New York City is a 400-year story told in steel, stone, and neon. Founded by the Dutch as New Amsterdam, it blossomed into a global crossroads where languages mingle, cultures thrive, and ideas take flight. From Ellis Island’s immigrant heart to the soaring spires of Midtown, the city rewards curiosity around every corner.

Expect a blend of iconic sights and hyperlocal finds. You’ll stand beneath the torch of Lady Liberty, ramble through Central Park’s leafy paths, and trace brownstone-lined streets in Greenwich Village. Between stops, savor bagels that crunch and chew in equal measure, world-class pizza, Jewish delis, and inventive tasting menus that define modern American dining.

Practicalities: the subway runs 24/7 (tap in with OMNY), yellow cabs are easy to hail, and comfortable shoes are essential. Reserve popular restaurants in advance, especially for weekend dinners. For views, aim for golden hour; for museums, go early. You’ll cover a lot—pace yourself and let the city’s rhythm lead.

New York City

Skyscrapers meet pocket parks, and gallery-hopping flows into late-night jazz. The city’s greatest luxury is choice: several excellent ways to spend the same hour, block by block. This plan balances headline attractions with neighborhood wandering, so you’ll experience both the postcard and the pulse.

• Top sights: Statue of Liberty & Ellis Island, Central Park, Times Square, the 9/11 Memorial, the High Line, Grand Central, and cutting-edge observatories like SUMMIT.
• Food highlights: Classic delis (Katz’s), pizza (Scarr’s, Joe’s), Chinatown dim sum, Nolita’s modern comfort at Thai Diner, refined American at Gramercy Tavern, and old-New York steaks at Keens.
• Fun fact: Manhattan’s street grid dates to 1811—walk it north–south to feel the tempo shift from business-core bustle to residential calm, then hop across the river to Brooklyn for indie energy.

Getting there: Fly into JFK, LGA, or EWR. Search competitive fares on Trip.com flights or Kiwi.com. Typical nonstops: 1–2 hours from the East Coast ($150–$300 roundtrip), ~3–6 hours from the Midwest/West ($200–$450).

Airport transfers: JFK AirTrain + subway (~60–75 min; AirTrain approx. $8.25 + $2.90 fare). LGA bus (Q70 SBS) to subway (~35–50 min; $2.90). Newark AirTrain + NJ Transit to Penn Station (~40–60 min). Yellow cabs/ride-hails: 30–90+ min depending on traffic.

Where to stay: Browse stays on VRBO and Hotels.com. Notable picks: The Plaza Hotel (Central Park classic), The St. Regis New York (sumptuous Midtown heritage), Residence Inn by Marriott New York Manhattan/Times Square (suite-style convenience), and Pod 51 Hotel (value-friendly in Midtown East).

Day 1: Midtown Landmarks, Bryant Park, and Sunset at SUMMIT

Morning: Travel day. Touch down, drop bags, and grab a restorative coffee at Culture Espresso (house-baked chocolate chip cookies) or Devoción’s Midtown outpost for farm-to-cup Colombian brews.

Afternoon: Stroll Bryant Park and the New York Public Library’s marble halls, then dip into Grand Central Terminal to admire its celestial ceiling and bustling Vanderbilt Hall. Lunch nearby: Urban hawker-style flavors at Nom Wah NoMad (dim sum staples), or classic pastrami on rye at Zucker’s Bagels & Smoked Fish.

Evening: Time your entry for golden hour at SUMMIT One Vanderbilt—a mirrored, multi-sensory observatory with radiant city panoramas and playful installations. Nearby dinner in Koreatown (32nd Street): try Cho Dang Gol for homestyle tofu stews or Jongro BBQ for charcoal-grilled short rib; finish with soft-serve at Grace Street.

Day 2: Statue of Liberty & Ellis Island, the Financial District, and the Brooklyn Bridge

Morning: Board early for the Statue of Liberty and Ellis Island Tour. Lady Liberty’s museum decodes the statue’s symbolism; Ellis Island’s Great Hall tells moving arrival stories with original manifests and exhibits. Pre-ferry fuel at Leo’s Bagels (bright, chewy bagels; go for a whitefish salad on everything).

Afternoon: Explore the Financial District: the 9/11 Memorial’s twin reflecting pools, Oculus architecture, and cobbled Stone Street. Lunch options: Eataly Downtown (fresh pasta, focaccia) or Fraunces Tavern (Revolution-era atmosphere and hearty pub fare). Walk the Brooklyn Bridge for skyline photos—the span’s Gothic arches frame lower Manhattan perfectly.

Evening: In DUMBO, watch the sunset from Brooklyn Bridge Park. Pizza debate time: Juliana’s for classic coal-fired pies or Time Out Market’s rooftop for variety with views. Nightcap at Harriet’s Rooftop (1 Hotel) overlooking the East River glimmer.

