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Originally Posted by ExoticLocales
Can you tell me more about the Hamptons v. Palm Beach/Miami Beach, thanks.
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The east end of Long Island splits into a South Fork and a North Fork. The Hamptons are on the South Fork, which is a peninsula that has the Peconic Bays and Gardners Bay to the north and the Atlantic Ocean to the south.
There are two "Townships" in The Hamptons. There are multiple villages/hamlets/towns, but they are all either part of Southampton Township or part of East Hampton Township. Note that Southampton is one word and East Hampton is two words.
The town of Sag Harbor actually has parts in both townships, but if I'm being honest, Sag Harbor is not as upscale as many of the other towns. It is on the bay, but no part of the town reaches the ocean. The ocean is where most of the most upscale neighborhoods are located. The real estate agents use the term "south of the highway" and "north of the highway". The highway they are referring to is Rt 27, which is one lane in each direction through much of the Hamptons. Anything south of it, is considered to be near the ocean, and therefore, more expensive. While "north of the highway" is considered to be the opposite.
You don't want to be west of the Shinnecock Canal. Even though there are towns with the word "Hampton" there, like West Hampton and Hampton Bays, and they are technically part of Southampton Township, most Hamptons purists don't consider anything west of the Shinnecock Canal to be the "real Hamptons". And the prices reflect that.
The town of Southampton, not to be confused with the larger "township" of Southampton, is the first place you hit when you cross the Shinnecock Canal. This part of Southampton is industrial. It is the only part of the Hamptons where you will see fast food chains, 7-11, etc. You don't want to be too close to there. This may get confusing, but this is in the "town" of Southampton, which automatically puts it in the "township" of Southampton, but it is not in the "village" of Southampton. Anything between the Village of Southampton and the ocean is where you want to be looking.
So if you start there, and work your way east, along the ocean, you hit the hamlets/villages of Water Mill, Sagaponack, and Bridgehampton, which are all part of Southampton Township. The next town you hit is Wainscott, which is where East Hampton Township begins, then you hit East Hampton, and then Amagansett. If you are near the ocean in any of these places, you have large lots 1-5 acres, often surrounded by high hedgerows, with beautifully manicured landscapes, and of course, the ocean.
Once you pass Amagansett, there is a long stretch of road with the ocean on one side and the bay on the other. This leads to Montauk, which was a sleepy fishing town with cheap motels near the beach, but in the last 2 decades has turned into a hotspot for the twenty-something crowd. Those cheap motels still look like cheap motels, but now they charge $400 a night during the summer weekends, which, technically is still cheap for The Hamptons. The other towns dont really have many motels. It is mostly upscale Bed and Breakfasts.
The towns are quaint, founded in the 1600s by English settlers. There are many New England style beach houses. There are also a lot of farms and horse farms there, giving it The Hamptons a weird combination New England/Horse Country/Beach vibe. But somehow, it works.
The old money areas are mostly in the Village of Southampton and the Village of East Hampton. The village of East Hampton is more beautiful in my opinion, but there is more to do in the village of Southampton. In East Hampton, the roads to know are Lilly Pond Lane, and the surrounding roads, and Further Lane, which extends into Amagansett. In Southampton, Meadow Lane is my favorite, with many homes on the ocean, but with bay views on the other side. But you cant really go wrong with anything between the village of Southampton and the ocean.
As far as Palm Beach goes, I am more limited in my knowledge. My mother-in-law has a winter house there, so I do know the area somewhat. But my wife hates it there, so we don't go very often. Many of the people who spend their summers in The Hamptons, are the same people who spend their winters in Palm Beach. From my limited experience, anything in Palm Beach proper, is upscale. But once you go to surrounding areas, like West Palm Beach, it is a mixed bag, with upscale areas surrounded by middle class and downright seedy areas.
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