The most coveted reservation of the summer is not in Southampton. It sits at the end of a 150-year-old pier in Greenport. Still, this past weekend, Brooke Shields showed up there for lunch.

The Friendship Behind the Pier

Shields spent part of her weekend on the North Fork at Saylor Beach House. Specifically, the Mediterranean-inspired beach club sits at the iconic Claudio’s Marina. Taylor Dayne, the 80s pop icon and Grammy nominee, opened it this spring. She built it with Celeste Fierro, the STK co-founder and a pioneer of vibe dining.

Shields came to support Dayne, since the two are longtime friends. She rolled in with a group and settled in for a long lunch. Then she watched the Peconic Bay sunset do its thing.

Yes, There Is a Boat From Sag Harbor

Here is the part that should interest anyone summering on the South Fork. Saylor is not a far-flung field trip. It is a boat ride, after all.

Dayne and Fierro partnered with Yacht Hampton on a dock-to-dine service. The boats run Thursday through Sunday. They leave Sag Harbor between noon and 4 p.m. for a 40-minute, white-glove cruise across the bay. Round trip runs $75 a person. Add the $20 “Happy Saylor” picnic on board, and of course, you have officially arrived.

The Vibe, and the Lobster

The aesthetic is unapologetic European beach club. A giant yellow Adirondack chair guards the entrance. You walk in through an archway dripping with faux citrus. Inside, it is all yellow umbrellas and neutral linen couches. Dayne herself curates the soundtrack as music director. She treats every sunset like a headliner slot.

Of course, the menu earns the trip too. Specifically, think two-pound baked lobster, charred citrus shrimp skewers, and fried calamari. There are mezze boards for grazing and a raw bar pointed at the water. In fact, the name is a mashup of Dayne and Fierro. Of course it is.

Why the Shields Sighting Matters

What makes the Shields sighting more than a celebrity blip is what it signals. Initially, the North Fork played the Hamptons’ quieter, flannel-wearing cousin. But that story is over. When Brooke Shields gets on a boat to be somewhere, the geography of the summer has shifted. Meanwhile, the people who notice these things first are already booking the noon departure.

The smart money sees Greenport early. Everyone else will read about it in August.


Saylor Beach House sits at 111 Main St., Greenport. The Yacht Hampton boat leaves Sag Harbor Thursday through Sunday. The good tables go to people who plan ahead, and so do the good summers. Social Life covers the rooms worth being in before everyone else finds them. Want your brand, your face, or your next opening in front of the people who book the noon boat? Then the conversation starts at sociallifemagazine.com/contact.