Locals rarely mingle with the summer set, so to kick back and shoot a game of pool or darts alongside your lifeguard or plumber, seek out a dive bar. In Sag Harbor, Murf's Back Street Tavern is the place to go for beer, sliders, and pizza. Just don't drink too many pints—the Sag police station is next door (64 Division St., Sag Harbor; 631-725-8355). In East Hampton's Springs neighborhood (a neighborhood largely inhabited by locals) Wolfie's Tavern pours an all-American selection of beers and entertains with satellite TV, a jukebox, and a horseshoe pit (15 Fort Pond Blvd., East Hampton; 631-329-4800). Dress down or you will stand out, and how.

Dune has returned for summer 2008, as has its A-list crowd. Expect a summer-long slew of sizzling weekends and watch for the likes of Jay-Z, Leonardo DiCaprio, and Sean Combs to make appearances. The 6,000-square-foot space will host such over-the-top events as "Kiss n Fly Saturdays," with New York DJs like Berrie, Rocktakon, and Jus Ske hitting the turntables. Dress to the nines to make the cut at the door.

Open Fridays and Saturdays at 11 pm.

If you have cash to burn and will gladly drop $20 for a Bellini and a chance to ogle playboys and dolled-up socialites such as Kate Moss and the Duchess of York, then Nello Summertimes just might be the place for you. George Washington once slept at this 17th-century inn; now it's an offshoot of Madison Avenue's Euro hot spot, where surprise DJs spin until the early morning hours. Expect a long wait to get in, poor service, questionable cooking, and plenty of attitude, but take our advice and go once to experience the decadence; there's nothing else like it in buttoned-up Southampton.

With its cabanas and 6,000-square-foot beach, Pink Elephant is like a small slice of St. Tropez deposited in Southampton (if you squint, the pool almost resembles the Mediterranean). A NASA engineer built the sound system, so come prepared to dance, and to drop $350 on a bottle of Grey Goose for the privilege (bottle service is required if you want to sit). During summer 2008, Pink Elephant will host a series of charity events, ranging from barbecues to guest performances by star DJs, with a percentage of the proceeds going to worthy causes such as DIFFA (Design Industries Foundation Fighting AIDS) and the Christopher and Dana Reeve Foundation. Expect the likes of Jessica Simpson, Petra Nemcova, and the cast of Gossip Girl to make an appearance.

Located in the center of sleepy Amagansett, the Stephen Talkhouse is the closest thing to a CBGB-style roadhouse as you're likely to find on the East End. Since opening in 1970, this live-music venue has attracted a talented roster of musicians—including Billy Joel and Paul Simon. The summer 2008 lineup includes Beth Orton on July 3 and Suzanne Vega on August 24. Grab a beer at the long bar, check out the autographed photographs and memorabilia papering the walls, and get ready to rock out. Buy tickets well in advance.