Rule No. 1: Don't pack light. Pack smart.
Think of it as the Gilligan's Island approach to travel. You think those people packed light for their three-hour tour? No. They packed knowing that stuff happens when you're on the road and that it's always better to have extra than to need more. So think before filling your suitcase. Anticipate. And while you're at it, invest in a good piece of luggage. Something like this soft, water-resistant trunk, created by Argentine yacht designer Germán Frers with a ship's tight quarters in mind. (It unzips every which way to reveal a raft of compartmentalizing bags that separate your wares and maximize storage space.) Because you never know what you'll need if you're stranded -- on an island, aboard a boat, in a parasailing harness. You just never know.
Leather-trimmed canvas trunk ($4,790) designed by Germán Frers for Valextra; flip-flops ($108) by Coach; nylon swim trunks ($890) by Tom Ford.
Rule No. 2: There is no shame in festive swimwear.Because bright colors and bold prints are the best way to catch a woman's eye. Or, when stuck in a riptide, the lifeguard's eye.
Clockwise from top left: Nylon swim trunks by Tommy Hilfiger ($55); Sundek ($120); Vilebrequin ($205); Nautica ($45).
Rule No. 3: There's no one right way to dress up while dressing down.At left: Three-button wool blazer ($525) by J. Press; cotton polo shirt ($75) by Lacoste; cotton shorts ($70) by Brooks Brothers; leather loafers ($90) by Rockport.
Cotton shirt ($225) by Burberry
Rule No. 4: No socks with deck shoes. Bare ankles only, please.
Rule No. 5: One thing everyone can agree on is the navy-blue blazer.
And Scarlett Johansson. We can all agree on her, too.
Rule No. 6: Keep your favorite watch away from the water.
Do you have any idea what it feels like to watch an expensive timepiece sink to the bottom of a large body of water? Do you want to know? Right.
Stainless-steel Oyster Perpetual GMT-Master II watch ($6,825) by Rolex.
Rule No. 7: When at sea, never question the authority of the man in the hat.
Rule No. 8: Trust in the windbreaker.
If the weather turns and you're stuck outside, nothing is more useful than a nylon jacket with a hood. Except a roof.
Nylon windbreaker ($135) by Perry Ellis.
Rule No. 9: Aviator sunglasses are the Learjets of style.
Newer styles and shapes come and go, but you can't beat classic aviators (e.g., this pair in lightweight titanium, worn by the pilots at NetJets) for sheer, effortless cool.
Sunglasses ($325) by Modo for NetJets.
Rule No. 10: Sailing watches have the best names.
Top to bottom: Stainless-steel Aquaracer Calibre S watch ($2,600) by Tag Heuer. Stainless-steel Velatura Yachting Timer watch ($875) by Seiko. NST Chronograph watch ($225) by Nautica.
