Clare in cockpit

For going on ten years now Clare has each summer broached the idea of cruising down south of Cape Cod to Martha’s Vineyard and Nantucket, as she has never been to those places and so has felt culturally deprived. But she normally can only get a week off work at a time, and I have consistently urged that this makes for a tight schedule when sailing from Portsmouth, or worse from Portland, where Lunacy is normally moored. This year, however, we decided at last to give it a try, emboldened by the fact that we’d been offered a mooring in Wood’s Hole, where we could leave the boat for a while if necessary.

With the help of our prospective boat-buyers, Nico and Amy, I sailed Lunacy down to Portsmouth from Portland the Friday before last, thus deleting 40 miles off the distance Clare and I would have to sail to reach the anointed cruising ground. We set off late the following morning from Pepperell Cove in Kittery, just across the river from Portsmouth, bound for Provincetown, first motorsailing then beating under sail against a contrary southerly breeze that eventually topped up to just over 20 knots.

Fortunately, it didn’t do this for very long. By the time we were down in Massachusetts Bay east of Boston the breeze became more moderate, though it remained perfectly contrary, and we were at least more comfortable as we tediously zig-zagged our way through the night beneath a clear moonlit sky. After a 21-hour run we arrived at last at P-town the following morning and enjoyed a lazy breakfast aboard before we sauntered ashore to poke around.


At rest in Provincetown Harbor with the Pilgrim’s Monument in view

Here’s the thing about P-town: I love the place dearly, the very idea of it geographically, the pearl in the knurled fist of the Outer Cape, but every time I go I am disappointed. Is it just me, or has Commercial Street become so honky-tonk as to be a parody of itself? Is it some immutable economic law that every special place in the world must eventually become a theme-park shopping mall???

I have fond memories of time spent in P-town back in the late 1970s, back when I was a dissolute college student, and this of course pollutes my perception of the place. No doubt those who make the scene there now will likewise be repelled by whatever it has become 30 years on, or at least will be bemoaning a precipitous drop in real-estate values, as much of it may well be underwater by then.

Night crawl

The monument hides in the mist as denizens of Commercial Street do some night-crawling


The trendy restaurant well off Commercial Street where we had dinner after some careful research and recon work by Clare

No matter. P-town always looks good from the water, especially when you are sailing away from it bound for the Cape Cod Canal. This next phase of our odyssey was probably our best day’s sailing of the whole week: a strong northwesterly to sweep us across Cape Cod Bay in the mid-morning, just in time to catch favorable current that flushed us through the canal at speeds up to 11 knots, and so out into Buzzard’s Bay for a fine reach down to Wood’s Hole.

Hadley map

After the canal Wood’s Hole was the second tide gate we had to negotiate. We dropped anchor in Hadley Harbor, a most excellent spot just west of the hole, and waited a couple of hours for the current to ease before passing through the Strait

Little Harbor

Then it was on to Little Harbor, east of the big ferry landing, where we picked up my cousin-in-law’s mooring off the Coast Guard station just as the sun was going down

We had dinner shore again at Wood’s Hole–in an unremarkable yet very expensive restaurant unfortunately–and after a good night’s sleep headed east across Vineyard Sound not long after the sun came up.

About that mooring: it seemed pretty sketchy to me, and I had to wonder if it would be wise to leave the boat unattended there for very long. I was studying the long-range weather forecasts too and saw there should be a strong southwesterly wind at the end of the week. So Plan B began to evolve. Instead of coming back to Wood’s Hole after visiting the Vineyard and Nantucket and taking a bus home, perhaps we should instead just carry on all the way around the Cape.

Later I realized I had in fact circumnavigated the Cape before, with passages down to the West Indies and back thrown in, but I had never done a discrete circuit, so this scheme seemed inherently attractive.

Cape Cod satellite

The target defined. Ever since they dug the Canal in 1914 the Cape has technically been an island and thus circumnavigable

We arrived at Edgartown around noon, were lucky enough to pick up a first-come transient mooring, and soon went ashore for lunch. Again the scene in town was a bit much for us, so we developed a counter-scene scheme: a five-mile hike all the way across Chappaquiddick Island and back, a pilgrimage to the tiny bridge where Ted Kennedy made the big mess that cost Mary Jo Kopechne her life in 1969.

Dike bridge

As Ted would say: we’ll drive off it when we get to it. And yes, of course they have huge guard-rails on the bridge now, so you can’t do that anymore

Kennedy map

If you visit the scene of the crime, you realize just how badly Kennedy behaved. No way can you turn right off the main road on to the dirt road leading out to the dike bridge and the beach and think you are heading for the ferry landing, as Kennedy claimed, even if you’re drunk out of your mind, which he insisted he wasn’t. Then he wandered around for hours, even swam across the channel to Edgartown so he could crash in his hotel, before he reported the accident

Beach road

Road to the beach beyond the bridge. And a very fine beach it is!

Evening aboard

Back on the boat in Edgartown that evening for dinner aboard

The next morning we were off early again for a light-air sail to Nantucket. I had never been here before, ever, which is a bit remarkable if you consider how long I’ve been mucking around New England on boats. Again we were lucky and found a mooring, though we had no reservation, and again we found a fervent summer scene onshore, though it was much more muted and high-rent than on the Vineyard and at Provincetown.

Translation: yes, there are lots of stores here, but they are trendier and way more expensive. It is also not nearly as crowded, which I very much appreciated.

Mooring field

A portion of the expansive mooring field. Lunacy is out there somewhere!

Whale skeleton

Sperm whale skeleton in the whaling museum. This 46-foot specimen washed ashore on Nantucket and died back on New Year’s Day in 1998

Infected tooth

They reckon it died of a tooth infection

Fish sign

It really is a very buttoned-down place

We spent all of Wednesday afternoon and night at Nantucket, and most of Thursday too, and all this time I was mostly focused on what came next. I’d been watching the weather, of course, and the prospect of strong southwesterlies for Thursday night on into Friday had been well confirmed. We now felt committed to Plan B, the circumnavigation, and there was really only one thing I was worried about. Pollock Rip Channel, the thin little exit ramp leading northward across the shoal-choked eastern approaches of Nantucket Sound, was our third and last tide gate. Unfortunately, to avoid major contrary current there we had to pass through it after nightfall.

We departed Nantucket at about 1800 hours on Thursday evening, and the rest, as they say, was history.

Nose injury

Just to keep things interesting, I clubbed myself in the nose with a winch handle while raising the mainsail inside the harbor. Not on purpose, of course. The handle slipped out of the winch while I was grinding on it full tilt


Wing-and-wing set on the run from the Nantucket Harbor entrance up to Monomoy

Pollock Rip chart

The belly of the beast. Ugly seas can make up here in current-against-wind situations, and the shoals are constantly shifting, so no chart can be perfectly accurate. The current also sets across the channel in Butler Hole, where things get tightest less than a mile off the south tip of Monomoy. We saw some contrary chop on our approach, but by the time we were in Butler Hole things were pretty slack


Reaching north up the east coast of the Cape the next morning

Last leg

The last leg in total. We arrived in Portsmouth after an overnight passage from Nantucket of 21 hours and so closed our loop on the Cape

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1 Response
  1. Pete Hogan

    Nice piece. Spent the summer of 1974 on Nantucket and circumnavigated the Cape. Ran badly aground north of Nantucket. They were shooting Jaws in Egartown. Good luck with selling the boat. Hope you will keep up the blog.

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