Driving !-84 / I-81 / I-26 / I-95
Have taken that route often from CT and MA . . . From the Sturbridge toll it would take about 2 hours to reach NY border on I-84. Then 2 1/2 hrs to go thru NY and PA to reach I-81 in Scranton. 3 hrs to get thru PA on 81. 1/2 to get thru Maryland and WV. Then about 4 hrs thru VA till you get to I-77.
From I-81 split taking I-77 to Charlotte, NC around 3 hrs. from Charlotte to I-26 in SC about an 1 hr. another 1 hr. across I-26 to I-95 . . . 1 1/2 hrs from where you get on I-95 to the GA border. 2 hrs thru GA to FL line and 2 1/2 to 3 hrs to get to The Villages - there are many debated routes of which to take. . . . going the inland route is about 150 miles longer than taking a straight shot down 95, but you'll usually have less traffic, far less tolls, especially when going northbound, great scenery, and personally I like the gas stops and hotels along the route. Under normal conditions it should not
take you longer than 23 hours driving time.
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Watertown, CT + Duxbury, MA + The Villages 
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