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For me this seems to be a showdown between California, Florida, Texas, and Ohio. Florida has Tampa Bay, Pensacola, Tallahassee, Jacksonville, St. Petersburg, Fort Myers, Naples, Orlando, Daytona Beach, and Miami. Texas has Houston, Waco, Dallas, Fort Worth, San Antonio, Austin, Wichita Falls, Amarillo, and El Paso. Ohio has Cincinnati, Dayton, Toledo, Columbus, Cleveland, Akron, Canton, Youngstown, and Portsmouth. California has San Diego, Los Angeles, San Jose, Sacramento, and San Francisco. OHio has an astounding number of major cities for a state its size (it certainly is one of the smaller states as far as land area goes.
naples, FL has only a population of 21,000+. definitely not a major city. and it's not tampa bay, it's just tampa. tampa bay is the metro region.
portsmouth, OH is also only around 21,000. what about lima (40,000+ instead)? or even mansfield (50,000+, with a noticeable skyline too). just not portsmouth.
to answer the question though, i've always thought ohio as the #1, especially based on size ratio. but it's probably technically california or texas.
despite being small, and these cities being in the way of only 60,000-150,000 each, connecticut has a wide array of small cities. there's hartford, bridgeport, new haven, meriden, stamford, waterbury, norwalk, danbury, new london, etc.
For me this seems to be a showdown between California, Florida, Texas, and Ohio. Florida has Tampa Bay, Pensacola, Tallahassee, Jacksonville, St. Petersburg, Fort Myers, Naples, Orlando, Daytona Beach, and Miami. Texas has Houston, Waco, Dallas, Fort Worth, San Antonio, Austin, Wichita Falls, Amarillo, and El Paso. Ohio has Cincinnati, Dayton, Toledo, Columbus, Cleveland, Akron, Canton, Youngstown, and Portsmouth. California has San Diego, Los Angeles, San Jose, Sacramento, and San Francisco. OHio has an astounding number of major cities for a state its size (it certainly is one of the smaller states as far as land area goes.
I'd say California, though Texas is a close second.
LA
San Diego
San Francisco
San Jose
Oakland (bigger than New Orleans or Memphis)
Sacramento
Palm Springs
I'd say its a three-way tie between Florida, California and Texas. I count four major cities/metro areas in each. Florida is debatable, since I'm not sure Jacksonville qualifies as a major city.
Florida: Orlando, Miami-West Palm Beach, Jacksonville, Tampa-St. Pete
Texas: Houston, Dallas-Ft. Worth, Austin, San Antonio
California: San Francisco-San Jose, Los Angeles, San Diego, Sacramento
Ohio would be in the next tier with 3 major cities.
...
The more I look at my list, the more I don't agree with it. Should El Paso be considered in the Texas list? How bout Fresno? Are they comparable in size to Jacksonville?
I would say California is the #1 state with the most major cities: 1. Los Angeles, 2. San Diego, 3. San Francisco, 4. San Jose, 5. Oakland, 6. Sacramento, 7. Fresno. Long Beach and Anaheim are pretty big too. Anaheim is basically like the center of Orange County, and they have their own hockey team (and baseball until it became the "L.A. Angels of Anaheim"). Santa Barbara is also a decent size.
#2 would be Texas: 1. Houston, 2. Dallas, 3. San Antonio, 4. Austin, 5. Ft. Worth, 6. El Paso
Surprisingly, New York state doesn't have a lot of big cities. It just has NYC and Buffalo. Rochester, Syracuse, and Albany are kind of big, but I don't know if they would be considered major cities.
Tennessee is another state that has a lot of big cities for it's size. It has Memphis, Nashville, Chattanooga, and Knoxville which are good sized cities.
This isn't a very scientific method, but California has seven cities with major pro sports teams bearing their names: Sacramento, Oakland, San Francisco, San Jose, Los Angeles, Anaheim and San Diego. That has to say something for the size/significance of each.
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tampa bay is the metro region. 
