Amtrak Auto Train. VA to FL.

Nope, trips to Florida are much easier by plane believe it or not. Even from crazy Boston Logan airport.

Well, not really disputing the points made knocking rail travel, at least compared to the alternatives, but sometimes it's worth the premium IMHO.

For instance, my parents used to winter in FL (classic snowbirds!), at first in one of a series of campers quartered in a trailer park, then in a manufactured home (essentially a trailer w/o wheels, bolted on a foundation!) near my sister in the Orlando area. For the latter years without a camper, they'd load up their mini-van (and I mean, up to the roofline!) and drive it back and forth each year.

When the two day drive (from Maryland's Eastern Shore) became too much, they used the Autotrain to transport the loaded minivan back and forth, and avoid the strain of driving. After arriving, they'd drive to their FL house, unload the contents of the minivan, and would then have a vehicle to use for their winter months down south. The first year, they went cheap, just paying for seats on the train, but a night trying to sleep in those seats for the overnight trip convinced them to pay extra for a stateroom with fold-down beds. This worked well for my parents for several more years, until my sister's twin girls grew up and the annual migration became too much for them, even with the assistance of the Autotrain, and they sold (really, gave away!) the trailer -- err, manufactured housing -- and left the traveling and visitation to other family members for the rest of their lives!

This guy does a lot of video on train travel. The best so far is his Chicago to CA. Then from LA to Chicago. Anyone contemplating a long train trip and hasn't done one in a long time, a lot of info here. And yes, I wouldn't do Coach for anything longer then a day either.

We avoid flying at all costs. Its crowded, uncomfortable,you can't take much onboard and at the airport they treat you worse than a convict in prison. In the past 22 years we have taken Amtrak from East to West North to South and into the midwest. We have been very pleased with the service and feel that its the best way to travel as ladies and gentlemen.
As for the Autotrain from Lorton, VA to Sanford, Fl; we have taken about 8 trips. It leaves Lorton at 4PM and arrives in Sanford around 9 AM. Security doesn't bug you at all. You can leave all your heavy luggage in the car or take as much or as little as you wish aboard. By not driving it saves fuel, wear and tear on your car, a hotel overnight, you can bring almost anything on including food and snacks but most of all you save a car rental expense that can run hundreds of dollars. After departing, we enjoy a fresh prepared dinner in the dining car, relax a bit afterwards then have our bedroom made up for sleep. In the morning we wake up have breakfast and arrive early enough in Fl to spend the whole day at Disney, Universal or just relaxing.
Some will say that flying is better but you will still have the car rental expense, long term parking and/or airport transportation. Those costs can easily run you over $1000 + air fare.