Rapid City, South Dakota to Key West, Florida

[rt88]

Hi everyone, I'm planning a trip from Rapid City, South Dakota to Key West, Florida, this summer. I'm driving a 1999 Ford Crown Victoria which gets 24 mpg highway. These are the cities I am planning to drive by:

Rapid City, SD - Pine Ridge, SD - Alliance, NE - Omaha, NE - Kansas City, MO - St. Loius, MO - Memphis, TN - Birmingham, AL - Jackson, MS - New Orleans, LA - Mobile, AL - Jacksonville - Daytona Beach - Orlando - Tampa - Miami - Key West, FL (roughly 3300 mi)

I'm planning to sleep a lot in the car and in cheap motels. I'm either driving solo or with a friend. I have roughly 5-6 weeks to complete the trip. Do you have any suggestions to where to stop on the way?

I like scenic drives, famous landmarks, small towns, diverse culture. I'd like to experience different types of local foods, music, and people.