Cruising with Diana, Part II

Newly minted girlfriend/sailor Diana diligently checks, while driving, mainsail trim aboard Student Driver, the author’s J/24. Photo by Mark Barrett

By Mark Barrett
For Points East

No sailing season in New England would be complete without at least one weeklong adventure, and at least one trip to the island of Martha’s Vineyard. We blocked out Wednesday, Aug. 16 to Wednesday, Aug. 23 for this cruise abroad our J/24 Student Driver, which we’d turned into a mini-cruiser.

Hadley Harbor: I was hoping to get to Oak Bluffs, on Martha’s Vineyard – about 15 miles from Kingman Yacht Center, in Cataumet, Mass. – on the first day. However, we had “a couple of things” to do first, like going out to Diana’s favorite place for breakfast, choosing marble for Diana’s new shower threshold, attending to Diana’s daughter’s horse, and picking up provisions. We made it to the boat at 4 p.m.

With the late start, the current through Woods Hole would be wrong, so we headed for Hadley Harbor, nestled among Nonamesset, Uncatena and Naushon islands, near the Woods Hole entrance. The speaker blasted rock and roll, Student Driver reached maximum hull speed, and Diana grinned as she gripped the tiller. After some sweet sailing, we doused the sails and motored into Hadley’s.

As soon as we came around the corner past Bull Island, we saw that all the moorings were taken, and seven or eight boats were anchored in the tight confines. By the time we were securely anchored, it was almost dark, so I began setting up the grill. My mouth watered as I envisioned the juicy steaks we’d soon be eating. Then tragedy struck: I dropped overboard the L-shaped tube that connects the gas bottle to the grill. Not a few curse words were hurled into the night, and we had cold sandwiches for dinner.

The next morning, I woke up at dawn and poked my head out the hatch to see a sailboat motoring out of the mooring field. This prompted me to look at “Eldridge Tide and Pilot Book,” and I realized I’d read the tides for the previous day. The current in Woods Hole was going to turn against us at 7 a.m., and it was already 6:30, so we started the motor, pulled the anchor, and got to the Hole in time for slack tide. The wind in Vineyard Sound was northeast, 10 to 12, which was perfect for the reach to Oak Bluffs. We were able to sail all the way over, about six miles, on a single tack.

Oak Bluffs: The mooring field in Oak Bluffs Harbor is first-come/first-served, and it was crowded when we pulled in about 9 a.m. We couldn’t find a vacant ball, so we rafted up alongside an old, but lovingly restored, C&C 40 named Greyhound. Perry and Beth, from Scituate, Mass., were the friendly owners. They were about to leave, and soon we had the mooring all to ourselves.

While I set up our sun shade, Diana ordered the Magma grill part I’d dropped overboard in Hadley’s, and she arranged to have it delivered to Oak Bluffs that day, on the 2:30 mailboat. Around 10 a.m. we rowed to shore for breakfast at Linda Jean’s on Circuit Avenue, but there was an hour-and-a-quarter wait. We bagged that and grabbed coffee and breakfast sandwiches at Mocha Motts, a take-out place.

The mailboat was a seaworthy, steel-hulled vessel that carried, several times a day, two dozen passengers as well as mail and packages from the mainland. Our part for the grill was onboard. Once we had it safely tucked away, we rented bikes, destination Edgartown, a 40-minute ride along a busy bike path. Diana was on a mission to get a famous lobster dip at the Seafood Shanty, with its spectacular view of Edgartown Harbor from the upper deck. We passed on the cheese-laced lobster dip because I’m lactose intolerant. We did, however, wash down chicken wings and shrimp with their signature “Eddy-Go-Deeper” vodka drinks.

It was 6 p.m. by the time we got the bikes back to the rental place.

The dinghy dock at Oak Bluffs Harbor was packed with inflatables. Our little fiberglass dinghy had been moved to the back row, meaning we had to climb over several inflatables to get to it. No other rowing dinghies were at the dock; the rowing dinghy is apparently going the way of the dodo bird. Dinghy docks in every harbor were crowded with increasingly large inflatables.

Back on the boat, we installed the replacement part on the grill, and finally grilled the steaks, which were perfect. A meal like that – in the cockpit of a sailboat, with the sun setting, with beer and wine and music – beats any five-star restaurant in the world. I don’t care what Yelp says. After dinner, I won two games of cribbage to Diana’s one.

