/Where Should I Retire?: I’ll have $10,000 a month to spend and prefer a city with beautiful outdoors, warm weather and lots of culture — so where should I retire?

Where Should I Retire?: I’ll have $10,000 a month to spend and prefer a city with beautiful outdoors, warm weather and lots of culture — so where should I retire?


Savannah, Ga.

Dear Catey,

In 2022, I plan to retire. I am looking for that special place. The best way I can describe it is Chicago without the weather, taxes and high cost of living. If I never have to experience below-freezing temperatures again, I would be ecstatic.

I would also want close proximity to green space for hiking or meditation. I love to travel and want to do more of that once I am retired. I just have not found that perfect place the combines the culture, history and music of Chicago.

Through good choices and planning, I will have a monthly income of $10,000 and very little expenses. Any suggestions?


Dear C.S.,

First off, major props for those “good choices and planning” that will yield you $10,000 a month. This will give you myriad options that can meet most or all of the criteria on your checklist. And another pat on the back for the fact that, despite having $10,000 a month to spend, you’re still looking for a spot that’s cheaper than Chitown.

I hear your predicament (cold weather and high taxes), so you’re not alone in fleeing snow or a high cost of living. Of course, Chicago is a special place — it’s hard to beat the history and music it offers — but I think you’ll find that these two spots meet most of your needs.

Tucson, Ariz.


Sunset view of Tucson from Mount Lemmon.

If you pick Tucson, home to the University of Arizona, your dreams of never having to experience below freezing temperatures can come true (though summers are hot) — and it meets a lot of your other criteria, too. First, Tucson has a ton to do on the culture front: “A massive downtown revitalization, which hit its stride in 2014 with the launch of the SunLink Streetcar, includes new restaurants, the renovation of historic theaters, a vibrant arts community, and a handful of stylish hotels,” writes Travel & Leisure. It also has a rich multicultural history, was the first city in America to become a Unesco World Heritage City of Gastronomy, and offers plenty on the music front, too. (Here’s the New Times of Phoenix on why cool bands often go to the much smaller Tucson rather than Phoenix.)

“Pairing that urban renaissance with Tucson’s surrounding natural beauty means visitors find themselves enveloped in vibrant desert magic from the moment they arrive,” Travel & Leisure continues. And indeed, Tucson’s location in the gorgeous Sonoran desert is great for the hiking and meditation you want to do; Outside magazine, in fact, named Tucson one of the best towns of 2019, citing, among other outdoor perks, that “Mount Lemmon offers more than 3,000 climbing routes.”

And the cost of living is appealing: It’s cheaper to live here than the average U.S. town, with the median home priced at under $200,000, and Arizona is one of the most tax-friendly states in America. Added bonus: There’s an international airport to make your travels easier.

Savannah, Ga.


A verdant Savannah streetscape.

This friendly, Spanish moss–laced city offers plenty of perks that you’ll likely love. First, the history: There’s the “world famous Historic District” with “more than 20 cobblestoned blocks [that] contain striking antebellum mansions, historic churches, manicured gardens, and parks shaded by towering live oaks. There are 22 historic squares, each with a different personality,” explains National Geographic.

That’s mixed with a vibe that’s decidedly “in the now,” writes Condé Nast Traveler, with “buzzing coffee shops, mind-blowing farm-to-table [dining] and an avant-guard art scene.” (The city is home to the renowned Savannah College of Art and Design.)

There’s also a lively music scene, with plenty of venues to see live shows.

Savannah isn’t quite the hiking town Tucson is, but there are trails you can hit up, and you can enjoy the beach, as well (beautiful Tybee Island is just 18 miles away). What’s more, it’ll save you plenty to live in Savannah versus Chicago, with a much lower cost of living and cheaper real estate.

Lonely Planet sums up the many joys of this Southern charmer: “Rife with elegant townhouses, antebellum mansions, green public squares, pristine tidal freshwater marshes and mammoth oak trees bedecked in moss, Savannah is a beautiful and culturally rich city.”

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