The Sunday on Labor Day weekend Capt. Avram Ludwig and I sailed the sailboat back from Martha’s Vineyard across open water to Orient Point, Long Island. It was about 75 miles of open sea. Big seas, big, big wind. That was really exciting. I’d left my plane and dog on Martha’s Vineyard, so I needed to get back and pick them up. Originally, Avram and I actually had this plan that we would tow an 11-foot dinghy behind the sailboat and when we got to Orient, we would take the 11-foot dinghy back through the 75 miles of open sea to Martha’s Vineyard. Just really insane (although the weather was supposed to be calmer on Monday). It would not have been possible on Sunday in the huge seas. Even on our 40-foot boat, we were getting tossed around all over the place.

I have this rule of thumb with Avram that I learned from many a misadventure: If at least one other person is willing to do something (like try to sail an 11-foot dinghy 75 miles across open seas) then that usually gives you a little bit of confidence. It’s just human nature — it’s certainly my nature. But I’ve discovered that Avram’s willingness to do something adventurous doesn’t give me any more comfort than my willingness to do it alone. His willingness to endorse a potentially reckless escapade simply doesn’t count; I still need to find a second, non-Avram person willing to do it, just to know that it’s not insane. In this particular case, I didn’t need another person because the night before we were supposed to leave, I was just running the idea by people, saying, “What do you guys think about 70 miles in the open ocean in an 11-foot boat?” and even Avram was like, “Well … the weather is getting worse” — and if Avram thinks that something is not a good idea, then it’s really not a good idea.

Avram and I did that same crossing in our sailboat a couple years ago during Hurricane Katrina with another friend of ours, John Christie, in 18-foot seas, with 40-knot winds and torrential downpours, at night (this time we did it during the day.) That was an example where John Christie was willing to do it, so it wasn’t just me and Avram, so that counts as two people who think the adventure is not suicidal. I arguably don’t know that much about sailing, but John Christie knows a lot, and he’s a parent, so if he says it’s OK to do, it must be OK. That time, all these people were coming to the dock as we were getting ready to leave Memensha at Martha’s Vineyard. I happened to be at the back of the boat, loading it up, and this old guy came up to me goes, “You guys settin’ out?” And I go, “Yeah,” and he goes, “You check the weather?,” and I go, “Yep.” And he goes, “And you’re still goin?,” and I go, “Yep.” And he goes, “Mind if I ask why?,” and I was like, “You gotta talk to one of those two guys; I’m just crewing the boat.” And so he went to talk to John Christie because he’s the one who’d said it was safe to do. And then three more people came up to us during the course of the couple of hours that we were getting things down, including the harbor master. Then the Coast Guard came and gave us a spot inspection to see if they could keep us from going. And a retired Coast Guard officer was like, “Look it’s my friends that will have to come out and rescue you, so don’t go.” But the bottom line was, John Christie said it would be fine, so we went.

The weather this year was dramatic enough that it kept everyone home, but we’d done that same crossing during a hurricane, so compared to that it’s nothing: It’s 20-25 knot winds and six-foot seas compared to 40-knot winds and 18-foot seas.

That said, we finally decided that while crossing in our 40-foot sailboat was no problem, crossing in an 11-foot boat wasn’t a good idea. So, no dinghy trip. Instead, I hired a pilot from Martha’s Vineyard to pick me up at Orient in a two-seat plane. And as we headed back, the whole time as we’re flying low and slow over the ocean, I’m looking down at the water thinking, “We could have done this.” It would have been a great piece for this blog.

Good thing there’s always next year!

More Doug Posts:

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Read — Screening Fair Game for the CIA, and Why Cheney Is like Jaws

Read — Science Fact: On the Moon, You’re Superman

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Read — Doug Liman Blog — Running With Jake Gyllenhaal

Read — I’m Getting Hitched: Making a Commitment to Untitled Moon Project

Read — I’m An Action Hero?!!?! My Hudson River Rescue: Birthday Pie with a Side of Boat Crash

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• Doug Liman Blog: Ladies and Gentlemen, the Captain Has Turned Off His Sense of Caution. Feel Free to Cower in Your Seats.
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