Cruising with Diana

Diana at the helm. Seasickness? Fear of heeling? Remarkably they were non-issues during the indoctrination process. Photo by Mark Barrett

By Mark Barrett
For Points East

“Hey Diana, how do you feel about sailing?” I asked my new girlfriend.

“Well, I’m not really a boater,” she responded. “I get seasick, and the way a boat leans way over freaks me out. And I really don’t like being on the ocean.”

Those were some major red flags, but Diana was such a good catch it was worth trying to convert her to a cruising sailor. The conversion process would have been easier if I still owned the late-model Catalina 350, but that boat was gone, the casualty of an expensive divorce. Instead, I had a J/24, vintage 1978. The boat once belonged to a sailing school, hence the name Student Driver.

Student Driver was hardly a comfortable cruising boat: The accommodations were spartan, to say the least. The vintage 1978 cushions were mildewed. Standing headroom? There was barely sitting headroom. The toilet was a plastic bucket. The old J/24 needed some sprucing up before I introduced Diana to her.

When Diana and I started dating, the New England boating season was over, so, I had time to make many improvements to Student Driver. I sprang for new navy-blue Sunbrella berth cushions. I installed a marine head and holding tank. I bought a hand-pump so we could brush our teeth and wash our hands in the little sink, even though we had to kneel to do it.

I bought a Magma gas grill to attach to the stern rail so we could grill steaks. I had a dodger made that provided a small area of standing headroom while at anchor. Luckily, Diana and I were still together when spring rolled around, and it was time for our first cruise.

Cuttyhunk: At the very tip of the Elizabeth Islands chain, close to Martha’s Vineyard, is a little island called Cuttyhunk. It’s a popular cruising destination because of its pristine, well-protected harbor, and the charm of its tiny island community. Although Diana liked the nightlife and a lot of action, I thought she might, for a change, enjoy a place with no distractions. I pictured us sitting in the cockpit with nothing to do but watch a gorgeous sunset and bond with each other.

We took off from Kingman Yacht Center, in Cataumet, Mass., on a June Friday, planning to sail down to Cuttyhunk in one shot and return on Monday. Diana was doing just fine with sailing that day. She had taken Dramamine and was wearing special bracelets. She even used the marine head while we were under way – a huge milestone. However, after beating into the 15- to 20-knot southwest wind for five hours, we decided to head to New Bedford Harbor for the night.

About 3:15 p.m., we motored through the hurricane barrier at the entrance to New Bedford, and we pulled into our slip at Pope’s Island Marina. We walked a block down to Fathom’s restaurant, and we drank Tito’s and soda with a splash of cranberry and split a grilled-salmon salad for dinner. It was perfect. Back aboard, we broke out the cribbage board and played a couple of games.

The next morning, we took an Uber from the marina to Yelp-recommended Margaret’s Restaurant, in Fairhaven, for a great breakfast. Diana was happy; breakfast was her thing. By the time we got back, it was raining, so we waited it out below. The dodger allowed us to keep the hatch open during the downpour.

We left the dock at 1:30 p.m. Outside, in the bay, it was blowing a steady 15 knots out of the southwest. Diana took the helm, and we sailed close-hauled, on a starboard tack, all the way to the RW “CH” bell just outside Cuttyhunk Harbor, a run of 12 miles. We picked up a mooring close to the dinghy dock; our dinghy had no motor.

Diana was anxious to get ashore and find a waterfront pub for a drink and something to eat. And that was when I told her there was no such place on the island. She didn’t believe me at first. When it finally sank in, she was incredulous. “What!” she said. “A place with no bar?”

“You can’t even buy liquor here,” I said. “It’s a dry island.”

She dove below to evaluate our liquor supply: a third of a bottle of red wine, an eighth of a bottle of vodka and three beers. “There’s no way in hell we’re staying here for two days and nights,” she said. “I can’t believe you didn’t provision better, knowing we were going to a dry island.”

“Don’t worry, you’re going to love this place,” I said. I kept repeating that as I rowed us to shore in our dinghy.

I was taking her to the only dinner spot on the island, a romantic open-air restaurant (BYOB) I went to years earlier. As we walked up to it, I got a sinking feeling: If it still was a restaurant, it definitely wasn’t open. Diana was not in a great mood. The lone gift shop was open, but Diana wasn’t interested in purchasing anything that said Cuttyhunk on it. She was worried that we’d have to survive the night on the potato chips and granola bars.

All was not lost, however. At the take-out place on the pier, we bought lobster rolls, stuffed scallops and shrimp cocktails, which we took back to the boat to savor to the accompaniment of a spectacular sunset. We listened to blues music and put a fatal dent in our liquor supply while playing three hands of cribbage. Diana won two out of three, and this, combined with the sunset and the wine, lightened her mood.

I still had my ace in the hole: an incredible breakfast experience the next day at The Cuttyhunk Fisherman’s Club. In the morning, we rowed ashore, walked up the hill to the club, and I got that sinking feeling again: No one was on the porch having breakfast. An employee broke the news: It wouldn’t open for the season for another two days. Two lousy days!

