The Ultimate 5-Day New York City Itinerary: Where to Stay, Eat, and Explore

11 min readSep 10, 2024

New York City has something for everyone — whether you’re looking to take in iconic landmarks like Times Square, enjoy hidden gems in SoHo and Chinatown, or explore world-class museums. In this 5-day itinerary, I’ll guide you through the best neighborhoods, tourist spots, and local favorites. You’ll also get insider tips on getting flight deals, how to navigate the city, and where to stay for an unforgettable trip to the Big Apple.

How to Get Cheap Flights to New York City

How to Find Flight Deals

The first step in planning your New York adventure is booking your flight. I highly recommend using Skyscanner to compare fares and find great deals on flights. Skyscanner lets you set up price alerts, so you’ll get notified when prices drop for flights to New York’s three major airports: JFK, LaGuardia (LGA), and Newark Liberty International (EWR).

Use American Express for Points

If you’re looking to fly in first-class or business-class, don’t forget to maximize your American Express Gold and Platinum cards. By signing up for the Gold card first, you can score up to 90,000 miles, and then move on to the Platinum card for an additional 150,000 points. These miles can be used to upgrade your economy ticket or cover the full cost of your flight, turning your New York trip into a luxury experience without breaking the bank.

Day 1: Arrive and Explore Times Square

Which Airport to Arrive At

When flying into New York City, JFK International Airport is your best bet for international flights and long-haul domestic routes. If you’re flying from within the U.S., LaGuardia (LGA) is often more convenient for domestic travelers, while Newark (EWR) is a good alternative if you’re staying in lower Manhattan or Brooklyn.

Getting to Your Hotel

From JFK, LaGuardia, or Newark, the easiest way to get to your hotel is by Uber. While New York’s public transport system is extensive, after a long flight, nothing beats the convenience of a private ride that takes you directly to your hotel. Avoid taxis that don’t use meters or offer “special deals” to unsuspecting tourists — this is a common scam. Uber gives you a flat rate and peace of mind.

TWA Hotel at JFK: A Fun Visit, But Don’t Stay Here

The TWA Hotel at JFK Airport is worth visiting if you have time — it’s a retro masterpiece, with its 1960s-themed design and rooftop infinity pool overlooking the runway. However, I recommend not staying here for your trip — it’s far from the main attractions, and commuting from the airport daily is time-consuming. Instead, visit the hotel for a drink at the Connie Cocktail Lounge or to explore its museum-like interior, then head to Manhattan for your actual stay.

Where to Stay in Times Square

For a central location that puts you right in the heart of the action, check into the Renaissance New York Times Square Hotel. With its sleek rooms and incredible views, it’s just steps from Broadway theaters, restaurants, and major landmarks. If you prefer a boutique experience, The Knickerbocker Hotel offers a historic setting with modern luxury.

Explore Times Square

After checking in, take your time exploring Times Square. The bright lights, towering billboards, and the endless hustle are unlike anywhere else in the world. Make sure to visit the TKTS Booth for discounted Broadway tickets — up to 50% off same-day performances. Be cautious of street vendors offering tickets or “free” souvenirs — they often mark up prices or ask for tips after taking photos with you.

Dinner at Ippudo Ramen (East or West Location)

End your first night with dinner at Ippudo Ramen, which has both an East Village and West Side location. Known for its rich tonkotsu ramen and mouthwatering pork buns, it’s a must-try for any foodie visiting the city. Make sure to get there early, as this place is always packed.

Day 2: Downtown — SoHo, Chinatown, and Little Italy

Morning in SoHo

After breakfast, head downtown to explore SoHo. Famous for its cobblestone streets and luxury shopping, SoHo offers a blend of trendy boutiques and charming galleries. It’s a great place to window shop or splurge on high-end fashion.

For lunch, stop by Best Thai in SoHo, which serves some of the freshest, most flavorful Thai food in the city. Their spicy papaya salad and pad Thai are crowd favorites and perfect for a light, delicious meal.

Afternoon in Chinatown and Little Italy

From SoHo, it’s a short walk to Chinatown. Wander through the bustling streets, visit herbal shops, and stop by Joe’s Shanghai for their famous soup dumplings. Chinatown is a cultural feast, offering everything from dim sum to bubble tea.

Next, head over to Little Italy, a small but vibrant neighborhood filled with Italian restaurants and cafés. For lunch or dinner, stop at Bierria, known for its delicious pizzas and rustic Italian dishes. If you’re in the mood for something sweet, grab a cannoli at Ferrara Bakery, a local favorite since 1892.

Day 3: Museums, 9/11 Memorial, and Statue of Liberty

Morning at the 9/11 Memorial & Museum

Start your third day with a visit to the 9/11 Memorial & Museum. The Memorial’s two reflecting pools, built in the footprints of the Twin Towers, serve as a solemn tribute to those who lost their lives. Inside the museum, you’ll find a collection of powerful exhibits that recount the events of September 11, 2001, through artifacts, photos, and personal stories.

Afternoon: Statue of Liberty & Ellis Island

From the 9/11 Memorial, head to Battery Park, where you can catch a ferry to Liberty Island. The Statue of Liberty is a symbol of freedom and one of the most iconic landmarks in the world. While you’re there, be sure to visit Ellis Island, where millions of immigrants passed through in search of a better life. Book your ferry tickets in advance through Statue Cruises to avoid long lines.

Evening at the Balloon Museum

For a fun, family-friendly activity, visit the Balloon Museum located near the Brooklyn Bridge. This whimsical, interactive museum is filled with vibrant balloon installations, perfect for kids and adults alike. Afterward, take a stroll along the river and snap some photos with the Manhattan skyline in the background.

