A Very Merry NYC Champagne Crawl: A Grown-Up Guide to Viewing 5th Avenue’s Holiday Windows

Stop 1: Grand Central & The Waldorf Astoria

Meet at Grand Central—the prettiest entry point to NYC is always beautifully dressed for the holidays, and this year’s Christmas Market is particularly strong. Walk to Peacock Alley at the newly renovated Waldorf Astoria for your first bottle of champagne. This iconic cocktail bar has expanded to full-service dining, but Queen Victoria’s ornate clock and Cole Porter’s Steinway piano still anchor the historic lounge, which dazzles with new life after nearly a decade of renovation. After champagne, head down 50th to see the tree at Rockefeller Center—you’ll pass St. Patrick’s Cathedral on your way.

Stop 2: Fifth Avenue Windows & The St. Regis

Work your way up Fifth Avenue from Rock Center, taking in the holiday windows as you go. The St. Regis at 55th had my favorite hotel lobby decorations this year—live red and white striped amaryllis among the tinsel and baubles. Settle into the King Cole Bar for your second bottle under the famous Maxfield Parrish mural. This bar is an icon for good reason, and the lobby alone is worth the visit during the holidays.

Stop 3: 57th Street fashion windows & The Four Seasons

Continue up Fifth to the Tiffany flagship at 57th—if you have time, I can arrange a personalized arts and culture tour of the building. Then turn right onto 57th Street, where some of my favorite windows live. The fashion houses here—Chanel, Louis Vuitton, and especially Dior—create windows with incredible storytelling and craftsmanship that often surpass the more famous Fifth Avenue displays. The Four Seasons’ Ty Bar makes a perfect third stop, right as you’re finishing the 57th Street stretch.

Stop 4: Bergdorf Goodman & The Plaza

Head back to Fifth Avenue for your grand finale at Bergdorf’s spectacular windows, which will lead you directly to The Plaza. I strategically saved this for last because The Plaza has the strictest door policy—officially limited to residents, hotel guests, and confirmed reservations. During the holiday season, they watch closely, so book your Plaza reservation first and work backward to time the rest of your afternoon. The over-the-top holiday decor here is the perfect ending to your crawl.

If you’re not embarking on the full champagne crawl, here are some solid spots for eats and drinks along the route:

• Cafe Grumpy in Grand Central: Coffee options in this area usually prioritize speed for commuters over quality, but Cafe Grumpy will make you a nice cup of pour-over in a ceramic mug.

• Monkey Bar: If you’re wondering where the characters from Mad Men would get into trouble in 2025, the answer is Monkey Bar. Think hearty portions, plush red booths, and a very famous cheeseburger.

• The Whitby Bar: When I scouted this route solo, I skipped the champagne but rewarded myself with a deliciously boozy Scofflaw Tea at The Whitby Bar. Tucked into a quiet stretch of 56th with a bit of an industrial exterior and a decidedly artsy vibe inside, The Whitby will make you feel like you’ve been transported downtown to SoHo in the very best way. When I asked the bartender if he could charge my phone, he directed me to the host stand where they have a beautiful cabinet full of chargers and gave me a coatcheck ticket while I left my phone with them—incredibly chic.

• The View: A little further west than these stops, Danny Meyer’s Union Square Hospitality Group is serving up NYC nostalgia inside of a rotating restaurant perched above Times Square. Wagyu pigs-in-a-blanket, a martini inspired by Katz’ Delicatessen, and a slice of New York Cheesecake might be just the thing to cap off your holiday stroll.