Lake Montauk to Sag Harbor

It was a bright, sunny day for our circumnavigation of Gardiners Island enroute to Sag Harbor. We were able to sail some despite the winds being light and not always in our favor. Gardiners Island has 27 miles of shoreline and covers 3,300 acres (6 miles long and 3 miles wide). It is the oldest family estate in the United States. King Charles I granted the island to Lion Gardner in 1639 and it became the first English settlement in what is now New York State. It is the only real estate in the United States still held by a royal grant from the English crown. The island is privately owned by descendants of Lion Gardiner, Lord of the Manor. Only family members and their guests are allowed on the island. Private property - No Trespassing.

One of the guests on Gardiners Island was the pirate/privateer Captain William Kidd. He came to Gardiners to bury some treasure prior to his appearing in English courts in Boston where he hoped he could clear himself of all charges against him. The treasure with the exception of a large diamond retained by Lord Gardiner was sent to Boston as evidence in the trial. Captain Kidd was convicted, sent to London and hung.

Anchored with Some Big Toys in Sag Harbor Anchorage

The Gardiners have always been a wealthy and powerful family. In 1844, Julia Gardiner married President John Tyler. Her mother was not pleased as she felt her daughter was marrying below her station to someone not rich enough to marry a Gardiner.


Sag Harbor gave evidence that there are still many very wealthy people in the neighborhood of Gardiners Island. There was insufficient room in the inner harbor for all the mega-yachts visiting Sag Harbor. As a result, the outer harbor was occupied by a dozen or more vessels ranging between 60 and 100 feet in length. We dropped anchor a short distance from those closest to shore hoping the shallower water would keep the larger craft from anchoring too close to us. It also put us closer to the breakwater and side entrance to the harbor. We later discovered this put us in the traffic pattern of the tenders ferrying guests and crew to and from the mega-yachts and the inner harbor docks.

In 1789, Sag Harbor was declared the first official port upon entering the United States. More ships from foreign ports came into Sag Harbor than New York City during the earliest years of our country. The custom house in Sag Harbor collected huge sums to finance the US government.

Sag Harbor was also engaged in the whaling industry early in the 19th Century.