In 2008 I teamed up with one of the Sailing Club’s other skippers to organize my first trip to Martha’s Vineyard and Nantucket. I’d only been to Martha’s Vineyard once before for a weekend, and I’d never visited Nantucket. That meant lots of research was required to make a plan that would suit twenty-four sailors on four boats for a week. Like every sailing experience, the trip provided ample learning opportunity for me and many others.
Our first challenge was accessing the boats. They live on moorings in Benton Cove near Fort Adams National Park. The plan was to checkout the boats, and then move them to a marina to load luggage and provisions, and then move cars to Fort Adams where they’d stay for the week. Traffic in Newport and inconvenient parking at the marina disrupted this plan.
As a result, loading was an unimaginable mish mash of inspecting and moving the boats and making dinghy runs and car runs with gear. Ultimately, everyone managed to leave their cars in the park and get their bodies and stuff on the boats across the harbor. Lesson learned about logistics when chartering in Newport!
After an 0700 skippers’ meeting, Perfect Summer departed for Cuttyhunk at 0730. Cuttyhunk is notoriously crowded, with a very limited number of moorings in the inner harbor (the “Pond”). Our only chance of getting a couple (to which we could tie two boats each) was to get there in the early afternoon. The rest of the fleet hung around until the marina office opened at 0800 in order to buy ice.
Perfect Summer had a great run under main and jib most of the way from Newport to Cutty. With the wind nearly at her back, the crew rigged a preventer on the main so that everyone who wanted could take a turn at the helm.
Trying to remain optimistic, they approached the Cuttyhunk channel. About sixty feet wide, and eleven feet deep at the center, the channel is a very strange experience for a keelboat sailor. Motoring slowly through, it seemed as if I could reach out and shake hands with people who were standing in waist deep water just a few feet away. To add to the fun, two Lasers were tacking their way up the channel just ahead. Fortunately, no traffic came out while I was negotiating Perfect Summer’s beamy hull through.
“Summer Magic, some are not”– Jack Buckley
A tour of the incredibly crowded pond confirmed our worst fears: there was not a free mooring to be had, and many already hosted two-boat rafts. Back out the channel we went, once again passing the frolicking beach-goers a few feet to port. Sharp eyes spotted a couple of open moorings in the outer field and we made a bee-line right for one of them. The moment we were secure, I changed into a swimsuit and jumped into the dinghy, driving it over to the adjacent empty mooring. This was a sneaky trick that might be challenged, but it was the only way to guarantee at least two moorings for our four-boat fleet. I tied the dinghy to the mooring, took a deep breath, and rolled over the side into the cool water, raising the bar on trip leader sacrifice to a new high (remember, Perfect Summer had also sailed without a supply of ice).
Over (tepid) cocktails the crew watched anxiously as other boats approached the mooring field, but fortunately none questioned the one guarded by the dinghy. Within the hour Imagine reached the anchorage and took up the other mooring, moving Perfect Summer’s dinghy to her stern (but not returning it. Soon after Hey Jude came along side Perfect Summer and Summer Magic joined Imagine.
Expeditions were sent in through the channel to the town dock where live lobsters, oysters on the half shell, and other local delicacies were obtained. The challenge of how to cook the big crustaceans was met in various ways: Hey Jude boiled them in pairs in their largest pot, Perfect Summer split and grilled some and boiled some to expedite the process. Summer Magic’s crew got the ingenuity prize: they sent a crew back ashore to borrow a big steaming pot from the lady on the dock who sold the lobsters.
In the morning, dense fog and a grim weather forecast, forced us to scrap the plan to go to Hyannis, 45 miles east. Instead we’d go to Vineyard Haven on Martha’s Vineyard. Radar was fired up and three boats set out for Quick’s Hole, a passage between two of the Elizabethan Islands from Buzzard’s Bay, where we were, to Vineyard Sound.
I was concerned about contrary current and breeze and the heavy fog, instead opted to circle around the western end of Cuttyhunk, thus giving the crew their first taste of motoring through heavy swells. Upon turning the corner to head east, however, conditions were fair for another downwind run, albeit through pea soup fog.
