4 Walkable Cities Perfect for a Weekend Getaway

Just add walking shoes!

What if your weekend getaway didn’t require a single car trip? No rentals, no rideshares. That’s
the appeal of walkable cities. On top of saving money, it’s also about freedom. The freedom to explore at your own pace, to take a detour down a charming street, to linger in green spaces. And everything you could possibly want to see is close enough to reach on foot.

Check out these destinations for a weekend that’s worth the walk!

• Chicago, IL

  Windy walkability!

  Chicago is one of those spots where you can spend the entire weekend walking around without ever feeling limited. Some of Chi-town’s most exciting experiences are clustered near the lakefront trail. So it’s easy to hit Millennium Park (home of the famous bean), the Art Institute, Field Museum, Shedd Aquarium, and the Riverwalk all in the same day. And the skyline views along Lake Michigan never get old!

  Chicago’s packed with fun, funky neighborhoods that are especially fun to discover on foot. Wicker Park is all about vintage stores, brunch spots, and record shops, while Fulton Market has some of the city’s best restaurants. And yes, a deep-dish pizza stop somewhere in between is basically part of the itinerary!

  Pro Tip: Chicago is also one of the top dog-friendly cities, so go ahead—bring your furry bestie along!

• New York City, NY

  The ultimate walk-everywhere weekend!

  With the country’s best public transportation, there’s no doubt that NYC is also one of the top walkable cities. The Big Apple is built for long weekends without a car. Start your day with bagels or coffee from a corner spot (or bodega) and head to Central Park, the Highline, or other green space. Then just… wander.

  Pop into high-end boutiques, stop by art galleries. Stroll along museum-filled 5th avenue. Walk across the Brooklyn Bridge, with its elevated pedestrian walkway and iconic views of Manhattan. In the evening, hop around rooftop bars, grab late-night pizza, or sip cocktails in the West Village. With a subway that runs everywhere, it’s easy to cover the majority of the city in just a few days!

• Portland, OR

  Coffee shops and brewery stops!

  One of our favorite walkable cities, Portland is made for wandering slowly and aimlessly. You can spend days walking around without needing a plan. Easy to explore neighborhoods are filled with coffee shops, breweries, and vintage stores. Powell’s City of Books, the world’s largest independent bookstore, can easily take a few hours to explore.

  Other walkable neighborhoods include the fashionable Pearl District, with its trendy restaurants and high-end shopping. The Alberta Arts District is another fun walking option, featuring numerous art galleries, eclectic shops, and colorful murals. Need a break from city strolls? Hop on the Express Shuttle to Washington Square’s zoos, gardens, and miles of walking trails.

• San Francisco, CA

  Postcard views on every walk!

  In San Francisco, even the most casual walks can turn into a scenic route. A quick coffee run can mean passing colorful Victorian homes or catching sight of the Golden Gate Bridge between buildings. Or climb a steep hill—there’s plenty of them!—for the stunning bay views at the top. And because the city’s layout is so compact, it’s easy to explore multiple neighborhoods in a single day.

  Golden Gate Park alone can fill your afternoon, with its gardens, museums, and walking trails. Or head to the Embarcadero, filled with shops, seafood restaurants, and views of Alcatraz across the Bay. Sip some of the stellar local wines and enjoy a visit with the city’s famous (and famously noisy) sea lions.

These highly walkable cities make exploring easy-peasy and give you a feel for the destination, without ever needing a car.

And to really lean into that go-with-the-flow mindset, ship your bags ahead to your final destination with LugLess. No hauling bags to the airport, no wasting time at baggage claim. Just land and start exploring!