Sooo...let's put aside the fact that we may be crazy for taking a 14 hour road trip to Florida with LO. What time of day have you had the most success leaving for a long trip? Early in the morning? Overnight? Drive all day?
We have a few weeks, but I am already thinking of ways to keep LO occupied in the car as much as possible, but want to maximize his happiness (my sanity) on the trip.