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Photo Diary: My Favorite Cities to Visit [1]

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Date: 2025-02-15

Back while I was traveling around the country in a DIY campervan, I visited over 150 cities and towns in 47 states. I’ve often been asked “which one was your favorite?”, and it’s a difficult question to answer. I’ve never been in any city that I flat-out didn’t like, though of course some cities are … um … less nice than others. Once you’ve spent a couple weeks in, say, Trenton, every other city starts to look pretty good. (I intend no offense to Trenton—I liked it there and had a great time.) But I have found that every place has a story, and every city has its share of interesting places to see. Every place is different: while Savannah GA would sip sweet tea and chat with you on the porch, Pittsburgh would slam down an Iron City or four with you, and Chicago would be happy to fight you in a bar. And I loved them all.

So here is my (very subjective) list of the ten cities and towns which I think I liked the most.

Key West FL

My very favorite place, ever. I love everything about Key West, from the laid-back island vibe to the smart-ass demeanor of the locals to the aquamarine tropical surroundings to the “sunset party” every night at Mallory Square to the feral chickens and iguanas running around everywhere. I think I’d be living here if it wasn’t such a frightfully expensive place (it is $pendy here not only because it is a tourist haven but also because it is way out on the end of the island chain and everything has to be trucked all the way down from Miami).

Some of the places I liked here: the Aquarium, Hemingway House, Mallory Square (alas, the Cat Man has now retired and is no longer doing shows), Fort Taylor, Butterfly Conservatory.

Chicago IL

Chicago is a bare-knuckle working class town that remembers its history. Al Capone, the Haymarket Riot, John Dillinger, the first nuclear reactor, a Nazi submarine—it’s all here. The best deep-dish pizza in the US, and some of the best museums in the world.

Some of the places I liked here: Field Museum, Shedd Aquarium, Adler Planetarium, Museum of Science and Industry, Chicago History Museum, Navy Pier, Willis Tower (screw those Brits—it’s the Sears Tower, dammit), Millennium Park, Lincoln Park Zoo, Boat Tours.

Savannah GA

The nickname “Slow-vannah” fits this town. It’s laid-back and unhurried, with classic Southern hospitality. There’s a ton of history here—some of it not so honorable—and some of the loveliest tree-lined streets that you will ever see. And make sure to ask one of the locals about the lost nuclear bomb.

Some of the places I liked here: Tybee Island, Fort Pulaski, Museum of the Eighth Air Force, Georgia State Railroad Museum, Oatland Island Wildlife Center, Wormsloe Historical Site, Forsyth Park, Savannah National Wildlife Refuge.

Las Vegas NV

The polar opposite of “Slow-vannah”, Vegas has energy like a hyperactive kid who had too much sugar for lunch. There’s a reason why this place is called “Sin City”. There are slot machines in every gas station and pizza parlor, and I couldn’t walk half a block without someone handing me an ad for “private adult entertainment”. Most of the tourists here never leave The Strip, but there’s a lot to see that is outside of the neon glitz if you want to stay away from the one-armed bandits.

Some of the places I liked here: Neon Museum, Atomic Testing Museum, Mob Museum, Nevada State Museum, Springs Preserve.

New York City

There’s no place like the Big Apple. I’ve been here dozens of times since I was a kid and every time has been an adventure, whether it was getting arrested at a protest rally on Wall Street or visiting the American Museum of Natural History or walking around Times Square to see the human show. A microcosm of the USA, and whatever you like, you can find it here.

Some of the places I liked here: Statue of Liberty/Ellis Island, Central Park, American Museum of Natural History, USS Intrepid, Times Square, Coney Island.

Charleston SC

If you like “history”, then Charleston is like a candy shop to a kid. It played a central role in both the Revolutionary War and the Civil War. It also has lots of Southern charm and hospitality.

Some of the places I liked here: Fort Sumter, Submarine Hunley, SC Aquarium, USS Yorktown, Charleston Museum, Magnolia Plantation, Dorchester State Historic Park.

Washington DC

Another place that I’ve been to dozens of times, for plain ole vacation visits and for political and protest rallies. More “history” than one could ever ask for, and the best museums in the world, bar none. One of my favorite places to visit.

Some of the places I liked here: Smithsonian Museums (all of them), Monuments and Memorials on the Mall (lots of them), Fords Theater, International Spy Museum.

Pittsburgh PA

Whenever I say I liked Pittsburgh, people always wrinkle their nose and reply “Ewwwww, Pittsburgh?” But I liked it here. Pittsburgh was nothing at all like I expected it would be. Having grown up in Allentown PA, a former industrial center now turned into a rusted-out shell of what it once was, I expected Pittsburgh to be the same. I was mistaken. Pittsburgh has made the transition from industrial town to a cultural and historical center, without forgetting its working-class roots.

Some of the places I liked here: Carnegie Museum, Pittsburgh National Aviary, Heinz History Museum, Phipps Conservatory, Frick House, Science Museum, Fort Pitt Museum.

Austin TX

A tiny little dot of bright blue in an ocean of blood red, Austin has the feel of a town in California rather than Texas. In addition to being the state capitol, it is a university town and a cultural center with a thriving music scene. It also has one of the coolest places I ever visited: the “Museum of the Weird”. It is … well … weird.

Some of the other places I liked here: LBJ Presidential Library, Bullock History Museum, Texas Memorial Museum, Zilker Botanical Garden, Austin Aquarium, O Henry House.

Kansas City MO

I may be a wee bit biased towards KC because my childhood hero was Lenny Dawson, quarterback for the Kansas City Chiefs (not my namesake, alas—I was a Junior and was named after my dad because my parents had no imagination whatsoever). But the self-styled “Paris of the Plains” had a lot of cool things to see, and I had a great time here. It’s a big city, but it has a small-town feel to it.

Some of the places I liked here: World War One Museum, Steamship “Arabia” Museum, Union Station, Lakeside Nature Center.



Some “honorable mentions” that I liked a lot but couldn’t fit into the list: Philadelphia PA, San Antonio TX, Boston MA, Los Angeles CA, New Orleans LA, Buffalo NY, St Augustine FL, Denver CO, Phoenix AZ … My “top ten” has around twenty-odd entries.

So how about it—what’s YOUR favorite city to visit?

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