One Year, One Boat, One Epic Family Sailing Adventure

We had the right boat: Searcher, a Bowman 57 ketch. I’d already made two voyages to the Caribbean on it. I had just turned my business over to a nonprofit and retired. Our two kids were the right ages: Our daughter, Ren (short for Renaissance), was 10, while our son, Havana, was 8. They’d been brought up on Searcher and could swim, row a boat, paddle kayaks, and sail a dinghy.

But my wife, Julie, still needed convincing that this was the perfect time to move aboard and spend the winter in the Caribbean. I gave her a copy of Don Casey’s book Dragged Aboard: A Cruising Guide for a Reluctant Mate. Besides, I told her, when I had turned over the school I’d founded, the house went with the deal. What choice did we have?

Getting Searcher to the Caribbean would mean a three-week offshore voyage of 1,500 miles through the Bermuda Triangle—our family’s first such voyage. I had already made the offshore passage from Maine to the Caribbean and back a dozen times on various boats. I knew it would be scary and perhaps dangerous, but I had a plan: We’d first spend early fall wandering along the New England coast. We’d spend a month on Martha’s Vineyard, and then cruise over to New Bedford, Massachusetts, before arriving in Newport, Rhode Island, to join the North American Rally to the Caribbean.

And before all that, I would spend the summer getting Searcher ready. We moved aboard in May. Julie was none too thrilled about living in a construction zone as I tore up the worn-out teak decks and replaced them with cork. We overhauled the rig and engine, installed a new charter plotter and radar, and added a Wi-Fi antenna, booster, and router. The cost of replacing the outdated refrigeration system was prohibitive. We’d just fill up the fridge with ice.

In early September, Searcher was ready. We loaded up and sailed away from our home port in Rockport, Maine. Hours later, the autopilot quit, and since it was old, it could not be fixed. A replacement was too expensive. We’d just hand-steer. For a year. 

We spent that fall living full time on the boat, exploring ­villages and small harbors. They were mostly vacant at ­season’s end as we got used to shipboard life and boat-schooling. We visited museums, ­libraries and boatyards, and took the dinghy up small creeks, poking around.

With no autopilot, we’d need extra crew for the offshore voyage. I spread the word on Hank Schmitt’s crew network, sailopo.com. From the dozen or so résumés I received, we landed on Rob and Emily, recent college grads. Rob had sailed his family’s sloop on Long Island Sound; Emily had been brought up on Castine Harbor in Maine. The couple joined us on Searcher for a weekend, and by the time they left, they’d been kid-approved.

The last day of October, we brought Searcher into the docks at Newport Yachting Center to join 30 other boats in the rally. We took on fuel, water and provisions. Rob and Emily joined us in hoisting the dinghy, securing it on deck along with the kayaks and bikes. At dinner that evening, we met the other crewmembers. 

The next morning, the skippers met at the Newport Yacht Club for a weather briefing. Conditions were blustery that day, with northeast winds of 30 knots and building seas. Most of the 30 boats left that afternoon. Since I had a green crew making their first offshore voyage, I decided to wait until the next morning, when we had 20 knots of wind on the beam. 

We crossed over the Gulf Stream without even knowing it. Two days later, a strong cold front caught up with us, with northwest winds gusting to 35 knots and seas building to 15 to 20 feet. Searcher was in its element, surfing down the face of large waves at 12 knots. My young crew was as thrilled as they were terrified. We entered Town Cut, heading into St. George’s Harbor, Bermuda, safe and sound—640 miles and four and a half days out of Newport.

Bermuda had so much to see and do that we spent a week there, then departed on the 850-mile voyage to the Caribbean. We caught fish, played games, read books, made journal entries, and stopped to refuel other rally boats halfway down the course. It was delightful, and it more than made up for the cold, raw weather, and seasickness of our first days at sea.  

In the British Virgin Islands, we stopped in Jost van Dyke to see my old friend Foxy Callwood, and to celebrate my 70th birthday. We spent Thanksgiving anchored in Kelly’s Cove off Norman Island. Rod and Emily departed to start careers in New York City, and the Lyman family got down to a few weeks of ­serious gunkholing in the US and British Virgin Islands.

Mornings were for boat-schooling—well, most mornings—and afternoons were for exploring caves on Norman Island, visiting old sugar mills on St. John, snorkeling amid coral canyons around Pelican Island, and beachcombing on Sandy Cay. Friends invited us to celebrate a round of birthdays with them on Bequia, located 370 miles south. We could easily make the voyage in two days if we sailed nonstop, but we instead elected to hop down the island chain, anchoring each night to sleep. We’d just raise the quarantine flag, stay on the boat, and leave the next morning. 

We waited a few days for the wind to go north of east, and then left the BVI from Round Rock Passage one afternoon in mid-December. We sailed all night. Julie and I shared watches at the helm. We slid past Saba Island in the dark, beneath a sky full of stars, a lone white light flashing from the hills. We then sailed southeast all the next day, with 15 knots of wind on the beam, making a steady 7 knots. 

The islands of Statia, St. Kitts and Nevis slid by off to port, each topped by a white cloud. Montserrat, with gray ash streaming south from its volcanic summit, lay ahead. Julie dug out the geography book we’d brought along, and class was in session. We skirted the exclusion zone marked on the chart plotter but did not escape the ashfall. In order to see and breathe, I strapped on a dive mask and snorkel. The family went below and closed all the hatches. We anchored that night off Deshaies, a small harbor village on Guadeloupe. The next morning, it took me an hour to wash off the ash, but not before the kids had scooped up samples to show their pals back home.

