5 Days in New York City

Here’s the 5-day New York City itinerary, designed to give you a deep dive into NYC’s culture, neighborhoods, and hidden gems, while maximizing sightseeing and minimizing travel time.

 

5 Days in New York City

 

Day 1: Essential NYC Highlights

1. Statue of Liberty & Ellis Island

Address: Liberty Island, New York, NY 10004

Cost: $23.50 (ferry ticket)

Time: 2-3 hours

 

2. Wall Street & Charging Bull

Address: Bowling Green, New York, NY 10004

Cost: Free

Time: 20-30 minutes

 

3. 9/11 Memorial & Museum

Address: 180 Greenwich St, New York, NY 10007

Cost: Memorial free; Museum entry $26

Time: 1.5-2 hours

 

Lunch: Eataly Downtown

Address: 101 Liberty St, New York, NY 10007

Cost: Entrees $15-$30

 

4. Brooklyn Bridge Walk

Address: Start at City Hall Park (Park Row and Centre St.)

Cost: Free

Time: 30-45 minutes

 

5. Times Square

Address: Manhattan, NY 10036

Cost: Free

Time: 30 minutes

 

Dinner: Joe’s Pizza (Moderate Option)

Address: 7 Carmine St, New York, NY 10014

Cost: $4 per slice

 

Luxury Dinner Alternative: The Modern

Address: 9 W 53rd St, New York, NY 10019

Cost: Prix fixe around $188

 

Day 2: Midtown and Museum District

1. Central Park Highlights (South Section)

Address: Start at 5th Ave & E 59th St.

Cost: Free

Time: 1-1.5 hours

 

2. The Metropolitan Museum of Art

Address: 1000 5th Ave, New York, NY 10028

Cost: $30 for adults

Time: 2-3 hours

 

Lunch: Sarabeth’s Central Park South

Address: 40 Central Park S, New York, NY 10019

Cost: Entrees $20-$35

 

3. Rockefeller Center & Top of the Rock Observation Deck

Address: 30 Rockefeller Plaza, New York, NY 10112

Cost: $40 for adults

Time: 1 hour

 

4. St. Patrick’s Cathedral

Address: 5th Ave, New York, NY 10022

Cost: Free

Time: 30 minutes

 

Dinner: The Smith Midtown (Moderate Option)

Address: 956 2nd Ave, New York, NY 10022

Cost: $20-$40 per entree

 

Luxury Dinner Alternative: Marea

Address: 240 Central Park S, New York, NY 10019

Cost: Prix fixe around $125

 

Day 3: Downtown Neighborhoods & Unique Experiences

1. West Village Exploration

Starting Point: Bleecker St, New York, NY 10014

Cost: Free

Time: 1.5 hours

 

2. High Line Park

Starting Point: Gansevoort St, New York, NY 10011

Cost: Free

Time: 1 hour

 

3. Chelsea Market

Address: 75 9th Ave, New York, NY 10011

Cost: Free entry; food prices vary

Time: 1-2 hours

 

Lunch: Los Tacos No. 1

Address: 75 9th Ave, New York, NY 10011 (inside Chelsea Market)

Cost: Tacos $4-$6

 

Luxury Lunch Alternative: Le Coucou

Address: 138 Lafayette St, New York, NY 10013

Cost: Entrees $30-$60

 

4. SoHo Shopping & Art

Address: Start near Spring St & Broadway

Cost: Free (shops and galleries vary)

Time: 1.5 hours

 

5. Empire State Building

Address: 20 W 34th St, New York, NY 10118

Cost: $44 for main deck

Time: 1 hour

 

Dinner: L’Artusi (Moderate Option)

Address: 228 W 10th St, New York, NY 10014

Cost: Entrees around $30

 

Luxury Dinner Alternative: Daniel

Address: 60 E 65th St, New York, NY 10065

Cost: Tasting menu $275

 

Day 4: Arts & Culture

1. Whitney Museum of American Art

Address: 99 Gansevoort St, New York, NY 10014

Cost: $25 for adults

Time: 1.5 hours

 

