Sag Harbor's favorite coffee shop right on Main Street.

Founded in 1846, this is the longest continually operating hotel in the United States. A premiere wine list anchors its landmark restaurant on Main Street in Sag Harbor.

Located in Sagaponack (a short drive from both Sag Harbor and East Hampton), Wolffer is the East End's most commercially successful Vineyard. Enjoy a flight at the main Estate or the roadside Wine Stand.

A 2025 addition to the Hamptons map, Sagaponack General Store is a quaint (but high-end) market for sandwiches, coffee and housewares.

An upscale Italian trattoria with 3 large TVs playing sports, right on Newtown Lane in East Hampton.

Previously a private estate with a rare outdoor art collection amidst beautifully landscaped grounds and a koi pond, the property was bequeathed by its late owner and is now open to the public. The extraordinary collection includes famed modern artists, including Ai Wei Wei.

Built in 1845 as the private estate of whaling magnate Benjamin Huntting II, the estate is currently part Masonic Lodge and part whaling museum. Sag Harbor, once the port of entry to the United States during the 17th century, was a famed whaling town and was even featured in Moby Dick. The museum is right in town and a great stop if going on a stroll down Main Street.