My Perfect Day: New York City Holiday Edition

Independent/Jessica Mackin-Cipro

There’s nothing like a visit to New York City during the holiday season. The East End may be just as beautifully decorated — and the prize goes to Southampton for being the most festive — but for those who want to venture out of the area for some holiday cheer, I’ve created a “My Perfect Day” holiday edition filled with all the festive fun in the Big Apple.

When it comes to New York City during the holidays, I find it’s best to stick to the classics. If you don’t, you might find yourself waiting in a two-hour line for a “holiday themed lounge,” which is actually just a dive bar with extra holiday decorations and barely drinkable eggnog. You’ll give up shortly after a group of children start throwing snowballs at you from across the street. Yes, I am speaking from experience. Trust me when I say I’ve done the research. Here are some of my top holiday destinations:

Tiffany Blue Box Café

Located on the fourth floor of the New York City Flagship Tiffany & Co, the café serves American classics. If you can get a reservation, it’s definitely worth the visit. I went last year and, spoiler alert, there were multiple ladies dressed as Audrey Hepburn, a site worth seeing.

The Plaza Hotel

Independent/Jessica Mackin-Cipro

Every year I stop by The Plaza for a glass of champagne and some holiday cheer. It’s the quintessential New York holiday experience. You can even honor The Plaza’s most famous fictional resident with an Eloise-themed tea in The Palm Court.

Bergdorf Goodman Windows

Independent/Jessica Mackin-Cipro

After The Plaza, be sure to stop and gaze at the Bergdorf window displays, entitled “Bergdorf Goodies.” From giant candy canes to gingerbread houses, the window displays celebrate all things sweet, along with fantastical storytelling.

The Lodge At Gallow Green

The McKittrick Hotel presents its winter hideaway, The Lodge at Gallow Green. When the weather turns cold Gallow Green turns into a cozy mountainside escape on the hotel’s rooftop. Discover an indoor-outdoor ski cabin in a secluded forest of pine trees. Guests can warm up with a selection of hot drinks, potent handcrafted cocktails, and seasonally-inspired small plates by Executive Chef Pascal Le Seac’h.

Flour Shop

Amirah Kassem’s Flour Shop confections took New York by storm last year with the signature rainbow cake. For a holiday themed experience, stop by Flour Shop in Soho for a holiday mini cake.

Ice Skating

My choice rink would be Central Park’s Wollman Rink. Stop by the Central Park Carousel while you’re there.

Serendipity 3

The legendary restaurant and general store was founded in 1954 and later became the backdrop for the 2001 film Serendipity with John Cusack and Kate Beckinsale. I went the other day ended up sitting at the movie table and have never felt more special. Of course we ordered the famous Frrrozen Hot Chocolate.

Catch A Show

Although your initial reaction might be to avoid midtown this time of year, it’s worth the hustle and bustle to see The Rockettes at Radio City Music Hall, a Broadway play, or The Nutcracker at Lincoln Center.

The Tree

Go see the Rockefeller Center Christmas tree. My suggestion is to take the trip later at night when the crowds have died down. It’s worth fighting sleep to get the tree all (or partially) to yourself.

Moxy Times Square

Go for a drink and the pink festive scenery — who doesn’t love a pink Christmas tree? The Moxy also has an ice cream vending machine, a photo booth, a revolving carousel, and putt-putt golf. Need I say more?

Holiday Shopping:

There’s always holiday shopping to add the list. Here are a few stops you can make, during your day of festivities.

Swarovski Ornament

Independent/The Shops at Columbus Circle

Swarovski brings on the glam for its annual limited-edition ornament. This year’s handmade, mouth-blown globe is covered in crystals and features a delicate shooting star to symbolize wishes and dreams. Available at The Shops at Columbus Circle. ($99)

MarieBelle Chocolates

Independent/Sylvain Gaboury/© Patrick McMullan

The bean-to-bar chocolate company is wrapping its most decadent gourmet chocolates for the holidays at MarieBelle’s flagship store in Soho. MarieBelle artfully customizes luxury candy confections. Gift artisanal ganache, lavish truffles and bars, or the Aztec Hot Chocolate. Also available at MarieBelle at the Kitano Hotel in Midtown, and Cacao Market by MarieBelle in Brooklyn.

Alexis Bittar Bangle

Independent/Alexis Bittar

A bangle from the Alexis Bittar DYO Capsule Collection allows customers to design their own piece in thousands of color combinations for a style that is truly one-of-a-kind. Available at The Shops at Columbus Circle. ($130)

Gucci Books

Gucci Wooster Bookstore celebrates Soho’s creative heritage. It’s a Gucci bookstore curated by David Strettell of Dashwood Books. According to Vogue, the store holds about 2000, mostly avant-garde and photography themed, titles with a prices range from $20 to $1000. Visit

Sant Ambroeus Treats

Independent/Jessica Mackin-Cipro

Stop by Sant Ambroeus in Soho or the Upper East Side (my two favorite locations outside of Southampton) for some traditional Italian holiday products. Try the Panettone or cookie tin. And remember, shopping is always better while sipping a Sant Ambroeus latte. It’s been a long day, you deserve a little pick-me-up.

Sugarfina x Tipsy Elves

Independent/The Shops at Columbus Circle

Sugarfina has teamed up with Tipsy Elves to create this adorable candy version of the ugly Christmas sweater. Open the box to find a pop-up ugly sweater scene complete with sweet treats. Available at The Shops at Columbus Circle. ($30)

Nirvanna Designs


Nirvanna Designs knit winter accessories can be found at the Union Square Holiday Market (pictured here), as well as Holiday Shops at Bryant Park, Columbus Circle Holiday Market, and its Times Square Pop-Up Shop. The winter accessory brand is inspired by the knit crafts of the Himalayan people. Every item purchased helps support the economy of Nepal through its craft. Visit

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