Ultimate 10-Day New York City and Washington DC Itinerary: Iconic Sights, Fun Birthday Night & Day Trip

Day 1: Arrival & Relaxation

New York City, USA on October 2, 2025

10:50am

Flight from Malta to JFK

Depart Malta on Turkish Airlines flight at 10:50am to JFK with arrival late at 10:40pm NYC time.
Included in ticket, Approx. 11h50m flight

10:40pm

Arrive at JFK Airport and transfer to hotel

After arriving, take a taxi or shuttle to Intercontinental New York Times Square for check-in and rest to adjust to time zone.
Taxi approx. USD 70, 30m

11:30pm

Check-in and unwind

Settle into your hotel to recover from the flight, prepare for the next day of sightseeing.
Hotel accommodation, Rest overnight
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Day 2: Midtown Icons

New York City, USA on October 3, 2025

8:00am

Breakfast at Pershing Square

Enjoy a classic NYC breakfast at Pershing Square, an elegant spot near Grand Central Station, serving hearty American breakfast dishes.
Approx. USD 20 per person, 1h

9:30am

Visit Grand Central Station

Explore this iconic architectural marvel with its beautiful celestial ceiling and historic market. Open daily 5:30am-2am.
Free, 1h

10:45am

Empire State Building Observatory

Head to the 86th-floor observatory for panoramic NYC skyline views. Open daily 8am-midnight. Purchase tickets online to avoid lines.
USD 44, 2h

1:00pm

Lunch at The Smith Midtown

This American brasserie offers delicious, comforting dishes in a lively atmosphere, perfect for a midday break.
Approx. USD 30 per person, 1h

2:30pm

Bryant Park & New York Public Library

Stroll Bryant Park's gardens and visit the adjacent historic New York Public Library, open 10am-6pm daily.
Free, 1.5h

4:15pm

Stroll 5th Avenue Shopping

Window shop and enjoy the vibe on 5th Avenue, the famous shopping street stretching several blocks north-south.
Free, 1.5h

6:00pm

Dinner at Milk Bar (Midtown location)

Treat yourselves to creative desserts and savory snacks at the famous Milk Bar, open until 11pm.
Approx. USD 15-20 per person, 1h

7:30pm

Evening at Times Square

Experience the dazzling lights and vibrant crowds of Times Square. Best seen after sunset for full effect.
Free, 1h
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Day 3: Statue & Lower Manhattan

New York City, USA on October 4, 2025

7:00am

Breakfast at Leo's Bagels

Start early with classic New York bagels from Leo's Bagels in Midtown, open from 7am.
Approx. USD 10 per person, 45m

8:00am

Statue of Liberty & Ellis Island Tour

Take the ferry from Battery Park to visit both iconic landmarks. First ferries depart at 8:30am. Reserve tickets online in advance.
USD 25.50 per person, 4h

12:30pm

Lunch at Fraunces Tavern

Historic Colonial tavern close to Battery Park serving classic American dishes.
Approx. USD 30 per person, 1h

2:00pm

Visit Wall Street & Charging Bull

Walk through the Financial District seeing the New York Stock Exchange and iconic Charging Bull statue. Free and open all day.
Free, 1h

3:15pm

9/11 Memorial and Museum

Reflect at the Twin Towers Memorial and visit the museum nearby (open 9am-8pm). Tickets recommended in advance.
USD 28, 2h

6:00pm

Dinner at Eataly Downtown

Italian marketplace with restaurants offering diverse authentic meals, located near the memorial.
Approx. USD 35 per person, 1.5h
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Day 4: Central Park & Museums

New York City, USA on October 5, 2025

8:30am

Breakfast at Sarabeth’s Central Park South

Enjoy upscale breakfast overlooking Central Park, famous for fresh, classic dishes.
Approx. USD 35 per person, 1h

9:45am

Central Park bike ride

Rent bikes and explore Central Park’s scenic loop, including The Great Lawn and Bethesda Fountain. Bike rentals available from 9am daily.
USD 20 approx. per bike, 2h

12:00pm

Lunch at The Loeb Boathouse

Eat lakeside with beautiful views inside Central Park. Open daily 11:30am-4pm for lunch.
Approx. USD 30 per person, 1h

1:30pm

Visit The Met (Metropolitan Museum of Art)

Explore the vast art collections from ancient to contemporary art. Open 10am-5:30pm on Saturdays.
USD 30 suggested donation, 3h

5:00pm

Roosevelt Island Tramway

Take this scenic tram ride across the East River with stunning Manhattan views. Operating hours 6am-midnight.
USD 2.75 (metro card fare), 30m

6:00pm

Dinner at The Water’s Edge Restaurant on Roosevelt Island

Relax with waterfront dining overlooking Manhattan skyline for a romantic birthday eve dinner.
Approx. USD 40 per person, 1.5h
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Day 5: Brooklyn & Birthday Night

New York City, USA on October 6, 2025

5:30am

Brooklyn Bridge Sunrise Walk

Start early to walk the Brooklyn Bridge enjoying spectacular sunrise views of Manhattan and Brooklyn.
Free, 1h

7:00am

Breakfast at Almondine Bakery in Dumbo

Enjoy fresh pastries and coffee at this popular bakery in historic Dumbo neighborhood.
Approx. USD 15 per person, 1h

8:15am

Explore Brooklyn Heights Promenade & Manhattan Bridge View

Stroll the promenade for stunning skyline views and photography near the Manhattan Bridge.
Free, 1h

