The Ultimate 5-Day New York City Itinerary for December (Holiday Magic & Hidden Gems)

New York City lit up for the holidays – a magical December experience

New York City during the holidays is pure magic. With twinkling lights, skating rinks under skyscrapers, and the smell of roasted chestnuts in the air — this 5-day itinerary gives you the perfect December experience filled with iconic spots, local tips, and hidden gems. Whether you're planning a romantic escape, a family adventure, or your first time in the Big Apple, this curated itinerary ensures you capture the best of the city's holiday magic without the overwhelm.

Day 1: Downtown & Holiday Vibes

• Morning: Free Staten Island Ferry past Statue of Liberty, then explore Battery Park, SeaGlass Carousel, and the Charging Bull
• Midday: Reflect at the 9/11 Memorial, explore the Oculus, and take in city views from One World Observatory
• Afternoon: Visit Grand Central Terminal and Winter Village at Bryant Park for ice skating & shopping
• Evening: Try Carmine's or Ellen's Stardust Diner — or catch the Radio City Christmas Spectacular for peak holiday vibes!

Day 2: Midtown Magic & Fifth Avenue

• Morning: Visit FAO Schwarz and marvel at Fifth Avenue's famous holiday window displays
• Lunch: Options include Serendipity 3 (book ahead), The Halal Guys, or The Plaza Food Hall
• Afternoon: Summit One Vanderbilt for breathtaking views, then explore Hudson Yards' festive markets
• Evening: Dyker Heights Christmas Lights tour in Brooklyn (the most extravagant holiday displays in NYC)

Day 3: Museums, Markets & Broadway

• Morning: Intrepid Sea, Air & Space Museum followed by a walk through Little Island
• Lunch: Chelsea Market favorites: Los Tacos No.1 or Very Fresh Noodles
• Afternoon: Walk the High Line or take the East River Ferry to DUMBO for skyline views
• Evening: Broadway show (Aladdin, Lion King or Harry Potter) or late-night pizza at Pizza Suprema

Day 4: Central Park & Cozy Downtown

• Morning: Central Park highlights: Bethesda Terrace, Alice in Wonderland statue, and Belvedere Castle
• Midday: Skating at Wollman Rink or visit Central Park Zoo. Lunch at Shake Shack or Eisenberg's Diner
• Afternoon: Flatiron Building + Union Square Holiday Market or browse Strand Bookstore
• Evening: Washington Square Park & dinner at John's of Bleecker Street (legendary coal-fired pizza)

Day 5: Liberty Island to Empire Views

• Morning: Statue of Liberty pedestal access & museum (book tickets in advance)
• Midday: Lunch at Ellen's Stardust Diner (singing waitstaff!)
• Afternoon: Roosevelt Island tram + Four Freedoms Park for unique skyline perspectives
• Evening: Empire State Building observation deck at sunset, dessert at Junior's

Where to Stay: Hotel Hendricks

Hotel Hendricks – A boutique escape in Midtown, perfect for a cozy yet stylish NYC stay.

This centrally located boutique hotel offers the perfect blend of comfort and style during the busy holiday season. Its midtown location puts you within walking distance of Rockefeller Center, Times Square, and Fifth Avenue shopping.

Pro Tips for NYC in December

Must-Try Winter Eats & Drinks

• Joe's Pizza: Classic $3 New York slice that never disappoints
• Wafels & Dinges: Belgian street waffles at Bryant Park's Winter Village
• Rolf's Restaurant: The most over-the-top Christmas décor in NYC (reservations essential)
• Devoción: Rich Colombian-style peppermint hot chocolate
• Levain Bakery: Warm, gooey cookies perfect for cold days

Optional Add-On Days

• Harlem Soul: The Met Cloisters, gospel brunch at Sylvia's, and Sunday concert at Abyssinian Baptist Church
• Queens Adventure: Museum of the Moving Image, Astoria's diverse food scene
• Brooklyn Escape: Prospect Park skating, Brooklyn Botanic Garden, and holiday lights at Borough Hall