The next day, Friday, was a layover day, so we stayed on the mooring. We rowed to shore and put our name in at Linda Jean’s for breakfast – a one-hour wait again – so we looked at the gingerbread houses. These are tiny Victorian houses built on an old Methodist campground. There are 300 of these “carpenter-gothic” cottages, and each one more elaborately carved and painted than the next. After breakfast, we took the bus to Vineyard Haven. The Vineyard’s bus service can take you all over the island for a couple of bucks.

There is a rather old-fashioned movie theater in Vineyard Haven, and we decided to see “The Big Sick,” a true story by a comedian from India, that was funny and touching. After the movie, we took the bus back to Oak Bluffs and went straight to the dinghy because the sky was ominous and thunderstorms were predicted.

We got out to Student Driver just before the storm hit.

The loud drumming sound the rain made on the cabin roof, only inches over our heads, was awe-inspiring. It was oddly satisfying to stay dry in a little sailboat during such a storm, although we had to bail out the compartment under the V-berth.

In the morning, we rowed to shore and got in line at Yelp-certified Biscuits. After breakfast, we returned to the boat to find that another vessel had rafted to us – a 32-foot Regal powerboat with two couples on board. After that heavy breakfast I really wanted to lie down and digest, but that wasn’t going to happen: The Regal crew were there to party, and they wanted us to join in. The two guys aboard were cruising with their girlfriends, and, by noontime, they were on a mission to get plastered.

We had planned to stay through Sunday night to see the famous Oak Bluffs fireworks, but rafting up to this boisterous company for two nights was not especially appealling. Instead, we decided to leave Oak Bluffs for the night and return on Sunday for the fireworks. At 2:30 we said goodbye to our new friends and dropped the mooring, bound for Osterville, about 11 miles away on the mainland. Out in Vineyard Sound, a 10- to 12-knot wind blew out of the southwest, so we raised the main and the working jib, Diana at the helm. Sometime after 5 p.m., we reached the narrow entrance to West Bay and Osterville.

Osterville: Our destination was Crosby Yacht Yard, where we planned to get a slip for the night and go to the Chart Room at Crosby’s, a sister restaurant to the Chart Room at Kingman. We passed through the Osterville drawbridge, and soon learned that Crosby had no available transient slips, but we could pay a dollar per foot per hour to tie up at the fuel dock – almost $50 to park our little boat for a couple of hours. But, hey . . . .

The Chart Room East was a lot smaller than the Chart Room at Kingman. And it was more upscale, which you’d expect, being in Osterville, one of the wealthiest towns on the Cape. We got two seats at the bar. We knew Kevin the bartender, who used to work at the other restaurant, so it was a lot of fun. We met Pat Lynch, a stylishly dressed elderly woman who told us she sat at the end of the bar every day in the summer to drink a martini and watch the sunset.

After cocktails, in the dying light, we motored through North Bay and around Grand Island into Cotuit Bay. The Cotuit launch was running, and when I radioed the driver, asking about a mooring, he said there were no transient moorings, adding, “but do whatever you feel is necessary.” We picked up a vacant mooring, got the grill going, and cooked chicken for dinner. It was a clear night, the sky was full of stars, and we took turns looking at the Milky Way through our binoculars.

In the morning, we rowed to shore on a quest for breakfast. Just up the street from the town dock, we encountered a craft fair – ecstasy for Diana – but though she examined every item, she didn’t buy anything. Breakfast was foremost on her mind, and the only place close by for coffee was The General Store, a few blocks away. There, we bought coffee, water, bananas and zucchini bread, which we ate on a picnic table.

We were out in Nantucket Sound by midmorning, and it was a gorgeous day for sailing back to Oak Bluffs. The wind was out of the southwest, 10 to 12, and we went with reefed mainsail and storm jib. Three hours and two tacks later, we were in Oak Bluffs.

Oak Bluffs, again: The harbor was more crowded than before, and we rafted up to Amorita, a big Gulfstar that was already tied up to another boat. The owner was Percy, a slender black gentleman with a snow-white beard and wearing a wide-brimmed straw hat. He was cruising with his wife and another couple. They also were in Oak Bluffs to see the fireworks. We sat on our respective decks and engaged in the banter sailors fall into while rafted up.

Percy was impressed that we were cruising in such a small boat. He related adventures he’d had in his first sailboat, a 30-footer, back when he didn’t know what he was doing. Eventually, he and his wife moved up to the 42-foot Gulfstar, which they kept in Quissett Harbor. Percy was familiar with Kingman Yacht Center, and he was acquainted with boat owners we knew. It’s a small world among cruisers after all.

Around 6 p.m., we rowed to shore and dined at Sharky’s Cantina, where the shrimp tacos and chicken wings were delicious. From Sharky’s we walked to Ocean Park to find a spot to watch the fireworks. I’m not a big fan of crowds – 15,000 people must have been there – but the fireworks were spectacular.

