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1.
. . . is larger? (area)
Florida: 65,757.70 sq mi
New York: 54,554.98 sq mi
Source
2.
. . . has a greater population?
Florida: 21,538,187
New York: 20,201,249
Source
3.
. . . has the greater difference in elevation between its highest point and its lowest point?
Both have their lowest point at sea level, but New York's highest point is Mount Marcy (5,343 ft) and Florida's is Britton Hill (345 ft).
4.
. . . has the larger largest city?
New York: 21,800,000
Miami: 6,350,000
5.
. . . has the larger capital city? (metropolitan statistical area)
Albany: 886,188
Tallahassee: 382,627
6.
. . . has more cities with population greater than 1 million?
Florida: 6
New York: 1
7.
. . . has more water area?
Florida: 12,132.94 sq mi
New York: 7,428.58 sq mi
Source
8.
. . . has a greater average annual precipitation?
Florida: 54.5"
New York: 41.8"
Source
9.
. . . was settled by Europeans first?
Florida: 1500s
New York: 1600s
10.
. . . has the least distance between its capital and the capital of a foreign country?
Albany > Ottawa: 214.21 miles
Tallahassee > Havana: 519.62 miles
11.
. . . has the tallest building?
New York: One World Trade Center (1,776 ft)
Florida: Panorama Tower (868 ft)
12.
. . . has more "Big 4" professional sports teams?
They're tied on MLB, NBA, and NFL teams, but New York has 3 NHL teams to Florida's 2.
13.
. . . has a higher Hispanic/Latino population (by percentage)?
14.
. . . has a higher African-American population (by percentage)?
15.
. . . is "taller"? (greater distance between northernmost and southernmost points)
16.
. . . is "wider"? (greater distance between easternmost and westernmost points)
17.
. . . borders more U.S. states?
18.
. . . has the busiest airport?
19.
. . . has more interstate highway mileage?
20.
. . . has a city named Long Beach?