The sounds of motors, buoys, bells, and horns came from all directions in the haze. Radar on each boat warned of hard obstacles all around. Still, the sight of a large fishing boat or ferry looming out of the fog was alarming. Aboard Hey Jude the rumble of an engine was their only warning before one of the one hundred largest yachts in the world (someone looked it up later) came charging through the mist. To Hey Jude’s startled crew My Shanti looked like an ocean liner.
Miraculously, as the fleet approached Vineyard Haven the fog cleared and the breeze increased. Imagine, Summer Magic, and Hey Jude immediately trimmed the sails and got underway amid a crowd of other sailors enjoying the sunny afternoon. Aboard Perfect Summer, however, something was wrong: Just as the lunch crew was passing out papaya halves for dessert, I felt the steering tighten up.
No, it wasn’t the wheel brake tightened by accident, nor the auto helm engaged in error. I turned it side to side, growing more and more alarmed as it became harder and harder to move, until it froze completely.
“Traveling roughly – Truffeling”– Crew of Hey Jude
“Want a papaya Mia,” some poor, unwitting crew asked.
“No! Not now!”
While first mate Jack aimed a flashlight into lazarettes and aft cabins looking for access to the steering mechanism, I continued trying to turn the wheel while declining additional offers of papaya from other crew. I can always tell the sailors from the passengers in these situations–the sailors pay attention to problems on board. The passengers offer papaya.
Perfect Summer was a brand new boat, and Jack could find no easy access to the quadrant beneath either helm – which meant he could not check to see if something was binding the steering, but also meant that it was unlikely some stray gear had fallen into the area.
With continued coaxing the wheel loosened a little, and a little more until it was possible to turn into the wind and douse the sails. Apologizing to the crew for the missed sailing opportunity, I engaged the motor and pointed the boat toward Vineyard Haven.
That morning, along with Summer Magic, we’d reserved a slip at the Black Dog Marina. Hey Jude and Imagine had opted for moorings in the harbor. Now I hoped that it would be an easy approach without sharp turns. The team at the Black Dog was not terribly instructive on the radio, and the marina did not feature a large sign, so while I tensely steered the crew looked up its location in relation to the ferry dock. Right next door, it turned out. And it also turned out that the instruction to “come along the north side of the dock” meant be ready to back into one of the slips there.
As the crew hurried to deploy lines and fenders on both sides, I used engine and bow thrusters to turn Perfect Summer’s stern toward the dock where a hand stood waiting. The steering cooperated.
“Watch out for your dinghy there,” he called out, reminding me that I’d meant to appoint a dinghy captain for the maneuver, but nobody was available when I thought of it, and then other exigencies took priority. Even as the dockhand spoke, Perfect Summer’s stern was swinging past the dinghy, putting the painter under the counter and dangerously near the propeller. The dinghy was cleated on the port side, but now located on starboard. I shifted into neutral.
“Jit! Get in the dinghy,” I ordered the novice crew standing on deck just above where the small boat now sat. “Right now. Get in the dinghy right now. Helen,” I turned to another crew, who was in the cockpit. “Uncleat the dinghy. Right now.”
Bewildered, but game, Jit dropping the dock line he was holding and climbed over the lifelines and down into the dinghy. Meanwhile Helen made quick work of uncleating the painter.
“Now let it go, completely,” I added to Helen, meanwhile risking a small shot of forward gear to keep away from the docked boats. “Jit, pull in that line.” He lay belly down on the bow of the dinghy to fish the line out of the water and pull it in.
With the little boat safe I focused on the big one and the hard surfaces all around it. My last instruction to Jit as the dinghy was carried forward along Perfect Summer‘s hull, “You need to lower the engine …” Then I had to turn my attention to the docked trawler growing closer on my starboard beam.
Needing some way for steerage, I put the boat in gear pointing back out of the harbor. Within seconds the crew on the bow was shouting:
“The dinghy! The dinghy!”
Jit had drifted quickly and Perfect Summer was motoring right at him. He was madly waving an oar, terror in his eyes.
