One week in the United States: a multi-city route
New York and Boston by rail, then a flight west to Chicago, San Francisco, and Seattle.
Photo by Maarten van den Heuvel on Unsplash
Interactive map of the route. The full stop list below works without it.
Owned inter-city distance across covered legs: 5750.1 km
How do you spend a week in the United States?
An east-to-west route that starts in New York and ends in Seattle by way of Boston, Chicago, and San Francisco. Train the first leg, fly the middle legs, and ride the Coast Starlight or a short flight up the Pacific coast. It is built for people who want the country's densest walking cities, not a windshield tour, and every stop has covered Wayside walking routes waiting.
- Days 1 to 4
New York City: start with the densest block
Start in New York and give it the most nights on the trip. The covered walks do the heavy lifting: the Midtown loop from Grand Central Terminal's celestial ceiling to Central Park's Mall, the Downtown Villages walk through Washington Square, Stonewall, SoHo, and the High Line, and the Oldest Mile from the Battery across the Brooklyn Bridge to DUMBO. Base yourself in Midtown or lower Manhattan and use the subway between walk start points. The first onward move is the one leg with no airport involved.
- TransitAmtrak runs direct trains from New York's Moynihan Train Hall to Boston South Station. The Northeast Regional takes about three and a half to four and a half hours with coach fares from about $29, and the Acela does the same run in about three and a half hours with Business Class from around $120.SourceTrain From ToAmtrak
New York City one-day itineraryNew York City walking tours
Next leg · 305.8 km
- Days 4 to 7
Boston: the compact counterweight
Boston is the payoff for doing the eastern half by rail. It arrives as a walkable counterweight to New York: the downtown Freedom Trail walk from Park Street Church to Faneuil Hall, the North End route from the Paul Revere House to the Bunker Hill Monument, and the Beacon Hill loop through Acorn Street to the Public Garden's swan boats. Stay near the Common or Back Bay. When you leave, Logan Airport is a short ride from downtown and the Chicago flight is the fastest hop of the long moves.
- TransitNonstop Boston to Chicago flights run about two hours 30 minutes at their fastest and typically around three hours. One-way economy fares often land between $60 and $275.SourceGoogle FlightsExpedia
Boston one-day itineraryBoston walking tours
Next leg · 1367.7 km
- Days 7 to 10
Chicago: the tall-building capital
Chicago earns its stop for the skyscraper story alone. The Skyscraper's First Mile walk ties the Rookery, the Monadnock, and Willis Tower into one argument about how the modern tower was invented, and the lakefront walk from Cloud Gate to Buckingham Fountain shows why the city's front yard stayed open to everyone. Leave an afternoon for Pilsen's 18th Street murals and tacos, or Bronzeville's Black Metropolis walk. Then it is a nonstop flight west to San Francisco; book that ticket with the other long hops.
- TransitNonstop Chicago to San Francisco flights take about 4 hours 30 minutes at the fastest and usually between 4 hours 45 minutes and 5 hours. One-way economy fares often start around $80, and the route's average one-way fare is about $134.SourceGoogle FlightsFareCompare
Chicago one-day itineraryChicago walking tours
Next leg · 2983.4 km
- Days 10 to 13
San Francisco: the walking city
San Francisco is the country's best big-city walking town, and the covered routes pick the right seams: the Chinatown alleys from the Dragon Gate to the fortune cookie factory on Ross Alley, the North Beach walk from City Lights up the Filbert Steps to Coit Tower, the Mission's Balmy Alley murals, and the Golden Gate's east sidewalk from Crissy Field. Spend one day on the waterfront from the Ferry Building to Ghirardelli Square, one in the hills, and one on the bridge. The Coast Starlight then runs overnight to Seattle, or you can take a short flight.
- TransitThe Amtrak Coast Starlight runs daily between the Bay Area and Seattle. The northbound train leaves Emeryville at 9:41 pm and reaches Seattle's King Street Station at 7:51 pm the following day; Wanderu lists one-way coach fares on the Seattle to Emeryville corridor from about $112.SourceTravels with KevWanderu
San Francisco one-day itinerarySan Francisco walking tours
Next leg · 1093.2 km
- Days 13 to 15
Seattle: the Pacific finish
End in Seattle, where the covered walks do two jobs at once. The market and waterfront route goes from Pike Place Market down the new Overlook Walk to the Olympic Sculpture Park, and the neighborhood routes split between Pioneer Square's Gold Rush story, the Chinatown-International District's three communities, Fremont's troll and Lenin, and the Space Needle to Kerry Park view. Leave a morning for Ballard's locks and a Scandinavian lunch. Seattle is a soft landing after the bigger metros and the natural place to tag on the Honolulu add-on.
- TransitNonstop Seattle to Honolulu flights run about 6 hours 15 minutes. One-way fares typically range from about $145 to $490 depending on season and how far ahead you book.SourceGoogle FlightsExpedia
Less time?
If you have less time, cut Chicago and keep the coasts. Do New York and Boston by train, fly straight from Boston to San Francisco, and finish with the Coast Starlight or a short flight to Seattle. That leaves a shorter loop with the two eastern powerhouses and both Pacific cities, and you lose only the middle hop.
Planning your route
Do I need to fly between the regions on this route?
You fly the long middle legs and the train handles the bookends. Amtrak runs direct from New York to Boston, flights are the practical choice from Boston to Chicago and Chicago to San Francisco, and the Coast Starlight or a short flight covers San Francisco to Seattle. That keeps the airport time to three hops.
Should I reverse the direction?
You can, but east to west works better for the body clock. Flying west buys back hours of afternoon, and finishing in Seattle leaves the relaxed Pacific coast for the end. Going west to east turns the long flights into time-losers and pushes the busiest cities to the final days.
Is the Coast Starlight worth a whole day of travel?
Only if you want the scenery more than the speed. The northbound train leaves the Bay Area at 9:41 pm and reaches Seattle the following evening, with daylight through the Cascades and, in season, Mount Shasta. A sleeper room adds real cost; a coach seat keeps it close to a flight price.
Where does Honolulu fit?
Add it at the end, not the middle. From Seattle or San Francisco it is one long overwater flight, and it deserves a few nights on its own rather than a rushed two-day detour inside the mainland loop. Honolulu has its own covered walks, from Iolani Palace to Waikiki's royal shore.
More of the United States
- Walking toursWalking tours in the United StatesThe United States is too big for one trip, so the right first visit is a region. This page builds one coherent first trip: New York and Boston on the eastern end, a flight to Chicago, then the Pacific coast through San Francisco to Seattle. Each covered city carries Wayside walking tours that turn the big country into walkable days. Honolulu is a separate add-on, a long overwater flight from the West Coast that earns a few extra nights. Miami, Orlando, Los Angeles, and Las Vegas are covered here too, and they work better as their own trips or extensions than as detours on this loop.
- Know before you gothe United States essentialsThe national need to know for a first United States trip: entry rules, dollars and tipping, trains and flights, plugs, holidays, and when to go.
Do it yourself
Follow it in the app
Walk New York, Boston, Chicago, San Francisco, and Seattle with a local's routes already loaded in the app.
Provenance · last verified August 20, 2026
Researched and routed by Wayside, with inter-city detail checked against the source.
SourcesBudget Your TripTrain From ToAmtrakGoogle FlightsExpediaGoogle FlightsFareCompareTravels with KevWanderuGoogle FlightsExpedia
Photo by Maarten van den Heuvel on Unsplash