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New York and New Haven · 9 Days

Experience the ultimate Northeast corridor journey, blending the high-energy landmarks and diverse neighborhoods of New York City with the historic Ivy League charm and coastal culinary delights of New Haven, Connecticut.

9days
27stops
197km

The route

Tap a day or a town

You sleep in New York — start in New York, end in New Haven.

DAY01

Times Square → Bryant Park

2.1 km · 20m driving · Overnight in Bryant Park
  1. 09:00
    Times Square· start
  2. 1.4 km · 10m
  3. 12:00
    ⭐ Empire State Building
  4. 0.7 km · 10m
  5. 15:00
    Bryant Park· overnight
DAY02

Central Park → Columbus Circle

6.9 km · 30m driving · Overnight in Columbus Circle
  1. 09:00
    ⭐ Central Park· start
  2. 0.4 km · 10m
  3. 12:00
    The Metropolitan Museum of Art
  4. 2.4 km · 10m
  5. 15:00
    Columbus Circle· overnight
DAY03

The Battery → Oculus at World Trade Center

11 km · 30m driving · Overnight in Oculus at World Trade Center
  1. 09:00
    The Battery· start
  2. 1.2 km · 10m
  3. 12:00
    ⭐ 9/11 Memorial & Museum
  4. 0.2 km · 10m
  5. 15:00
    Oculus at World Trade Center· overnight
DAY04

The High Line → Little Island

6.2 km · 30m driving · Overnight in Little Island
  1. 09:00
    ⭐ The High Line· start
  2. 0.8 km · 10m
  3. 12:00
    Chelsea Market
  4. 0.5 km · 10m
  5. 15:00
    Little Island· overnight
DAY05

Brooklyn Bridge → DUMBO

6.2 km · 30m driving · Overnight in DUMBO
  1. 09:00
    ⭐ Brooklyn Bridge· start
  2. 0.5 km · 10m
  3. 12:00
    Brooklyn Bridge Park
  4. 0.7 km · 10m
  5. 15:00
    DUMBO· overnight
DAY06

Grand Central Terminal → Frank Pepe Pizzeria Napoletana

137 km · 1h 42m driving · Overnight in Frank Pepe Pizzeria Napoletana
  1. 09:00
    Grand Central Terminal· start
  2. 129 km · 1h 22m
  3. 12:00
    ⭐ New Haven Green
  4. 1.3 km · 10m
  5. 15:00
    Frank Pepe Pizzeria Napoletana· overnight
DAY07

Yale University → Yale University Art Gallery

2.4 km · 30m driving · Overnight in Yale University Art Gallery
  1. 09:00
    Yale University· start
  2. 0.4 km · 10m
  3. 12:00
    ⭐ Beinecke Rare Book & Manuscript Library
  4. 0.6 km · 10m
  5. 15:00
    Yale University Art Gallery· overnight
DAY08

East Rock Park → Lighthouse Point Park

15 km · 30m driving · Overnight in Lighthouse Point Park
  1. 09:00
    ⭐ East Rock Park· start
  2. 2.2 km · 10m
  3. 12:00
    Yale Peabody Museum
  4. 9.3 km · 10m
  5. 15:00
    Lighthouse Point Park· overnight
DAY09

Louis' Lunch → Union Station

11 km · 30m driving
  1. 09:00
    Louis' Lunch· start
  2. 1.2 km · 10m
  3. 12:00
    ⭐ Wooster Square
  4. 1.3 km · 10m
  5. 15:00
    Union Station
Booking timeline
Book these before you go
  1. Days 1–5Stay in New York · Nights 1-5
  2. Days 6–8Stay in New Haven · Nights 6-8
Heads Up
  • Book Amtrak or Metro-North tickets in advance for the best rates between NYC and New Haven.
  • July is peak summer; expect high humidity and carry water during city walks.
  • Many Yale University libraries and museums have specific public visiting hours; check schedules before arrival.
  • Reservations are highly recommended for famous New Haven pizza spots like Frank Pepe or Sally's.