The perfect seaside town for history buffs, Sag Harbour is the most northern of the charming Hamptons towns, just across from idyllic looking Shelter Island. Once a whaling town, Sag Harbor’s simple, narrow streets disguise its historic importance - Sag Harbor used to be America’s first official port, and it’s name checked in Moby DIck! Most of the best places to stay in Sag Harbor offer wonderful views and a vintage feel.
Many of the best places to stay in Sag Harbor have some link to this town’s past as a whaling port. There are the converted mansions and port-side cottages, but some of the commercial whaling buildings have also been renovated into hotels. At one stage, around the turn of the 19th Century, Sag Harbor had more tons of square-rigged vessels engaged in commerce than New York City.
The wetlands and dunes surrounding Sag Harbor are largely protected, and are home to a surprising number of endangered species, and in the woodlands you might catch a glimpse of deer, muskrat, red foxes, coyote and woodchuck. And out beyond the sprawling stretches of sand you might spot dolphins or harbour porpoises.
Sag Harbor’s Whaling Museum is one of the town’s main sights, but there’s also a Whaler’s Church, several very fascinating cemeteries, the Jermain Library and the ‘Umbrella House’, which is the town’s oldest house, known to have housed British troops during the American Revolution.
There are also a couple of Yacht clubs.
Sag Harbor is also known for being the home of John Steinbeck.
Our pick of the best places to stay in Sag Harbor is a charming townhouse conversion right in its centre.
Sag Harbor (New York State)
1846 townhouse has eight rooms, a popular and lively restaurant and an award winning 85-page wine list. Rooms are comfortable with American antiques and private bathrooms. French classical is on the menu, and the staff are top notch. Hop on to the owners 75 foot John Trump houseboat for the day.