Long Island extends for more than 100 miles from Brooklyn and Queens in New York City all the way to Montauk on the far east end. The island protects the coasts of mainland New York and Connecticut from the open Atlantic Ocean, and the resulting 10-20 mile wide sound between the mainland and Long Island features flat water and pastoral scenery.

Sag Harbor wildlife

That scenery along the coast of Long Island Sound belies the population density of the island itself, which is home to almost 8 million people. Of course many of those live in New York City itself, but even excluding those city-folk there are still almost 3 million residents of Long Island.

Old fashioned glazed donut from Grindstone in Sag Harbor

With its proximity to NYC, the financial capital of world, Long Island Sound was a playground for the rich and famous, and it remains that today. After stops along Long Island’s “Gold Coast” in Oyster Bay (home of Billy Joel) and Port Jefferson, Madrone entered the rarified air of the Hamptons at Sag Harbor.

One of the numerous Long Island mansions

Mansions dotted the shore, and Madrone was dwarfed by a steady stream of superyachts – one night we counted 23 boats larger than 100′ in length around us. Multi-million dollar day boats streamed in and out of the harbor, and Madrone was surely embarrased that her crew didn’t fit in by wearing uniforms.

New friends- Coco, Annette and Sharon

But everywhere we go, we meet great people. In Sag Harbor, we got some helpful local tips from Therese and Cody aboard S/V Vinyasa, who are raising their new baby while refilling the cruising kitty by working for the summer aboard charter yachts. And we had a great evening aboard the beautiful motoryacht Cloud Nine with Annette and Sharon, while their dog Coco found a new best friend in Angie.

Annette’s beautiful Sabre, Cloud Nine