Manhattan 5-Day Itinerary

July 14-18, 2025 | From The Gregorian Hotel
Created by Oliver and Claude
Day 1 - Midtown Icons
Day 2 - Upper East Side
Day 3 - Downtown Historic
Day 4 - SoHo & Village
Day 5 - Modern Art
Essential Info

Day 1 (July 14): Midtown Icons

Morning (9:00 AM)

Times Square - FREE
📍 42nd St & Broadway
From Hotel: Walk north 7 blocks (10 minutes)
Bryant Park - FREE
📍 42nd St & 6th Ave
🌐 bryantpark.org
2-minute walk from Times Square
New York Public Library - FREE
📍 5th Ave & 42nd St
🌐 nypl.org | 📞 (212) 340-0863
2-minute walk from Bryant Park

Lunch (11:30 AM)

The Smith - $$ ($20-30/person)
📍 1150 Broadway at 28th St
🌐 thesmithrestaurant.com | 📞 (212) 644-7700
15-minute walk south or subway

Afternoon

Empire State Building - $45-65
📍 350 5th Ave at 34th St
🌐 esbnyc.com | 📞 (212) 736-3100
8-minute walk (1 block from hotel!)
BOOK AHEAD: Skip-the-line essential
Grand Central Terminal - FREE
📍 89 E 42nd St
🌐 grandcentralterminal.com | 📞 (212) 340-3395
Subway 6 train from 33rd St (3 stops)
Chrysler Building exterior - FREE
📍 405 Lexington Ave
3-minute walk from Grand Central

Late Afternoon

Top of the Rock - $42-47
📍 30 Rockefeller Plaza
🌐 topoftherocknyc.com | 📞 (212) 769-8000
15-minute walk or subway
BOOK AHEAD: Book 6:30 PM sunset slot

Dinner (8:00 PM)

Joe Allen - $$ ($25-35/person)
📍 326 W 46th St
🌐 joeallenny.com | 📞 (212) 581-2908
Return to Hotel: 12-minute walk or taxi ($8-12)

Day 2 (July 15): Upper East Side Culture

Morning (9:00 AM)

Metropolitan Museum of Art - $30
📍 1000 5th Ave at 82nd St
🌐 metmuseum.org | 📞 (212) 535-7710
From Hotel: Subway 6 train (15 minutes total)
BOOK AHEAD: Timed entry recommended
Focus: European Paintings, Egyptian Art, American Wing, Met Roof Garden

Lunch (1:00 PM)

Sarabeth's - $$ ($18-28/person)
📍 1295 Madison Ave at 92nd St
🌐 sarabethsrestaurants.com | 📞 (212) 534-5900
10-minute walk up Madison

Afternoon

Madison Avenue Shopping (60th-80th Streets) - Varies
📍 Madison Avenue (60th-80th Streets)
Central Park - Bethesda Fountain, Bow Bridge - FREE
📍 Central Park (72nd St entrance)
🌐 centralparknyc.org
Neue Galerie - $25
📍 1048 5th Ave at 86th St
🌐 neuegalerie.org | 📞 (212) 628-0200
Austrian/German art, famous Café Sabarsky

Evening

Via Quadronno - $$ ($22-32/person)
📍 25 E 73rd St
📞 (212) 535-5600
Return to Hotel: Subway or taxi ($15-20)

Day 3 (July 16): Downtown Historic Manhattan

Morning (8:30 AM)

9/11 Memorial & Museum
📍 180 Greenwich St
🌐 911memorial.org | 📞 (212) 312-0195
Memorial: FREE | Museum: $33
From Hotel: Subway R/W (12 minutes)
BOOK AHEAD: Timed entry required for museum
One World Observatory - $47-54
📍 285 Fulton St
🌐 oneworldobservatory.com | 📞 (844) 322-4726
BOOK AHEAD: Skip-the-line recommended

Lunch (1:00 PM)

Stone Street Tavern - $$ ($20-30/person)
📍 52 Stone St
🌐 stonestnyc.com | 📞 (212) 691-9900
8-minute walk through historic Stone Street

Afternoon

Wall Street & Federal Hall - FREE
📍 26 Wall St
🌐 nps.gov/feha | 📞 (212) 344-8000
Trinity Church - FREE
📍 75 Broadway
🌐 trinitywallstreet.org | 📞 (212) 264-4550
Brooklyn Bridge - FREE
📍 Park Row & Centre St (Manhattan entrance)
🌐 NYC.gov Brooklyn Bridge
South Street Seaport - FREE
📍 12 Fulton St
🌐 southstreetseaport.com

Evening

Staten Island Ferry - FREE
📍 Whitehall Terminal, 4 South St
🌐 siferry.com | 📞 (718) 727-2508
Best free Statue of Liberty views! Take 6:00 PM ferry
Lombardi's Pizza - $ ($15-20/person)
📍 32 Spring St
🌐 firstpizza.com | 📞 (212) 941-6330
Return to Hotel: Subway (12 minutes)

Day 4 (July 17): SoHo, Village & Flatiron

Morning (9:30 AM)

SoHo Shopping - Varies
📍 Start at Broadway & Prince St
From Hotel: Subway N/Q/R/W (10 minutes)
Spring Street & Broome Street boutiques
Housing Works Bookstore Café - FREE
📍 126 Crosby St
🌐 housingworks.org | 📞 (212) 674-9922

