Anniversary Blowout

The wet and wild view from Bailamos, the authors’ S2 9.1. On this trip the boat, for the first time ever, would take enough water over the bow to reach the cockpit. Photo by Jackie Llewellyn

March/April 2021

By Jackie Llewellyn
For Points East

We steamed out the narrow channel that leads from the harbor in Westport, Mass., into Rhode Island Sound, and we couldn’t believe the sea state that greeted us off Horseneck Beach. Gigantic breakers, like the “white horses” you see in the Gulf Stream, rendered us speechless.

We avoided the local-knowledge shorter route through the Hens and Chickens and set out for the green can farther out. The waves were gigantic. The wind was from the northeast, and it was twice what it was forecast to be. Our 30-foot S2 9.1 Bailamos was powering up seven-foot waves, and surfing down them at 8.5 knots. It was too late to head back to Westport; the seas there looked more dangerous.

We had a handkerchief of a jib out to help stabilize the boat, and we motored across the western end of Buzzards Bay, bound for Vineyard Haven. By the time we were in the middle of the bay, the waves were 10 to 15 feet high, and the wind was a steady 28-34 kts. We’d never had water in the cockpit – ever! – during our years of sailing, and now some four inches sloshed in it as waves crashed over the bow.

We’d just begun the second week of a three-week southern New England cruise, and we were shaking our heads, thinking it wasn’t supposed to be this way.

My husband Dan and I had put many thousands of miles under the keel of Bailamos, including a yearlong cruise to the Bahamas and back. Both licensed boat captains, we’d sailed from Panama to the Galápagos Islands, and Dan had crossed the Pacific to French Polynesia. So it was a shock when a three-week cruise, in local waters, presented the worst conditions we’d ever experienced – the biggest waves and the most consistent gale-force winds. And all this produced way too much adrenaline and, in my case, downright fear.


Dan and I usually take a September sail to celebrate our wedding anniversary on the 19th of the month. During the summer of COVID-19, racing had been cancelled, ports were either too crowded or unavailable to us, and we couldn’t go to Maine or Nova Scotia. Each time we made a plan, the virus was in the way. It saddened us to see Bailamos sitting on her mooring and not being used, so we decided to stay local for our September cruise – head south from our Hull, Mass., homeport, bound for Buzzards Bay.

We packed the boat with provisions, fuel, water, linens, and the like in one day, and, on Sept. 9, 2020, we headed for the Cape Cod Canal. It was an easy motor sail in familiar waters. We got a mooring at Parkers Boat Yard, in Red Brook Harbor, and marveled at the dense schools of fish jumping around us, creating a crazy, silver glittering sea.

By the end of Day 1, Dan and I were both filthy. The boat had not been used much during the summer, and when you’re not living on one, there can be a lower standard of cleanliness. Over the long slog from Hull to Red Brook, I spent four hours cleaning Bailamos, getting her shipshape, and, after that, my clothes were unwearable. Dan started out with dirty clothes, having packed in haste.

After a day in the rain on the spectacular Shining Sea Bike Way – between North Falmouth and Woods Hole – we set out for Hadley Harbor on Naushon Island, just off Woods Hole. We had never been to Hadley’s, but we had heard a lot about this famous harbor. One aspect of sailing that I love is what I call the “privileged access” it affords. Opportunities abound to see, up close and personal, beautiful homes, wildlife sanctuaries, private schools, and protected habitat blocked from the public who travel by road. Sailors can see what motorists and cyclists cannot because of fences, landscaping and Do Not Enter signs.

Hadley Harbor’s Inner Harbor presented a beautiful view – plus the clear message that we could look, but not go ashore. Having said that, Bull Island, outside, is open to the public for hikes and picnics.

We sailed over to Woods Hole, which we’d transited many times. Trying to figure out where to drop a hook in Woods Hole or rent a mooring, we wound up in Eel Pond, which was quiet and delightful. In this COVID-19 summer, at season’s end, many marinas and boatyards were not answering the phone or radio, so all we could do in Eel Pond was find the slimiest unused mooring in the basin and tie up. We stayed for two nights. Anchoring is not allowed in Eel Pond.

This had been one of the windiest Septembers on record. As I wrote this piece, on Sept. 22, there had been so many named storms that the folks who name them were at Tropical Storm Beta, on the second round of the alphabet. The sailing in between these systems was pretty darn good, with little motor-assist required. From Woods Hole we practically flew to Menemsha, excited that the Martha’s Vineyard Striped Bass and Bluefish Derby was in full swing.

Cuttyhunk was next. We’d been there five years earlier, when we hid from a storm and were stranded on Bailamos for 36 hours. This time our issue was man-made, in which we experienced mechanical failure. Upon leaving Cuttyhunk for the Sakonnet River, the faint smell of burning rubber sent Dan on high alert. We turned back to the inner mooring to change the failed engine belt. Dan is a mechanical genius, and he always has backups upon backups of equipment that sooner or later will need replacing.

With the exception of Newport and Block Island, we always passed Rhode Island ports. However, in the summer of 2020, where we all stayed closer to home, it was the perfect time to do some short-jump exploring. Third Beach, on the Sakonnet River, is a great anchorage, and our fold-up bikes got us to the Sachuest Point National Wild Life Refuge. We savored lobster rolls from the Easton’s Beach Snack Bar, and gathered more provisions.

