An island of wealth, Palm Beach is the winter home of celebrities, politicians, moguls and folks with supersized bank accounts. Life is different here, and a visit to this elite island city, where shiny Rolls- Royce cars and pampered pedigree pooches are everyday sights especially during season, can be otherworldly.

1  Parade of Homes

Take a dreamy drive along Billionaire’s Row, South Ocean Shore Drive, where the most exclusive and luxurious estate properties rise up between the Atlantic Ocean and the Intracoastal Waterway. Entrances marked with ornate gateposts, carved stone finials and towering privacy hedges lead to homes priced upward from $10 million, with some reaching $70 million and climbing.

2  The First Millionaire

Palm Beach has been synonymous with high society since 1896 when oil tycoon Henry Flagler built his first luxury hotel on this slender 18-mile- long barrier island and lured those who had the means to escape winter’s wrath. The home he built for his third bride was named Whitehall, house of marble. Meticulously preserved, it is now the Flagler Museum and tells the story of not only Flagler’s accomplishments, but of life on Palm Beach during the Gilded Age, through its exquisite architecture and historic furnishings.

3  The Ultimate Shopping Experience

Worth Avenue has the most prestigious shops in the world—Cartier, Tiffany & Co., Louis Vuitton, Gucci to name a few—brimming with elegant merchandise. No doubt there’s some serious designer and brand- name shopping going on here. But even if you don’t have super-deep pockets, you’ll still find a few stores on the avenue or hidden in the vias, little gardenlike passageways, where a purchase or two won’t break the bank.

4  The Scene

Enjoy a cocktail, lunch or dinner at any of the restaurants on or around Worth Avenue that cater to the nip-and-tuck clientele sporting saucer- size sunglasses. The go-to lunch spot for decades is Ta-Boo, where a mixed crowd of regulars and visitors can always be found, and for cocktails, the Leopard Lounge, in the Chesterfield boutique hotel, is another traditional venue famous for its catlike decor. But other spots like chef Clay Conley’s Buccan keep the culinary offerings fresh and the vibe modern.

5  The Grandest of the Grande Dames

Palm Beach’s most famous hotel is the Breakers, a historic treasure still operated by Henry Flagler’s heirs. To experience this opulent property, book a night or two. But if that’s not in your budget, then come for Sunday brunch in the cavernous Circle Room where 30-foot frescoed ceilings and murals of Tivoli Gardens add even more opulence to the experience. Don’t leave without looking up: Renaissance-style artwork adorns the Breakers arched ceilings along with elaborate crystal chandeliers.

6  Winter Feasting

Quickly rising to the top of Florida’s list for foodie festivals, the December Palm Beach Food & Wine Fest draws top talent like chefs Daniel Boulud, Scott Conant and David Burke along with Food Network celebs. Chef talks, high tea and four-course dinners are held at the Four Seasons, the Breakers and other venues around town, with the Grand Tasting on Worth Avenue the most delicious finale.

7  Walk the Avenue

A dapperly dressed Rick Rose leads the curious on a Historical Walking Tour of Worth Avenue every Wednesday. Not just a famous shopping street, Worth Avenue has a fascinating history and Rose’s animated tours spill all. Expect the scoop on how eccentric Addison Mizner became the signature architect of old Palm Beach and why Lilly Pulitzer set up shop here to sell her rainbow-colored resort wear.

8  The Beach

With a bustling social scene, one can almost forget the beach. But that would be a shame, so you’ll want to head to the public stretch right off of Worth Avenue by the big tower clock. It’s perfect for a stroll and of course, if you stay at any of the oceanfront hotels you have a swath of sand and crashing waves.

9  Hotel Hopping

Palm Beach doesn’t have a huge inventory of hotels, but what it does have is some of the classiest properties. Shoppers prefer boutique hotels steps from Worth Avenue: the Chesterfield, where they can enjoy a high tea after shopping, the Colony, with evening cabaret shows at the Royal Room, and the Brazilian Court, a private spot hidden by tropical foliage on a side street. Big resorts from the Breakers to the Four Seasons and the Eau Palm Beach Resort & Spa to the Omphoy Ocean Resort provide the cabana and beach experience.

10  Summer Bargains

When temperatures rise, seasonal residents shift to the Hamptons. And that’s when Palm Beach is especially appealing to those of us further down the wealth spectrum. The weather may be hot, but the Gulf Stream ushers in a breeze. Resorts offer deep discounts, and Worth Avenue stores slash prices. All are good reasons to go.