What you'll do
This 5-day itinerary is designed for couples who want to experience the romance and festive charm of New York City during the holidays without rushing from place to place. With a budget-friendly approach, you’ll enjoy iconic Christmas sights, enchanting strolls, cozy dining, and world-class art — all while saving your big splurge for a memorable Broadway night. Days are kept intentionally slower, allowing you to savor each moment together while still capturing the magic of the season.
From gazing at the Rockefeller Center tree, ice skating hand-in-hand, and admiring Fifth Avenue’s sparkling windows to exploring the city’s finest art collections and sipping cocktails in beautiful holiday bars, this itinerary balances romance with holiday cheer. With a hotel budget of under $400 a night, we’ve chosen a stylish mid-range property that offers comfort, convenience, and a romantic atmosphere.
Day 1
Arrival & Holiday Sparkle
Morning/Afternoon:
Arrive in NYC, check in at Walker Hotel Tribeca, drop bags.
Evening:
Head to Midtown to see the Rockefeller Center Christmas Tree, walk along Fifth Avenue holiday windows, and enjoy a cozy dinner at Lillie’s Victorian Establishment (lavish holiday décor, romantic atmosphere).
Walker Hotel Tribeca
hotel
Stylish boutique hotel in Tribeca
Walker Hotel Tribeca
A stylish micro-luxury property with 152 efficient guest rooms. The lobby doubles as a coworking/social hub with regular programming. Its location makes SoHo, Chinatown, and Tribeca easily walkable.
Perks for booking through me:
Complimentary daily breakfast
$50 food & beverage credit (min. 2-night stay)
Waived facility fee
Early check-in/late check-out
Room upgrades (when available)
To book this property with these perks, message me or email ryan.jones@fora.travel
Macy’s Herald Square Christmas Windows
Sightseeing
Iconic New York City department store
Though not on Fifth Avenue, Macy’s is iconic when it comes to holiday windows. As the world’s largest department store, Macy’s goes all out with elaborate themed displays tied to its Miracle on 34th Street fame. Pair your visit with a stop inside for Santaland, which requires advance reservations.
Saks Fifth Avenue Holiday Windows
Sightseeing
Luxury department store in NYC
The crown jewel of New York’s holiday windows, Saks Fifth Avenue unveils an extravagant theme each year, paired with a dazzling nightly light show across its entire façade. Expect long lines and heavy crowds at peak times, but the magic of the animated windows and synchronized music is worth it.
Bergdorf Goodman Holiday Windows
Sightseeing
Luxury department store in NYC
Just steps from Central Park, Bergdorf Goodman’s windows are known for being the most artistic and imaginative in the city. Each display is a meticulously crafted work of art, often with whimsical or couture-inspired themes. It’s a must-see for design and fashion lovers.
Rockefeller Center Christmas Tree
Sightseeing
Iconic Midtown plaza with shops & rink
The Rockefeller Center Christmas Tree is the ultimate symbol of the holidays in New York City and a must-see for any Christmas itinerary. Towering over the plaza, the tree is decorated with thousands of twinkling lights and crowned with a dazzling Swarovski star, creating one of the most photographed holiday backdrops in the world. While the area can be packed with visitors, timing is everything—arrive very early in the morning or late at night to enjoy the magic without shoulder-to-shoulder crowds. Pair your visit with a stroll past the nearby Fifth Avenue holiday windows or a skate on the Rockefeller Rink for the full Midtown holiday experience.