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Montauk is an intimate seaside hamlet set at the tip of Long Island’s South Fork. Sometimes referred to as “The End”, others would prefer to call it “The Beginning”. A fascinating historical area, Montauk is home to the oldest operating lighthouse in the country as well as the oldest working cattle ranch.

But Montauk offers more than just history. Home of a small community during the winter months, Montauk is a laid-back beach town that explodes during the summer months. Undeveloped beaches, parks, soaring cliffs overlooking rolling ocean waves, sandy beaches, and natural and fresh water ponds abound.

Montauk has something to offer everyone. With natural beauty so prominent many fall in love with Montauk from their first experience. Its no wonder Montauk continually attracts beach-goers, surfers and fishermen and water enthusiasts worldwide.

Amagansett, tucked between East Hampton and Montauk, is a simpler hamlet of the Hamptons, whose name is derived from the American Indian word meaning “place of good water,” which still holds true.

Just a stone’s throw from the ocean you will find an enclave of quintessential beach cottages, affectionately known as “the dune”. Along the prestigious Bluff Road original homesteads rise high above hedge grow for picture perfect ocean vistas.
North of the highway is the Bell estate area, which offers hilly landscapes and windy roads, Devon area, and Lazy Point – all with easy access to Gardiners Bay and Fresh Pond. Surely water enthusiasts find this town one that offers endless opportunities.

As designated historic district, the village of Amagansett is lined with boutiques, restaurants, coffee houses, galleries, a farmers markets, and night time entertainment.

Stroll down picturesque Main Street and immediately it is apparent why East Hampton Village is at the top of America’s Most Beautiful Main Streets list. Bookended by Town Pond and Hook Mill, one is reminded of the historic significance, as the windmill dates back to 1806. These distinctive facets of East Hampton conjure up images of a distant past and add a unique layer to the village charm.

To match this charm are sandy beaches that have been recognized as the world’s best. Within the estate area are famed Main Beach and Georgica, favorites for many looking to catch a sliver of sun and relaxation. On the north side of the town is the lush land of Northwest Woods providing the utmost in privacy.

Artists to corporate CEOs, Academy Award winning actors and directors, local carpenters, bankers and more, can’t help but fall in love with East Hampton. After all as John Howard Payne wrote “… be it ever so humble, there’s no place like home.”

Bridgehampton, a richly diverse town comprised up of farm fields, vineyards, horse farms, community and commerce, all leading easily to its pristine ocean beaches. Thought by many to be named because it bridged Southampton to East Hampton, Bridgehampton was actually named after the bridge over Sagg Pond, which was commissioned in 1686.

This is a village replete with fabulous shops, galleries, enticing restaurants, miles of sandy white ocean beaches, and of course, the famed Hampton Classic Horse Show and Bridgehampton Polo. One cannot forget the historic significance associated with Bridgehampton either, with the Bridgehampton Historical Society, founded in 1956, sitting right in the middle of town.

Regardless of your personal attraction to Bridgehampton, everyone who comes to this special section of the Hamptons agrees it’ is really a bridge to a special way of life.

The name Sagaponack, like so many others in the Hamptons, is derived from the Shinnecock Indian Nation and meant “land of the big ground nuts” or potatoes. Potato farming continued until the late 20th century but today those fields are home to huge estate. It is these estates that have ranked Sagaponack as the number one most expensive zip code.

Sagponack offers sublime natural beauty in its abundance of ponds along with miles white sandy ocean beaches. Open land prevails as well with farm field vistas, horse farms a plenty, and Wolfer Vineyard.

Originally just a stretch of open fields connecting Southampton to East Hampton, Sagaponack is now considered one of the smallest, yet wealthiest communities in the US. Just a small town with your basic needs, you have Southampton, Bridgehampton and Sag Harbor for entertainment and dinning. The rural abundance of Sagaponack is what makes this area so picture perfect.

A stroll through the Village of Sag Harbor allows a look at early colonist’s Capes, whaling captains’ Greek Revivals, and wealthy industrialists’ Victorians. In the late 1700’s, Sag Harbor was one of the busiest whaling ports, which peaked in the 1840s. Today visitors are still enchanted with the village’s historic significance, charming and century old architecture, quaint street and shops, and overall charm of yester year.

The maritime history is rooted at the foot of Main St., with the harbor and Long Wharf, which is now home to major yachts and sail boats, just as it was home to whaling vessels decades ago.

This rustic yet sophisticated hamlet offers a variety of old town charm with its local stops combined with fine dining restaurants, historical museums, and cultural events.