We motored all that day down the mountainous flank of Guadeloupe, sailed through Îles des Saintes and down the lee of Dominica, and anchored that evening off the village of Saint-Pierre on Martinique. The next morning, we motorsailed down the green, lush side of this large island, but by the time we’d reached St. Lucia, the wind-slot effect between the two islands had pulsed too far west for us to make it into Rodney Bay. It was late afternoon when we did manage to anchor in the tiny, narrow harbor of Marigot.

The next morning, our third since departing the BVI, we left Marigot and passed the Pitons—two volcanic spires that look straight out of Jurassic Park. All afternoon, we sailed down the west coast of St. Vincent, and at 9 that night, with radar, we entered wide-open Admiralty Bay off Bequia. We dropped the hook near Lower Bay Beach, away from the crowded inner harbor, and stayed there for a month.

Bequia is the winter home for many liveaboard boaters. It’s a nice place to be, with a welcoming community ashore and lots to see and do. Bequia has always been a sailor’s island. We enjoyed birthdays, Christmas, bodysurfing, exploring the reef, and boat-schooling before it was time to get going again.

The Grenadines is a chain of small islands south of St. Vincent. Each is worth a visit, but we headed for the Tobago Cays, a popular anchorage on a shallow, reef-filled bank. We found it too popular, and after an hour, we sailed on to Clifton Harbor on Union Island to clear out for our final ­destination: Grenada. 

All the following day, we sailed past Carriacou, then down the green coast of Grenada. According to Chris Doyle’s guidebook, Prickly Bay on the south coast is an ideal anchorage. There we found a customs office, two marinas, a chandlery, and a pub with a dinghy dock. We spent three weeks anchored there. We rented a car and drove deep into the mountains and rainforest to find waterfalls, a cocoa plantation, and a rum factory. We took part in the annual workboat regatta and began to ­embrace island life. I could have moved there permanently.

By late February, it was time to begin the voyage back up the island chain. I wanted to be in Antigua by mid-April to cover the Classic Yacht Regatta. We provisioned at the open-air market where Ren got her hair braided. We also took on fuel and water at the yacht club, and then we set sail.

Because the family had gotten a look at each of the islands on our way down, we had a good idea of the islands we wanted to explore on the way back north. Havana wanted to see the wooden-boat builder on Carriacou, so we stopped there and hailed a taxi to the east side of the island, where we found two sloops under construction. They’re still built here using traditional tools, techniques and a seasoned eye. Later, in Antigua, we’d see them racing more-modern yachts.

The Pitons on St. Lucia were a must. We anchored under the towering peaks and ran a stern line ashore. We spent three days there while the kids mucked about in hot mud pools, hiked, and explored the old town of Soufriere. Julie wanted to park ashore for a while, so we moved to Rodney Bay Marina. It was like being back in the States.

It’s a daysail from Rodney Bay up to Saint-Pierre on Martinique. We anchored beneath the cliffside statue and cleared in at French customs using the computer at the town hall by the dock. The town is worth a week, but we spent four days. We rented a car and explored the lush island interior, with its mountainous rainforests. We found rivers, pools and waterfalls to splash in. We visited Fort-de-France and took the coastal road back to the boat. The French Islands are well-supported by their home country, so the roads and infrastructure are like driving through the South of France—a stark comparison to the islands that the English left to fend for themselves.

After a 50-mile sail north to Dominica, we anchored in wide-open Prince Rupert Bay, up near Portsmouth, and cleared in at the commercial pier. We explored the island’s mountainous interior with a guide, bathed under Emerald Falls, and met “Mr. Nice,” a local farmer who introduced us to all that Dominica grows. A man named Albert rowed us up the Indian River into the ­island’s jungle interior, recounting his life as a West Indian living in this tropical paradise. 

From Portsmouth, it’s 20 miles—a four-hour sail—to the small French archipelago of Îles des Saintes. We were getting near the deadline to be in Antigua, so we pressed on to Deshaies at the northern tip of Guadeloupe. I could’ve spent a month here, but we were off the next morning to clear into Antigua in Jolly Harbour, where there’s a fuel dock, storage yard, chandlery, well-stocked supermarket, and Wi-Fi for the price of beer. Nearby is Five Islands Bay, a quiet and mostly vacant anchorage. Falmouth and English harbours are a three-hour sail away. In late April, the yachting world gathers in these two ports for the Antigua Classic Regatta, followed a few days later by Antigua Sailing Week.

We spent a month anchored off Pigeon Beach and joined all the action ashore. The kids were off sailing dinghies with other kids from the yacht club while I photographed the classic yachts for a magazine story.

All of this ended too soon, as our six months came to its conclusion. Boats were leaving Hurricane Alley and heading north. We picked up two extra hands for the voyage back to Maine, and we were off in the middle of May, arriving on Memorial Day weekend—tan, fit and wiser.

By then, the kids were 11 and 9. Ren told us that she knew exactly what she wanted to do with her life: “I want to attend Maine Maritime Academy and go to sea.”

That’s exactly what she is doing now. Havana had loved the lines and shapes of the boats we’d passed, so when we got to Bequia, he spent a week in a model-boat workshop, building his own model. He has it in his bedroom now. He recently graduated from Southampton Solent University in the UK with a degree in yacht design. One of his first jobs was as an architect on the salvage team who extracted Dali, the ship that struck the Francis Scott Key Bridge in Baltimore in March 2024. 

Julie went back to her ­career in film, and I became a ­full-time soccer dad. I also ­returned to my former career as a ­photojournalist and continued to write books and stories for magazines. And I’ve never met a family or a person who has spent a year or more at sea on their own boat and regrets a moment of their experience.

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