Now that you’ve had the opportunity for a lovely sober day out (well sober if you didn't go too crazy at the wineries!) Here’s where the real fun starts. These top five Long Island spots have the best of both worlds. With good old fashioned beach fun for the day, and a booming night life, you can’t really go wrong.  

5. Nautical Mile, Freeport
   Take a charter boat for the evening, aka a booze cruise. There are plenty of outdoor bars that line Woodcleft Canal. Among favorites are E.B Elliots and Hudson & McCoy. You can wine and dine, or just get wasted. For the more conservative crowd, The Mile’s got some lovely little art galleries and boutiques.

4. Long Beach
  Known for its great beaches and nightlife, Long Beach is lined by a two mile long boardwalk. It’s what a beach experience should be, surf, volley ball, and great bars.
As far as nightlife goes, Whale’s Tale and Minnesota’s are among favorites for partygoers.
 

3. Fire Island, Ocean Beach

   Because there are no roads, there are no cars.  Which means, yes, there is actually a place on Long Island that doesn't have the daunting possibility of unpredictable traffic.  You can take the ferry from Bayshore, and though the price for parking is pretty steep ($8 dollars on weekdays, $41 on weekends), just pack your car full of pals and demand for everyone to throw down.  There's the beach of course, spas, shopping, and restaurants that turn into bars and clubs come night.

2. Montauk

  It wouldn't be summer on Long Island without Montauk.  By the way, I can't help but think that town names like these contribute to our "Lawnguyland" accents (Montauk, Wantagh, Setauket. Think about it...)  Here you can find countless restaurants, bars, fishing, resorts, cheap motels, or just crash on the beach by a bonfire.  It's the closest you're going to get to a beach vacation around these parts, so enjoy it.   Ladies, the Surf's Lodge sounds like an ideal place to pick up some surfers.

1. The Hamptons

  This, of course, is number one; because, really, where else can you go on this little island where you can run into Sarah Jessica Parker or P. Diddy?  (Oh what I would give to run into SJP...)  You've got options here.  There's West Hampton, South Hampton (Great shopping), East Hampton (A bit on the ritzy side, but hey, there's a Tiffany's.)  Bridge, Sag Harbor, Hampton Bays (Home to the White House club.)  The famous Neptune Beach Club is located in East Quoge.  Don't feel threatened by that exclusive vibe.  If you fit in with it, that's great, but even if you don't...It's always fun to pretend to be rich for the day.