The Ultimate Upper East Side Saturday With Claire Distenfeld of Fivestory

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As one of New York's youngest entrepreneurs, Claire Distenfeld might have you thinking she's all business. After all, she is the owner of Fivestory, the department store-meets-boutique that refreshed the high end shopping scene. But when we joined Claire for a Saturday stroll through her Upper East Side neighborhood, we learned that she's more than just an expert in local sartorial taste.

She also knows where to get the best cocktail, the best gelato, and the best frites within steps of her boutique. The discerning taste and innovative eye she's demonstrated at Fivestory are just as helpful when she's showing you where you want to be, especially in the sophisticated stretches of Madison Avenue.

FIVESTORY: 18 East 69th Street

We met Claire at Fivestory, the dream land of any fashion fan that fuses the timeless allure of uptown polish with a fresh twist on trends and statement pieces. It's probably one of the only places you can feel the magic of a place like Bergdorf's and the intimacy of a small boutique, complete with the excitement of new labels and cult favorites to discover, from Delfina Delettrez and Edie Parker to Sabine G and Alexandre Birman. To put it another way, you'll do damage on your credit card here, and you'll love every second of it.

"To me, retail experiences are something that should be emotional and engaging," Claire says. "I wanted to take the customer on a journey, engulf the senses and allow them to escape the noisy, hectic city and just explore new designers, new music, and new smells in a comfortable and inviting, yet decadent environment."

LE CHARLOT: 19 East 69th Street

We can now vouch for the elegant people-watching you can engage in at the almost-too-lovely outdoor tables of Le Charlot. The pretty French bistro defines tradition with a simple menu of classic dishes done right—we took Claire's advice on the fresh hearts of palm and avocado salad, the mouthwatering Cajun mahi mahi, and the addictive frites.

"Authenticity is kind of my mantra in life," our guide explains. "[Le Charlot] has some of the best food on the Upper East Side and is extremely authentic. The owner is always sitting outside or around the table inside with his friends smoking and drinking wine, which to some sounds cliché, but to me is just adorable."

CREEL AND GOW: 131 East 70th Street

"My second mantra is discovery and exploration," Claire explains when she leads us to Creel and Gow. The small shop feels huge—global, even: curiosities, antiques, taxidermy, and more take you around the world in a few steps. It feels like you're in a museum, so it's even more thrilling when you remember you can invest in one of these rare treasures and take it home.

"I literally could spend hours and hours [here] conjuring up amazing life adventures that these items had," Claire says when we're face-to-face with the likes of a stuffed zebra and stunning peacocks. We especially love the hammered gold jewelry, antique French furniture, and an incredible Royal Brighton Pavilion model made from matchsticks.

SANT AMBROEUS: 1000 Madison Avenue

Deciding it's time for a gelato break (when is it not?), we head to classic uptown hangout Sant Ambroeus. We agree with Claire that every little detail of this place is aesthetically pleasing as its chocolate mousse is delicious.

"I grew up across the street from Saint Ambroeus my whole life, and was always obsessed with their wrapping paper and little cakes and uniforms and literally everything about the place," she says. It's definitely the perfect spot to unwind for a moment with an expertly crafted cappuccino and some pistachio ice cream, all with a decidedly more elegant feel than your average café.

Bemelmans Bar, 35 East 76th Street

What better way to end the day than sinking into a seat at Bemelmans with the perfect martini? The sounds of live jazz don't hurt, either, which Claire tells us happens every night from 5:30pm to 8:30pm. You instantly feel transported to the Art Deco days of the 1920s, or perhaps to a quintessential New York scene from a Woody Allen movie (speaking of which, Allen's band is one of the regular musical acts).

The decor doesn't hurt in making this spot special, either. "The wall murals are amazing and were done by illustrator Ludwig Bemelman, who conceived one of my favorite children's books, Madeline," Claire explains. Tucked into the regal Carlyle hotel, Bemelmans is easily one of the most sophisticated ways to relax and chat over cocktails.