Day 3: Central Park, Museum Mile, and Broadway

Morning: Breakfast at Ess-a-Bagel (legendary, generously schmeared bagels) before a Central Park ramble: Gapstow Bridge, the Mall, Bethesda Terrace and Fountain. Consider a narrated pedicab ride if you want to cover more ground and hear park lore.

Afternoon: Choose your masterpiece fix: The Met (Egyptian Temple of Dendur, Impressionists) or the American Museum of Natural History (T. rex, dazzling gems). Lunch ideas: The Modern Bar Room near MoMA (polished but relaxed) or a casual stop for Levain Bakery’s famous walnut-chocolate chip cookies on the way.

Evening: See a long-running phenomenon: Wicked on Broadway. Book a pre-theater dinner: Joe Allen (industry haunt with American classics), Sardi’s (caricature-lined walls), or Carmine’s (family-style Italian; great for groups). Post-show, stroll Times Square’s lights briefly, then retreat to a quieter bar like Dante West Village for refined cocktails.

Day 4: The High Line, Chelsea Market, Williamsburg, and a Harbor Dinner Cruise

Morning: Coffee at Blue Bottle or Stumptown near the High Line entrance, then walk the elevated park’s landscaped path past murals and Hudson Yards art. Early lunch at Chelsea Market: Los Tacos No. 1 (adored adobada tacos), Miznon (overflowing pita), or Very Fresh Noodles (hand-pulled biang biang).

Afternoon: Subway or East River Ferry to Williamsburg. Browse indie shops on Bedford Avenue, grab a latte at Devoción’s atrium, and pastry at Bakeri. If it’s weekend, Smorgasburg adds dozens of pop-ups; otherwise, try Lilia (reserve early) for wood-fired Italian or have a snack at Peter Pan Donut & Pastry Shop.

Evening: Dress for an elegant night afloat on the New York City Dinner Cruise with Live Music. Glide past the Statue of Liberty and under city bridges while the skyline shimmers—arguably the best way to see NYC after dark.

Day 5: West Village to SoHo, Last Bites, and Departure

Morning: Ease into the day in the West Village. Breakfast at Buvette (buttery croque madame, airy waffles) or La Cabra (Danish pastries, immaculate cappuccinos). Wander tree-lined streets to Washington Square Park and its arch.

Afternoon: Quick, memorable lunch options before you depart: Katz’s Delicatessen (hand-carved pastrami), Scarr’s Pizza (naturally-leavened slices), or Xi’an Famous Foods (spicy cumin lamb noodles). If you have an hour, browse SoHo boutiques or the New Museum’s contemporary exhibits, then head for the airport—allow 60–90 minutes transit time from Manhattan.

Evening: Departure day—no late-night plans suggested. If you’re staying, celebrate with a classic steak at Keens (order the mutton chop) or modern Thai at Thai Diner in Nolita (crispy garlic chicken and coconut pancakes).

Practical Tips & Getting Around

• Transit: Use OMNY to tap into subways and buses ($2.90 per ride). Walking is often fastest within neighborhoods.
• Timing: Reserve observatories for sunset. Start major museums at opening. Book restaurants 2–3 weeks ahead; walk-ins possible at off-peak hours.
• Neighborhood strategy: Cluster sights to minimize crosstown rides—Midtown (Day 1), Lower Manhattan/Brooklyn Bridge (Day 2), Uptown/Central Park (Day 3), West Side + Brooklyn (Day 4), Downtown shopping/eating (Day 5).
• Seasonal notes: Winter brings holiday lights and cozy dining; spring/fall are prime for park strolls; summer offers rooftop bars and ferry breezes.

Optional add-ons (if you have extra time): Top of the Rock for classic Empire State views; the Edge for an outdoor sky deck; a food tour in Chinatown & Little Italy; or a helicopter flight for epic aerials.

Bookable highlights in this itinerary (curated picks):

• SUMMIT One Vanderbilt: Experience ticket
• Statue of Liberty & Ellis Island Tour: Guided options
• Broadway (Wicked): Reserve tickets
• NYC Dinner Cruise: Evening sailing

To fine-tune this plan, pick a home base that matches your style: Midtown for convenience to Broadway, the Village for cozy streets and cafes, or Brooklyn for creative energy and skyline views back to Manhattan.

Where to book stays again: VRBO – New York City | Hotels.com – New York City

Flights: Compare on Trip.com and Kiwi.com.

Five days in New York City blends the unforgettable—Lady Liberty, Broadway, skyline sunsets—with neighborhood flavor, from Village cafes to Williamsburg roasters. You’ll leave with a camera roll full of views and a short list of spots to revisit next time.