“It’s a dinghy, it bounces!” I shouted back, nonetheless backing off on the throttle and easing into reverse. Out of the corner of my eye I saw a small local boat heading out from the dock and hoped it was a local going to Jit’s rescue. Apparently, being a novice, he did not know how to lower and start the dinghy engine.
On the second attempt, sans dinghy, Perfect Summer eased into the slip, crack crew deploying bow and spring lines to the pilings as they passed. By the time she was secure, the local boatman returned with Jit and the dinghy in tow. I thanked him sincerely as he handed me the painter, but his expression was somewhere between annoyance and disdain for bareboat charterers. Meanwhile, the young man on the dock said to Jit: “Don’t know how to drive a dinghy, huh?”
And welcome to Martha’s Vineyard!
To top it all off, during the entire episode, Perfect Summer’s helm had handled perfectly.
“Vinyl Haven, are you there?”– Cecilia Sweeney
Imagine had similar experience with the non-communicative locals, but perhaps for good reason. First mate Cecilia called again and again, “Vinyl Haven Marina, Vinyl Haven Marina,” and oddly got no answer. “Geez, I wonder how far these radios really go.”
Stocked with fresh provisions and well-earned Black Dog shirts and hats, we set out the next morning for Nantucket, about twenty-eight miles away. The southwesterly breeze continued, and the seas in Vineyard and Nantucket Sounds were calm, making for another good run east. At the turning point to head south toward Nantucket’s channel, we thought to heave-to for lunch before resorting to motor. But no sooner did we backwind Perfect Summer‘s the jib and achieve that peculiar holding pattern than Jack noticed the dark color of the sky to the south. Time to run for cover!
One by one the fleet motored into a driving squall with rain stinging faces and eyes peeled for the next ferry in the narrow channel. Conditions improved inside Nantucket Harbor, where rows of gigantic motor yachts – including My Shanti –cut the wind. Nantucket Boat Basin dock staff welcomed each boat via VHF and provided detailed directions to its slip. In no time all four boats were secure. And moments after that a dock hand had relocated the boarding ladder on the fixed dock to better align with each boat’s gate. Amazing!
“I brought a beer”– Mia, displaying a five-liter Heineken mini keg
My first Nantucket activity was to look for On the Waterfront, a geocache hidden right in the marina. As I was poking around on a seawall, my first mate Jack came along and, thinking something must be amis, asked what was going on. I gave him my short Geocaching explanation and the description of the cache and he joined in, all the while exclaiming at how silly it was. Even after he found it!
That afternoon I gathered my crew for a dinghy lesson. One by one, I had them lower and raise the engine, prime the fuel tank, and start the motor. Each one took a turn driving the little boat around in the marina.
Everyone crowded into Perfect Summer’s cockpit for that evening’s appetizer party. We even invited the people from neighboring boats, although they seemed just a bit intimidated by our raucous crowd. Beer flowed from the Heineken mini keg, and then Steve arrived with his blender pitcher full of piña coladas. Food and drink disappeared and laughter was the loudest sound around. Many enjoyed a late evening stroll on the “private” dock, visiting the row of monster yachts all flying Cayman Islands flags.
For our layover day on Nantucket, Vic had organized bicycle rentals. To our delight, the morning dawned gloriously sunny and dry. We broke into groups to visit the island’s attractions, starting with the whaling museum and moving on to other historic sites. I convinced Steve and Henry to join me riding across the island to Sconset to look for the Sconset Walk geocache. The ride back felt longer, with Henry and I slowing down some by the time we got back to return the bikes.
Everyone reconvened in the evening at Nantucket Lobster Trap for dinner. The menu included individual clam bakes – each pot overflowing with perfectly steamed mussels, clams, sausage, corn, potatoes, and a lobster. Needless to say, nobody went home hungry.
“Don’t hesitate – Macerate!”—Larry Sherwood
The next morning the fleet set out for Edgartown on Martha’s Vineyard. The southerly breeze continued, so we ran north out of the channel then turned west for a pleasant reach. Coming up on Hey Jude’s stern, I raised Perfect Summer’s pirate colors and dodged to windward to cut the other vessel’s breeze. Skipper Larry warned me off with a threat to macerate (all holding tanks were equipped with macerators that could be used to empty them when outside the three-mile limit).
