New York City Itinerary – The Manual

Yesterday, I dove deep into some of my favorite places in the city to wine and dine like the locals in an elevated and indulgent way. Of course, an indulgent weekend in New York City is more than just eating and drinking (despite how much I wish that could be the case). You also need to find great places to lay your head and things to fill your time. I am not talking about the usual suspects. No, I am talking about the ways you can get an authentic, indulgent experience in New York City.

Here are my picks for where to stay and what to do for the man who wants to deeply indulge in the best New York has to offer.

Where to Stay 

You can throw a rock in any direction and hit a hotel, Airbnb, or hostel claiming to be the best in the city, offering a new and unique twist on the story of New York City. For me, these are the ones to spend your nights diving deep into the NYC feel.

The Ritz-Carlton New York, NoMad

The Ritz-Carlton New York, NoMad

The only North American Ritz-Carlton built from the ground up in over a decade, The Ritz-Carlton New York, NoMad is a sky-high sanctuary of urbane luxury. The sleek glass tower houses three gourmet restaurants created in partnership with José Andrés, the celebrated Spanish chef and humanitarian. Zaytinya specializes in mezze and the clean, citrusy fare of the Levant. The Bazaar is an old-school steakhouse with a Spanish accent. Don’t skip a nightcap paired with panoramic skyline views at Nubeluz, the penthouse lounge.

Guest suites have floor-to-ceiling windows in front of the beds. The views are as intoxicating as the aged Sherry at Bazaar Bar, the lobby watering hole. After dinner, pour a New York whiskey from the minibar and settle into the marble bathroom’s jacuzzi—big enough for two.

Thompson Central Park  

Thompson Central Park   / Hyatt

A Modernist perch in Midtown, Thompson Central Park is a quick stroll away from cultural landmarks like Central Park, Broadway, Carnegie Hall, and the Frick. 

The handsome rooms are quiet and private, with uninterrupted views of Central Park. Enjoy live music with dinner or pre-theater martinis at Parker’s, the flagship restaurant. After a big night on the town, stumble into Burger Joint, a graffiti-walled smashburger speakeasy behind a thick velvet curtain off the lobby.

Faena New York

Faena NYC / LOUIS XIII Cognac1

Opened in 2025, Faena New York is the city’s latest luxury fever dream. Designed by Danish starchitect Bjarke Ingels, it makes both design nerds and jet-setting bon vivants swoon. 

The dining matches the splendor of the decor. The Living Room must burn through more caviar in a night than a Romanov imperial banquet. Try it on the fish ‘n’ chips—fried fish topped with jet-black Beluga pearls. 

Mingle with the famous, rich, and beautiful at the lobby’s marble horseshoe bar. The exuberance is so contagious that you might feel tempted to order a pour of Louis XIII Rare Cask 42.1 Cognac—a spirit so rare it borders on myth. The amber nectar reposes in a black Baccarat crystal decanter, glassware that looks smuggled out of Versailles Palace. 

What to Do 

Like any city, there is an endless list of things to do to occupy your time in The Big Apple. However, NYC specifically has a feeling, a vibe, if you will. Forget the toursity things. Forget Times Square, Freedom Tower, and the Statue of Liberty. These things here are the day-to-day things that will give you the street-level NYC feel for a true New York City indulgence.

Iconic Timepieces

Image used with permission by copyright holder

High-end jewelry stores were once like semi-private parlors. You booked an appointment, received a glass of Champagne upon arrival, and admired the beautiful objects on display at your leisure. No crowds, no pressure, just a friendly tête-à-tête with the owner. Alas, nothing gold can stay—unless it’s a gold Rolex from Iconic Timepieces. 

In a sunlit showroom overlooking Bryant Park, owner Allon Zohar has assembled a collection of the world’s most coveted watches. Mechanical marvels from Patek Philippe, Cartier, and Audemars Piguet gleam in the cases, alongside the sort of microbrands serious collectors cross oceans to track down.

If you’re not ready to sell your firstborn son to acquire a watch, consider commissioning an engraving on your timepiece from Zohar. His skill at embellishing precious metal is enough to make Albrecht Dürer hang up his tools.

Barberino’s

Barberino’s

I find a good haircut as uplifting as a spa treatment—especially in a handsome barbershop with an espresso in hand. No one tends to the masculine mane quite like the Italians. Their technique diverges from the American school: no buzzers, just scissors and sprezzatura.

The boys at Barberino’s, a marbled temple of grooming in Midtown, are as slick with shears as Michelangelo was with his paintbrush. I left looking so sharp that I briefly considered moving to Milan and trying my hand at freelance modeling. The shop in front carries high-end Italian hair products and colognes.

Oh, Mary!

OH, MARY! / Emilio Madrid

In your course of gobbling and swilling across New York, make time for a dose of cultural vitamins. There are excellent museums across the nation, but no other American city rivals New York’s theater. 

If you’re going to see one play while in town, make it Oh, Mary! It’s deliriously funny, delightfully irreverent, and surprisingly informative about American history. I haven’t laughed so hard since watching Borat after taking an edible.  

Spin

SPIN / SPIN

I’m so viciously competitive at bar games that I’ve had to swear off billiards and darts. You don’t want me gripping a potential weapon in the heat of joie de combat, with Jim Beam egging me on. These days, I stick to ping-pong, provided the paddles are plastic and incapable of inflicting blunt-force trauma.

Spin, a cavernous subterranean lounge in Midtown, has enough ping-pong tables to outfit the entire campus of Zhengzhou University, China’s largest university system. When you’re not smacking aces like Richard Nixon facing off against Chairman Mao, try your hand at giant Jenga. After clinching glory at the tables, sink into a plush leather sofa with a margarita and the Korean fried chicken sandwich. 

The Stand 

The Stand

Among comedy clubs, The Stand’s standing is god-tier—a stage that has hosted the likes of Dave Chappelle, Bill Burr, Seinfeld, and countless other immortal jesters. It also quietly has one of New York City’s finest whiskey libraries, including some holy grail Scotches that could make Sotheby’s envious. 

Show up early, order a wood-fired pizza, and post up at the bar with a pour of Birthday Bourbon. Just don’t get so sloshed you start heckling the comics—it doesn’t end well.

Michael Andrews Bespoke

Michael Andrews

Is there anything in the world more New York than a custom suit made specifically for you? There are few cities in the world that are more iconic in the fashion world than New York City. And that means you can’t come here and not elevate your wardrobe. My favorite? Michael Andrews Bespoke. Great suits. Speakeasy vibes. And a true New York feel that would make Harvey Specter feel right at home.

Get a new suit, get an iconic luxury watch, and take in a Broadway show. If you don’t think this is New York enough, everyone else will.