Well I made it in and out of Woods Hole about ten times before I ran into a problem. Went out for a sail on Saturday with my girlfriend and sister. Everything was going great until the wind pooched around 1300. I dropped the hook off Falmouth, had a sandwich and waited for the wind to finish clocking and fill in. I wasn't in a hurry as slack water in WH wasn't until around 1530. I felt the air start to stir around 1430 so I started making my way toward the channel going into WH. Then the wind completely died. I mean force 0 died. I was lined up perfectly for the channel but the current in Vineyard Sound had me and was pulling me SW at about 3 knots. It was no biggie, there was plenty of water around me and I could have just dropped the hook again once clear of the channel. However, my sister had somewhere to be so I got a tow back into great harbor from a nice guy in a Bene. Of course the second I climbed back in the tender to row ashore the wind filled back in at around 10kts. Damn.
Is the lesson here that one needs an engine to sail here? Nah. I think the lesson is to leave one's sister on shore!
I will say that that's the first tow I've ever gotten in 16 years of sailing, several of those professionally with no engine. Somehow I think I'll end up having another one or two before the season's over....