Long Island unfolds like a coastal dream winding through harbour towns, vineyard-covered hills, and over 193 kilometres of shoreline. When summer crowds fade, harvest and holiday seasons shine, with local food, wine and seaside charm keeping the island alive year-round.

Beacon Trail / Guiding Light

On the region’s South Fork in the hamlet of Montauk (often called “The End”), head to the top of historic Montauk Point Lighthouse for panoramic views of the Atlantic Ocean. On the region’s North Fork, Horton Point Lighthouse in Southold provides a bird’s-eye perspective of the Long Island Sound, home to seals and sea turtles.

Coastal Cuisine & Signature Sips

The culinary journey between lighthouses is as rich as the scenery, making every meal from seaside shack to a fine-dining experience part of the adventure. In Amagansett, The Lobster Roll has been a local staple since the 1960s, serving buttery lobster sandwiches in a casual setting. Greenport’s Frisky Oyster delivers sea-to-table favourites like lobster quesadillas and Crab Louis that pair with local wines. North Fork Table & Inn, an island institution led by a MICHELIN-starred chef, highlights the island’s waterways and vineyards, with a few elegant rooms for overnight stays.

Sip on a pint of handcrafted pumpkin cider at Riverhead Ciderhouse or grab a flight of pumpkin beer at Tap Room. Boasting over 60 wineries, savour small-batch wines with sweeping bluff views at Kontokosta, or raise a glass at crowd-pleaser Wölffer Estate, or cosy up by the fire pit at Osprey’s Dominion with award-winning pours.