Day 4: Brooklyn’s Hidden Gems

Morning in Williamsburg

Head over to Brooklyn and start your day in Williamsburg, a neighborhood known for its artsy vibe and trendy coffee shops. Grab a cup at Devoción, a favorite for its chic ambiance and Colombian-sourced coffee. Take a leisurely walk along the Williamsburg Waterfront, where you’ll get spectacular views of the Manhattan skyline.

Lunch at Juliana’s

If you’re a pizza lover, stop by Juliana’s Pizza in DUMBO. Often competing for the title of the best pizza in New York, Juliana’s coal-fired pies are a Brooklyn institution. While in DUMBO, don’t miss snapping a photo of the Manhattan Bridge from Washington Street, one of the most iconic views in New York.

Brooklyn Museum & Prospect Park

After lunch, spend the afternoon exploring the Brooklyn Museum, home to impressive art collections from around the world. For a nature break, take a stroll through Prospect Park, a beautiful green space designed by the creators of Central Park.

Day 5: Central Park and Upper East Side

Morning in Central Park

No trip to New York is complete without a visit to Central Park. Rent a bike or take a leisurely walk through the park’s winding paths, and be sure to visit Bethesda Terrace and the Loeb Boathouse. If you’re up for it, row a boat on The Lake, or simply relax by the water.

Afternoon: Museums and Shopping

Spend your final afternoon at one of New York’s world-class museums. The Metropolitan Museum of Art and the American Museum of Natural History are both excellent choices, depending on your interests. If you prefer shopping, take a stroll down Fifth Avenue and explore the luxury flagship stores.

Dinner & Final Broadway Show

For your last night in New York, indulge in one more Broadway show — this time, with a great seat thanks to the TKTS Booth or your advance ticket purchase. End your evening with a fine dining experience at Le Bernardin, or enjoy a hearty Italian meal at Carmine’s in Times Square.

Getting Around Safely with Uber

While New York’s subway system is extensive, Uber is the easiest and safest way to get around, especially when visiting multiple neighborhoods in one day. It’s convenient for families, groups, or when you want to avoid crowded trains. Plus, it offers door-to-door service, ensuring you make the most of your trip.

Conclusion: Discover the Best of New York City

New York City is more than just a collection of landmarks; it’s a vibrant, dynamic place where every neighborhood offers something unique. From exploring Times Square and Central Park to the hidden gems of Brooklyn and Chinatown, this 5-day itinerary will help you make the most of your time in the city while avoiding the common tourist traps. Whether you’re here for the pizza, the Broadway shows, or the rich history, New York is a destination that will stay with you long after you leave.

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Until next time here’s to smooth skies, good company, a journey full of happy memories. I’m your Travel Hack Guide to affordable luxury tips. Catch you later. Peace

Travel Hack Guy

ZachusTravel.com & YouTube.com/zachustravel

Bonus: Why You Need to Visit New York City at Christmas

As amazing as New York is all year round, there’s something truly magical about the city during Christmas time. The streets transform into a winter wonderland, decked out with twinkling lights, festive decorations, and holiday cheer that fills the air. If you’ve never experienced New York City during the holiday season, here’s a little teaser of what awaits you — and why you’ll want to plan your next trip for December.

1. See the Rockettes at Radio City Music Hall

One of the most iconic New York holiday traditions is seeing the Radio City Christmas Spectacular, featuring the legendary Rockettes. This high-kicking, synchronized show is a must-see for the entire family. Tickets sell out fast, so be sure to grab yours early on Ticketmaster or through the Radio City Music Hall website. The dazzling performance, complete with dancing Santas and an appearance by the big man himself, Santa Claus, will leave you full of Christmas spirit!

2. Ice Skating and Decorations at Rockefeller Center

Another classic holiday activity is ice skating beneath the towering Rockefeller Center Christmas Tree. The tree, often standing over 70 feet tall, is covered in thousands of lights and is one of the most iconic Christmas symbols in the world. Even if you don’t lace up your skates, walking around Rockefeller Plaza and taking in the holiday window displays and sparkling decorations is enough to fill your heart with joy.

3. Holiday Shopping on Fifth Avenue

For the ultimate shopping experience, stroll down Fifth Avenue, where the world’s most luxurious department stores put on stunning window displays. You’ll find high-end brands like Saks Fifth Avenue, Bergdorf Goodman, and Tiffany & Co., all decked out in their holiday best. Whether you’re window shopping or looking for the perfect gift, Fifth Avenue is the place to be.

4. Visit Bryant Park’s Winter Village

For a more family-friendly experience, head to Bryant Park’s Winter Village, which features a massive ice skating rink, holiday markets, and cozy food stalls where you can sip hot chocolate or enjoy festive treats. The Winter Village is a great spot for picking up unique, handmade gifts and soaking in the holiday atmosphere.

5. Explore the Holiday Markets

New York’s Christmas markets are perfect for finding one-of-a-kind gifts, ornaments, and holiday decor. The Union Square Holiday Market and Columbus Circle Holiday Market are two of the most popular, with stalls offering everything from handmade crafts to gourmet treats. These markets are ideal for a leisurely afternoon stroll with the family.

6. See the Dyker Heights Christmas Lights

If you’re looking to get off the beaten path, take a trip to Dyker Heights in Brooklyn. This neighborhood is famous for its extravagant Christmas light displays, with homeowners going all out to turn their homes into festive masterpieces. The whole family will be amazed by the over-the-top decorations, which attract visitors from all over the world.

With so much to do and see during the holiday season, New York City at Christmas is nothing short of magical. From seeing the Rockettes to ice skating under the stars and shopping for unique gifts at holiday markets, it’s an experience your family will never forget. So why not plan a winter getaway to the city that knows how to celebrate Christmas in style?