My 5 Favorite U.S. Cities

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a city with a body of water and a bridge

I don’t live in a city, and don’t ever plan to. Coming back to my tiny hometown is still a special part of any trip away. After living in this lovely northern California valley for 25 years, nowhere else on earth will truly be home.

But I do enjoy visiting other parts of the United States, especially cities. Some I’ve enjoyed far more than others, and each is unique. Here are my top five favorites of those I have visited:

a street with palm trees and a white tower

Charleston

Charleston may not make the true city definition in some people’s books (including the metro area, it doesn’t even hit a million residents), but it certainly does in mine. I visited Charleston for the first time at the end of 2018 and instantly fell in love. The rich history and charming beauty make it a gem of the South.

While the purpose of my one visit was work, I would love to return for a few days to enjoy this lovely city. I took an awesome walking tour of the city with a very knowledgeable guide, but had time to do little more than wander the streets and eat out well every night. Charleston has no shortage of excellent restaurants, something to keep in mind if you’re a foodie.

Seattle

Aside from San Francisco (which did not make my top 5 favorite U.S. cities), Seattle is the city I’ve visited most. From my trip as a kid with my family, to more recent visits, it is a place I’ve always enjoyed.

Pike Place Market is one of my favorite spots and should be among the top three things to do in Seattle on any list. The spot you might not know about, however, is Storyville Coffee, a highly preferred alternative to the nearby original Starbucks. Avoid a long line and enjoy a much better coffee in a warm, cozy atmosphere with views of Elliott Bay.

a lake with trees and a city in the background

New York City

The largest city in the country is usually at or near the top of most people’s favorites. The Big Apple has such a wealth of things to see and do that it is impossible to exhaust, even if you visit many times. From the history, to the food, to simply the energy of the city around you, visiting is such an enjoyment. And even when it becomes too intense, you can take a break in Central Park, almost forgetting there is a bustling metropolis all around you.

All three times that I’ve visited NYC have left me wanting to return. There is no other city quite like it.

Washington D.C.

It’s been too long since I’ve visited our nation’s capital. Way back in 2005 I had the opportunity to see it for several days over two separate trips, but I haven’t made it back since. I spent two whirlwind days touring with our Boy Scout Jamboree troop, which consisted of a visit to the Smithsonian National Air and Space Museum and the Museum of Natural History, besides visits to monuments, Arlington cemetery, and a photo-op with our congressman. It was insanely fast-paced.

Which made me appreciate the chance to visit for another week later that year at a much more leisurely pace. Washington has so much to offer as our nation’s capital, and it is still one of my favorite U.S. cities that I have visited.

chicago skyline

Chicago

I finally made it to Chicago for the first time this year, to the consternation of my dad. He had visions of us getting riddled with bullets. We moved on to Detroit just days later, making it a double whammy. But no, we didn’t hang out in the south side looking for trouble.

I’m sure anyone familiar with Chicago knows that the downtown and Magnificent Mile are both entirely safe and excellent parts of town. We had a blast. My first deep dish pizza at a place called Lou Malnati’s was amazing. My son and I also loved the Adler Planetarium and exploring the city by water taxi.

Chicago impressed. That’s all I can. I would love to go back again.

Other cities?

Closely following these are Portland, San Diego and Atlanta. I had so much fun in Atlanta with one of my boys last year, and San Diego we’ve visited multiple times, as my wife has family in the area. With beaches and weather in the 70s almost continuously, SD is hard to beat. Plus, the zoo is ridiculously amazing.

Boise, Denver, Detroit, New Orleans, San Antonio, Sacramento, and San Francisco fill out the middle of the list, in no particular order. A couple of others, St. Louis and Philadelphia, I haven’t visited recently enough to have a valid opinion. Phoenix is near the bottom of my list, right above Los Angeles and Las Vegas. Not sure which of those last two comes in dead last.

Top of my list that I haven’t seen: Boston.

What are your favorite U.S. cities to visit? 

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Mark Ostermann

In no particular order:
Nola
Denver
NYC
I don’t know why but I always have a BLAST in Cleveland and it is my favorite ball park so far
I also think Kansas City is very underrated

I haven’t done much of the west coast but that is coming over the next couple of years.

Least favorite – Atlanta – hands down worst place on earth!
Most overrated – Boston

Jason Brandt Lewis

In *alphabetical* order…

Top Five: Chicago, New Orleans, New York, Seattle, Washington DC.
Next Five: Boston (*not* during the summer!), Charleston, Las Vegas, Los Angeles, Portland (OR).

1) San Francisco is not on my list because I live here.
2) Las Vegas, IMHO, is no longer the Land of Buffets but a truly *great* food destination city (though perhaps not for kids).
3). Having grown up in LA, it’s fun to go back and visit for 2-3 days at a time, but heaven knows I never want to live there again.

Grace

Boston, New York City, Orlando, Charleston and San Diego are my top 5!

Chuck Griffin

I tend to like smaller, “walkable” cities. With that in mind and in no particular order:

1. Billings, MT
2. Portland, ME
3. Burlington, VT
4. Palm Springs, CA
5. San Juan (Old Town), PR

Joy

Thank you for mentioning St. Louis, even though you have no opinion yet. At least this s we St. Louisans know to stay away from, or drive through fast with the Lord’s Prayer on our lips. But majority of the metro area is safe, and family friendly. St. Louis’ unique City/County layout does not help. In a metro area of almost 3 million, the city is only 300K. So the crime rate in the city, which is
very high, is only aggregated over the 300K figure. That makes our crime figure very disproportionate.

The Unaccompanied Flyer

Going to second that. We often get put on the most dangerous cities list but I’ve lived here my whole life and crime is minimal in most of the area. City and county are quite unique. I suggest checking out the Central West End or The Grove. In the county, Kirkwood, Webster, and Clayton are three cities to check out as well.

Jason Brandt Lewis

In the FWIW mode, St. Louis is *not* unique re: “city/county layout.” It is the “City and County of San Francisco.” St. Louis itself covers (on land) 66.1 square miles, versus just 46.9 sq. mi. for SF. But both are great places…

Christian

Check into St. Augustine some time. Even though I’m from Florida, I didn’t visit until after I turned 40. My loss.

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