The Boats, The Plans & The Families

A trio of New Englanders with different boats sets sail on a Caribbean sabbatical, and learns important lessons about themselves and the cruising life.

May 12, 2016
Family Matters
For the Smith family, the schooner Rebecca of Vineyard Haven was a vehicle for adventure. Jesse Smith

After six months in the Caribbean living aboard his 43-foot cruising catamaran, Fabuloso, with his wife and two young sons, Mike Zani was more than in his ­element. With winter behind him, before the northward passage home to New England, he hosted a rum-punch competition with a potluck dinner. As Zani passed out soft drinks to the children through the forward hatch, a friend who had been taking a similar family ­adventure — but on a traditional wooden schooner — popped below. “You are really the master of your domain,” said Jesse Smith, who had been living aboard his Gannon & Benjamin 60-footer, Rebecca of Vineyard Haven. “Yes,” said Zani, jokingly, “now get out of my kitchen.”

Zani and Smith, two friends from Rhode Island, had been exchanging notes all season on what constitutes the ideal cruising setup. Like a deer catching the faintest scent of an upwind human, Zani was acutely aware of anything out of place (or in his way). Along with the Gonsalves family of Massachusetts — ­also on a family sabbatical, aboard a 46-foot performance cruiser called Meridian — both he and Smith were winding down from what by all ­accounts was a once-in-a-lifetime trip through the Leeward and Windward islands with their wives and children.

How-to articles about realizing your dreams of cruising and living aboard are familiar in sailing magazines. The mainstream media often prefer to unveil the darker, riskier side of voyaging with live coverage of aborted family ocean passages, like last year’s rescue of the Kaufman family from their cutter, Rebel Heart, when an ill toddler and failed systems forced a Coast Guard recovery off the coast of California.


The story of these three relatively concise and successful liveaboard trips on Fabuloso, Meridian and Rebecca, however, reveals a more conservative and thoughtful approach to the same goal. Here were three strikingly different budgets and approaches with a common outcome: an unmatched experience of tuning in with spouses and children.

Family Matters
On the island of Dominica, the Smith girls, Teal and Selah, flank Orly and Asa Gonsalves near a beach where scenes from the movie Pirates of the Caribbean were filmed. Jesse Smith

Wheels In Motion

I f there was a single spark that ignited an inextinguishable adventurous flame, all three families agreed it was a dinner ­party on a frosty New England winter night ­several years ago. A casual discussion over steaming hot lasagna with circumnavigators George and Rosa Day took off in many directions as the questions started flying.

“How old were your children?”


“Was it hard to make healthy meals?”

“What about home schooling?“

“Did you ever want to quit?”


The practical queries came from the wives: Smith’s bride, Annice Kenan; Conley Zani; and Mege Gonsalves. Near the end of the evening, the three had cornered Rosa Day for even more information.

The three women had decidedly different backgrounds. Kenan, for instance, grew up in North Carolina. Her only exposure to sailing was aboard a colorful, spunky little Sunfish on a lake at summer camp. Though she had the propensity for seasickness, she knew that, at least for Selah, their older, 11-year-old daughter, a new schooling approach was needed. “The thought was just to pull her out,” she says. “It’s healthy to get out in the world.” “We always wanted to take a family adventure outside the ­socialized norms,” says Smith, who learned to sail through racing nine years before this trip. “When our second daughter, Teal, was born, I didn’t want to lose touch with her and get roped into the system of school and sports.”

Though they had taken three trips chartering in the British Virgin Islands, Conley Zani says that she married into the vision of “taking off with the family.” She grew up on Kentucky’s ­bucolic Lake Cumberland, water-skiing and fishing. As a kid, Mike had cruised the Florida Keys and Cape Cod on a Tartan 37 with his family, and later embarked on a trip around the world that was cut short when his stepmother was scared off after an Atlantic storm. Life got in the way of Mike’s further voyaging until he sold his company in 2012 and was looking to buy another. But his thirst for voyaging had never been quenched. “When you talk about something for 10 years, does it become a family dream?” he says. “Then we went to that cruising dinner. The seed was planted, and Conley liked the idea, so I started to take her to boat shows to look at boats.”

Family Matters
The young daredevil Asa Gonsalves catches big air. Courtesy of the Gonsalves Family

The Zanis say that educating their boys, Wake, 8, and Wyatt, 6, was not a primary factor in their decision to go cruising. In fact, Conley confesses that they dreaded that part the most. But they shared their friends’ desire to spend dedicated time together as a family, and saw the confined space of a boat — and the broader expanse of the blue Caribbean — as their salvation.

For the Gonsalveses, the motivation to take their children through the Caribbean chain ran deeper. Before they had children, Jeff and Mege served as captain and cook on charter boats in the same waters. They wanted to revisit these special ­places and show son Asa, 8, and daughter Orly, 11, the colorful West Indian culture and the French colonial influences in St. Barts. But they also wanted to expose them to the more challenging ­issue of poverty in the Caribbean.

“The original vision was a two-year gig to the South Pacific, going to places we haven’t been,” says Jeff, a marine ­surveyor. “Suddenly we realized that the destination didn’t matter. Everything would be new to them. It was more about spending time with the kids, and a more modest itinerary helped make that a much more attainable goal.”

While they came from different backgrounds, the families ­also had much in common, including kids in school ranging from the first to fifth grades. For everyone, weekends were packed with birthday parties and sports. Weekdays consisted of the ­usual dash to and from school, followed by hours of homework. “I realized that, ‘Wow, this allows for so little family time,’” says Kenan. “This wasn’t the lifestyle we had envisioned. Childhood is too precious and fleeting.”

