For millions of people around the world, retirement is just a dream. The cost of living is high, housing is scarce, and loneliness creeps in. If you’re a boomer looking to retire, you might want to live in a city that has it all. But, do you know where to start? We’ve made a list of cities that offer everything from the affordability of a retirement income to the warmth and friendliness of a small town. From the beach towns to the mountains, these places are sure to have everything you need for a happy and healthy retirement. Read on as we look at the best places for single boomers to retire in America.


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Philadelphia is the 5th largest city in the USA and is located in the state of Pennsylvania. Its people, buildings, and landmarks are all unique to its culture. From Benjamin Franklin to Rocky Balboa, you can find traces of Philadelphia in movies, songs, and artwork.

Pennsylvania’s biggest city is a great place to meet other seniors. Over 58% of women and 33% of men aged 65 and older are currently single in the city. 16% of women and 12% of men are single due to divorce. And, a third of women and 12% of men are widows or widowers. Around 8% of seniors in Philadelphia have never been married. 


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Miami is in southeastern Florida. It has warm weather and beautiful beaches. Miami is famous for its cuisine, nightlife, culture, and the Lincoln Road Mall, which is one of the top Miami shopping destinations in the country.

Retirees are drawn to Miami’s beaches and warm climate. In the Miami metro area, 62% of women and 35% of men are unmarried. Many Miami retirees are widows (34%) and widowers (11%), and around 19% of women and 14% of men are divorced. Close to 8% of people aged 65 and older in Miami have never been married.


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Chicago is the biggest city in Illinois, and is located at the southwestern tip of Lake Michigan. Chicago has a strong history and sense of community, unique architecture, much to see and do, and wonderful shopping.

Though you’ll need to bundle up for Chicago’s winter, there are plenty of opportunities to meet new people. 58% of women and 33% of men aged 65 and older in Chicago are single. Many people are single due to the death of a spouse. Divorce is a common reason to be single at age 65 or older. 16% of women and 11% of men are divorced. About 8% of seniors in Chicago have never been wed.

Los Angeles

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Los Angeles is known as the entertainment capital of the globe. This city attracts tourists from all over with its historic sites, picturesque settings, and celebrity homes. It also has the best weather in all of America.

Retirement in LA brings the excitement of living near Hollywood. The area has top-ranked medical centers that draw people to live there. Almost 59% of women and 33% of men are currently single in LA. And, about 9% of seniors in the Los Angeles metro area have never been married. 

New York

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New York – it’s the center of the universe, the heart of the country, and the city that never sleeps. From its skyscrapers to its museums, it’s a city that just begs to be explored.

The NY metro area is home to over 1 million seniors who are currently unmarried. In New York, 61% of women and 33% of men aged 65 and older are single. The state has an unusually high proportion of people who’ve never gotten married, but many older residents are also divorced or widowed.