There are few places in the world that capture the spirit of the holidays quite like New York City in December. The moment the first wreaths appear along Fifth Avenue and the facades of Manhattan’s grand stores begin to shimmer under cascading lights, the city transforms into a scene of cinematic magic.

Nothing signals the start of the festive season more than a weekend spent here: strolling beneath the glittering garlands, the chill in the air softened by the glow of shop windows and the scent of roasted chestnuts drifting through the streets.

And nowhere embodies that magic better than Bergdorf Goodman. Each year, the legendary department store turns its windows into miniature works of art that elaborate tableaus of crystal, silk, and imagination. It’s an annual ritual for New Yorkers and visitors alike: to pause, gaze, and let the sparkle of the season unfold before you. Just across the street, the Cartier mansion gleams beneath a brilliant red ribbon of lights, the entire building wrapped like the world’s most glamorous gift. Together, they anchor the city’s most enchanting holiday block, where every twinkle seems to whisper Christmastime in New York!

Below is my ultimate guide to a holiday weekend in the city that balances timeless glamour with indulgent ease, celebrating the art of slowing down in a place that never does.

WHERE TO STAY

For the quintessential experience, choose a Midtown hotel steeped in character and history…the kind where marble floors echo with decades of whispered stories and the lobby glows beneath towering trees adorned with Baccarat ornaments.

The Plaza Hotel
A landmark of opulence overlooking Central Park, The Plaza is the definition of New York grandeur. Its soaring ceilings, gilded detailing, and famed Palm Court tea service make it a destination in itself. During the holidays, the lobby sparkles with a towering Christmas tree and the faint scent of pine mingling with Champagne from the bar.

The Carlyle, A Rosewood Hotel
A timeless Upper East Side sanctuary where Old New York elegance lives on. The Carlyle’s art-deco interiors and impeccable discretion have made it a favorite of presidents, artists, and icons alike. The warmth of the staff and the hushed intimacy of its hallways make you feel as though you’re part of a very refined secret.

The Peninsula New York
At the corner of Fifth Avenue and 55th Street, The Peninsula fuses classic design with contemporary sophistication. Its Pen Top Bar transforms into a holiday dreamscape, complete with a fully lit Christmas tree on the rooftop terrace, framed by panoramic views of the city’s skyline. From up here, the lights of Fifth Avenue shimmer below like a river of gold.

The St. Regis New York
Home to polished marble columns, impeccable service, and the original Bloody Mary, The St. Regis is the epitome of timeless glamour. During December, garlands wind up its grand staircase and live jazz hums softly from the King Cole Bar, creating a warmth that feels distinctly Manhattan.

EVENING DRINKS: WHERE THE LIGHTS ARE LOW AND THE MARTINIS COLD

There’s perhaps no greater New York luxury than a perfectly stirred martini or, if you’re me, a skinny margarita enjoyed in a storied hotel bar, where time slows, conversation lingers, and every drink feels cinematic.

Bemelmans Bar, The Carlyle
Walls hand-painted by Ludwig Bemelmans, the creator of Madeline, surround guests in golden whimsy while live music fills the air. The room is filled with those who understand that true New York glamour comes softly—one martini and jazz standard at a time.

Pen Top Bar & Terrace, The Peninsula
High above Fifth Avenue, this rooftop bar channels 1930s Shanghai elegance with mirrored accents, velvet seating, and panoramic views. In December, a glittering Christmas tree illuminates the terrace, glowing against the skyline as the city’s lights twinkle below. It’s one of the most atmospheric places to toast the season.

The Palm Court, The Plaza
Famed for afternoon tea, The Palm Court becomes even more enchanting at night. Beneath its stained-glass ceiling, order a Champagne cocktail or a Manhattan and take in the hum of conversations rising beneath the grand arches.

The Bar at Baccarat Hotel
A decadent blend of crimson velvet, mirrored walls, and crystal chandeliers. The martinis are ice-cold, served in hand-cut Baccarat glassware that refracts the light like jewels. It’s dramatic, intimate, and unmistakably Parisian in spirit—a sparkling refuge from the chill of the city streets.

Because truly, there’s nothing quite like a dark and sexy hotel bar in December.

WHERE TO DINE

With the city at its busiest, securing the right table is part of the thrill. These dining rooms capture the mood of the holidays—polished, glowing, and indulgently warm.

The Polo Bar
Ralph Lauren’s private club for the stylish set, tucked just off Fifth Avenue. Mahogany paneling, equestrian paintings, and tartan banquettes create the feeling of a Manhattan country house. The burger is legendary, but it’s the atmosphere—glamorous yet intimate—that makes dinner here feel like a privilege.

Gallagher’s Steakhouse
Since 1927, this Midtown institution has perfected the art of the classic New York steakhouse. The aging room lined with cuts of prime beef is iconic, and inside, the mood is all convivial energy, clinking glasses, and rich, old-school charm.

Monkey Bar
A Midtown favorite that blends history and playfulness with its mural-lined walls and glittering crowd. It’s the kind of place where you can linger for hours over a martini and a perfectly crisp schnitzel, watching New York characters drift in and out.

Each of these rooms offers its own slice of Manhattan tradition, an elegant reminder that dining in this city is as much about the setting as the cuisine.

SATURDAY: CURTAIN UP

No December weekend in New York is complete without a Broadway performance—or a night at Radio City Music Hall for the world-famous Christmas Spectacular starring the Rockettes. For nearly a century, the Rockettes have defined New York’s holiday season with their precision, glittering costumes, and choreography so sharp it feels like a snowflake come to life. The show is dazzlingly nostalgic and absolutely worth experiencing at least once.

A Saturday matinee on Broadway is the perfect complement, a way to slip into another kind of magic. Longtime classics like Wicked deliver comfort and grandeur, while newer productions such as the brilliantly irreverent Oh, Mary! prove that New York theater remains daring and unpredictable.

After the show, stop at L’Avenue at Saks. From its glass-lined dining room overlooking Rockefeller Center, sip an espresso martini as you watch skaters glide beneath the famous tree. It’s one of those moments that feels like living inside the very holiday scene you came to experience.

SUNDAY: FIFTH AVENUE AND THE ART OF HOLIDAY STROLLING

There is a rhythm to Fifth Avenue in December, from the murmur of carolers to the hum of shoppers and the glittering reflections in every window. Begin at 59th Street and make your way south, passing Tiffany & Co., Louis Vuitton, Dior, Prada, and Bergdorf Goodman, each adorned in their festive best.

Step inside Prada’s Fifth Avenue boutique to warm up and take in the season’s collections. The space feels like a jewel box of Italian modernism, all sleek marble and soft lighting. If you visit, ask for Arief, whose impeccable taste and service make every stop feel personal and unforgettable.

Then stop at Ralph’s Coffee inside the Ralph Lauren flagship for a peppermint mocha and a brief escape from the cold. Linger beneath the glow of Cartier’s iconic red-ribbon façade, the city’s most photographed holiday moment and one that never loses its magic.

These small rituals—walking, watching, and simply being—are what make a New York Christmas weekend unforgettable.

THE FINAL NOTE

A Christmas weekend in New York is not just a trip; it is a tradition. It is the hush of snow outside The Plaza’s doors, the clink of crystal at Bemelmans, and the glitter of Cartier’s bow shining down Fifth Avenue. It is a sensory celebration of luxury and nostalgia that can only exist here.

With thirty days until December, now is the time to reserve the rooms, tables, and moments that will define your holiday season.

Because in New York, the holidays don’t simply arrive. They shine.