down the same time on our Beneteau 40 De Life and will follow the counter clockwise route once or twice, weather willing. We've been out in the past and have had strong winds and swell one week and almost no wind the following week. Sometimes you have to adapt your plan! We keep the cruising guide handy and check the weather before we head out.
The one anchorage that we've found we need to arrive early is Cooper Island. We do love the northernmost mooring right under the house with its webcam. It is somewhat protected there, but you will roll there if anywhere. We planned to stop there in November, but a big squall blew through as we approached and we just kept going to Trellis Bay.
If its blowing, Little Harbor at Peter Island is very calm and a nice swim/snorkel. Trellis Bay is calm as well, but there is not much room to anchor (we end up near the ferry wharf) and we won't swim there. We prefer to anchor at Marina Cay between the mooring field and the reef and use that as our jumping off point to North Sound via The Dogs - George Dog if its rough or Great Dog/The Chimney if its calmer.
Finding space to moor/anchor in North Sound is not a problem. We anchor along Prickly Pear Island and stay on the dock at Leverick Bay.
For Anegada we prefer to anchor off of Setting Point as the mooring field is shallow and any swell would have us pounding our keel. We used to be able to anchor between the mooring field and Setting Point, but its gotten shallow for our 6' 5" draft. In November there were a half dozen monohulls anchored east of the last red channel marker in 12'; many of them tried to anchor closer in and had to back off the sand.
Consider Diamond Cay on the east end of JVD for a wonderful anchorage with many turtles and access to Sandy Cay, Sandy Spit, B-Line, Foxy's Taboo and the Bubbly Pool. Little Harbor is another protected harbor with restaurant options.
Cheers, RickG
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