9:30am

Visit The Bean and The Bull

Stop by The Bean for a great coffee and The Bull for brunch or relaxed bites in Brooklyn.
Approx. USD 20 per person, 1h

11:00am

Return to Manhattan and rest

Head back to hotel to relax or freshen up before birthday celebrations.
Taxi approx USD 15, 30m

3:00pm

Birthday Afternoon Free Time

Optional shopping or relaxing in Bryant Park or nearby museums.
Varies, 2h

6:30pm

Birthday Dinner at The Press Lounge

Dine at this rooftop bar and lounge with sweeping sunset and skyline views; perfect for a special occasion. Open until 1am on Sundays.
Approx. USD 65 per person, 2h

9:00pm

Speakeasy Bar Experience at Please Don't Tell (PDT)

End the night with cocktails at one of NYC’s most famous speakeasies, reservation recommended.
Approx. USD 20-30 per drink, 2h
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Day 6: Washington DC Day Trip

Washington, D.C., USA on October 7, 2025

6:00am

Depart NYC to Washington D.C.

Take an early Amtrak train from Penn Station to Washington Union Station (approx 3h15m).
USD 60-120 roundtrip, 3h15m

9:30am

Walk National Mall & Visit Lincoln Memorial

Explore the central park area with iconic monuments including the Lincoln Memorial and Washington Monument.
Free, 2h

11:30am

Visit Smithsonian Museums

Choose between the National Air and Space Museum or National Museum of American History, open 10am-5:30pm.
Free, 2h

1:30pm

Lunch at Union Station Food Court

Wide variety of food options in grand historic train terminal.
Approx. USD 15-20, 1h

2:30pm

White House Photo Stop & Library of Congress Visit

Take photos outside the White House and explore stunning Library of Congress interior, open until 4:30pm.
Free, 1.5h

4:00pm

Return to NYC by train

Catch return train from Union Station to Penn Station.
Included in roundtrip fare, 3h15m

7:30pm

Relaxing Dinner near Hotel

Casual low-key dinner at Urbanspace Vanderbilt Food Hall near hotel for a variety of choices.
Approx. USD 20 per person, 1h
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Day 7: Shopping & Culture

New York City, USA on October 8, 2025

8:30am

Breakfast at Buvette

French-style café in West Village serving perfect croissants and coffee, opens at 8am.
Approx. USD 20 per person, 1h

9:30am

Explore 5th Avenue & Rockefeller Center

Walk along 5th Avenue for iconic shopping and visit Rockefeller Center, including St. Patrick’s Cathedral. Rockefeller Top of the Rock open 8am-12am.
Top of the Rock ticket USD 45, 3h

12:30pm

Lunch at Rockefeller’s Sea Grill

Enjoy seafood with central Manhattan views.
Approx. USD 35 per person, 1h

2:00pm

Visit American Museum of Natural History

Explore vast collections including dinosaur fossils and planetarium. Open 10am-5:45pm.
USD 28 suggested donation, 3h

5:30pm

Return to hotel rest

Take time to freshen up before evening plans.
Free, 1h

7:00pm

Drinks in Hell’s Kitchen Bars

Explore lively nightlife with bars like Rudy’s Bar & Grill or The Pony Bar.
Varies, 2h
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Day 8: Sports & Beachside Fun

New York City, USA on October 9, 2025

8:00am

Breakfast near hotel at Best Bagel & Coffee

Classic NYC bagels with various toppings, open early.
Approx. USD 10 per person, 45m

10:00am

Visit Coney Island

Relax on historic beach, boardwalk, and visit amusement park. Accessible by subway, approx 1h ride.
Free entry to beach; rides extra, 4h

3:30pm

Return to Manhattan and refresh

Rest at hotel before evening game.
Free, 1h

5:30pm

Travel to MetLife Stadium

Take transport to East Rutherford, NJ for NFL game - New York Giants vs Philadelphia Eagles, kickoff ~7:00pm.
Game tickets TBD, 4h event + travel
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Day 9: Ferry & Final Explorations

New York City, USA on October 10, 2025

9:00am

Staten Island Ferry

Enjoy free ferry ride to Staten Island and back, with great Statue of Liberty views. Runs 24/7, every 30 minutes.
Free, 1.5h

11:00am

Visit Madison Square Park & Flatiron District

Relax in park, then explore iconic Flatiron Building and nearby restaurants.
Free, 2h

1:30pm

Lunch at Eataly Flatiron

Diverse Italian food market and eateries for casual dining.
Approx. USD 25 per person, 1h

3:00pm

Visit The Edge Observation Deck

Experience thrilling views from NYC’s highest outdoor sky deck. Open 8am-midnight, last entry 11pm.
USD 48 per person, 1.5h

5:00pm

Evening drinks at rooftop bar The Crown (Lower East Side)

Celebrate final night with skyline views and elegant cocktails.
Approx. USD 20-30 per drink, 2h
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Day 10: Departure

New York City, USA on October 11, 2025

5:30am

Early breakfast at hotel

Light breakfast before departure.
Included with hotel, 30m

6:00am

Transfer to La Guardia Airport

Taxi or shuttle to LGA for flight to Chicago, check-in in advance due to early flight.
Taxi approx. USD 40, 30m

7:00am

Flight LGA to Chicago

Depart NYC early morning for Chicago, ending New York trip.
Included in ticket, Approx. 3h
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