We walked dejectedly back down to the docks, bought breakfast at the take-out place, then hiked up the hill in the middle of the island to the observation platform. From there we had a breathtaking 360-degree view of Buzzards Bay, Vineyard Sound and the Elizabeth Islands. We could see the boats on moorings, and Student Driver looked tiny from there, compared with the other boats. As we walked down the hill, Diana called her daughter on the phone, and I overheard her say how beautiful Cuttyhunk was, and how much fun she was having. I smiled inwardly.

We sailed out that afternoon, bound for a mooring at The New Bedford Yacht Club, which is actually southwest of New Bedford, in Padanaram Village. Once in the harbor, we contacted the NBYC launch, which directed us to a mooring. Ashore, we checked out the clubhouse, a stately old building with gorgeous half-hulls on the walls. We had cocktails at The Sail Loft and a dinner of salmon bellies at The Black Bass.

On Monday, we left the mooring at 12:21. It was blowing 16 to 20, southwest, with the three- to four-foot seas. But it was a downwind leg and a pure delight. We surfed past Cleveland Ledge Lighthouse, eventually reaching our home mooring, and already thinking about our next cruise.

We would sail to the tip of Cape Cod in July.

Provincetown: We got off the mooring at Kingman at exactly 5 p.m. Our route would take us through the Cape Cod Canal, where the current is strong, vessel traffic heavy. Our destination that evening was Sandwich Marina at the canal’s east end. It was three miles from our mooring to the start of the canal and another seven or eight to the marina. We were able to sail in light air to the Hog Island Channel, where we lowered the outboard and started motoring.

I’d consulted the current tables for the canal in “Eldridge’s Tide and Pilot Book,” which said we’d have a strong, fair current at that time of day. Sure enough, as soon as we got into the canal our speed over the ground jumped up to just over eight knots. All three bridges – the Railroad Bridge and the Bourne and the Sagamore – were shrouded in fog. Diana steered the entire trip through the canal, and the four-horse Suzuki ran flawlessly. We arrived at Sandwich Marina at 7 p.m., only two hours after we left the mooring at Kingman.

Diana’s house was in the Town Neck section of Sandwich, a mile or so from the marina. She put on her running shoes and jogged home, got into her Pontiac Solstice – the little red convertible she called “Lolita” – and came back to pick me up. Diana was turning out to be a really good girlfriend.

We had her daughter’s dog, Dozer, to attend to, and decided to stay overnight at her house. Dozer, a lanky mutt, was coming to P-Town with us on our little sailboat.

Fortified with breakfast sandwiches from Mary Lou’s Coffee Shop up the street, we left the dock at 10:15, before the start of the 10:30 foul tide.

Provincetown Harbor was about 23 miles across Cape Cod Bay from Sandwich Marina, and we wondered how Dozer would fare for four or five hours. Diana had bought him a bright-yellow life jacket, which contrasted nicely with his jet-black fur.

We had a calm start that morning, a dead run from the end of the canal straight toward P-Town. Dozer lay down awkwardly at our feet in the cramped cockpit. Diana worried about the intensity of the sun, so she held our beach umbrella over him.

The breeze remained light, so after a couple of hours creeping along at three knots, I started the outboard and boosted our speed up to a blazing five. About 14 miles into the trip the wind picked up from the southwest, and we sailed her in, past Long Point Light and up into Provincetown Harbor.

Once we were past the breakwater, we radioed the marina, and the launch driver showed us our mooring right off the beach. We quickly went ashore because Dozer had to relieve himself. He boarded the launch like a veteran boat dog, and soon we were strolling down Commercial Street.

Diana researched the dog-friendly restaurants on her phone, and we went from one to the other having drinks and appetizers. Dozer was nervous about the crowds of people, and every 50 feet we had to stop to let someone pet him. Dozer could not have cared less about these people. Whenever somebody stuck a hand in his face, he’d turn away. I was liking him more and more.

Later, after maybe one-too-many cocktails, and snuggling on the beach during a gorgeous moonrise, Diana asked, “What time do we have to leave tomorrow?”

“Nine in the morning.”

“Nine? Why so early?”

“We need to leave then so we can hit the current in the canal at the right time,” I said.

“But I want to go out to breakfast in the morning. I Yelped it, and there’s this really good place we have to try.” The ambience turned way sour after that, with Diana threatening to get a hotel room and take an Uber back home in the morning. It was a calm, beautiful night on the mooring, with a sky full of stars and a breathtaking view of the illuminated Provincetown Monument. I talked her into playing cribbage, and she beat me handily two games in a row. Everything was fine after that.

First-off in the morning, we took Dozer to a section of beach where dogs can run free. Diana’s compromise regarding breakfast was that instead of a big, sit-down affair, we grabbed greasy breakfast sandwiches from a take-out place in order to catch the tide.

We dropped the mooring at 10 a.m. A light wind blew out of the west, so we were able to sail with the full main and jib for a couple hours, but then the wind dropped to nothing and we started the motor. Cape Cod Bay was a flat, undulating sea of blue glass. The little outboard hummed monotonously as we headed southwest toward Sesuit Harbor, some 15 miles away.

