The Best Places to Retire

Aaron Crowe
Written by
Aaron Crowe
Read Time: 2 minutes

Where you choose to live during your post-working days will greatly influence the success of your retirement years. Here are three of the best cities to hang your hat when your coat hook is no longer at the office.

When Frank Sinatra sang Cy Coleman's "The Best is Yet To Come," he may have been talking about his retirement days. After all, it was the last song he ever sang in public back in February 1995. And Ol' Blue Eyes did have the saying imprinted on his tombstone.

For Sinatra, Rancho Mirage, California proved to be city of his dreams. Do you know where yours will be? If not, here are three of the best candidates to ensure that you have a healthy and happy retirement.

1. Portland, Oregon. Constantly appearing on "best cities" lists, Portland may be the most perfect city for anyone, including retirees. Its 227 parks, 146 miles of hiking trails, and 277 miles of bike paths give active people recreation at every turn. There's skiing on Mt. Hood, kayaking on the Clackamas River, and a vibrant music and art scene. In addition to coming in second on CookingLight's "top 20 cooking cities," it was rated fourth in the best cities to walk. While not an inexpensive city, it is affordable, and retirees will enjoy their expansive public transportation system and 30 senior centers. Smart Money ranks it fifth on their list of "places to retire during an economic downturn," because there are job opportunities for seniors seeking part-time employment.

2. San Francisco, California. When Tony Bennett left his heart in San Francisco, he knew that it would be a good place to retire when his velvet vocals crooned no longer. While city living isn't for all retirees, those who enjoy excitement might find it the haven of their dreams. Developers are preparing for an influx of baby boomers by building high-rise condos downtown that are equipped with fitness centers, and are only a few BART stops away from the opera and symphony. has voted it second on its list of most walkable cities, and it's in the top five on "Best Places to Retire with Allergies." If you're looking for an athletic, artistic, and pollution-free retirement, and aren't intimidated by hills, San Francisco may be the place for you.

3. Delray Beach, Florida. No overview of best places to retire would be complete without an entry from the Sunshine State. South Florida's Delray Beach has everything a retiree wants and needs, including vast cultural opportunities, a thriving downtown district, easy beach access, substantial healthcare systems, and golf and tennis. In addition, it's ranked higher for "quality of life" than any of Smart Money's top 10 "Best Places to Live." It's smaller and less intimidating than South Florida's larger cities of Miami and Ft. Lauderdale, but large enough to find virtually any type of amusement or service that you seek.

The most important thing is to choose a location that makes you happy. Whether it's a beachfront condo in Delray, or a home in bustling Portland, the right place will make a significant difference in how you spend the rest of your life. Sinatra found his dream place in Rancho Mirage-but for you, just choose a place where you can be your own Chairman of the Board.

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