I'm in central Florida, so I have a 200 mile shot to get Tampa, Jacksonville and Miami, luckily no mountains to go over. I have a 50 foot crankup tower that's been up since the 70's.
I've always been happy with Wineguard antennas. The good antennas are directional so you will need a rotator. Also there are amplifiers available to further increase the signal. Make sure you get the antenna as high as possible and away from trees. Also make sure you ground the antenna outside, lightning is not your friend!
I would also recommend a good grade of coax cable for your signal and a coax grounding block installed near the entry point on your house.
If it sounds like a lot of work... it is, but the sound quality is worth it. Also, a good installation will last for years with little to no maintenance.
Good luck with it!