Seattle to Orlando,and to the KEYS questions

All of the good diagonal routes, whether across the northern Midwest and starting down through Chicago, or going through Salt Lake City, through Colorado, Kansas, Oklahoma, Arkansas to reach the Gulf Coast in Louisiana or Mississippi, are about 3500-3600 miles, 50-55 hours driving time. Because I don't drive in winter conditions after dark (too difficult to assess road surface conditions) that would be 5-6 days each way for me. You will be in winter driving conditions shortly after leaving the Pacific Coast until you reach the Gulf Coast. Major highways are kept clear, except during actual storms when the crews are trying to catch up. You may have to wait out those situations, sometimes 2-3 days.

You can avoid most, but not all, of the winter driving going down along the coast to southern California and across I-10, which will be subject to freezing winter weather only between Arizona and Louisiana. This route is much longer, maybe 70+ hours drving time. It is popular for folks making seasonal moves, with time for leisurely travel and schedule flexibility, but does have less risk of delay.

Drug stops? I've no experience with that, but any travel route within 100 miles of a U.S. International border is fair game for immigration checks, whether random stops or checkpoints where all traffic is stopped for inspection. I've had to go through inspection at the permanent (but not always open) Homeland Security checkpoint on I-10 east of El Paso. I've also had to stop for agricultural inspection, several states do this, including Florida, but timing is random.

If this is a drug run for you, I suggest running through the middle of the country, and keeping your nose clean on traffic behavior, rather than trying to get across the areas where checkpoints are common.

I travel by road in winter from the middle of the country to the Great Lakes, to the Gulf Coast, and to Florida. In the winter I can manage 300-400 miles a day, adjusting routes and speeds to weather. Summer trips to same places, with 14-16 hours of daylight and only thunderstorms to dodge, I make 600-800 miles a day.

Your trip sounds like 5-6 travel days each way in the best of conditions, unless you have enough drivers to do it non-stop, the 3-4 days.

And if you want to see much of anything in Florida, consider that a trip from Central Florida to Key West and back was a week long for my wife and I, going down the Atlantic Coast from Cocoa and coming back through the Everglades and south central Florida. Things move slowly in Florida.

I think I'm going to go ahead and fly. I do have airline reservations,and rental car. Driving dose not bother me. I'm retired,and would have adjusted my time for the trip.. Maybe this summer I well drive back down to Florida

Lots of people love to drive versus flying. I'm ex-Air Force aircrew and a current pilot, but given the choice I'd much rather drive across the Country than fly.

I agree with those who say fly and rent a car, and I'm a guy who generally prefers to drive if it's at all doable compared to flying.

Just head South on 5 and then over. It's 500 miles further, but would have the best weather. But there are still some mountains through there. Carry chains or I personally like cables better than chains. Make sure you know how to put them on before leaving and make sure they fit. On your dates I assume you mean you are leaving to drive back on the 14th? Not that you have to be back in Seattle by the 14th?

Do you have two drivers or just one? I can do 1000 miles a day with two drivers, but just me driving my limit is about 750 in one day. But I've never tried that many miles that many days in a row. Sounds like you know how far you have to go so if you would rather drive than fly that's a decision for you to make.

I would fly unless I had longer to stay. You will have weather concerns that time of year getting across the central US unless you go south to 8 & on to 10, the long way around.

I've crossed the country kitty-corner in the opposite way a couple times, from Vermont to San Diego, along with taking various other long car road trips. That direction is a little shorter (around 3000 or so miles) and took me five full days, some very full. I don't like to drive more than about ten or eleven hours in a day as my alertness and general driving skills start to drop off pretty rapidly soon thereafter. Obviously, people differ in how long they can safely drive, but that's my limit.

At any rate, I'd plan on six days for Seattle to Orlando. Usually the interstates are kept fairly well passable as a general rule, but certainly pay attention to the weather and adjust as needed. (Do be aware that Florida is deceptively long, and it's several hours more from Orlando to Key West.)

As others have said, unless the road trip is part of the fun, it would probably make a lot more sense to fly and frankly may be less expensive to boot (depending partly on how many people are traveling). Even Amtrak might be quicker than driving and of a similar cost (at least if one doesn't get a sleeper).

With that time frame all you are going to do is drive. I would wait until there was more time available.

Is this a gag?
If not, X2 on flying and renting a car. BTW do you have reservations?
Google Maps shows 45 hours of driving time each way!

The shortest route I90, I29, I24, I75 is 3,474 miles around 6 days plus.

The warmest way staying out of most bad weather I5, I10 I75 is 4,049 miles around 7 days plus.

Why waste all of that time driving 7-8K miles in that short time?
Get on the plane in Seattle and fly to Orlando, then rent a car.
Drive to Key West and back to Miami or Fort Lauderdale and fly back home.
And spend up to 10-12 more days in Warm Florida.