Navigating the Upper Crust of the East End

Southampton

With a history dating back a few hundred years, Southampton is considered by many to be the social center of the Hamptons. Not only does it have seven miles of oceanfront with 11 beaches—including Cooper’s Beach, which was just named the No. 1 beach in the U.S.—its quaint town center offers a plethora of restaurants, shopping boutiques, and art galleries that visitors and locals alike flock to.

Dining

Even in the Hamptons, the ladies-who-lunch set can enjoy all that they have come to expect at Nello’s on the Upper East Side, thanks to Nello Summertimes (136 Main St.; 631.287.5500) serving up its signature inimitable Italian fare. If it’s a scene you’re craving, the space transforms into a thriving nightlife enclave after dark. A little more low-key is Savanna’s Southampton (268 Elm St.; 631.283.0202), which serves delectable eclectic cuisine (with a focus on local seafood) in inviting surroundings. The Driver’s Seat Restaurant (66 Jobs Lane; 631.283.6606) has one of the region’s longest histories; the building that is now the front bar room was built in 1888, and the restaurant first opened in 1960, albeit under different ownership. The current proprietors took over in 2005 and restored the facilities and updated the menu, which calls to guests looking for superior food in that coveted laid-back Hamptons environment.

Shopping

The allure of treasure hunting in Southampton comes from the unique boutiques and antique stores filled with goods you won’t often find elsewhere. For fashion, trend-setting beauties should pop into Theory (60 Jobs Lane; 631.287.5121) where model-types can find coveted jeans and pants with long and slim cuts, and Alice + Olivia (56 Jobs Lane; 631.204.0164), whose clothing appeals to the likes of Sarah Jessica Parker and Mena Suvari. This year, British luxury company Asprey delighted shoppers by opening a pop-up store, dubbed Asprey Summer Shoppe (45 Main St.; 631.488.4016). The concept for the boutique is a walled-in English garden, achieved through back-lit white lattice walls and antique stone garden tables. The 1,500-square-foot space is filled with signature sterling silver gifts, crystal, china, jewelry, leather goods, and iconic games such as backgammon.

Bridgehampton Polo

Once again, Bridgehampton Polo Club will host the Mercedes-Benz Polo Challenge at Blue Star Jets Field (849 Hayground Road, Bridgehampton). The season will kick off on July 24 and continue for the subsequent six Saturdays. As has come to be tradition, merely attending a match is not enough; the “hautest” ticket in town gives access to the exclusive VIP tent that will welcome the host of notables, celebrities, and media who flock to the field every year.

Sag Harbor

With an abundance of quaint charm, many people choose to call the two-square-mile Village of Sag Harbor their year-round home rather than just a seasonal address, so property is a hot commodity. While the real estate market dipped a bit in 2009, this year already saw a record-breaking $13.75 million sale close. The historic maritime village is on a port that has hosted everything from whaling boats of yesteryear to today’s grand yachts, which dock right on the edge of town. Sag Harbor Yacht Club (27 Bay St.; 631.725.0567) has one of the few marinas in the Hamptons equipped to handle vessels more than 200 feet in length, and Sag Harbor’s centrally located Malloy’s Waterfront Marina can handle boats up to 195 feet. (However, it only has 10 slips available for transients, so reservations are recommended during peak summer months.)