I prefer to ride the backroads rather than super highways, so my trips always include towns along the way. I figure on riding 300 miles a day, so I choose to fly from central Florida to an area I want to ride. It lets me try out other bikes and saves mileage on my Vulcan 1600, which already gets 10,000 miles added to the odometer each year. This page is full of places you can fly to and rent a bike nearby.
Manchester, NH is 50 miles south of Laconia, and 95 miles to the Kancamagus Scenic Byway in Conway. EagleRider is just 4 miles from the airport and rents Harley, Honda, Indian, Victory and more. The Killington Classic event in August is just 2 hours from the airport. Consider riding western Massachusetts and eastern NY also.
Appleton, Wisconsin, near Green Bay has a regional airport and Harley rentals. Michigan's Upper Peninsula is 80 miles north. Wisconsin and Minnesota have plenty of rural getaways to enjoy.
The Texas hill country is 50 miles northwest of San Antonio. Caliente Harley-Davidson is 14 miles from the airport, with great rental rates. Rent an Electra Glide Ultra 2 days in April 2014 for under $150/day, including insurance.