If you’ve spent any length of time in New York City, it’s plausible that you’ve already grown weary of the kitsch, crowds, and surge pricing characteristic of it’s more popular tourist zones. Especially on blustery winter afternoons, you may be seeking a more mild, more authentic New York experience.

The Flatiron District is home to residents and office buildings, yes, but it’s also brimming with dining and shopping experiences that in and of themselves easily qualify as sightseeing. The itinerary below reveals the best way to spend a windy, chilly afternoon in New York – with cappuccino in-hand, ambling through one of city’s most interesting and entertaining neighborhoods. Bundle up and explore.

A Wintery Afternoon in New York's Flatiron District
Flatiron Building, 23rd & Broadway

Stop #1: Madison Square Park & The Flatiron Building

Madison Square Park, like Madison Avenue, that borders it to the West, is named after fourth U.S. President. James Madison. While always picturesque, it’s generally devoid of formal events and activity during the winter season. Outdoor art installations rotate throughout the year and weave around stretches of park benches. Currently on display is a piece by internationally-renowned artist Teresita Fernandez – a 500-foot-long sculpture built in 6 sections throughout the park. (It’s pretty impossible to miss.) If the weather is mild, it’s a great place to stop and map out the rest of your afternoon. The park is quite small and can be transversed in it’s entirety in under 10 minutes.

At the northeast corner of the park – E. 23rd Street and Broadway – is the Flatiron Building, unmistakable due to it’s nose-like shape darting out onto the sidewalk. Twenty-two stories tall and named for it’s resemblance to a cast-iron clothing iron, the building is a combination of residences and offices, and, sadly, outside visitors aren’t allowed in. Not to worry – it’s intricate exterior more than makes up for that.

Stop #2: Lunch

A Wintery Afternoon in New York's Flatiron District
Lunch at KOA

Some of the most famous chefs in the world have housed their restaurants in the Flatiron District. (Think Jean-Georges’ ABC Kitchen or Daniel Humm’s ElevenMadisonPark). I can’t tell you they’re not worth the price point, but, if you’re like me, these types of establishments are reserved for special occasions / winning the lottery. There’s absolutely no reason why you can’t get a delicious meal for less. Be sure to pace yourself, this itinerary is packed with opportunities to indulge so there’s no need to fill up right away.

If you’re in the mood for classic fare with incredible ambiance, head to Kat & Theo. The roaring fireplace well warm your fingers and toes and the simple lunch menu leaves indecision at the door. The small plates are delicious but my favorite continues to be the Quinoa Salad and Chicken Soup – $30 with tax and tip

If you’re like me and immediately associate wintery weather with a steamy bowl of ramen, then KOA is an obvious choice. Order the Chashu Ramen lunch set (it includes a small salad and a veggie egg roll), the pork belly literally melts in your mouth. #heaven – $20 with tax and tip

If you’re in budget mode, the best-tasting meal for your money can be found at Shake Shack – and I mean that almost universally. There are fewer institutions that are more New York than this and lucky for you, the chain’s flagship location is planted in Madison Square Park, the heart of the Flatiron District. Dig on into a Shack Burger (a cheeseburger with lettuce, tomato, and the famous “shack sauce”) and crinkle-cut french fries. – $10 with tax

Stop #3: Shopping on 5th Avenue

Necessary for walking off the onset of a food coma, there are some gems along this stretch of 5th Avenue for the mid-range shopper. A few of my favorite chains? Madewell (check out their drool-worthy Pinterest boards), the Nike Running store, and Zara. Though it never hurts to pop into the Victoria’s Secret, Sephora, and H&M that are also in close proximity. Go HAM, ladies. I love this stretch of 5th Avenue shopping because the stores are tucked in around office buildings and other commercial properties, which keeps crowding to a minimum.

Stop #4: Idlewild Bookstore

Climb a squeaky staircase to the second floor and you’ll find Idlewild Bookstore, home to travel guides, literature, and language books that cover destinations from all over the world. The obvious publications from the likes of Frommer’s, Lonely Planet, and Rick Steves are there, but so are the work of travel writers, backpackers, bloggers, and adventurers both famous and up-and-coming. If you fall in love with this place like I did, then you may want to inquire about brushing up on your foreign language of choice – Idlewild offers classes that teach Spanish, French, Italian and German.

Stop #5: Dough

Boutique donuts… what could possibly be more New York? Right next door to the Idlewild bookstore, Dough is impossible to resist. With signature flavor combinations inspired by the creator’s Latin American roots, patrons can and do enjoy a wide range of options – from the classic cinnamon sugar cake doughnut, to the trendy Chocolate and Sea Salt Caramel, to the exotic Hibiscus. Prices range from $3-$6 per doughnut, but don’t worry, they’re the size of your head.

Stop #6: Fishs Eddy

Swing back west and prepare for a jaw-dropping experience at Fishs Eddy – a veritable cornucopia of kitchen-ware. Named after a town in upstate New York, this place has something for every shopper and every style – serveware, flatware, glassware, and accessories both modern and vintage. Looking for a cup and saucer from a 19th century New York hotel dining room? It’s here. Need a quirky coffee mug and a vintage set of measuring spoons? They have it. For similarly unique finds, check out the nearby Whisk.

Stop #7: The Cellar at Beechers

At this point, you’ll need real sustenance. I get it. I promise that Beecher’s Cheese Shop and Cellar will wow you. Everyday happy hour is from 3-7 p.m. I recommend letting your server pick your wine and appetizer pairing, but if you’re skittish, you can’t go wrong with the house red and cheese plate –  $28 with tax and tip.

Stop #8: The Museum of Sex

Now that you’ve been properly lubricated, you’ll be ready to enjoy New York’s Museum of Sex which houses exhibits and information that, I hope, is fairly self-explanatory. Besides, it’s a museum so it qualifies as a cultural experience. This will not be enjoyed by the squeamish, the sheepish, or the shy. But if that’s not you (and I’m assuming it’s not) it’s an entertaining – and interactive – experience.

Stop #9: 230 Fifth

There’s no better way to end your perfect afternoon in the Flatiron District than with a cocktail and view – and 230 Fifth has both in spades. Despite it’s reputation as a tourist hotspot, it has arguably one of the best skyline views in all of New York City and keeps the rooftop open year-round. You can spend your wintery evening under a heat lamp and blanket – provided at no extra charge. Get there with enough time to watch the sky turn from blue, to pink, to black, and watch the lights burst to life all around you. You’ll pay for the view (here’s the cocktail menu) but, trust me, it’s worth it.

Still feeling sprite? Good for you, over-achiever! Here are a few….

More Things To Do in New York City’s Flatiron District

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