The sun beat down mercilessly, but Dozer seemed happy in the shade of his umbrella. Diana reclined on one of the folding cushion-chairs, resting one hand on the tiller to steer. We had the Jack Johnson station playing on the Bluetooth speaker, and the boat rocked gently as the outboard droned on. I kept a lookout, but there was nothing to see except the occasional fishing boat off in the distance.

I called Diana and got no response. Her hat was pulled down low over her eyes, and her sunglasses reflected the blue glare off the water.

I called her again. “Huh . . . what?” she said as she looked at her watch. “Jeez, I’ve been asleep for 20 minutes!”

Sesuit Harbor, in Dennis, was narrow and there were no moorings or places to anchor, although Northside Marina and the Dennis Municipal Marina had slips. We tried calling Northside first, but they had no vacancies. The harbor was packed with boats, but we found an empty slip where we could get off the boat. We put Dozer on his leash and walked up the ramp.

I entered the dockmaster’s office and asked a gentleman in a uniform if any transient slips were available, to which he answered, apologetically, in the negative. “Where are you now?” he asked. We told him, and he said we could stay there until he found a slip for us. We secured the boat, then ate lobster rolls and salad at the Northside Marina restaurant. Later, we had cocktails and fish tacos at the Marshview Restaurant. Back on the boat, we played a hand of cribbage before hitting the sack. Diana skunked me.

In the morning we had breakfast at Northside. My old friend Dave MacTavish, who worked there as a mechanic, stopped by to say hello. We left the slip by 10 a.m., bound for Sandwich Marina. A gusty southwest wind was blowing, but, in the lee of the land, the seas were flat, and we beam-reached at six knots. We arrived at the mouth of the canal at 2:30, with a fair tide and two- or three-foot standing waves.

Diana’s friend Amy met us at Sandwich Marina to help us ferry Dozer and her bags to her house. Currently, all logistics were driven by Diana’s eyelash appointment, which was crucial because she was going away on a business trip the next day. I would take Student Driver back to Kingman by myself.

After a rough and trying passage – stiff wind against strong tide, standing waves, and the small matter of a car carrier in the canal – I was back on my home mooring by 6:30 p.m. I was glad Diana was getting her eyelashes done and had missed this last leg. Otherwise, she might have turned down the next cruise: an overnighter to a quaint little harbor on the other side of Buzzards Bay.

Onset: It was Friday, July 21. Diana and I had planned an overnight trip cruise to the village of Onset, at the top of Buzzards Bay, about eight miles from our mooring. At 5:30 p.m., the launch delivered Diana and Dozer, and three grocery bags of food, out to the boat. After provisions were stowed, we motored off the mooring and headed out.

Halfway down the fairway, the outboard died. I frantically pulled the cord and fiddled with the choke, to no avail. We drifted up against a moored sailboat and hung on while I tried to rejuvenate the motor. After half-dozen pulls on the cord, it started up again and ran fine. Phew.

In the bay, the wind was blowing 15 to 18, southwest. With a reefed main and no jib, we sailed down Hog Island Channel until it branched off toward Onset. Onset Harbor offered several vacant town moorings, but all were far from the dock, so we picked up a private mooring that was closer. This would be Dozer’s first time in the dinghy, and we didn’t want to row any distance.

Ashore, we walked Dozer, then stopped at the Quahog Republic for a drink. Diana had her heart set on a pizza from iconic Marc Anthony’s, and we carried it over to a gazebo in the waterfront park for supper. Having Dozer along kept us out of another bar – probably a good thing – so we returned to Student Driver. We played a hand of cribbage before going to bed, and I skunked Diana.

In the morning, we woke to a perfectly calm harbor. At 8:30, we rowed to shore and found a dog-friendly café, where we had coffee and muffins. Back to the dock, we were alarmed to see the Harbor Patrol boat alongside Student Driver. Long story short, the patrolman said we were on a private mooring, and that we needed to take a town mooring, at $30 a night. I apologized and asked if I should pay him, to which he replied, “Don’t worry about it; just remember for next time.”

We moved over to one of the town moorings near Wickets Island, then rowed to the islet, where once there’d been a house and a stone pier. A large sign said the island was for sale, so Diana looked it up on her phone: For only $700,000 we could own it. There was a nice, sandy beach, and Dozer had a blast playing in the water.

At 2 p.m., we dropped the mooring. The wind had died by that time, so we motored the eight miles back to our mooring. We didn’t want to leave the boat, so we mixed cocktails, attached the Magma grill to the rail, and grilled the steak and chicken Diana had brought. After dinner, Pandora played blues music while we slow-danced in the cockpit. A boat passed by, and someone onboard yelled, “Hey, get a room!”

It would have been a perfect trip, except that Diana hit a big planter in the Kingman parking lot and put a dent in the bumper of her Denali. But now that she had experienced three short cruises, we planned something a little longer to find out what she was really made of. Stay tuned.

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, as does Diana. These days, they sail their J/30 Mojo out of Red Brook Harbor, in Buzzards Bay. Part 2 of “Cruising with Diana” will appear in the Midwinter 2020 issue.