This only includes cities I visited during the decade; specific sights, museums, etc. and non-urban attractions (Grand Canyon, Petra, etc.) will be separate categories. And Chicago doesn't count since I live there, but still ranks as my favorite city.
North America
1. New York - I was in the Big Apple 10 times during the decade and it never lost its bite. Broadway is amazing and there's always some place new to explore.
2. Philadelphia - Don't think I'd want to live there, but for 3 days, Independence Hall, the Liberty Bell, related historical sites, great museums (including the little known but fabulous Barnes Foundation), awesome cheesesteaks and a new ballpark make for a great trip.
3. Washington, DC - All the things to see and do on the National Mall and beyond make this a great place to visit.
4. New Orleans - Sadly, I first went in 2007 and the devastation of Katrina was still readily apparent. But the French Quarter is spectacular and a tour of the hurricane-affected areas was harrowing. Also, the food is as wonderful as touted, even if Antoine's wasn't quite.
5. Nashville - Somewhat surprising how much I enjoyed all the historic music sites, honky tonks (free music bars) and even the replica Parthenon.
6. Boston - Is the Big Dig over yet? I was there in 2000 after first going in 1993 and the construction was still going on, slightly diminishing the joy of this amazing walking city.
7. San Francisco - A beautiful city but a bit short in top-notch interactive tourist experiences (museums, etc.) rather than simply enjoying the beauty/allure of Golden Gate, Lombard St., the non-tourist Wharf, Haight-Asbury, North Beach, etc. But it does have the #1 new ballpark of the 2000s.
8. Pittsburgh - Home to the second best new ballpark in America, some top rate museums, the enjoyable Mt. Washington overlook (and Duquesne Incline) and delectable sandwiches that feature fries and slaw atop the meat. Also the closest city to Frank Lloyd Wright's amazing Fallingwater.
9. Montreal - I enjoyed all 3 of Canada's major cities, including Toronto & Vancouver, but I think Montreal was the coolest.
10. Seattle - Ahead of some of the honorable mention cities by only a small margin, but the Experience Music Project and Space Needle, nice new ballpark and the old "underground" tours made this a very enjoyable visit. I also saw the pre-Broadway visit of Hairspray here, and instantly predicted it would win the next Tony, which it did.
Honorable Mention:
Denver (some of the best sites in Boulder, Rocky Mountains & beyond); Kansas City (surprisingly great museums: Negro League Baseball museum, Jazz museum, Hallmark museum and Nelson-Atkins art museum are all top notch); Austin (like Nashville, a great city for walk-in free music, but a bit short of daytime attractions); San Antonio (loved the Alamo & Riverwalk); Toronto (much like Chicago except for the skyline); Milwaukee (Calatrava's art museum expansion and Miller Park added greatly to MKE's allure this decade); Detroit (much maligned for all the lasting blight, but the Henry Ford Museum & Dearborn Village are among the top US museums, the art museum is good and both the new baseball & football fields are enjoyable); Grand Rapids (undergoing massive construction when I was there, making the home to a nice new art museum and a great open-to-the-public Frank Lloyd Wright house, a city on the rise); Las Vegas (mass artifice but enjoyably so); Los Angeles (liked it better as a visitor than a resident)
Others to mention:
Vancouver, San Diego, Cleveland, Louisville, Indianapolis, Madison, Oklahoma City, Toledo (surprisingly stellar art museum)
Rest of the World
1. London - Magnificent history, theater, museums and vibrance. If only the food was better.
2. Florence - All the Italian cities I saw were spectacular, but I think I liked this best, just over...
3. Venice - Probably the most beautiful place I've been
4. Bilbao - Sparked by Frank Gehry's new Guggenheim museum in 1997, this city felt fresh and revitalized when I was there in 2005, and still had many massive construction projects underway. I hope to get back someday to see the results.
5. Paris - I was only there for less than 2 days in 2000 (after a longer trip in 1993) but still got quite an Eiffel
6. Rome - Easily overshadowed by how much one can enjoy the more quaint Florence, Venice, Siena & Pisa (and elsewhere I didn't get to), but Rome itself, with the Colisseum, Forum, Vatican and more, is truly mind-blowing
7. Barcelona - The architecture by Antoni Gaudi, capped by the spectacular yet still far from finished Sagrada Familia, is out of this world
8. Dublin - Typically just seen as a gateway to the rest of Ireland, it truly is an enjoyable world-class city
9. Prague - A number of enjoyable sites, but more just the beauty and vibe make it tremendous
10. Amsterdam - High art, low class, hidden homesteads and everything in between
Honorable Mention:
Melbourne, Liverpool, Jerusalem, Copenhagen, St. Petersburg, Stockholm, Brussels, Sydney, Cairo, Helsinki, Madrid, Toledo/Siena (both were awesome as day-trips from bigger cities)
No Hancock? Oh, I guess technically it's not a city, so you are off the hook. - tgem.
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