I just wrapped up my nearly annual pilgrimage to Manhattan. Like usual, I tried to time it during that perfect, dazzling window of time tucked between Thanksgiving and Christmas, when the city truly earns its title as the most glamorous place on earth (and somehow, again, SantaCon).

December in NYC isn’t about endurance; it’s about execution. The city’s cultural calendar is packed, the sidewalks are full, and the margin for error is slim. This 72-hour holiday blitz was built around one goal: maximum spectacle with minimal friction. When the plan is right, the city feels electric instead of exhausting.

Every trip I take is a strategic puzzle. For this NYC trip I wanted the lights, the history, the shows, and the food. And I wanted it without wasting time crushed in Times Square or Rockefeller Plaza. To make this happen, we focused on the essentials: Broadway, holiday glamour, and experiences that simply hit different in New York. True luxury here isn’t splurging indiscriminately; it’s moving seamlessly from a matinee curtain call to an exceptional dinner without ever feeling rushed.

The difference between an unforgettable holiday weekend and an expensive, crowded headache comes down to planning. Consider this your blueprint.

Day I — Conquering New York City Traffic (Friday Evening)

We executed a flawless late-afternoon landing. And here is my first, non-negotiable for NYC:

The Subway is Your Best Friend

Times Square Subway

TCT Tip: Skip car services in Manhattan (especially in December). I stopped using them years ago after spending two hours crawling ten miles through gridlock. The subway is faster, more predictable, and drops you exactly where you need to be. Bonus: it throws you straight into real New York energy the moment you arrive.

Our priority for Friday evening, after dropping our luggage, was a quiet, exceptional dinner away from the immediate Times Square crush. If I’m going to eat in New York, I want an experience I can’t easily replicate at home which is why I always go for French food when in New York.

We settled into a small, French place in Hell’s Kitchen. New York is one of the few places in the States where you can consistently find truly authentic, high-caliber French food, and I adore the formality and precision of it. It was the perfect, elegant counterpoint to our more recent culinary adventures (we ended up eating Trash Can Nachos in Vegas - thanks Guy Fieri).

Day II — Hamilton, Sushi and a metric ton of Santas (Saturday)

Saturday was designed for peak cultural immersion, with a perfectly calibrated mix of history, world-class theater, and a very strategic light viewing.

The Museum of Broadway

Museum of Broadway

We started the day with a deep dive into the industry that built this part of the city. The Museum of Broadway is a fascinating journey through the history of theater, moving chronologically from its birth to the present day. The museum features some incredible pieces from theater history. For example, some costumes from the legendary Ziegfeld Follies are over a century old and were famously found in a dressing room at the New Amsterdam Theatre (they are now on loan from Disney).

Fun Fact: When you visit the exhibit dedicated to The Phantom of the Opera, look closely. It’s reportedly decorated with exactly 13,917 crystals—the precise number of performances the show played up to its original closing date. That’s the kind of logistical dedication I can respect.

Hamilton Matinee

Hamilton

Next up: a matinee of Hamilton. For a show this iconic, this in-demand, and during the holidays, we booked our seats months ago. That’s the definitive way to guarantee a seamless, front-row experience. But, if you find yourself booking at the last minute (a situation I try to avoid, but, hey, life happens), here is a trick that can save your view and your wallet:

The Solo Ticket Trick: The single greatest secret for high-demand shows like Hamilton is to use the seating map to search only for a single ticket. The digital ticket matrix hates leaving one seat stranded, so it often releases premium single seats (such as those stuck between two groups of people) at reasonable prices. Search for one, then have your travel partner do the same nearby. You might not be next to each other, but you’ll both have a killer orchestra view for a fraction of the pair price. This trick is invaluable for those last minute seats.

The Early Dinner Pivot

This is the moment where we solve the two biggest Saturday challenges: securing an incredible dinner and avoiding the 7 PM tourist crush at the Rockefeller Tree.

1. Early Dinner

Omakase

After Hamilton, we executed a strategic early dinner. Many mid-afternoon theater-goers run into the problem of trying to find a decent, high-quality meal at 5:30 PM. We solved this by heading directly to Zama Omakase.

The concept of Omakase is the ultimate expression of trust in culinary expertise. The word itself means “I leave it up to you,” and it refers to a dining experience where you simply trust the chef to serve a selection of their best dishes, often determined by the freshest ingredients of the day. It’s the definition of adventure. Zama Omakase is a smart, more affordable entry point to high-quality Omakase near Midtown. Booking an early seating meant we had an intimate, precise, and utterly sublime experience where we could decompress and refuel before the evening chaos began. This is the luxury of timing: amazing food, no crowds.

2. The SantaCon Collision and The Strategic Retreat

As we left dinner and started heading toward the Rockefeller Center area, we ran right into it: SantaCon.

I swear, every time I plan a December trip, I somehow manage to perfectly time it with the annual organized chaos of thousands of people dressed as Santa, elves, and various holiday creatures out visiting the bars. (Honestly, I think I have a gravitational pull toward large, highly inebriated group events. It’s an adventure, I guess.)

