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.