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The 15 best trips to take alone in America

Who needs a travel buddy to enjoy a vacation? Here are the best trips to take alone across America for guaranteed fun.

Powell California
San Francisco
By Tolly Wright |

Need some solo time? Want to explore the country on your own? Whether newly single, in need of decompressing following time spent on one of the best family cruises leaving from America or looking to make use of those credit card points towards a stay at the best hotels in America, we’ve got you covered: Here are the best trips to take alone across America for guaranteed fun times (you’ll probably also want to bookmark our list of best Italian restaurants in America—in case a craving for pizza suddenly kicks in while traveling).

Asheville, North Carolina
Photograph: Courtesy CC/Flickr/Ken Lane

Asheville, NC

Nestled in the Smoky Mountains, this western North Carolina city is a favorite among artists and outdoor lovers alike. The cool, tranquil waters of the French Broad River, located within the city limits, are perfect for a kayak trip, while the nearby mountains offer plenty of great hikes and look out spots for photographers and nature enthusiasts. If you’re looking for a more refined experience, check out the fairy tale castle-like Biltmore Estate, the largest privately owned house in America, where visitors are invited to explore the meticulously maintained gardens and interior. A fan of beer? You’re in luck: Asheville has more breweries per capita than any other city in America. Cheers!

Belmont Park
Photograph: John Bahu

San Diego

San Diego is all about those natural beaches, amazing surf waves and California burritos. The 1,200-acre Balboa Park deserves a full day (or two) of your attention. Here, you’ll find gardens, museums, theaters and the world-famous San Diego Zoo. All that amazing culture will be perfect fodder for your conversation on the boat to your scuba diving expedition.  

Chicago, Illinois
Photograph: Shutterstock


With top-notch museums, parks and a public transportation system that rivals any other across the country, Chicago is a winning bet for a vacationer still unsure about the pros of solo traveling. For some much needed me-time, go shopping along the Magnificent Mile (North Michigan Avenue) or visit an amazing spa. Looking for company? Check out the city’s top comedy clubs, including Second City, the iO Theater and the Laugh Factory.

Powell California

San Francisco

In a city that fully embraces free spirits, your desire to fly through local museums, restaurants and scenic neighborhoods solo will certainly be celebrated. We suggest hopping aboard one of San Francisco’s historic cable cars and discovering this West Coast city one gorgeous sunset at a time.

Public Garden
Photograph: Elan Fleisher


While Boston might loom large in American history (it is the oldest city in New England, after all), with a good pair of comfortable shoes, you’ll be able to walk the narrow winding streets and explore the relatively small city in a day. The nearly 400-year-old town is full of hidden treasures that can be discovered while on one of the many walking tours. Tired of walking? Try one of the trolley tours—the guides are top notch and you might just make some friends while aboard the bright vehicles.