On the trip itself it's a pretty flat run going from Punta Gorda up the west coast of Florida, Interstate 75, cutting across Florida to Jacksonville from Gainesville, then straight up Interstate 95. I will take my time doing it in two days.
Here are my weight projections:
2005 Boston Whaler 170 Montauk & 2010 E-Tec 115HO
Weight Pounds
Boat 1,400
Motor 390
Fuel 225
Battery 75
Oil 30
Trailer 550
Spare Tire 40
Misc 100
Anchor 50
Total 2,860
2015 Ford Escape AWD
Weight Specifications
Car AWD GCWR 7,626
Curb Weight 3,769
Trailer Hitch 100
Fuel 129
Driver 200
Tools 100
Total Weight (Car) 4,298
Total Boat+Car 7,158
The actual combined car and boat weight compared to the GCWR is only leaving about a 468 pound buffer.