Setting Sail: Our First Adventure Aboard the New Catamaran

After completing their American Sailing Association (ASA) 101 and 103 certifications at Nanny Cay on Tortola, Conor and Kelly Malone took the decisive leap into liveaboard family voyaging. Stepping aboard their newly acquired Leopard 62 Custom catamaran, The Big Dog, the Idaho family began an intensive week-long shakedown cruise through the British Virgin Islands. Though the 62-foot blue water multihull had operated in charter service off and on since the previous December, this passage marked the first time the owners had spent more than an hour aboard her decks.

Joining Conor, Kelly, and their teenagers Finn and Maddie were Captain Terry and First Mate Ruth, seasoned professional mariners who had maintained and skippered the yacht since Hurricane Irma. With decades of combined Caribbean seamanship, the professional crew served as onboard mentors, guiding the family through the catamaran’s complex sail plans, deck hardware, and mechanical systems. As chronicled on Sailing Big Lost, the voyage transformed theoretical coursework into practical ocean seamanship across the Drake Channel and out to the coral reefs of Anegada.

Crossing the Channel to Norman Island

Leaving the docks of Nanny Cay Marina behind, The Big Dog motored south across the Sir Francis Drake Channel toward Norman Island. Dropping anchor outside The Bight for their inaugural night at sea, the family immersed themselves in the immediate rhythms of boat life. Underwater hull lights illuminated the clear Caribbean water, turning the surrounding sea into an aquarium where shrimp and small reef fish darted through the glow.

At dawn, the crew set off on a steep overland hike to the ridge of Norman Island, hoping to beat the midday sun. Recent tropical downpours had left the atmosphere thick with humidity, turning the rocky ascent into a grueling, sweat-drenched climb. Along the ridge trail, they navigated past native barrel cacti laden with bright magenta fruit before reaching the summit, where Finn deployed his drone to capture aerial perspectives of the fleet resting at anchor below.

Back aboard, Captain Terry initiated Conor into the daily disciplines of catamaran deck management. Standing beside the boom, Terry walked through the proper technique for opening and securing the mainsail stackpack zippers, demonstrating how to lash down running lines and halyards so they remain clear of the sail track and avoid flogging in offshore breezes.

Marina Cay Moorings and the Granite Labyrinth of The Baths

Setting sail northward, the catamaran picked up a mooring ball in the protected lee of Marina Cay, just off Beef Island. Positioned within sight of the airport runway lights and the distant silhouette of Virgin Gorda, the mooring field offered a tranquil anchorage reminiscent of maritime RV camping. AIS displays lit up with familiar cruising vessels as the family settled into their evening routine.

Before launching their dinghy excursions, Captain Terry delivered an essential safety briefing regarding Caribbean mooring tackle. He instructed the family never to grab or brush against the submerged mooring painter ropes while swimming, pointing out that colonies of stinging hydroids establish themselves on the fibers and deliver painful skin welts. Instead, the crew practiced diving cleanly beneath the lines whenever entering the water.

On Virgin Gorda, the family ventured into the natural wonder of The Baths, a mile-long shoreline dominated by massive weathered granite boulders piled along white sand beaches. Taking the Cathedral Pool Trail, they wound their way through dramatic rock grottos, squeezing through narrow tidal crevices and climbing wooden ladders surrounded by crystalline seawater pools. Escaping the midday crowds, they later retreated north to a quiet pocket beach outside Leverick Bay in North Sound, enjoying deep shell-strewn sand and calm swimming.

Thirteen Nautical Miles to Anegada

Departing Leverick Bay, The Big Dog set out across open water on a 13-nautical-mile passage north to Anegada. With consistent trade winds filling the sails, Conor took the helm to experience how the 62-foot catamaran handled under working sail, learning the tactile responsiveness of the twin rudders and tracking leeway across the rolling swell.

