"We took a motorboat to this amazing private island—it had a ladder built into the rocks so we were able to climb up and sightsee. But the best part was diving back down."
Swim trunks, $89, VENROY, venroy.com.au. Boxer briefs, $40 for four, TOMMY HILFIGER, macys.com.
"The head of the polo team at the resort gave me his best-looking, most athletic horse," he says. "Growing up I had a friend with a ranch and a few horses, so I had some experience riding. I was a little nervous in the beginning, but I got comfortable pretty fast."
Shirt, $98, POLO RALPH LAUREN, ralphlauren.com. Pants, $120, SEAN JOHN, macys.com. Dredoso T-shirt, $55, HUGO, hugoboss.com. Rookie socks, $12, RICHER POORER, richer-poorer.com. Hiking boots, $1,425, HERMÈS, hermes.com.
"The last time I rode a horse was 12 years ago. Sprinting across a polo field was freeing."
Syrma Fleece, $365, DIESEL BLACK GOLD, diesel.com. Braddom jeans, $298, DIESEL, diesel.com. Hiking boots, $1,425, HERMÈS, hermes.com.
"Jessie and I explored the old town on the property. The cobblestone streets and antique buildings were beautiful. I’ve never been to Italy, but it felt like an old Italian village."
Long-sleeve polo shirt, $795, BURBERRY PRORSUM, burberry.com. Pants, $168, TOMMY HILFIGER. Lace-up shoes, $625, TOD'S, tods.com.
Decker made a swift return to Denver (the hometown of his team at the time) thanks to an on-property airport that serves international JetBlue flights. Direct flights from New York JFK are also offered three days a week. For more details go to jetblue.com.
Robe, $6,750, TOM FORD, 212-359-0300. Pants, $495, EMPORIO ARMANI, armani.com. Boxer briefs, TOMMY HILFIGER. Hat, SUPREME, supremenewyork.com. Sunglasses, $375, GUCCI, solsticesunglasses.com. CEO Tech David Coulthard Edition watch, $925, TW STEEL, twsteel.com.
Groomer: Giselle Jimenez.