Our tour of the Hamptons starts in Southampton Village, at the western edge of the South Fork of Long Island.
One of the most prestigious communities on Long Island, Southampton is also the most residential, with tons of bars, restaurants, and luxury boutiques. Tree cover is dense, hiding the celebrity summer homes of celebrities like Rachael Ray, Howard Stern, George Soros, Kelly Ripa, and Tory Burch.
To the east of Southhampton is Bridgehampton, a smaller hamlet. It's a bit more low-key, but no less ritzy. The Hampton Classic horse show is held here every year.
Heading east over Sagaponack Pond, we land in Sagaponack, NY, which was named the most expensive small town in the country in 2010.
The East End's long heritage of family farming lives on in Sagaponack at the Foster Farm, which grows potatoes.
A tour of Sagaponack wouldn't be complete without a look at junk bond king Ira Rennert's gigantic house on the waterfront.
A 110,000-square-foot home on 63 acres, Rennert's Hamptons mansion is considered one of the largest occupied pieces of residential real estate in the US.
Based on his nearly $400,000 tax bill, the house could be worth up to $198 million dollars.
To the east of Sagaponack, on the border of East Hampton Village and Wainscott, this lagoon area enclave is known as Georgica Pond. Site of the famous Grey Gardens house, the community is steeped in high society history.
Famous homeowners around Georgica Pond include Steven Spielberg and Ronald Perelman, who throws the most legendary, star-studded parties at his 57-acre estate.
Cruising down the shoreline the mansions get more and more impressive.
Between 1998 and 1999, former President Bill Clinton vacationed in a summer house on Georgica Pond. It was his "summer White House." The Clinton family still gets out to the Hamptons just about every summer. Last year they rented a house in Amagansett.
Flying east from Georgica, the estates of East Hampton Village come into view. Not far from these princely properties is the Maidstone Golf Club, whose membership criteria (and pricing) is kept notoriously close to the vest.