Since we had already completed our early dinner, we had the freedom to execute a strategic retreat. We slipped into a nearby, upscale hotel bar (one of the few bars safe from the roving Santas) for a leisurely post-dinner cocktail. This was the critical moment of rest and recuperation, allowing the initial, frantic wave of Saturday evening revelers and the bulk of the Santa army to pass.

3. The Rockefeller Anti-Chaos Trick

Rockefeller Christmas Tree

Refreshed and refueled, we executed our final, strategic move of the night: the late-night Christmas tree viewing.

You cannot, I repeat, cannot simply wander into the Plaza at 7:00 PM on a Saturday. That is a tactical failure not to mention a mistake possibly leading to being crushed to death. To see the Tree and the lights like a local (or like someone who values her personal space), you must go late.

  • Arrive Late: We arrived closer to 10:00 PM. The Tree is lit daily until midnight. By that time, the massive early-evening crowds, the tour buses, and the day-trippers are largely dissipated. You can actually walk right up, take a breath, and enjoy the magic.
  • The Fifth Avenue Approach: Do not try to enter from the side streets. The most iconic, beautiful, and strategically sound view is from Fifth Avenue, looking west through the Channel Gardens. You get the horn-blowing angel sculptures lining the walkway, perfectly framing the Tree and the building behind it.
  • The Saks Two-for-One: After you get your classic shot, turn around and face Saks Fifth Avenue. Its façade is wrapped in a brilliant, synchronized music-and-light show that plays every 10 minutes from 5 PM to 11 PM. It’s a world-class spectacle, and one of my favorite parts of NYC at Christmas.

Day III — History, Heels, and Hilarity (Sunday)

Sunday was dedicated to the sheer, unadulterated, and historical glamour of the holidays.

The Department Store Grand Tour

We started with the world-famous window displays. This is not shopping; this is experiencing New York’s commitment to theatrical holiday art (okay, maybe a little bit of shopping). We started at Saks (to see the windows up close) and then headed to Macy’s Herald Square.

Macy's Wooden Escalator

Macy’s is a mandatory stop because it’s a living museum of retail history, and it’s one of the largest department stores in the world.

Fun Fact: Head deep into Macy’s (I recommend floors two through nine) and look for the escalators. The store still operates some of its original wooden escalators, made of oak and ash, that were installed nearly 100 years ago between 1920 and 1930. They are reportedly the last functioning wooden escalators in NYC, and they emit a unique, antique clacking sound as they carry you up. You’re not just shopping; you’re taking a ride on a piece of New York retail history.

But if you want to shop… Make it to the top floor! The flagship store dedicates a massive, glorious section of its upper levels to an unbelievable Christmas store, making it a spectacular way to wrap up your window-gazing tour and grab those last minute holiday gifts.

The Camp-Fabulous Matinee: Death Becomes Her

Death Becomes Her

Our Sunday afternoon saw us diving into the new musical, Death Becomes Her. Adapted from the cult-classic film, this show is pure high-gloss camp, sharp satire, and theatrical spectacle. The story of two vain rivals and a magical potion promising immortality is wickedly funny and perfectly modernized. It’s a riot of brilliant costume design (it won a Tony in 2025), wit, and sheer performance power. Other than the costumes (I really wish I could pull off that many sequins!) The highlight is the show’s stagecraft. They perfectly recreate the film’s most iconic, visually complex scene: the famous staircase fall. This stunt alone is executed using dancers and theatrical doubles and is an excellent example of how live theatre can still compete with movie magic.

Day IV: A Calculated Exit (Monday Morning)

Monday brought a 10:00 AM flight, which is far from the ideal window (I prefer to leave either very early or mid-day, after the morning commuter rush, to avoid the bulk of airport congestion). However, this timing was a tactical choice: we were eager to get back to the kittens and, more critically, to avoid the risk of getting stuck in the canyon on the drive home during peak rush hour or, worse, after a fresh snowstorm. Trips are great, but getting home feels amazing.

So with this in mind, we left earlier than necessary for our Subway ride to the airport to bypass the worst of the commuter crush, knowing that on the other side we could unwind in one of my other favorite places - the airport lounge! This let us have a nice relaxing breakfast (and my traditional pre-plane mimosa) at the airport before boarding our flight.

Another seamless, high-value, and utterly glamorous 72-hour adventure complete.

Final Thoughts

This trip proved what I already knew: New York City is a puzzle that, when solved correctly, yields enormous rewards. By prioritizing strategic transport (subway forever!), leveraging expert dining options, and using my anti-chaos protocols for the most crowded attractions, we achieved maximal glamour and zero stress. It required sequins and warm boots, just as I predicted.

Next up on the docket? Since I’m back in the mountains and they’re covered in that lovely, lovely powder I’m going to do some crucial, local research. Expect a deep-dive review on the new Deer Valley East Village and the fancy heated lift seats (I do love a cozy tushie). After that, it’s another mother-daughter adventure - this time to the slopes of Winter Park via the Winter Park Express (choochoo!). Stay tuned!