6 North American Cities to Explore in 5 Days

Destination: North America, N/A – placeholder for non-country recordsCreated by: Moo_The_TrotterLast updated: 12th October 2026
Choose a five-day city stay: Chicago for architecture and the lakefront, Montréal for markets and old streets, or Mexico City for art and history. These six linked itineraries are alternative trips.
3
Major museums and architecture
Image of New York in 5 Days: Museums, Neighbourhoods and Skyline

New York in 5 Days: Museums, Neighbourhoods and Skyline

Itinerary · New York City
New York combines major museums with neighbourhood walks and skyline views. Choose it for a varied five-day introduction to a large city, with each day focused on a different area.
Image of Chicago in 5 Days: Architecture, Museums and the Lakefront

Chicago in 5 Days: Architecture, Museums and the Lakefront

Itinerary · Chicago
Chicago puts architecture, museums and Lake Michigan into five days. Pick it if the riverfront and lakefront appeal as much as the collections indoors.
Image of Washington DC in 5 Days: Museums, Monuments and City Walks

Washington DC in 5 Days: Museums, Monuments and City Walks

Itinerary · Washington
Washington DC centres the trip on museums, monuments and city walks. Choose it for American history and substantial collections rather than a skyline-focused break.
Neighbourhoods, markets and outdoor walks
Image of San Francisco in 5 Days: Bay Views, Parks and City Streets

San Francisco in 5 Days: Bay Views, Parks and City Streets

Itinerary · San Francisco
San Francisco pairs bay views with parks and distinctive neighbourhoods. It suits travellers who want outdoor walks and changing city scenery across a five-day stay.
Image of Montréal in 5 Days: Old Streets, Markets and Mount Royal

Montréal in 5 Days: Old Streets, Markets and Mount Royal

Itinerary · Montréal
Montréal combines old streets, markets and Mount Royal. Pick it for neighbourhood walking, food stops and a hilltop park within the same city trip.
Image of Mexico City in 5 Days: Art, Markets and Historic Streets

Mexico City in 5 Days: Art, Markets and Historic Streets

Itinerary · Mexico City
Mexico City brings art, markets and historic streets into five days. Choose it for a culturally focused trip with substantial museums and several different neighbourhoods to explore.