The next day, we sailed upriver to Tiverton, but it proved too windy – 34 mph – to tie up at the dock-and-dine Boat House restaurant, just north of the Route 24 bridge. So we went back downriver, and secured a mooring at Standish Boat Yard. The only ball available was a tangled mess, and after Dan tried twice to pick it up, we called the yard to see if the dock manager could get it undone. Ken came right out with his skiff, got the ball untangled in the howling wind, gave himself a victory pump, and then loaned us his truck the next day so we could get a new propane tank and more provisions. Now that does not happen on land.

Our end goal on this trip was Block Island, but first we headed over to Potter Cove, on Prudence Island. There were many unused private moorings, but instead of pirating one, we dropped the anchor. We rowed to shore with the folding bikes in our Gloucester Gull dory, and found that this is a charming place, especially at the end of the summer season. Prudence has one little store, gravel roads, and lots of protected land, which was vastly different from our next port, Newport.

And this was when the weather began to get a little dicey. The wind was out of the north – 20s and 30s, plus stronger gusts – and it was relentless. Being in cozy Narragansett Bay, we never thought we’d have to worry about the weather. The conditions were bad enough that even considering leaving Potter Cove assumed some boat-name attributes: endurance, courageous, tenacity.

We went to Newport because Jamestown Harbor, on Conanicut Island, is too exposed from the north, and we had plans to go to Block Island the next day. Sailflow ( said it would be a little calmer in the City by the Sea, and a good spot to find ourselves before more serious wind and seas built up. We did laundry in Newport – which was great – and we got to ride in the Newport launch; I always feel like a celebrity doing that. But there was no way we were going to make it to Block.

Sailors are obsessed with weather. We check Sailflow several times a day, and in the middle of the night. We listen to NOAA Weather Radio on the VHF, and once is never enough. It’s hard to go to Plan B when you want the thrill of the sail to Block Island, and crave a mudslide at The Oar. However, we convinced ourselves that sailing to Block in winds exceeding 30 mph, with seas over seven feet, in our 30-foot boat, would not be a good idea.

The extended forecast looked even worse, so we headed for Westport, Mass. And got our asses kicked. When you’re getting hammered by the sea close to shore, wearing your offshore PDFs (only worn when the conditions are intense, when you’re not talking much) you stop second-guessing.

Westport is tricky to get into with a 3.5-knot ripping current, so we anchored off Horseneck Beach, waited for a favorable tide, and took naps. Westport Harbor had hundreds of boats. Who knew? It is not a great place for transient boats, with few places, we believed, for anchoring in that kind of current, and few transient moorings for non-seasonal boats. And the anchorages appeared to be too far from the docks for a comfortable row ashore.

We spent our 33rd anniversary aboard, drinking Spanish Cava. In the morning, we learned that F. L. Tripp & Sons had a launch service for $1 per person. We needed a day off, so biked in an easterly direction, against the wind, and hung out on Horseneck Beach. The forecasters said the next day would be fine, the new “fine,” with winds in the mid- to high teens and gusts in the 20s. But the real danger would be on the following day, when a gale was predicted. We planned to set sail for the Vineyard in the morning, taking on fuel, water, clean laundry, propane, provisions . . . check, check, check.


Now it is the beginning of Week 2, and you already know that conditions were getting dicey. I tried to keep a lid on my fear, but my body knew the truth and trembled: My feet shook, and my knees were knocking. I was holding on to the dodger so hard with both hands that Dan would later say that if he’d tried to pry them loose, the dodger would have broken. From my perspective, the boat appeared to be sideways to the seas, but Dan said we were climbing, then tumbling, down the waves. Maybe the weather guys got the day of the gale wrong because we were in a gale, and it was relentless. We still had the waypoint for Cuttyhunk on the plotter, and it took a lifetime to reach it.

“What do you want to do?” I asked Dan, who was completely soaked and spent. “What? Are you kidding?” he replied. “We’re heading for Cuttyhunk, our harbor of refuge, once again.” And, after three attempts to snare a mooring, we were safe and sound in the protection of that little island. We’d stay there for 36 hours.

After stiff Dark ’n Stormie’s, we slept for 10 hours, exhausted, arms hurting from holding on for dear life. I thanked Dan for his navigational expertise and cool temperament in one of the worst crossings of our lives.

When we reviewed the historical wind data on Sailflow, it revealed that we’d made the crossing at the worst possible time, with winds steadily over 30; NOAA reported seas off Block Island at 19 feet. In the summer of COVID-19, we proved that you can find new ports, generous boat managers, and plenty of storytelling adventures right in your own backyard.

And, oh yes, Happy Anniversary, Dan.

United States Coast Guard-licensed Capt. Jacqueline Llewellyn sails out of Hull, Mass., on Bailamos, a 30-foot S2 9.1 sloop, built by S2 Yachts of Holland, Mich. She started writing about sailing during a one-year voyage between 2015 and 2016 with her husband, Capt. Dan. Check out