Where is your home port? I'm in Mt. Sinai.
I have been to Captains Cove a few times. You won't have any problems getting in or out, it's very simple. How are you at docking? If the place is crowded (not likely considering the time of year and weather forecast) you may have to fit into a smallish place. Last year I had to fit my 35' boat into what looked like a 36' space - and right behind giant power boat that burned more fuel in an hour than my boat costs! The dockhands were helpful and it wasn't too bad.
Regarding your sail question, you will be best off with a reefed main and a reefed headsail to match. If the wind is 15 kts or less you will want the entire headsail. If the wind gets to 20 kts, you'll want the headsail rolled up to a 100. If the wind goes to 25, then take down one of the sails, which ever is easier to lower (probably the headsail).
BTW, here is the latest marine forecast:
NW WINDS 15 TO 20 KT WITH GUSTS UP TO 25 KT EARLY IN THE
MORNING...BECOMING SW WITH OCCASIONAL NEARSHORE GUSTS UP TO 25 KT
IN THE AFTERNOON. SEAS 2 TO 3 FT.
SW WINDS 10 TO 15 KT. SEAS 2 TO 4 FT. A CHANCE OF
SHOWERS IN THE EVENING.
Unfortunately, that's not the best forecast for heading north in the morning and south in the afternoon. The apparent wind will be on the nose both ways.
Lastly, if you still want to make this trip note the tides. The westerly wind against the incoming tide will make a nasty short chop. High tide is around 10:30AM. So as the tide goes OUT, the waves will be down. As the tide comes IN (starting around 4:30) the seas will get worse.
Anyway, good luck with your boat and your trips.
Deep Blue C, 2002 C&C 110
Mt. Sinai, NY
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