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Two converging waves of luxury and hipness have created a traveller's sweet spot in this iconic New York neighbourhood

Customers dine at Shake Shack in Madison Square Park.

Oh, you're going to New York. Amazing!

Oh, you're staying in Midtown? Why?

The M-word has long seemed like the most verboten thing about New York for anyone but a certain type of bright-lights, wide-eyed tourist, or young families pulling their brood toward Olive Garden in Times Square. And recently, Trump Tower's new-found political symbolism – and associated security measures – has taken even more shine off the area's most iconic avenues.

"Oh, you want to meet all the way up there?" texted a friend who lives in Brooklyn. I could sense Aaron's sarcasm from a borough away, but the lingering dot-dot-dot ahead of his follow-up message told me there were mental gymnastics happening as he calculated how to meet my wife and me at our Midtown hotel.

"Dinner on us if you can make the arduous subway ride," I replied. Once he arrived – rather quickly on a Friday night, getting out at a 28th Street stop – Aaron had no problem choosing a great spot, vetted by his industry-insider sister. Less than an hour after his initial textual trepidation, we walked across Broadway and were catching up over too many unfiltered rice beers and massive family style plates at Hanjan (36 W 26th St., hanjan26.com), a modern interpretation of a traditional Korean traveller's tavern – a concept we apparently took literally. Somehow we managed to finish the dessert of black sesame ice cream and watermelon sorbet. We did pay, though Aaron returned the favour on his home turf before our trip was over.

The makeup of Midtown has grown ever fuzzier on its southern end, which, most importantly, has made the area great again. More luxury hoteliers are dipping below 34th Street to find new digs still in walking distance of Broadway's twinkling marquees. Meanwhile, food, drinks and shopping long associated with lower Manhattan's hipper enclaves have crept up the island. These two converging waves, just north of Madison Square Park, have created a traveller's sweet spot that's become my new favourite New York neighbourhood.

Eat

From an Italian ice to a sit-down meal, diners and shoppers can find essential Italian food at Eataly.

A real estate agent will sell you on this being NoMad. You can even stay at the NoMad hotel, the place that helped cement the area's hipster-approved name. I like to think of it more as just North of Our Two Favourite Food Institutions.

They've grown to be culinary stalwarts now, but we were still giddy to be in walking distance of both the original Eataly (200 5th Ave., eataly.com) and Shake Shack (Madison Avenue and East 23rd Street, shakeshack.com). As Toronto's Eataly outpost is still what seems like eons away from opening, Mario Batali's flagship mega-emporium of Italian food remains one of the few places in the world where adults get to feel like a kid in the candy store. That is, if you replace sugar and confection with salumi and pasta, and spread it across 50,000 square feet. And though Danny Meyer's burgers have taken over the United States and the world (except Canada, of course) since opening in Madison Square Park in 2004, there's that same kid-again feeling about queuing outside the shack that started it all.

That line was looking too long for adult Cliff and Maggie, though, we noted on our walk home from Korean dinner. But that's the beauty of the growing number of hotel options in the area. Instead of arriving from afar and feeling obliged to wait an hour for food (your incredulity at craving a burger after dinner is noted), we decided to wait out a quieter moment another day.

Save for one special trip to the East Village to eat at Gabrielle Hamilton's Prune, our lower Midtown address saved us from that New York tyranny of trying to muscle our way into the best restaurants at the worst times. The lamb burger at April Bloomfield's Breslin on the west side of 29th; Meyer's new pizza place Marta on the east side; the Korean fried chicken at Bonchon up Fifth; the spicy cumin lamb noodles at the Xi'an Famous Foods outpost down on East 23rd: We came, we ate, we waited nary a minute to do it.

The Breslin: 16 W 29th St.; thebreslin.com. Marta: 29 E 29th St.; martamanhattan.com. Bonchon Chicken: 325 5th Ave.; bonchon.com. Xi'an Famous Foods: 38 E 23rd St.; xianfoods.com.

Stay

The rooms at the James New York’s new NoMad location are spacious and as well-appointed as one would expect from a hospitality group that made its name in SoHo with a retro-modern aesthetic.

We weren't far from anything we desired while at the James New York's new NoMad location (rooms starting from $275 U.S.). Although still in a preview phase during renovations (there will be a flagship Scarpetta Italian restaurant on the ground floor when all is done) it served as a welcome home base. The rooms are spacious and as well-appointed as one would expect from a hospitality group that made its name in SoHo. The aesthetic is retro-modern: I couldn't keep my eyes off the raised marble sink in the bathroom, or the gold-plated minibar that anchored one corner.

The key is to ask for a room in the back of the building. You never expect one with a view in New York, unless you're paying for it, but the James has the pleasant distinction of having a very well-off next-door neighbour, where the amenities include a large courtyard that extends that property's rectangular footprint across an entire block. Snag one of these courtyard-facing rooms and you'll be treated to that rare Manhattan experience: not having that rich person's apartment window two feet from yours.

The location, on the corner of Madison and East 29th, also offers a reprieve from the city's more bustling dividing line one block over. It was Pride on the weekend of our stay, and the parade down Fifth Avenue was a glorious party to stumble upon returning home. We got to see Alexander Wang give out condoms while wearing a "Protect your Wang" T-shirt! But when we had enough, and had pocketed enough free condoms, it was a relief that the thumping bass of the parade was nowhere to be heard in our secluded room.

22 E 29th St.; jameshotels.com

Location, location, location

Pedestrians walk at the intersection of Broadway and 5th Avenue in midtown Manhattan.

When you can in New York: Walk. But when you can't, and traffic renders hailing a cab impossible, you brave the MTA. You'll never beat the overworked subway system that tests everyday citizens. But staying just off 28th Street, within walking distance of three different stops, feels like a weekend-getaway victory.

Elsewhere, subwaying always felt like a daring adventure of "how long must I spend underground before I faint?" The upper West and East Sides might as well be two different universes of subway; the chasm between Times Square and the cobblestone streets of downtown Manhattan can be measured in transfers and cars "holding." And Brooklyn? You better make like a hipster and pack your rolled up copy of The New Yorker for that hour-long haul. Those 28th Street stops are a happy equilibrium between all things New York, just close enough to our favourite places in more familiar neighbourhoods. But mostly, we stuck to our slice of Midtown.

Hidden gems

We've always loved walking and gawking at the high-end shopping of Fifth Avenue, including the Marimekko design flagship off Madison Square Park. But "buying" isn't usually a verb that befits our bank account when we're on Fifth. That is, until we discovered, around the corner from the James, the literally named 260 Sample Sale (260 5th Ave., 260samplesale.com).

Around since 1999, the retail space operates as a weekly pop-up selling different discounted luxury brands. The weekend of our trip, the store was deep into a J.Crew/Madewell sale. If you remember that scene from Friends, when Monica takes the crew to go bargain wedding-dress hunting and all hell breaks loose amongst rival brides-to-be – this was that sitcom chaos come to life. And it was thrilling, especially for Maggie, to find this past season's best shirts and dresses for 50 per cent off their retail price.

The Madison Square Park Shake Shack is where the chain got its start.

We walked out, delirious with that "that was so cheap!" feeling. How would we celebrate? By spending our new-found savings on burgers. We ambled down the street, our stomachs set on only one thing: Shake Shack. We arrived; you could count the number of people in line on one hand. Not 10 minutes later, we were stuffing our faces with Double Shackburgers.

The writer paid a reduced rate at The James New York - NoMad. It did not review or approve this article.