2. Greenwich Village & Washington Square Park

Address: Washington Square, New York, NY 10012

Cost: Free

Time: 1 hour

 

Lunch: Minetta Tavern

Address: 113 Macdougal St, New York, NY 10012

Cost: Entrees $20-$45

 

3. Museum of Modern Art (MoMA)

Address: 11 W 53rd St, New York, NY 10019

Cost: $25 for adults

Time: 1.5-2 hours

 

Dinner: Gramercy Tavern (Moderate Option)

Address: 42 E 20th St, New York, NY 10003

Cost: Entrees around $30-$45

 

Luxury Dinner Alternative: Per Se

Address: 10 Columbus Cir, New York, NY 10019

Cost: Prix fixe $325

 

Day 5: Diverse Experiences

1. Brooklyn Heights Promenade

Address: Montague St, Brooklyn, NY 11201

Cost: Free

Time: 1 hour

 

2. DUMBO Exploration & Manhattan Bridge Views

Address: Washington St, Brooklyn, NY 11201

Cost: Free

Time: 1-1.5 hours

 

3. Brooklyn Museum

Address: 200 Eastern Pkwy, Brooklyn, NY 11238

Cost: $16 for adults

Time: 1.5-2 hours

 

Lunch: Juliana’s Pizza (Moderate Option)

Address: 19 Old Fulton St, Brooklyn, NY 11201

Cost: Pizzas $20-$35

 

Luxury Lunch Alternative: River Café

Address: 1 Water St, Brooklyn, NY 11201

Cost: Prix fixe $50-$100

 

4. Prospect Park & Brooklyn Botanic Garden

Address: 990 Washington Ave, Brooklyn, NY 11225

Cost: Botanic Garden $18 for adults

Time: 2 hours

 

Dinner: Peter Luger Steak House (Moderate/Luxury Option)

Address: 178 Broadway, Brooklyn, NY 11211

Cost: Entrees $60+

 

This 5-day NYC itinerary dives deep into the neighborhoods, history, and culture of New York City, offering a rich balance between iconic sights and local experiences.

Hotel Recommendation:

If price is no option... we recommend The St. Regis New York, located at 2 East 55th Street at Fifth Avenue.

Why The St. Regis?

 Iconic Elegance: Known for its classic opulence, The St. Regis combines old-world grandeur with modern amenities. It is one of the city’s most iconic luxury hotels, offering impeccable service and a sophisticated ambiance that has attracted dignitaries, celebrities, and travelers seeking the height of luxury.

 Location: Situated in the heart of Midtown Manhattan, right next to Fifth Avenue, you are in close proximity to top attractions like Central Park, The Museum of Modern Art, Broadway, and shopping destinations like Saks Fifth Avenue.

 Rooms & Suites: Rooms here are spacious and lavishly designed, offering rich furnishings, exquisite marble bathrooms, and stunning views of the city skyline. The suites, including the King Cole Suite and the Royal Suite, offer an ultra-luxurious experience with expansive living spaces, fine art, and bespoke touches.

 Personalized Service: St. Regis is known for its butler service, which offers guests personalized attention to make every stay memorable. Whether you need a restaurant reservation, a customized tour, or unpacking and pressing services, their butlers are there to cater to your every need.

 Fine Dining: The hotel features Astor Court, offering classic New York fare, as well as King Cole Bar, known for its signature cocktail, the Bloody Mary (it’s said to have been invented here).

 Amenities: Guests enjoy access to the state-of-the-art fitness center, a full-service spa, and exclusive experiences like private shopping tours.

 

You can also find your own favorite spot here:


 Annual Events in Paris to Consider:

Here are some of the most popular annual events in New York City that attract travelers from around the world. Each offers a unique experience and a chance to see the city at its most vibrant. If you’re planning a trip, considering these events can help you decide the best time to visit:

 

January

 New Year’s Day in Times Square – Times Square, Manhattan

 Kick off the year in NYC with the famous ball drop at midnight on New Year’s Eve, followed by a New Year’s Day celebration.

