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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.

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Q: Toll cost from Boston Massachusetts to Orlando Florida?
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