To say that Bob Giles enjoys cruising is an understatement. Ask him where he’s cruised aboard his Nordhavn 96, VivieRae, and he’ll list countries and islands representing nearly every letter of the alphabet. There’s Australia, the Bahamas, Bali, Costa Rica, Indonesia, Fiji, the Maldives, Panama, Tahiti, Thailand, Vanuatu and of course the United States—for starters. Amid the familiar names are unusual places like Mexico’s Revillagigedo Islands, which have the greatest concentration of tropical marine megafauna (think manta rays, hammerhead sharks and whale sharks) in North America.

Considering that Giles took delivery of VivieRae in 2017, the breadth of cruising is astounding. More astounding is that the yacht covered 21,000 nautical miles in just her first year. From being the guest of remote villagers at kava ceremonies to diving famous battleship wrecks, Giles has seen and done more since then than most people do in a lifetime. He continues to create itineraries in global regions that he and his wife have yet to explore, too.

“I’ve always loved to go places where most people won’t go,” he says. “The further from land and the more remote, the better I like it. As my wife says, I wasn’t born with the fear gene.”

Born to a boat-loving father, he grew up waterskiing, cruising and fishing in Texas before buying a 24-footer immediately upon college graduation. He worked six days a week for his father’s car dealership, taking his boat out on dive trips with paying customers on day seven to help defray his ownership costs.

In his 30s, he bought a Roughwater. “Most guys in their 30s would want something fast and flashy, but I wanted something that I could go long range aboard,” he says. He wasted no time, either, cruising from Lafayette, Louisiana, to the Virgin Islands. During the ensuing years, multiple boats followed, some of which he owned with friends.

When he was 58—he’s 69 now—Giles and one of those friends considered buying yet another boat, for exploring together. Unfortunately, his friend died before they could turn the idea into reality. The loss hit Giles hard. “I said, ‘I’m gonna buy a boat. I could be dead tomorrow, and you never know,’” he says.

He met a broker at the Palm Beach boat show and mentioned that he was seeking a 100- to 120-foot explorer. “There weren’t a lot of boats there,” Giles says, adding that the broker repeatedly recommended seeing a Nordhavn 86. “I kept saying, ‘It’s not big enough.’” But, by the end of the day, Giles hadn’t seen anything meeting his desires. The broker remained resolute. “He said, ‘Bob, let’s just walk on the boat. Just five minutes. If you don’t like it, we’ll leave.’ And I walked on the boat, and it felt much bigger than an 86. It had the range and was in incredible condition. It was only a few years old.”

Six months later, after cruising aboard a few days with his wife in Martha’s Vineyard, the 86 was his.

That VivieRae was quite the explorer, putting 20,000-plus nautical miles under her hull in a few years. When Nordhavn came out with a 96 a few years later, Giles signed on for Hull No. 3. He owned both yachts for about 10 months before selling the 86—and after taking a maiden voyage aboard the 96 from the Nordhavn shipyard in China to Bali, about 3,000 nautical miles.

Visits to nearly every Bahamian and Caribbean island followed, and then, his love of adventure persuaded him to cruise the world. In January 2021, VivieRae headed through the Panama Canal for the first of hundreds of adventures. Giles planned his first trip on a spreadsheet, noting miles and times to spend at each location. His captain thought the schedule was pretty aggressive, but Giles says “we executed it to the day.”

Not surprisingly, people often ask Giles what his favorite place is. “I can’t come up with one,” he says. “It’s always been three.” Namely, they’re Indonesia, for its extraordinary sea life; Vanuatu, for the friendliness of the villagers, who live the way their ancestors did centuries ago in the South Pacific; and the Tuamotu Islands of French Polynesia, for the ability to dive with a wall of hundreds of sharks at once.

What makes Indonesia all the more noteworthy is that it nearly resulted in the catastrophic loss in March 2023 of both VivieRae and her custom 38-foot tender, Ricochet.

VivieRae’s captain and crew were en route from Horn Island in northern Australia to Indonesia’s Raja Ampat archipelago, about an 800-nautical-mile trip, when Ricochet broke loose. When his captain called with the bad news, “I said, ‘You can’t just let it drift, y’all got to go try to get it.’”

The captain’s next call delivered more bad news. The towline had fouled VivieRae’s portside prop. Also, a fishing net wrapped around the starboard prop. VivieRae was in 200 feet of water just past Papua New Guinea. Winds were sustained at 40 knots and gusting to 55 knots, and seas were 10 to 15 feet off the port bow. Her anchor wasn’t holding well despite 300 feet of chain. A government vessel at a peninsula about 30 miles north offered to tow VivieRae into the lee of the land so the crew could free the portside prop, but conditions were just too rough to make it safely to the yacht’s position.

A few days passed, and with conditions still poor, Giles’ captain called to say an oil tanker was offering similar towing assistance. After the conversation, Giles realized it was 5 a.m. where the yacht was. Believing it was better for them to wait until daybreak and have the tanker approach on VivieRae’s leeward side, he texted his captain, asking him to call. “Well, the next call I get is, ‘Bob, the tanker just crashed into the side of the boat.’” The 600-foot vessel came up on her port side, and was forced into her by the wind and seas.

Remarkably, there was a silver lining: “It was cosmetic damage on the superstructure and some damage on the hull, but no structural damage to the boat whatsoever,” Giles says.

After the Royal Australian Navy sent a ship to evacuate VivieRae’s crew, Giles and his former captain flew to Indonesia to rescue the Nordhavn. By the time they arrived, the weather had broken. Even more luck was on their side, because the same naval ship took them out to the yacht, where they freed the propellers.

“Right after we get that done, we’re on the boat having lunch and my cellphone rings,” Giles says. “It’s the Australian Coast Guard, telling me that a pilot boat off Horn Island has spotted Ricochet.” She was 275 miles south of VivieRae. The captain of the pilot boat put Ricochet on a mooring buoy, where Giles later found her in “perfect condition.” Initially, they’d thought her tow eye had pulled out, but they learned that her pin and shackle weren’t connected properly.

“In hindsight it probably was a good thing,” Giles says. “I was rushing through the best part of the world because of the timing, trying to get to the Med by June.”

Giles certainly isn’t rushing anymore. Nor is he slowing down. With the Maldives and maybe the Red Sea in his sights the next several months, he’s still dreaming up bucket-list trips.

“Today, with the tools that are available with navigation and Google Earth, it’s very easy to plan a trip,” he says. “You can visit areas virtually before actually going there, and do some research on where you might want to go.”

All without even the slightest fear of the unknown. 

This article was originally published in the March 2024 issue.