I've driven down there a few years prior from Springfield and if you're thinking of doing it to save money versus flying, especially if you have more than 3 people going, do it. Plus you'll be able to sight-see more of the US. Anyway for toll cost, it all depends on the route you follow. If you follow the "quickest" way, I95, it'll be in upwards of $30 or more dollars one way in toll as you have to get into and out of Boston and NYC (including one or two bridges in NYC,) the New Jersey turnpike, Delaware turnpike, and the JFK Memorial Highway in Maryland. One way of avoiding this and minimize the toll cost I found is following 91 South to 84 East (from Boston it's 90 East to 84 East,) then 81 South to 77 South. Once on 77 South, take the route to South Carolina where it merges back into 95 South bypassing all of the tolls. End result; a bit more drive time but less than $10 in tolls, money and hassle saved not flying, and more time spent with family while seeing more of the US.
260 miles taking Florida's TURNPIKE (toll) - SOUTH.
100 miles taking this route:Take SR-60 WEST from Vero Beach to Florida's Turnpike (toll); stay left past the toll booth on the entrance ramp to get onto Florida's Turnpike (toll) NORTH to ORLANDO.Take Florida's Turnpike (toll) NORTH to Orlando.
92 miles taking this route:Take I-91 SOUTH from Holyoke to I-90 MASSACHUSETTS TURNPIKE (toll) to BOSTON and ALBANY, NY at EXIT 14. Follow signs to I-90 MASSACHUSETTS TURNPIKE (toll) EAST to BOSTON.Take I-90 MASSACHUSETTS TURNPIKE (toll) EAST to Boston.
190 Miles taking Florida's TURNPIKE (toll) - NORTH.
The Florida Turnpike does not go to the Gainesville area of the state. You would have to take I-75 to get there from the Orlando area.
75 miles taking this route:Take I-75 SOUTH, from Orlando, to Florida's TURNPIKE (toll) - SOUTH to ORLANDO off EXIT 328.Take the TURNPIKE (toll) - SOUTH to Orlando.
73 miles taking this route:Take I-75 SOUTH from Ocala to Florida's TURNPIKE (toll) SOUTH to ORLANDO off EXIT 328.Take the TURNPIKE (toll) SOUTH to ORLANDO.
200 miles down the TURNPIKE (toll) SOUTH.
Take I-75 SOUTH from Atlanta to FLORIDA'S TURNPIKE (toll) SOUTH to ORLANDO at EXIT 328 in FLORIDA. To bypass MACON, take I-475 SOUTH (EXIT 177 off I-75 in GEORGIA).Take FLORIDA'S TURNPIKE (toll) SOUTH to Orlando.
178 miles taking Florida's TURNPIKE (toll).
Take US-231 NORTH to I-10 EAST.Take I-10 EAST to I-75 SOUTH to TAMPA at EXIT 296A.Take I-75 SOUTH to Florida's Turnpike (toll) SOUTH at EXIT 328 (LEFT EXIT).Take Florida's Turnpike (toll) SOUTH to ORLANDO.
438 milesThis is the route:Take I-75 SOUTH, form Atlanta, to Florida's TURNPIKE (toll) - SOUTH to ORLANDO at EXIT 328 in FLORIDA, via I-475 SOUTHaround Macon (EXIT 177 off I-75 to get onto I-475 SOUTH - BYPASS to I-75 SOUTH to VALDOSTA).Take the TURNPIKE (toll) - SOUTH to Orlando.