Cruising Cape Cod and Martha’s Vineyard

Cape Cod. Just saying the words evoke wonderful summery images: sand dunes, seasonal jobs, soft air, and the glassy still anchorages of my gloriously misspent youth. My parents brought us as kids—I was the adorably demonic child that scared the crap out of them by literally sailing off over the horizon in the Sunfish. And my awkward adolescence was made even awkwarder by the proximity of bikini-clad girls on the Cape’s outer beaches. And ah, yes…..the summers away from college. I’ve faint memories of waiting tables, fake ID’s, awkward eagerness around more bikini clad girls, and exalting in the loving lap of summer on The Cape—at least until it was time to go back to school. Right after college, I even spent a summer living like a savage aboard a palatial, 60’s vintage, 24-foot Bahama Islander with 4-foot headroom, and a 4-foot draft fixed keel that I ran aground on every damn sand bar the Cape had to offer. But that was, um, some time ago.

So, even into my adult life, this Cape-centric view of summer meant that the numerous other cool summer hotspots in my native northeast—coastal Maine, “The Islands” of the Cape and the Islands, and even such far off exotic destinations like…Narragansett Bay—went virtually uncruised, until friends and soon-to-be charter companions, Nick and Tery, made a remarkable suggestion. We were kicking around some remote, have-to-fly-to-get-there summer charter destinations when they simply said: “Why don’t we just cruise around the Cape and Islands?”

Duhh. We all live in the Boston area. My wife was newly pregnant and we all agreed that we needed to go sailing to “chill out”. So, chartering a boat—literally in our back yard—and cruising to places in the Preppie Promised Land like Martha’s Vineyard and Nantucket (that yours truly, Mr. Experienced Cruiser/Cape Cod Lover/sorta-psuedo-preppie, had never actually cruised to), sounded a lot more relaxing than trying to get four extremely busy people to Greece so we could Med-moor and “chill out” with every other Euro on “holiday.” I’m glad someone was thinking. Let the chillin’ begin!

And chill we did as soon as our the owner of the nearly brand-new Jeanneau Sun Odyssey 42 we’d chartered from Swift Yachts, concluded his lengthily pre-departure orientation. Like all charter companies operating in cruising grounds that have high seasons spanning weeks rather than months, the good folks at Swift Yachts don’t own the boats they charter. But they did deftly facilitate our charter with the person who did. He checked to make sure we checked out. We did, eventually, and were off. But in the spirit of relaxation, we didn’t want to sail too far. Our first day goals were simple, stow our copious provisions, get off the dock where we picked the boat up in Warren, Rhode Island, on the northwestern shores of Narraganset Bay, and be in a pretty anchorage by nightfall. Easy. The cruising guide and our helpful owner suggested picturesque Dutch Harbor on Jamestown Island as our first stop. It was only 10 miles down the Bay.

A pleasant voice over the radio directed us to our mooring for the night, and the same pleasant voice welcomed us to Dutch Harbor in person when she picked us up in the launch to bring us into “town.” The “town” of Jamestown is a pleasant walk up the road from Dutch and has all the things you need—quaint houses, smiling locals, and a few restaurants and ice cream shops—when you go ashore during a summer charter. We returned to the boat with full bellies, relaxed minds, and a plan for the week that had taken shape over dinner. Our first day was a short one, but the next was going be longer. We all wanted to visit Cuttyhunk, and Martha’s Vineyard, on our week-long chill out charter, but, over dinner, we also agreed that we really wanted to sail too. So, the adventure of trying to get all the way out to Nantucket (well over 75 miles away) and back, was a possibility too. The weather forecast looked good, and if we were lucky, we’d have just enough time to pull it off, but only if we covered some significant ground almost every day. So, we planned on making a bee-line for Cuttyhunk in the morning.

The broth-like fog.

As is often the case when you get back to cruising after its been a while, we all breathed a bit easier as we putt-putted out of the marina and into the sailing playground that Narragansett Bay becomes on a sunny Saturday afternoon in Mid-July. We exhaled even deeper when we set the sails, shut the engine down, and were left with only the sounds of our gurgling wake. Just perfect. The southerly sea breeze was strong enough to move us along, but not so stiff as to require any great effort to trim sails and slice our way to windward. Since it was a steamy afternoon, and we didn’t have too far to go, a quick swim off Prudence Island was in order. Any remaining land-based cares melted away as we bobbed off the stern. Then it was on to dinner and the sunset off the western side of Jamestown.

When we awoke, the boat was enveloped in a summer haze the constancy of weak broth. The haze provided an eerie backdrop, but wasn’t too tough to navigate through until if finally, several hours after we departed Dutch, the muggy broth burned off, and Cuttyhunk came into view. Each of us had quickly settled into the peaceful rhythm of  motorsailing over the flat seas—easy autopilot passages are way conducive to chilling out—but we were excited about or upcoming landfall as well. Nick had been to Cuttyhunk Harbor many times before, but the narrow entrance, and the boats that get packed in like sardines, and even the crazy airstrip next to the harbor channel where we actually saw a small prop plane land as we were getting our mooring sorted out was new to the rest of us. Our 0630 start in Narragansett Bay allowed us to cover the roughly 35 miles get to notoriously crowded Cutty early enough to find an available mooring. We grabbed it, then grabbed a late lunch in the cockpit, and then loaded up our backpacks for a run into shore. We newbies were eager to experience the Cuttyhunk coolness that Nick raved about when we planed our itinerary, and it didn’t disappoint.

