Summer in Southampton: Bluebloods & Greenbacks

There's no place quite like Southampton in the summertime. Sprawling green lawns are dotted with pink and blue hydrangea, tall privet hedges are trimmed to perfection, and the gabled rooflines of grand estates peek out from windswept dunes.

In town, chic new shops pop up for the season, flowers tumble out of window boxes, American flags wave in the breeze, and the smell of money fills the air.

Nowhere is that smell more overwhelming than in Southampton's estate section, home to the town's wealthy bluebloods. Whether it's tree-lined Halsey Neck Lane, oceanfront Gin Lane, or ultra-exclusive Meadow Lane, the estate section is where polite society reigns . . .

And where impolite society must resort to stalking in order to sneak some photographs, given that these folks have spent untold millions on their spectacular homes, only to obscure them from prying, ill-bred eyes like mine with all manner of hedges, gates, cameras, and intercoms.

Still, you didn't really think I was going to let a handful of trespassing citations and three nights in jail stop me, did you?

I'm kidding, of course. It was only one night in jail.

In all seriousness, though, you know you've abandoned all sense of dignity when you pull your leased Honda onto the shoulder on Gin Lane, jump out in your flip-flops, and start taking paparazzi shots of the Old Guard's houses while the drool runs down your chin.

The private estate at the end of this long driveway is called Fairlea. Fairlea Expensive, that is. Gravel ain't cheap, ya know.

I guess this is the high-class version of that old bumper sticker, "My Other Car is a Lamborghini."

There's one in every neighborhood: that guy who doesn't cut his grass, or leaves his Christmas lights up all year. In Southampton, it's the guy with the windmill in his yard.

Or the guy with the O.K. Corral security gate.

Or, worst of all, the poor sap who couldn't afford a separate entrance for the help. How gauche.

Behind this hedge is the venerable Meadow Club, which was established in the 1880s and is known for its meticulously maintained grass tennis courts. The Wasps, they'll use any excuse to hire a groundskeeper.

Like this poor guy, who was apparently hired to spend the day on his hands and knees in a mile-long gravel driveway, pulling the weeds out with a tweezer.

Or this one, who probably trained with Cirque du Soleil before pulling off this feat.

Despite being manicured to within an inch of its life, Southampton has a tiny bit of natural beauty, too.

Because it is a sin to have more money than God, Southampton also has its fair share of lovely churches.

The only thing a church needs more than an iron pot? A cannon.

I'd have taken some pictures of the church interiors, too, but I'm not a big fan of bursting into flames.

In town, Southampton is chock-full of tony shops where residents of the estate section can burn through some of the money that's falling out of their pockets.

It's a sad day when you discover that a town's library is way nicer than your house.

Even the old library.

I don't know what I'm pointing at here, but it's a pretty good bet that I can't afford whatever it is.

If a shopping spree hasn't relieved you of the burden of a full wallet, one of the best places to lighten the load is at Tutto Il Giorno, a restaurant whose name means "all day" in Italian, and also describes how long you'll want to spend in Tutto's gorgeous, Tuscan-style garden.

Angel and I started by sharing the burrata . . .

. . . and ended by thumb-wrestling over the last of the tomatoes.

Then it was on to the spaghetti for me, and the ravioli stuffed with bitter herbs, Parmigiano-Reggiano and sage sauce for Angel. It's a shame they both look so unappetizing.

Oh, you think I forgot something? Don't be silly.

The lovely decor was designed by fashion designer Donna Karan's equally-talented daughter, Gabby. My family is really talented, too, but there isn't much money in bickering.

Another spot we like in Southampton is Le Chef, a small bistro for the ladies-who-lunch crowd.

One of the things I love about Le Chef is that they give you a free bowl of soup with your lunch entree. Free! In Southampton! This day's soup was spring pea with basil. Did I mention it was free?

Angel ordered the local flounder, while I had one of my favorite sandwiches, the sundried tomato with goat cheese, cucumber, field greens, and basil-walnut dressing on 8-grain toast.

As I was photographing our entrees, one of the ladies a few tables over gasped loudly to her dining companions: "That young lady is taking a photograph . . . of her sandwich!!" Little did she know that the real shocker was how many vegetables I ate in one sitting. Between the soup and that sandwich, I might have actually eaten a day's worth of vegetables in a single day, instead of spreading it out over a month or two like I usually do.

Of course, not every place in Southampton caters to such highbrow tastes. This is the Golden Pear, a popular local mini-chain of cafes where you can grab a coffee, some breakfast, or a light lunch all year round.

The Golden Pear has the distinction of being one of the only restaurants within 100 miles of New York City where you can allow people to pour their own coffee without fear of someone getting trampled to death.

Of course, you might still be in danger of a stampede, given the lines that stretch out the door in the summer.

But at least you'll be trampled by the very well-heeled.

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