Out of curiosity I just created a quick planning route from Rockport to the CC Canal to see how far you are. Was surprised to find out you're at least 160nm from there, and that's if you stick to the rhumb line (which of course, sailboats don't typically do). With all that great coastline to explore it's a push to get to the RI and Southern MA coast on a two week vacation. With a schedule like that (especially considering the prevailing winds) you'd need to be pretty lucky with the weather fronts to avoid extensive motoring.

This September's trip for us from Western CT to P-town and back was "charmed" with respect to the winds. It's a bit under 180nm each way by the rhumb lines. We departed on a Saturday (after Earl came past on Friday), in 35-knot westerlies. The trip East in LIS was a quick one under double reefed Genoa (alone) trying to slow the boat due to the large waves (we were hitting 15+ when surfing and around10/11 going uphill from the troughs). The westerlies continued for a few days to get us into Marion, MA, (I don't think I've ever seen more sailboats in one place) then turned to SW as we coasted NE in a downwind run through the CCC and Provincetown.

For the return trip through Buzzards Bay we were lucky we didn't have the dreaded day of motoring I expected in the prevailing SW winds (and the accompanying chop that can develop there if the tide is ebbing). Instead, our trip back treated us to NW winds 15-20 to Onset, then again next day NW 15-20 let us average about 9-11 knots from Onset Harbor to Block Island in one close reach. The wind dropped to under 3 knots the last few miles north of BI and we motored in. We stayed in BI a few days to meet up with friends on other boats, and then had SW winds to let us sail a reach to Stonington, CT. There we holed up a few days to enjoy the Stonington/Mystic area (ashore, with assistance from local taxis) while a well-predicted front assailed the local waters with strong westerlies that would have been headwinds if we pushed homeward. Then the winds veered NW and then S and we were able to sail a reach back to western LIS until the last few miles of motoring. We got in some excellent sailing. Wish it could always be that way.

As the saying goes; "it's better to be lucky than good" -- but when you're on a schedule you need to be lucky if you want to sail.