10 Free City Walking Tours

Chicago Architecture

Chicago’s monumental architecture takes center stage on this itinerary from Free Tours by Foot. Beginning at the country’s third-tallest building, the Willis (formerly Sears) Tower, and concluding at architect Frank Gehry’s Pritzker Pavilion and the Crown Fountain in Millennium Park, you’ll amble along the 1.25-mile Riverwalk to the waterfront through a skyscraper-littered route through Chicago’s downtown Loop. Marvel at works by the father of modern American architecture, Louis Sullivan, and the Modernist pioneer Mies Van der Rohe.

Duration: 2 hours

Frequency: Daily; check for specific dates

Reserve: Freetoursbyfoot.com​

Capitol Hill, Washington, D.C.

Visit the heart of political power in our nation’s capital with a tour of Capitol Hill from DC by Foot. Admire the legislative and judicial seats of government: the imposing white marble Capitol, Supreme Court and Library of Congress. While the buildings are closed to the public, you can listen to stories and trivia that bring these historic landmarks to life and find the best vantage points for photo ops. (The tour is not wheelchair accessible.)

Duration: 1.5 hours

Frequency: Daily; schedule released up to four months in advance

Reserve: Freetoursbyfoot.com

Chinatown, San Francisco

Admire Chinese temples (the country’s oldest), landmark pagodas and a dragon’s gate in the oldest Chinatown in North America and the largest outside Asia on this tour from Guruwalk. Watch older residents perch on cardboard boxes in Portsmouth Square, the community’s “living room,” to play cards or Chinese checkers. Spot the hospital where Bruce Lee was born. Get a personalized fortune cookie (a San Francisco invention) at the Golden Gate factory and then ogle the hanging duck and dried starfish at the Stockton Street Market. Bonus: Walk to the SOMA neighborhood and ride the gondola to the lush, 5.4-acre rooftop garden park above the Salesforce Transit Center. 

Duration: 2.5 hours

Frequency: Mondays and Fridays

Reserve: Guruwalk.com

​Historic Charleston

Learn the fascinating story of one of the country’s oldest cities — from the settling of Charles Towne in 1670 to the churches and spires that give the Holy City its nickname. On this itinerary, you’ll cross cobblestone streets and cut through back alleys to discover the beautiful mansions, elegant churches and old graveyards of Charleston’s historic center. You’ll also get a glimpse Fort Sumter in Charleston Harbor, whose capture by Confederates triggered the Civil War.

Duration: 2 hours

Frequency: Several times a week; frequency changes monthly

Reserve: Freetoursbyfoot.com

​Seattle Market Experience

It’s considered the “soul of Seattle,” but the nine-acre Pike Place Market is much more than just a farmers market. Shop for unusual products, including Nepali imports, cigar-box guitars and clothing from Iran. Snap a photo of the original Starbucks. Applaud the waders-clad fishmongers slinging hefty salmon across the fish stalls to be weighed and boxed. Get the signature mac ’n’ cheese at Beecher’s and drizzle it with white truffle oil from the Truffle Queen, or try the Russian piroshki popularized by Anthony Bourdain. Listen to star busker Carly Ann Calbero belt out a tune that belies her petite size. And leave your mark by adding your wad to the multicolored gum wall that grows up to four inches a year. 

Duration: 70 minutes

Frequency: Daily

Reserve: Seattlefreewalkingtours.com

​Boston Freedom Trail

On this classic Boston tour, stroll the iconic 2.5-mile Freedom Trail’s cobblestone streets, past colonial stone houses and ancient cemeteries, while hearing tales of rebellion, war and American independence. Every step tells a story of America’s birth, including the Boston Massacre and the Boston Tea Party, in a city where Sam Adams, Ben Franklin and George Washington once roamed. Stop at 16 sites, including the Boston Common, Old South Meeting House and Faneuil Hall.

Duration: 2 hours

Frequency: Daily

Reserve: Freetoursbyfoot.com

Old San Juan, Puerto Rico

Wrap yourself in Spanish colonial ambience as you admire two landmark forts guarding the harbor: San Cristóbal and El Morro. Follow the city’s cobblestone streets past shady plazas and centuries-old chapels to the narrowest house in America — just five feet wide — and to the bar that claims to have invented the piña colada. Outside the venerated Cathedral of San Juan Bautista, which, dating to 1540, is the oldest church on U.S. soil, listen to the guitarist-singer crooning “En mi viejo San Juan,” a haunting Puerto Rican anthem about missing one’s homeland. Finally, grab a fruit-flavored limber, Puerto Rico’s answer to the popsicle, which was named for Charles Lindbergh when he landed on the island in 1928. 

Duration: 2 hours

Frequency: Several times a week; frequency changes monthly

Reserve: Civitatis.com