Best Cities to Visit for a Multigenerational Family Reunion

Multi-Generational Travel

Some of the best cities to visit with your family tout diverse museums, restaurants, and all-ages attractions sure to please the entire group

A growing desire for experiences over material things and the need for togetherness among overscheduled families contribute to the trend. The biggest and best cities to visit for all ages will appease everyone in your troupe. Boomers eagerly want to share experiences with their grandchildren; Millennials and Xers love discovering different cultures; and GenZers seek “sustainable” adventure and interaction with local people. Tweens and toddlers just want to have fun! What destination works for a multigenerational vacation?

Some of the best cities to visit across the United States boast museums, theaters, concerts, parks, great restaurants, good public transportation and diverse neighborhoods. You’ll have plenty of choices for where to stay and what to do. We explore three of the top cities for multigenerational family travel for you to consider when planning a reunion.

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Boston, MA

Boston is a playground for the history buffs in the family. Walk the Freedom Trail or take a guided ghost tour of famous haunts. At Boston Harbor, you’ll find various boat tours, including some that will take you to the Charlestown Navy Yard, home of the USS Constitution. Originally built in 1797, “Old Ironsides” is the only active-duty ship in the U.S. Navy that has sunk an enemy ship.

Boston Harbor in Boston, Massachusetts, one of the best cities to visit with your family. Photo courtesy of Pixabay.

For sports fans, there’s Red Sox baseball at Fenway or Bruins hockey at “The Garden.” Boston and the surrounding area also are home to many of the finest colleges and universities in the country. Watch college rowing teams train on the Charles while the Gen Z grandchild tour campuses and meet with students and admissions officers. After the campus visit, regroup for a great Italian meal in Boston’s North End.

Chicago, IL

Birthplace of the skyscraper, Chicago boasts world-famous tall buildings, and tours on the Chicago River provide a unique perspective on the city’s architecture. Visit Navy Pier for a boat tour or take the kids to the Chicago Children’s Museum. Try a real Chicago hot dog (yellow mustard, pickle relish, onions, dill pickle, tomato wedges, hot peppers, and celery salt—but no ketchup!) The kids will savor deep-dish pizza while adventurous grandparents can sample global cuisine all over the city.

“The Bean” in Millennium Park, Chicago. Photo courtesy of Lance Anderson/Unsplash.

Take in a show at Second City, the launchpad of many SNL, television, and movie careers, or check out the award-winning Goodman, Chicago Shakespeare, or Steppenwolf theaters. Ride the “el” to Wrigley Field for a Cubs game or take in a Blackhawks game at the United Center. Music lovers will find everything from blues clubs and rock to the world-famous symphony and opera. Don’t forget to take a family photo in front of “The Bean” sculpture in Millennium Park to preserve memories of your trip to the Windy City.

San Diego, CA

In California, San Diego offers something for everyone. The San Diego Zoo rightly deserves a day to visit but save time for the rest of historic Balboa Park. Situated on a hill above downtown, the park has gardens, museums, theater (including a puppet theater), and many food options. Downhill along the harbor, a convenient light rail system connects you to the USS Midway Museum and the San Diego Maritime Museum, both of which boast exhibits and ships from sail to steam.

Metal art at Coronado Tidelands Park on Coronado Island. Photo courtesy of Bob Osias/Unsplash.

Try a hop on-and-off trolley tour to historic Old Town for a taste of Mexican culture or the Gaslamp Quarter for Victorian style buildings, shops, and nightclubs. Not for those afraid of heights, ride the trolley across the 200’ tall Coronado Bridge to visit Coronado Island, home of the historic Hotel Del Coronado and the Coronado Tidelands Park, offering breathtaking views of the San Diego skyline.

Whether it’s relaxation or activities, sightseeing or cultural exploration, America’s biggest and best cities to visit with family have something for every generation. Be sure to subscribe for FREE to Destination Reunions for more family travel insights and start planning your reunion today!

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