Lunch (12:30 PM)

Jack's Wife Freda - $$ ($18-25/person)
📍 224 Lafayette St
🌐 jackswifefreda.com | 📞 (212) 615-0032

Afternoon

Flatiron Building - FREE
📍 175 5th Ave at 23rd St
Subway 6 from Spring St to 23rd St
Union Square & Strand Bookstore - FREE
📍 E 14th St & Broadway
📍 Strand: 828 Broadway
🌐 strandbookstore.com | 📞 (212) 473-7300
Fifth Avenue Shopping
📍 Saks Fifth Avenue - 611 5th Ave
🌐 saksfifthavenue.com | 📞 (212) 753-8000
Rockefeller Center - FREE
📍 45 Rockefeller Plaza
🌐 rockefellercenter.com | 📞 (212) 769-8000

Evening Options

Broadway Show - $50-200+
🌐 broadway.com | 🌐 TodayTix app (discounts)
BOOK AHEAD: Popular shows book 2-3 weeks ahead
Lincoln Center outdoor events - FREE-$50
📍 10 Lincoln Center Plaza
🌐 lincolncenter.org | 📞 (212) 546-9200

Dinner

Gramercy Tavern - $$$ ($50-70/person)
📍 42 E 20th St
🌐 gramercytavern.com | 📞 (212) 477-0777
BOOK AHEAD: Reservations essential
OR Shake Shack - $ ($12-18/person)
📍 Madison Square Park, 23rd & Madison
🌐 shakeshack.com
Return to Hotel: 15-minute walk or taxi ($8-12)

Day 5 (July 18): Modern Art & High Line

Morning (9:30 AM)

Museum of Modern Art - $30
📍 11 W 53rd St
🌐 moma.org | 📞 (212) 708-9400
From Hotel: 18-minute walk or subway
BOOK AHEAD: Skip lines during summer
Focus: Floors 4-5 (Impressionist/Post-Impressionist)
MoMA Design Store - FREE to browse
📍 Same building as MoMA
🌐 store.moma.org

Lunch (1:00 PM)

The Plaza Food Hall - $$ ($15-25/person)
📍 1 W 59th St
🌐 theplazany.com | 📞 (212) 759-3000

Afternoon

High Line - FREE
📍 Gansevoort St entrance (Washington St & Gansevoort St)
🌐 thehighline.org | 📞 (212) 500-6035
From Plaza: Subway + 10-minute walk
Chelsea Market - FREE to walk
📍 75 9th Ave
🌐 chelseamarket.com | 📞 (212) 652-2110
Directly below High Line at 16th St
Meatpacking District boutiques - Varies
📍 Around 14th Street & 9th Avenue

Final Stop

The Morgan Library & Museum - $25
📍 225 Madison Ave at 36th St
🌐 themorgan.org | 📞 (212) 685-0008
4 blocks from hotel!

Farewell Dinner

Tavern on the Green - $$$ ($45-65/person)
📍 Central Park West & 67th St
🌐 tavernonthegreen.com | 📞 (212) 773-1447
BOOK AHEAD: Reservations essential
Return to Hotel: Taxi ($10-15)

Essential Booking Information

MUST BOOK AHEAD:

RECOMMENDED TO BOOK:

Money-Saving Apps:

  • TodayTix - Discounted Broadway shows
  • Groupon - Restaurant and attraction deals
  • Resy - Restaurant reservations

Hotel Location Advantages:

  • Empire State Building: 1 block away
  • Herald Square/Macy's: 2 blocks
  • Subway Access: 34th St-Herald Square (2 blocks)
  • Multiple Transportation Options

Cost Summary

Food Cost Guide:

  • $ (Under $20/person): Lombardi's, Shake Shack, food halls
  • $$ ($20-40/person): The Smith, Sarabeth's, Jack's Wife Freda
  • $$$ ($40+/person): Gramercy Tavern, Tavern on the Green

Transportation:

  • Subway: $2.90 per ride (€2.65)
  • 7-day MetroCard: $33 (€30)
  • Taxis from hotel: $8-20 most destinations

Attraction Costs:

  • Free attractions: Times Square, Central Park, Brooklyn Bridge, High Line, Staten Island Ferry
  • Museums: $25-33 each
  • Observation decks: $42-65 each
  • Broadway shows: $50-200+

European Payment Tips:

  • Most places accept contactless cards
  • Tipping: 18-20% restaurants, $1-2/drink bars
  • Total attraction costs: ~$200-300/person

Important Reminders

  • Weather: July in NYC is hot and humid - dress in layers, carry water
  • Air Conditioning: Venues blast AC - bring light jacket for indoors
  • Walking: New Yorkers walk 3-4 mph - comfortable shoes essential
  • Peak Times: Avoid rush hours (7-9 AM, 5-7 PM) on subway when possible
  • Broadway: Book popular shows 2-3 weeks ahead
  • Restaurants: Dinner reservations essential, lunch often walk-in

Your Hotel Details

The Gregorian Hotel
📍 42 W 35th St, New York, NY
🌐 thegregorianhotel.com | 📞 (212) 279-0017