Unlike the volcanic peaks of Tortola and Virgin Gorda, Anegada is a flat limestone and coral atoll covering 15 square miles, rising to a maximum elevation of just 28 feet. Early Spanish explorers named it Tierra Anegada, or “drowned land,” because its low profile makes it almost invisible from the helm until close aboard. After picking up a mooring ball at Setting Point, the family went ashore for an evening dinner at The Wonky Dog.

Exploring the atoll by rental car the following morning required Conor to adapt quickly to left-hand traffic, navigating past roaming livestock and strict rental reminders noting thirty-dollar penalties for sand or smoking inside the vehicle. The island’s ubiquitous feral goats, while comical to visitors, pose an ongoing ecological threat by stripping native brush required to sustain the endangered Anegada rock iguana (Cyclura carinata bartschi).

At Loblolly Bay on the northern barrier reef, the family experienced world-class snorkeling across labyrinthine coral canyons and centuries-old encrusted iron anchors. During their reef swim, they encountered a juvenile lemon shark patrolling the sandy channels. Meanwhile, the reality of running a land-based enterprise from sea played out on the beach: Kelly sat sheltered from the trade winds, drafting a condominium purchase offer for an Idaho real estate client back in Sun Valley while Conor and the teenagers swam.

Vessel Forensics: Choosing the Leopard 62 Over the Privilège 585

Enjoying an early morning coffee on the flybridge while watching a reef shark cruise the shallow flats, Conor reflected on the rigorous boat search that had culminated in the purchase of The Big Dog. The family had narrowed their global yacht search down to just two proven blue water catamaran designs: the South African-built Leopard 62 Custom and the French-built Privilège 585.

Their search took them across Europe and the Caribbean, inspecting two Privilège 585 catamarans in Spain and France, as well as two Leopard 62 yachts in the USVI and BVI. The Privilège models had captivated them initially with handcrafted mahogany interiors and a signature central master stateroom nestled between the bridge deck hulls. However, several critical operational and financial realities shifted their decision:

• Financial and Currency Pressures: A strengthening Euro against the US Dollar increased acquisition and closing costs on European hulls, making transatlantic transfers financially unfavorable.
• Vessel Maintenance and History: One European Privilège had passed through numerous owners and required extensive structural and systems refits, while the other had served only as a local day sailer whose seller remained reluctant to negotiate.
• Crew Pedigree and Caribbean Location: The Big Dog had only two previous owners and came with an impeccable maintenance log overseen by Captain Terry and Ruth, who knew every wire, pump, and valve aboard.
• Flybridge Architecture: While lower helm stations keep crew close to the main deck, the Leopard 62 Custom flybridge provided 360-degree navigational visibility, cooling trade wind ventilation, and freed up the entire aft cockpit for an expansive, shaded family living salon.

Mast Inspection Aloft and Passage to Peter Island

Anchored in the sheltered waters of Great Harbour at Peter Island, Conor and Captain Terry tackled essential aloft rig maintenance before heading back to Nanny Cay. To ensure smooth sail handling under reefed conditions, the mainsail track required thorough cleaning and marine lubrication.

Securing himself into a heavy-duty bosun’s chair, Conor was winched up the yacht’s towering 85-foot mast. Ascending toward the masthead against a golden Caribbean sunset, Conor lubricated the car slides along the extrusion, checked standing rigging tangs, and inspected the masthead wind instruments and VHF antenna. The aloft vantage point provided a breathtaking panoramic view across the surrounding islands and anchorages.

As the shakedown week drew to a close, Maddie and Finn reflected candidly on the lifestyle transition. While both teenagers cherished the swimming, drone filming, and wildlife encounters, they recognized the psychological shifts required when swapping a spacious home in Idaho for the compact quarters of a cruising multihull. With the initial shakedown sail deemed a resounding success, the family prepared to return to Tortola for their upcoming PADI Open Water dive training, taking their next confident steps toward full-time circumnavigation.

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