The sky was hazy and the oppressive humidity threatened some serious weather as the day wore on.
As Perfect Summer approached Edgartown I telephoned the harbor master about moorings. There were none available. Edgartown’s dockside accommodations are sparse, and couldn’t handle boats of our size and depth. The only option was to anchor outside of the harbor, in a very exposed location. I telephoned the marina in Oak Bluffs, a few miles north. Yes, they had a few open moorings and plenty to raft up. The true meaning of this seemingly encouraging news was only to become clear an hour later. All four boats found themselves weaving through Oak Bluff’s frighteningly tight, completely crowded mooring field like four Winnebagos cruising a Walmart parking lot during the holidays.
Summer Magic worked her way deep into the harbor and found a free mooring and another beside it. I joined her with Perfect Summer, noting with some trepidation the close proximity of the small sailboat off our stern. Shortly a harbor worker pulled up in a dinghy and explained that these moorings were for twenty-five footers. The folks on neighboring boats looked relieved when we dropped them and moved away.
Conversations with the harbor crew via VHF clarified the situation: they would allow up to four boats on a mooring and it was up to us to find someone – a stranger – to tie off to.
With the day coming to an end and no place to anchor, making a new best friend was imperative. Then the harbormaster came through, guiding Summer Magic and Imagine to a mooring that already held a brand new Beneteau 48. The owner of the Beneteau asked Summer Magic’s crew if they’ve ever done this before.
“No,” replied one of Summer Magic’s crew honestly, thinking the question to be personal. Skipper Steve talked fast and demonstrated his extensive rafting experience to alleviate the Beneteau skipper’s sudden case of anxiety.
Meanwhile Hey Jude made friends with a Connie and Henry on Decoy, a big Grand Banks with a well-cared-for, lived in look. Perfect Summer came up on her opposite side, creating a powerboat sandwich.
Finally secure, and having made the acquaintance of unexpected neighbors, some crews went ashore to explore Oak Bluffs. I continued my dinghy driving course. At sunset Vic once again serenaded the mooring field on his bagpipes, an act that had drawn a crowd on Nantucket and in Cuttyhunk as well.
The forecast for Thursday was ugly: A low pressure front was moving in, bringing high winds and rain. Our plan was to head for Padanaram in Buzzard’s Bay, but we considered making the run all the way to Newport – if it was going to be raining tonight, we might as well be in an interesting town. Plus, the boats had to be back there by early afternoon on Friday anyway. We deferred the decision until we reached Buzzard’s Bay, which required an early departure Thursday morning to run through Wood’s Hole with the current near slack.
At peak current, Wood’s Hole can be a maelstrom with five knots of current moving through a very narrow, twisted passage between mainland Cape Cod and Nonamesset Island. At 0845 the first of the fleet entered Wood’s Hole and found only a slight current. Timing is everything.
Once all four boats were through the passage and inside Buzzard’s Bay, the skippers confered via VHF radio and agreed to make for Newport. The sky was blue with just a hint of haze, and the predicted bad weather wasn’t due until close to noon. We could be most of the way home before it reached us.
Fortunately, the southwesterly we’d had all week continued, and it was steady around twenty knots. The fleet made a close reach west with reefed sails. The next couple hours were a delight as the crews took turns on the helms and watched the Elizabethian Islands slip past to port. Eventually Cuttyhunk, our first night’s stop, was abeam and then we were outside of Buzzard’s Bay with the open Atlantic abeam to the south.
The seas picked up immediately, an endless succession of rollers slightly abaft of the beam. To take them on our port bow we had to turn off course to the south. It became a game of turning into the bigger swells, then correcting back to course until the next big one rolled through. Aboard Hey Jude Vic Oburg got an unpleasant surprise when, during a particularly rough moment, the door to his cabin fell off its hinges and landed on him.
By 1100 the skies ahead and to the south were decidedly ugly. At the back of the fleet, Summer Magic reported dodging one squall that passed to the southeast. This was encouraging, but unfortunately an anomaly. Presently the full force of the low pressure system’s front line became apparent. The sea was foaming with whitecaps and the swells were growing higher and closer. Jibs were furled, engines were started, and life jackets were donned.