 Winter Jazzfest – Various locations in Manhattan

 This multi-day festival brings jazz musicians from around the world to various venues, offering top-tier performances.

 

February

 New York Fashion Week (Winter) – Lincoln Center, Manhattan

 One of the biggest events in the fashion industry, featuring runway shows and events from top designers.

 Chinese New Year Parade – Chinatown, Manhattan

 Celebrate the Lunar New Year with parades, cultural performances, and firecrackers.

 

March

 St. Patrick’s Day Parade – Fifth Avenue, Manhattan

 The world’s largest St. Patrick’s Day Parade, held annually since 1762, marches up Fifth Avenue with bagpipes, dancers, and green galore.

 

April

 Tribeca Film Festival – Various locations in Manhattan

 Founded by Robert De Niro, this festival celebrates independent films and attracts film lovers from around the world.

 Macy’s Flower Show – Macy’s Herald Square, Manhattan

 This iconic department store transforms its space with impressive floral displays, usually lasting two weeks.

 

May

 Fleet Week – Various locations in Manhattan

 A celebration honoring U.S. Navy and Marine Corps, featuring ship tours, military demonstrations, and events.

 Five Boro Bike Tour – All five boroughs

 America’s largest bike ride, taking cyclists on a scenic route through all five boroughs.

 

June

 NYC Pride – Greenwich Village, Manhattan

 One of the world’s largest LGBTQ+ pride celebrations, featuring a Pride March, parties, and events around the city.

 Museum Mile Festival – Fifth Avenue, Manhattan

 A one-day event where museums along Museum Mile offer free entry, featuring live performances and family activities.

 

July

 Fourth of July Fireworks – East River or Hudson River

 Macy’s Fourth of July fireworks are a spectacular show over the river, drawing crowds from across the city.

 Shakespeare in the Park – Delacorte Theater, Central Park

 Free outdoor performances of Shakespeare plays, drawing theater lovers from across the globe (runs through summer).

 

August

 New York International Fringe Festival – Various locations in Manhattan

 This annual arts festival features a wide range of performances, including theater, comedy, and dance.

 Harlem Week – Harlem, Manhattan

 Celebrates Harlem’s rich cultural history with events, food, music, and performances.

 

September

 New York Fashion Week (Fall) – Lincoln Center, Manhattan

 Another edition of NYFW, attracting fashion enthusiasts, designers, and celebrities from around the world.

 Feast of San Gennaro – Little Italy, Manhattan

 A lively Italian street festival with food, games, parades, and a cannoli-eating contest.

 

October

 New York Comic Con – Jacob K. Javits Convention Center, Manhattan

 One of the largest pop culture conventions in the U.S., celebrating comics, film, anime, and video games.

 Open House New York – Various locations across NYC

 A weekend of free access to many of NYC’s architectural landmarks and historic sites, often with guided tours.

 

November

 New York City Marathon – All five boroughs

 One of the world’s premier marathons, with 50,000+ runners covering a route through all five boroughs.

 Macy’s Thanksgiving Day Parade – Central Park West to Herald Square, Manhattan

 A beloved holiday tradition featuring massive balloons, floats, and performances watched worldwide.

 Radio City Christmas Spectacular – Radio City Music Hall, Manhattan (runs through early January)

 A holiday classic featuring the Rockettes and elaborate performances that capture NYC’s festive spirit.

 

December

 Rockefeller Center Christmas Tree Lighting – Rockefeller Plaza, Manhattan

 One of NYC’s most iconic holiday events, with a massive Christmas tree lit up with thousands of lights.

 Holiday Markets – Union Square, Bryant Park, and Grand Central Terminal

 These markets feature local vendors, food stalls, and holiday gifts in a festive atmosphere.

 New Year’s Eve in Times Square – Times Square, Manhattan

 End the year with NYC’s most famous celebration, culminating in the midnight ball drop and fireworks.

 

These events highlight the best of New York City’s dynamic culture, from fashion and film to music and holiday traditions. Whether you’re looking for a festive winter experience, an exciting summer event, or cultural celebrations throughout the year, NYC has something to offer every type of traveler.

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