Once they’d decided to take the plunge, Kenan and Smith hired an educational “coach” from California five months ­before the trip and started a home-schooling routine. The family ­also sold their home in Providence, Rhode Island, and jettisoned clothes, books and other clutter from their life. “By the time we left in the fall,” concedes Kenan, “I still didn’t feel ready. I was so busy packing and planning.” But at that stage, there was no turning back.

family matters
Aboard Rebecca of Vineyard Haven, dad Jesse keeps daughters Selah and Teal company as they tackle the books. To prepare for their trip, the family began a home-schooling routine months before departing. Courtesy of the Smith Family

Boats & Budgets

It almost sounds like the beginning of a sailor’s joke: A schooner, a catamaran and a high-tech cutter are rafted up in a tropical cove. And the unlikely combination of friendly families on differing vessels certainly piqued the interest of fellow cruisers. But boats reflect their owners, and in these examples, their respective family units.

Personal style, a tolerance (or lack thereof) for heeling and rocking, and budget all contributed to which boat the Zanis, Smiths and Gonsalveses each chose for their six-month Caribbean sojourns.

“Conley likes the looks of a classic, blue-hulled Hinckley,” says Mike Zani. “But she hates deep, dark saloons and feeling claustrophobic. Ultimately, visiting boat shows, we decided the biggest, worst-looking catamaran was better than any monohull she saw.”

The bulkier, modern catamarans didn’t appeal to Zani, so he focused on earlier-generation cruising cats. A “serial CEO,” he first searched diligently for an economical long-term charter. “I had been talking to a broker for two years,” he says. “He told me, ‘You’re looking for a white elephant.’” But a business mentor of Zani’s advised him to “just buy right.”

“Since I purchased things for a living, I made a spreadsheet of every modern catamaran for sale,” he says. “I bought on the flat part of the depreciation curve.” His model was based on the idea that demand for cruising catamarans had increased over the past five years on the East Coast and in the Caribbean, but that there was a shortage of inventory. He found the opposite to be true in the Med, where there was a large supply of privately owned cruising catamarans for sale, driving the price down overseas.

Ultimately, using his business savvy, Zani bought a 2002 Fountaine Pajot Belize 43 in the Canary Islands in October, sailed it with his father-in-law and friends to the Caribbean via the Cape Verde Islands, and, after his children were safely back for the last month of school that following May, sold the boat in Fort Lauderdale for 8 percent more than the original purchase price.

As was the case with the Zanis, Annice Kenan was not an experienced sailor.

“At first I thought, ‘Let’s pick the places we want to be and charter a boat, maybe a catamaran,’” she recalls. “Then I saw the look in Jesse’s eyes. That definitely wasn’t his dream.”

family matters
The Zanis sailed a Fountaine Pajot Belize 43, Fabuloso. Courtesy of the Zani Family

Smith owned a contemporary art gallery in Providence, and his first sailboat had been a 1930 International 6-Meter that he restored to original trim with sparkling varnish and custom bronze fittings. Like most sailors, to Smith, the classic, gaff-rigged Alden schooners looked like mystical ocean-touring craft. So when the traditional-style schooner Rebecca of Vineyard Haven, built in 2001, came on the market, he was hooked. After consulting with designer and builder Nat Benjamin of Gannon & Benjamin Marine Railway, on nearby Martha’s Vineyard, Smith undertook a complete overhaul of the rare 10-year-old wooden boat.

Smith and Kenan planned to share their cruising experience periodically with friends and family, and Rebecca‘s communal living spaces and varnished interior fit the bill. The stout schooner rig also proved useful on their delivery to the Caribbean from Rhode Island. Under reefed foresail and staysail alone, the crew reached along at 12 knots in a November gale, sipping tea and baking cookies.

If, on the spectrum of cruising boats, a boat could sit between a fiberglass catamaran and a wooden schooner, it would ­likely be Meridian, a Chuck Paine-designed 46-footer built in glass and Kevlar for offshore passagemaking. The Gonsalveses didn’t have the budget (or risk tolerance) to approach their cruise the way Smith or the Zanis did, but what they did have — professional sailing skills — landed them a perfect home for a season in the Caribbean.

Like Zani, at first Jeff Gonsalves searched for a seasonal charter of several months’ duration, but options reached the $80,000 mark for the season. “We were tipped off by a mutual friend that Steve Taylor would be interested,” he says. Taylor was a fellow New Bedford Yacht Club member and happened to be thinking about a cruise in the Caribbean.

“He loved the idea of making our dream of sailing with the kids a reality,” says Gonsalves. “Steve didn’t want to directly profit. He just wanted to come down and sail for a few weeks. I was named in the insurance, and the whole deal was a gentlemen’s verbal arrangement.”

As a former yacht captain, Gonsalves was well suited to care for Meridian. All Taylor asked was that he deliver the boat to and from the Caribbean and pay for fuel and any minor upgrades needed for the trip. A two-week vacation for Taylor and his family aboard the boat over the holidays gave the Gonsalveses the opportunity to step off and spend some time aboard Rebecca with the Smiths.

Read the rest of the story here.

Chris Museler has covered sailing as a journalist for 20 years. He regularly contributes to The New York Times, and his work, both in print and online, appears in a broad range of publications and media outlets. He lives in Portsmouth, Rhode Island, where he nurses a dwindling racing career and a growing family cruising schedule.


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