We were off the mooring by 7 a.m., and we motored around East Chop and up into Vineyard Haven Harbor, where we grabbed a mooring inside the jetty. We rowed in to the dinghy dock, and, after breakfast, we went to the little Stop & Shop, reminiscent of what grocery stores were like when I was a kid. We bought our usual provisions there, including a bag of ice so the beer would stay cold.

We left the mooring at 11:30, bound across Vineyard Sound toward Woods Hole. It was blowing 12 to 15 out of the southwest, so we flew the reefed main and the small jib. We hit the Hole at favorable peak flow, and it was scary being propelled past buoys forced horizontal by the tide. With the southwest wind on our nose, we tacked twice to stay in the narrow channel. We were a well-tuned machine by then, Diana on the helm and me working the jib sheets. We shot out into Buzzards Bay and set a course for Mattapoisett Harbor, a comfortable beam reach.

An eclipse of the sun was due sometime during our passage across Buzzards Bay, and Diana had made special eclipse glasses out of cardboard and aluminum foil. When the time came, we donned them in anticipation, but it was cloudy, and we didn’t see a damn thing.

Mattapoisett: We sailed for an hour and a half, on a beam reach, right into the mooring field in Mattapoisett Harbor, and it was lumpy in the open roadstead. The Mattapoisett Boatyard’s guest moorings had orange balls, and we grabbed one ($40 for the night) close to shore. When you have a tippy little dinghy, you want to be close to the dinghy dock. Once ashore, a one-mile walk through a beautiful residential neighborhood brought us to The Inn at Shipyard Park. We got a table for two on the porch, and had delicious grilled salmon and chicken with bucatini. OK . . . I’ll admit that the Yelp app can be a valuable tool when cruising. We returned to Student Driver, and she was bouncing all over the place. The idea of crawling up into that V-berth to sleep seemed ludicrous, but crawl up there we did. That Diana could tolerate sleeping in those conditions dispelled any notion she was susceptible to sea sickness.

In the morning, it was blowing 18 and still rough as hell, and we sailed right off the mooring with reefed main and smallest jib. We were close-hauled until we got around N “2” off Angelica Point, where we bore off on a broad reach for Sippican Harbor in Marion.

Marion: We didn’t drop the sails until we were at the narrow point of the channel between the mainland and Ram Island. From there, we motored down the channel, past beautiful sailing yachts and Tabor Academy, down to a vacant mooring off the docks of Burr Brothers Boatyard.

The wind continued to pick up during the day, but now we were in a protected harbor, in the lee of the Tabor Academy fieldhouse, and the water was flat. We took the Burr Brothers launch to shore to eat at Brewfish, with its craft beers and good chicken wings. We had to get to the launch before 8 p.m., when it stopped running. This was the downside of the launch versus the dinghy: you had a curfew.

Back on Student Driver, it was blowing a gale, and we needed weights on the cards to keep them from blowing away while playing cribbage in the cockpit. We each won a game.

On the last morning of our cruise, we took the launch to shore for breakfast at Uncle John’s, near Diana’s eyelash studio. Arriving someplace by boat that you normally go to by car changes one’s perspective. After breakfast, we got into the dinghy and rowed over to a large Leopard catamaran moored nearby. “Can we have a boat like that someday?” Diana asked wistfully.

“Sure, why not?” I said, unsure if we’d ever have a half-million dollars of disposable income, but I wasn’t about to discourage her. The fact that she was dreaming was a good sign.

We dropped the mooring about 9:45, and it was a quick sail across Buzzards Bay in 15 knots of wind out of the southwest. We couldn’t bear heading straight to our mooring, so we dropped the anchor off Bassetts Island and savored a great afternoon of cocktails, sandwiches and swimming. By 6 p.m., we had the boat back on our mooring, and were in the dinghy bound for shore.

And that’s how the cruising season ended. But Diana had earned her wings by cruising on a J/24, so it was time to move up. We sold Student Driver and purchased a J/30 that Diana named Mojo. We’re looking forward to cruising next season on our new boat, maybe up along the Maine coast.

We’ll let you know how that turns out.

Mark Barrett started at the bottom in the boating industry – literally – scraping, washing and painting all sorts of vessels. He currently works as a yacht broker for Cape Yachts in Dartmouth, Mass., and lives in Sandwich, with the now-famous Diana Donahue. They sail their J/30 Mojo out of Red Brook Harbor, in Buzzards Bay.