“I’m not suggesting that you put your lifejackets on, but it might be a good idea to get them out of the locker”—Jeff Hamer, as he dons his inflatable
And suddenly we were into it: driving rain gave the churning sea the appearance of grey velvet. The numbers on the anemometer went up and up and up, finally stopping at 39.5 apparent during the front’s initial blast. For a half hour or more each boat seemed to run in place – engines revving, speedometers and GPSs registering forward motion, but chart plotters showing hardly any progress over the bottom. Eventually the winds lessened from high twenties to mid and the tangle of wind churned chop calmed down a little. The boats were able to make progress. For a while the western sky lightened, a beacon promising an end to the storm for those who persisted. But it was a false promise, for the weather line was moving up from the south, and we were pelted with repeated waves of driving wind and rain. As the miles and hours wore on even that scrap of brightness was consumed by the grey.
The biggest, most dangerous swells came in sets of four close together, the first often breaking. I stayed on the helm, taking them on the port bow, driving up and over the first and then plowing through the second and third, with the fourth usually rolling under Perfect Summer‘s stern. After each set there would be a few minutes respite during which it was possible to turn northwest and make up for the course deviation. All of the time I steered–several hours–first mate Jack stood by the companionway looking aft.
All of our fleet, even the smallest boat at 42 feet, was capable of handling this weather – in fact, on the largest boat it was rather fun. But every crew did have one serious concern: our dinghies. This is what Jack was watching.
We hadn’t anticipated the severity of the weather based on the forecast, so none of us had removed the motors from the inflatables. Had we made the decision to go to Newport when we were back on the moorings in Oak Bluffs, we might have considered the distance – our longest leg of the trip – and thought to do it for that reason alone. But those of us with experience know how heavy a four-stroke outboard is and we don’t relish the task, so we had allowed ourselves to avoid it.
And now the sea was going to issue the ultimate reprimand.
Each breaking swell posed a threat to the small, buoyant crafts off our sterns. It wasn’t always possible to steer the bigger boat to position the smaller properly in the swells. Perhaps we were lucky that only one of the four little craft was flipped over by the seas. Quite suddenly Imagine was towing a sea anchor – the very unstreamlined, upside down inflatable with the very heavy outboard dragging down the stern.
She slowed to a crawl with the seas and wind still battering her. The crew tried to bring the overturned boat in close, and even tried to right her. Nearby, Summer Magic reduced her speed to sail in company with Imagine. Unaware of the loss behind them, Hey Jude and Perfect Summer were making as much speed as possible and already far ahead.
The two sailboats motored through the weather together for what seemed like ages, but was about two hours. And then a blessing in disguise: the dinghy painter parted. The dinghy immediately drifted away to leeward and vanished from sight in the grey seas.
Relieved of the tremendous drag, Imagine was able to accelerate and despite the terrible loss the crew felt a sense of relief.
Nearly twenty miles after passing out of Buzzard’s Bay, one by one the fleet turned stern to the marching swells and ran north into Naraganset Bay and Newport. I handed the helm of Perfect Summer over to Jack and allowed my shoulders to relax. As the biggest boat, we’d spent three hours in the weather, while Imagine and Summer Magic spent five. Their waiting moorings in sheltered Brenton Cove were a very welcome sight.
The rain never stopped that afternoon and evening, and very few of the twenty-four sailors hailed a launch to go ashore. Instead each crew enjoyed a traditional must-go party and everyone was able to begin packing for Friday’s departure. Sometime that evening said to me, “You were incredible through that storm. I will sail with you any time.”
As if to add insult to injury, Friday dawned a gloriously sunny, calm day. We could have been departing Padanaram and motoring to Newport in the sunshine. But as the morning’s chores went on we were glad we’d covered the miles yesterday. By noon most had finished packing, dealt with the last of the leftovers, took the boats to the fuel dock, offloaded the luggage in a succession of dinghy runs (or one crowded launch run), and had our final checkouts with the charter company. Some chose to extend their stay in the Newport area, but most headed home with fond memories of a great trip, even with its ‘ups and downs’.
A version of this account appears on The Sailing Club’s website.