Portofino, St. Barts, Southeast Alaska, and Nantucket have distinctive dress codes. From the latest spring and summer menswear collections—which feature wind- and water-repellent jackets, linen and cashmere knits, and a boatload of seaworthy accessories—we chose ensembles that are perfect fits for these prime yachting destinations. And we offer suggestions on how to spend your time in port. —Laurie Kahle
On a peak above Portofino’s harbor, a medieval fortress offers breathtaking views of the Italian Riviera. Named for Montague Yeats Brown, the 19th-century British consul to Genoa who made the castle his home, the Castello Brown has remained as unspoiled as Portofino’s cobblestoned square and pastel-colored villas. —William Kissel
WHERE TO STAY
Saying the name of the hotel will get you past the carabinieri who police the checkpoint on the road to Hotel Splendido (+39.0185.267.801, www.hotelsplendido.com). The former monastery has been a jet-set gathering place since it was transformed into a hotel more than a century ago.
WHERE TO DINE
The intimate harborside Ristorante Puny (+39.0185.269.037), named for its owner, Luigi “Puny” Miroli, serves the fresh catch of the day as well as other Italian seafood and pasta specialties. Request a table outside, on the Piazzetta di Portofino.
WHAT TO SEE
In the water near San Fruttuoso—a medieval abbey located around the peninsula from the harbor—a bronze statue of Christ was submerged approximately 60 feet to create an underwater memorial to mariners who have perished at sea.
WHAT TO PACK
Pal Zileri Sartoriale linen sport coat, $2,295; Hermès Faubourg Express large suitcase with cotton Champ de Courses lining, $5,350 (medium case, $4,825, and small case, $3,025); Loro Piana linen scarf (special order only), $465; Bulgari bowling bag, $1,850; Acqua di Parma 50 ml eau de cologne, $71; Harrys of London leather driving moccasins, $375; Jan Leslie 18-karat gold and pink enamel starfish cuff links, $2,500; Corum red gold Admiral’s Cup watch, $29,500; Valentini cotton trousers, $345; Brunello Cucinelli cashmere sweater, $935; Pal Zileri Sartoriale linen knit shirt, $425; Martin Dingman belt, $325; Cartier Panthère de Cartier sunglasses, $620.
ST. BARTS, FRENCH WEST INDIES
Because Gustavia Harbor on Saint Barthélemy (better known as St. Barts) is too small to accommodate the massive cruise ships that patrol the Caribbean, the low-key ambience of this 8-square-mile island has been preserved. Impressive yachts fill the port’s moorings, which include 60 dockside berths along St. Barts’ sole city of Gustavia. In town, at the isle’s villas, and on its beaches, the St. Barts lifestyle is casually refined and convivially French. —Lori Bryan
WHERE TO STAY
St. Barts’ nearly 60-year-old Eden Rock Hotel (+590.5220.127.116.11) rests atop a rocky outcropping in St. Jean Bay and features the island’s premier restaurant for fine dining, On the Rocks.
HOW TO UNWIND
Ligne St. Barth (+590.518.104.22.168, www.lignestbarth.com) will dispatch to your yacht a massage therapist bearing potions containing sea sand and the Caribbean tiaré flower (a type of gardenia).
WHERE TO DINE
Take a picnic to the beach with a basket containing Champagne and saumon au beurre de basilic (salmon with basil-flavored butter) prepared by Maya’s Restaurant (+590.522.214.171.124).
WHAT TO PACK
Valextra German Frers travel bag, $3,480; Etro cotton paisley print polo, $320; Hermès cotton crepe polo, $640; Etro nylon swim trunks, $190; Brunello Cucinelli linen throw, $675; Schedoni backgammon set, $7,500; Hermès patinated calfskin Qeros sandals, $650; Blinde by OSA International copper beryllium sunglasses, $375; Martin Dingman nubuck belt with brushed silver hardware, $195, and leather belt, $325; Cartier Pasha Seatimer 18-karat yellow gold and rubber chronograph, $38,400; Etro cashmere V-neck sweater, $620; Paul & Shark linen shorts, $200. [Ralph Lauren Home Collection desk, $16,801, and chair, $4,883.]
SOUTHEST ALASKA, INSIDE PASSAGE
Do not be daunted by the frequent rain and summer temperatures that, on average, are below 60 degrees Fahrenheit. Cruising the Inside Passage offers an abundance of natural spectacles: fjords surrounded by snowy peaks, soaring eagles, and breaching humpback whales. Rise early, and you might spot brown bears foraging for food along the shoreline. —Jill Bobrow
WHAT TO DO
Picturesque Petersburg displays the Norwegian heritage of its residents, particularly during a Norwegian folk dance festival. The town is home to the Petersburg Marine Mammal Center (907.772.4170, www.psgmmc.org), which focuses on preserving humpback whales.
HOW TO UNWIND
At Sawyer Glaciers, at the end of Tracy Arm, you can hear (and see) blue icebergs calving and watch seals and their pups float by on ice floes. This pristine spot, accessible only by boat, is ideal for sea kayaking.
WHERE TO PLAY
Ketchikan resembles an old mining town. Nearby, you can hike and climb amid Sitka spruce, western hemlock, and cedar. Then satisfy your appetite with succulent salmon, king crab, and halibut wraps at Annabelle’s Famous Keg and Chowder House, located in the Gilmore Hotel (907.225.9423).
