The Journey

Handmade in England from Smythson's scuff-resistant Panama calfskin, with gold-stamped pockets for his passport and boarding pass.

Grooved aluminum carry-on that picks up dents and stories with every trip.

Bose's lightest, quietest pilot headset, with three noise-cancelling modes and Bluetooth. For the owner who still likes to take the controls.

A titanium pilot's smartwatch with moving maps, METARs and NEXRAD weather on the wrist, plus automatic flight logging.

The story of Riva's legendary mahogany speedboat, the icon of the Italian Riviera. A perfect gift for a man who keeps his boat in Italy.

The inflatable slide from the upper deck to the sea that turns a week aboard into the trip everyone talks about. FunAir builds them for superyachts like the 59-meter Helios.

TechRadar's best action camera of 2026. Waterproof to 10 meters with no case, so it can ride along on the SEABOB or eFoil and film in 5.3K.

TechRadar's best 360-degree camera. Captures everything around him in 8K, waterproof to 15 meters, so he can choose the best angle later.

The foam mat that unrolls off the swim platform for lounging, jumping and kids at play. Rated 4.8 stars by owners.

Styled like a mid-century speedboat by Hinckley, the Maine yacht builder. T3 gave it its 'Recommends' award and loved the included carbon fiber paddle. Made for calm-water cruising off the boat.

OutdoorGearLab's Editors' Choice for best all-around paddle board of 2026. Testers said it stayed easy to stand on even with waves from every direction. Inflatable, so it stows on board.

OutdoorGearLab's top pick for a solid (non-inflatable) board: smooth glide and easy turning for the serious paddler. Note that the model may be discontinued.

A 'floating private island' for swimming, sunning and launching paddleboards off the stern. Holds up to 2,100 lb, rated 4.8 stars across 320 owner reviews, and folds down for storage.

An inflatable frame with a deep, weighted mesh net that keeps jellyfish out while sea water flows through. Firm enough to sunbathe on, and it rolls up into the tender garage.

Tide and anchor-drag alerts, live depth and wind, and voice control of a Garmin chartplotter, all from his wrist. Dive-rated to 40 meters.

The unlined suede loafer you'll spot on every deck from Portofino to Capri. Handmade in Italy and featherlight on the foot.

The 100 most remarkable yachts ever built, hand-bound in Assouline's Ultimate Collection. Pairs with the Library books on cars and Formula 1.

Rolex's sailing watch, from the title sponsor of the Fastnet Race and other great offshore races. This reference is in 18k Everose gold on the Oysterflex strap.

From the official timekeeper of the 2027 America's Cup: a blue ceramic bezel with a 10-minute regatta countdown and a seconds hand weighted with the shape of the trophy.

The cult-classic sailing jacket you'll see on docks from Newport to Porto Cervo, updated with feedback from professional sailors. Waterproof and smart enough for the spectator boat or the yacht club bar.

For the man who races, not just watches: Helly Hansen's offshore jacket with a best-in-class hood. Yacht magazine called it 'an oilskin that makes no compromises.' Too warm for summer coastal sailing.

German marine binoculars with a built-in compass, waterproof to 10 meters and fog-proof, with a 30-year warranty. Follow every tack from the spectator boat.

The original leather boat shoe, with non-marking soles for the deck and rawhide laces. Rated 4.4 stars by owners, and right at home at any yacht club.

Named for the Italian Riviera harbor: a slim, elegant 40mm automatic with a discreet date, made for linen shirts and long lunches by the water.

The swim shorts of Saint-Tropez since 1971, in the brand's quick-drying fabric and famous prints. What he'll see on every deck from Capri to Mykonos.

The unlined suede loafer you'll spot on every deck from Portofino to Capri. Handmade in Italy and featherlight on the foot.

Pure linen in midnight blue, made in Portugal. Sleeves rolled for lunch at the beach club, buttoned down for dinner in the harbor.

The Italian folding sunglasses Steve McQueen made famous. They fold small enough for a jacket pocket on the tender to dinner.

Fine Panama straw with a grosgrain band, handmade in Italy by the hatmaker founded in 1857. Sun protection with Riviera elegance.

'The first Italian cologne': Sicilian citrus, lavender and rosemary in the Art Deco yellow bottle, unchanged since 1916. Summer in Italy in a bottle.

The tailored swim shorts that go from the beach club straight to lunch, with side adjusters instead of a drawstring. The brand's best-selling cut.

Unlined suede on a rope sole hand-made in Spain. The quiet, barefoot-feeling shoe for the harbor in Portofino, lunch in Capri and the deck in between.

Choose the places that are his: Capri, the Amalfi Coast, Monte Carlo, St. Tropez, Mykonos, the Greek Islands and more. A shelf of his summers.

The oldest trophy in international sport comes to Naples: the Louis Vuitton Cup from May 22 and the Match July 10-18, 2027, raced close to the seafront. VIP hospitality hasn't been announced, so book the hotel on the bay now; rates are already climbing.

The great offshore classic starts from Cowes on July 24, 2027 and finishes in Cherbourg, Normandy. The start off the Isle of Wight is one of sailing's great spectacles.

March 17-21, 2027: the world's most beautiful superyachts racing around St. Barth, with parties ashore every night. Book the villa and the table at the dock.

The world's largest sailing regatta, per Guinness: up to 2,689 boats on one start line in the Gulf of Trieste, every October, with a week of concerts and events in the city.