Shephard doesn’t just take a bite out of his beloved Apple products, he basically owns the entire orchard. “I am such a nerd about it,” he says, noting that he totes his iPhone, iPad Pro, MacBook Air, Apple Watch and AirPods on his excursions. To monitor the whereabouts of all those collectables (and everything else), he uses his AirTags. “I keep them in all my bags,” he says.

For those long-haul overseas flights, “I definitely need my mask so I can sleep on the plane and be ready for the day ahead as soon as I land,” Shephard says. He singles out this one-size-fits-all mask from Tempur-Pedic, which contours perfectly to any face to achieve maximum sleep tranquility. And just to ensure excellent zzzs, Shephard also brings an accompanying Tempur-Pedic Neck Pillow.

On land, Shephard wears “nice and comfortable” Nike training shoes or flip-flops. On sea, he opts for classic Sperry boat shoes. Actually, it’s not an option. “We never wear shoes that you would wear on the street,” he says, adding that any inappropriate footwear is taken in the Parsifal gangway and stored. His go-to nautical shoes are designed to get wet and boast special traction. Plus, “The soles don’t mark up the decks.”

In his Dopp kit? Well, put it this way: “I don’t use a lot of fancy products,” he says. “I use a three-in-one shampoo for everything except toothpaste.” His no-fuss toiletries include a five-blade Gillette razor, Gillette gel shaving cream — he shaves every day — and a rechargeable Oral B toothbrush that sweeps away plaque via three modes. As he astutely notes, “manual just doesn’t cut it anymore!”

All smiles here: Shephard also packs his stainless steel foldable tripod to help him take steady selfies on his iPhone and capture all the beauty around him. “I love to take photos of my changing surroundings,” he says.

“I love photography and share a lot of my photos on my social media,” he says. (Check out his Instagram feed for proof!) Flash to this waterproof action camera, which offers double the average frame rate for smooth motion and pristine image quality. The captain recently snapped away in Cordoba, Spain, where he captured “a beautiful church that used to be a mosque. I love history.” 

Of course, those nifty cameras are useless if not properly charged. So Shephard never forgets his America to Europe and UK adapter — compatible in Germany, Italy, Greece, Iceland, Finland, Spain, Denmark, Israel and more. “I always need to power up something,” he explains.

Regardless of the destination or length of the trip, Shephard abides by an important travel law: “Don’t wait for bags.” So instead of checking luggage at the airport, he stuffs everything in two compact backpacks. The versatile Oakley Kitchen Sink features adjustable mesh-lined shoulder straps, a padded side-sleeve for access to his MacBook Pro, a bottom shoe department and “latches that look like parachute cords.” Its companion, the Bathroom Sink, is slightly smaller and holds his chargers and passport.

Because Shephard is a professional sun worshiper, he’s quite particular about his shades. “I need to protect my eyes,” he says. These sleek glasses from Maui Jim feature polarized lenses that block UV rays and cut down on glare. “These are really important when you’re sailing or boating because you can see the water and see what’s underneath the water.”