Palm Beach, Fla.
BACKSTORY: Oil Magnate Henry Morrison Flagler began speculating in Florida railroads in the 1880s. Enamored of Palm Beach Island, which sits between the Intracoastal Waterway and the Atlantic, he built a resort—the Palm Beach Inn—there. It became known as The Breakers in 1901, shortly before it burned down (twice) and was rebuilt.
BEST PLACE TO HANG OUT: Rented in advance, the white clapboard poolfront bungalows at each of the hotel’s three family-friendly pools keep you cool and entertained while the little ones play. If you’re more in the market for peace, quiet and frozen daiquiris, there’s a brand new adults-only pool with a pergola for shade.
CLAIM TO FAME: The guest list at this Italianate masterpiece reads like the New York Social Register. The Astors, Vanderbilts and Rockefellers were regulars. Andrew Carnegie and J.P. Morgan frequented the property, as did Henry James, who described the hotel as “burnished like a royal yacht, really immaculate and delightful.”
HOT DISH: You won’t need old money to eat at the high-concept HMF, but you will need money. Settle into an emerald easy chair and use the unreasonably long silverware to eat wild boar empanaditas and heirloom tomatoes with silky burrata cheese, followed by butterscotch panna cotta with rum-roasted pineapple.