I went to the keys for the first time about 25 years ago, not bad at all, as the years passed the traffic got worse and worse. I did not go for about 10 years and last year went to Key Largo (1st Key on way south) with a friend to pick up a boat. The traffic was freakin horrible, I don't know if something was going on or it is always like that.
I would think that 4 hours to Key West is rather optimistic. On one hand the traffic is terrible on the other it is a scenic drive. I would definitely spend the night and not try to make it in one day. Plus there use to be a lot of activity's along the water front in the evening, jugglers and musicians and clowns and sword swallowers and such, I don't know if they still do it but was a lot of fun!
I know of 2 option's, there are likely more. Boats can be rented in FL if you might enjoy that for the trip. There is also a Ferry from Ft Myers to KEy West, however Ft Myers is on the opposite side of the state from you (this is the way I will go if I do). There are no ferry's on the east coast of FL to Key West
Here it is, http://www.sunsetcelebration.org/
Yup stay the night!
Edited by Jester, 11 December 2016 - 10:03 PM .