WHAT TO PACK
Lochcarron of Scotland merino wool/angora fisherman sweater, $575; Christian Roth handmade acetate sunglasses, $260; Santoni handmade calfskin Gazelle sneakers, $485; Berluti baby goatskin dopp kit, $450; Beretta flat-front cotton trousers, $195, and baseball cap, $19; Avon Celli gray quilted silk/cashmere vest, $1,325; Lochcarron of Scotland cashmere scarf, $695; Martin Dingman woven cotton double D-ring belt, $195; Loro Piana suede blouson jacket, $3,275;Berluti calfskin Bel Ami weekend bag, $4,150. [Ralph Lauren Home Channing Stag candelabra, $1,995, and St. Germainwoven end table, starting at $2,145;Antler chair from Linda Horn.]
In Moby-Dick, Herman Melville wrote of a Nantucket whaler,”The sea is his; he owns it, as Emperors own empires.” The island’s time as a whaling capital is long past, yet you still can feel like an admiral of the ocean when docking here to explore the inns, boutiques, and restaurants housed in the more than 800 pre-1840 structures in Nantucket Town. —Mike Nolan
WHERE TO SHOP
Scout for vintage Georg Jensen flatware, accessories, and jewelry at Alastair Crawford (508.228.3635, www.alastaircrawford.com), located on Old South Wharf, just off Nantucket Town’s cobblestoned Main Street.
WHAT TO DO
Admirers of Melville’s novel can peruse the Nantucket Whaling Museum’s (508.228.1894, www.nha.org) collections of whaling memorabilia—from scrimshaw and harpoons to a 46-foot-long sperm whale skeleton.
WHERE TO STAY & DINE
Topper’s (508.228.0145, www.wauwinet.com), one of New England’s best seafood restaurants, is located at the Wauwinet Inn, a Relais & Châteaux property (with a recently opened full-service spa) that straddles a narrow strand between Nantucket Harbor and the Atlantic.
WHAT TO PACK
Versace deerskin belt with gold buckle, $430; Tardini alligator belt with nickel buckle, $750; Isaia rope belt, $170, white cotton five-pocket trousers, $225, and navy long-sleeved cotton piqué shirt, $215; Jack of Spades stretch cotton twill Outlaw trousers, $155; Martin Dingman crocodile and calfskin loafers, $1,450; Valextra Big Necessaire leather dopp kit, $1,600; Truefitt & Hill blue horn shaving set, $300; Robert Marc Collection sunglasses, $375; Morgan Grays suede-lined, American buffalo duffel, $895, and coordinating amenities kit (on chair), $425; Canali quilted nylon and Wind Tech jacket, $1,095; Lochcarron of Scotland striped cotton long-sleeved polo, $275; Isaia light blue cashmere/silk sweater, $675, and cotton chambray pants, $375; Loro Piana orange cotton sweater, $395. [Ralph Lauren Home Devonshire crocodile wing chair, price available upon request.]
Acqua di Parma, +39.02.5522.881, www.acquadiparma.it
Avon Celli, distributed by Mach III, 212.702.0136, www.avoncelli.com
Beretta, 212.319.3235, www.beretta.com
Berluti, 212.439.6400, www.berluti.com
Blinde by OSA International, 949.360.1010, www.osainternational.com
Brunello Cucinelli, 212.627.9202, www.brunellocucinelli.it
Bulgari, 800.285.4274, www.bulgari.com
Canali, 310.270.4200, www.canali.it
Carpathia for Just Cuff Links, 847.816.0035, www.justcufflinks.com
Cartier, 212.446.3459, www.cartier.com
Christian Roth, 212.244.4967, www.christianroth.com
Corum, available at Wynn Las Vegas, 702.770.3520, www.corum.ch
Etro, 212.247.1200, www.etro.com
Harrys of London, 212.217.2745, www.harrysoflondon.com
Hermès, 212.751.3181, www.hermes.com
Isaia, 212.245.3733, www.isaia.it
Jack of Spades, 212.398.3861, www.jackofspades.com
Jan Leslie, 212.679.5337, www.janleslie.net
Linda Horn, 212.772.1122, www.lindahorn.com
Lochcarron of Scotland, 603.356.3369, www.lochcarron.com
Loro Piana, 212.980.7961, www.loropiana.com
Martin Dingman, 870.422.7151, www.martindingman.com
Morgan Grays, 866.531.6447, www.morgangrays.com
Pal Zileri, 212.751.8585, www.palzileri.com
Paul & Shark, 212.452.9868, www.paulshark.it
Ralph Lauren Home, 888.475.7674, www.ralphlaurenhome.com
Robert Marc Collection, 212.675.5200, www.robertmarc.com
Santoni, 212.794.3820, www.santonishoesusa.com
Schedoni, 305.529.9999, www.schedoni.com
Schmidli Backdrops, www.schmidli.com
Tardini, distributed by Yvonne Guest Showroom,212.586.1186, www.tardini-accessories.it
Truefitt & Hill, 312.714.1111, www.truefittandhill.com
Valentini, distributed by Glazer Imports, 212.582.0042
Valextra, 212.826.8900, www.valextra.it
Versace, 212.317.0224, www.versace.com