Cuttyhunk is classic Cape and the Islands cool.

I don’t know if it’s part of every cruisers DNA, (like the compulsion to wear crocs or carry a rigging knife tied to a belt loop with a “lanyard”), but we were compelled to climb to the highest point of the island almost as soon as we set foot on dry land. Why is that? We all agreed that this was going to be our “chill out” cruise, yet there we were, driven, seemingly by some strange Yankee instinct to work up a sweat humping uphill in the heat of the day to take in “the view.” I hope some of you out there can relate to this curious compulsion. But, as it always seems to be in hindsight, it was worth it. Not only did we get a feel for this charming little island we’d spent several hours sailing through broth-like haze to get to, we also swapped sweaty stories under sunny skies with other like-minded “cruiser/climbers” we encountered who were obviously on similar expeditions. It was fun and made swimming off the beach over on the western side of the island even more refreshing. And then it was “time for tea.”

No, you’ve not happened upon an episode of Downton Abbey. Tea time is one of the many decadences that cruising makes possible for us busy people, and for us at least, it doesn’t get more “chill” than watching the sun start to set and the world go by in the late afternoon with tea or coffee and a chocolate treat under the bimini in the cockpit. Tea time flows effortlessly into cocktail hour. Dinner flows seamlessly out of that, and then we were gazing up at the twinkling stars, and talking about tomorrow’s destination—The Preppie Promised Land—Martha’s Vineyard.

Does this man look like a pseudo-preppie to you?

We knew we could swing the early morning departure, and we liked the mooring availability it afforded us in Cutty (the anchorage in Cutty fills up by the early afternoon  pretty regularly during the height of the summer), so we agreed that a getting an early start, and covering the miles to busy Edgartown Harbor would get us there in time for tea. And unlike the previous morning, we were treated to a classic, blue sky, warm water whitecap reach in 15 knots of breeze down Vineyard Sound. The Chamber of Commerce couldn’t have drawn up any better and we experienced why the cruising in this part of the world is so good—when the weather cooperates. The boat was sizzling along. The crew was happy. And the untamed beauty of the Vineyard and Elizabethan islands we barreled past was simply a sight to behold. We didn’t even need to harden up to much as we rounded the southern tip of the Vineyard and close reached past the touristy, ferry port towns of Vineyard Haven and Oak Bluffs on our way to preppie paradise in Edgartown.

We were basking in the glow of those perfect days that remind us why sailing is so cool, when another pleasant voice on the radio was directing us to a yellow mooring in Edgartown Harbor. And the college kid in charge of the mooring field called me “Cap’n.” I’m embarrassed to admit, but, I still like it when they call me “Cap’n,” and moreover, we’d arrived! There were friends in town we wanted to visit. And bikes we wanted to rent and ride. And ice cream cones we wanted to eat before they melted. And more than anything else, we were ready to roam among the preppies in their native habitat. Thankfully there was no real hill, apart from the social register, to climb. And we’d finished climbing.

The two days we’d allocated to visiting this vacation spot for presidents and media moguls alike, simply flew. We rode bikes all over town, and shopped, and ate at over priced, um, I mean, nice waterfront restaurants, and literally assimilated into the summer preppie scene. The land based friends and their cute kids said “Can’t you stay another day?” And Caroline and Tery admitted more time to do some shopping wouldn’t be all bad, but we still hoped to knock Nantucket off the list too. And that just wasn’t going to be possible if we dallied in Edgartown any longer.

The weather, however, didn’t really care about our “plans,” and the forecast—steady 30-40 knot winds with higher gusts—for the day we’d “planned” to make the jump over to Nantucket really made the decision for us. Sure we could have sailed in those conditions, and we did get up in the morning and take the launch out to the boat with the hope that things would be calmer than forecasted, but they just weren’t. The wind howled through the mooring field and the launch was elbow-to-elbow with folks like us who decided it just wasn’t worth it. Oh the horror! “Trapped” in Edgartown in July. It was like some crazy kind of reverse snow day. We indulged in a lazy lunch and “chilled out” in the shade on our land-based friend’s shore side deck like we were getting away with something. Brilliant.

But then we slowly started counting the bread crumbs and coming to terms with the fact that after three of our six available nights were spent in Edgartown, it was time to start heading back. Obviously it wasn’t as far as it would have been if we’d pushed on to Nantucket, but we still had to sail a good chunk of miles cover in order return the boat back to that marina in far off Warren, Rhode Island, on time.

No Biggie. We just planned on one big push to get from Edgartown back to where we started, essentially, Dutch Harbor in southern Narragansett Bay. We’d spend the night there before the final, 10-mile push to return the boat by the requisite 1000 check-in time. Yep, you guessed it. Early morning departure. Easy autopilot cruising. Lunch in the cockpit while the same islands we marveled at several days before, passed by on the other side of the boat. We punched through Quicks Hole (the narrow passage between the islands of Naushon and Pasque) in the early afternoon, pulled into Cuttyhunk for a quick top up of fuel (even if we’d had time to stay there were no available moorings), and then chased the setting sun back to Jamestown.

When we finally pulled up the same Dutch Harbor mooring we’d used on our outbound track, there was no need to go into town. It’d been a long day. We were tired and refreshed, and the sun was setting, spectacularly. Tea time was spent at sea, but we sure made it in time for cocktail hour. It was then, as we basked in the crazy golden light of our last sunset onboard, that we finally chilled out.

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