BoMag-Cliff-Jack-500In the course of my job, I get more seat time in high-caliber vehicles than dedicated staff at car magazines. That’s not to brag, but to illustrate the challenge I had. With a Rolls-Royce, Bentley, Mercedes, BMW, and Subaru’s new sports car all in one summer, I knew I’d need to produce something beyond a standard review. I pitched this road trip feature to Boston Magazine, the city’s premier luxury lifestyle magazine, and found myself driving 2,100 miles across New England — and occasionally, stumbling into the woods and having beers with a ukelele player. The result is a 12-page travel spread filled with lush photos from Dominic Casserly, who shot me and my dog out the back of an old pickup, after months of planning routes, researching towns and taking on my first big assignment after leaving the Globe that spring. It felt like freedom.