NYC Holiday Season: My Insider's Guide

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Aldany Diaz
Curated By

Aldany Diaz

  • New York City

  • City Travel

  • Weekend Getaways

  • Couples Travel

  • Solo Travel

  • Winter

Advisor - NYC Holiday Season: My Insider's Guide
Curator’s statement

I hate the cold. But I have a secret I need to share: New York City in December is my exception. Nothing puts me in a brighter mood than the electric energy of the holiday season here. From the iconic outdoor ice skating to tracking down the city’s most cozy and vibey cocktail bars, this trip feels like coming home. I’ve been here countless times, and you truly could visit a hundred times and still find new things to do. If you’re looking for the insider’s path to holiday magic, you’ve found it.

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Things to do in New York City

  • Rockefeller Center’s Tree & ice rink: You have to see the big tree—it’s the classic NYC holiday shot. Grab some hot cocoa and just chill for a bit, watching the ice skaters spin around. It’s the ultimate dose of holiday grandeur.

  • Window shopping on Fifth Avenue: Seriously, don’t miss the insane holiday window displays on Fifth Ave. Stick around for the Saks Light Show—they turn the whole building into a dazzling, synchronized spectacle!

  • Bryant Park’s Winter Village: This is my go-to for finding unique, actually cool gifts from local artisans. Plus, the ice rink here is way less chaotic and often has shorter lines than Rockefeller, making it the smarter choice for a quick skate.

  • Warming up in Grand Central: When the cold bites, duck inside this gorgeous terminal for the annual Holiday Fair. Even if you don’t buy anything, the sheer beauty of Grand Central’s architecture is worth the quick visit.

  • The Radio City Rockettes Show: This is a classic for a reason—the Rockettes’ Christmas Spectacular is truly unmatched. With a ton of showings all December, it’s super easy to snag a ticket and fit this dazzling show into your schedule.

Honorable mentions: When you leave Manhattan

  • Dyker Heights Lights (Brooklyn): Take a trip out to this neighborhood to see homes absolutely decked out in over-the-top, competitive holiday lights. It’s truly a sight—like a Christmas movie set in real life!

  • Lightscape at the Brooklyn Botanic Garden: For a more peaceful evening, stroll this mile-long path of beautiful, artistic light installations. It’s a gorgeous escape and a fantastic photo opportunity.

  • Holiday Train Show (The Bronx): Head up to the NY Botanical Garden to watch miniature trains chug past tiny versions of NYC landmarks. Everything is crafted from natural stuff—it’s totally charming and detailed.

Places to eat & drink in New York City

  • Guantanamera: Honestly, this is some of the best Cuban food I’ve ever had—it’s the perfect place to grab dinner before or after a Broadway show since it’s right there. Bonus: they often have fantastic live music to complete the experience!

  • Shy Shy: If you’re hanging out in Chelsea, this cute spot is a must-visit, especially if you love a good martini. For the bourbon drinkers out there, you absolutely have to try The Golden Finch—it’s phenomenal.

  • Jungle Bird: Just across the street from Shy Shy, this sister bar goes full tropical with a South East Asian twist. It’s got a super cool vibe, and their take on the classic “I’m Old Fashioned” cocktail is seriously next-level.

  • The Up & Up: Step into history at this intimate underground spot, which used to be the famous Gaslight Cafe (yes, the one from The Marvelous Mrs. Maisel!). Their cocktail menu features some of the most creative and unique drinks I’ve ever tasted.

  • 2 Bros. Pizza: Nothing screams New York like grabbing a quick, greasy slice of pizza on the go, and while you can score a good slice almost anywhere, 2 Bros. Pizza just happens to be my personal favorite. It’s cheap, fast, and always hits the spot.

Need to know

The holidays in NYC mean big crowds and big prices. My top tip: if you want to see a show or snag a nice dinner reservation, you have to book early, early, early. Don’t mess around!

Also, please remember the golden rule of the city: on escalators, stand on the right side! The left lane is for the people who are actually walking up (which is basically everyone running late). Keep that flow moving, and you’ll fit right in!

Aldany Diaz

Travel Advisor

Aldany Diaz

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