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Port Washington, NY
Port Washington sits on Manhasset Bay in Nassau County, and the adjacent Sands Point peninsula — home to former Gold Coast estates including one, Falaise, built for Harry F. Guggenheim — is widely cited alongside Great Neck as part of the real-world inspiration behind the mansion-lined shorelines of The Great Gatsby's fictional East and West Egg. The hamlet's downtown sits directly on the water, with a harborfront park and a Main Street built around the Long Island Rail Road terminus, giving Port Washington a genuinely walkable, marina-adjacent character that's distinct from the more purely residential feel of many nearby North Shore communities. That LIRR branch, the Port Washington Branch's namesake terminus, delivers commuters to Penn Station in roughly 35 to 40 minutes, and because the line terminates in Port Washington rather than continuing further east, the town functions as something of a natural gateway point between Nassau County's North Shore and the rest of Long Island. Sands Point Preserve, the former Guggenheim estate now operated as a Nassau County park, opens its Gold Coast-era mansion grounds and waterfront trails to the public, giving Port Washington residents direct access to a piece of the same Jazz Age estate landscape that helped define the area's literary and architectural legacy nearly a century ago.
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Southampton, NY
Southampton was settled by English colonists in 1640, making it one of the oldest English settlements in New York State, well over a century before the American Revolution — a founding history that gives it a genuinely different historical character from most of the rest of Long Island's suburban towns, most of which developed as commuter communities only in the 19th and 20th centuries. The village transformed through the late 19th and 20th centuries into one of the most prominent summer resort communities in the country, anchored today by sprawling oceanfront estates and a concentration of seasonal wealth that's made "the Hamptons" broadly, and Southampton specifically, a nationally recognized shorthand for high-end East Coast summer living. Unlike the rail-commuter suburbs closer to New York City, Southampton functions substantially as a seasonal and second-home market rather than a year-round bedroom community — the Long Island Rail Road does reach the village, but the roughly two-and-a-half to three-hour trip from Penn Station makes it impractical as a daily commute, reinforcing its identity as a destination rather than a straightforward suburb. The Southampton Historical Museum and the nearby Parrish Art Museum preserve and showcase the area's colonial history and its long-standing role as an artists' colony respectively, giving the town genuine cultural institutions layered on top of its reputation for beaches and seasonal wealth.
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