You can fly into Boston and make your way to Bar Harbor, over the course of 3-5 days. Of course, you can take longer if you want or shorten the trip into just day trips.
Alaska Route: Paxton, AK to Cantwell, AK
Camping is the most popular way to explore the road, but there are a number of rustic lodges and roadhouses along the way that caters to adventurous travelers. Bring your binoculars, camera, and be prepared for an Alaska road trip like the Alaskans do.
Arkansas National Scenic 7 Byway
Cruise down the California coast on what is one of the best road trips in the USA. And then work your way down to San Fransisco where you can enjoy walking across the Golden Gate Bridge.