There's nothing grand or challenging about driving 1,000 miles in a modern everyday vehicle, but grand touring and/or even racing in an exotic vehicle from any era can turn the 1,000 miles into something memorable and romantic.
THE MILLE MIGLIA, an open-road endurance race which took place in Italy twenty-four times from 1927 to 1957 (13 years before the war, eleven more after 1947). From 1953 until 1957, the Mille Miglia was also a round of the World Sports Car Championship.
Since 1977, the "Mille Miglia" has been reborn as a regularity race for classic and vintage cars. The route (Brescia-Rome round trip) is similar to that of the original race, maintaining the point of departure / arrival in Viale Venezia in Brescia. To thrill of reliving this legendary race in almost any vintage classic vehicle would be more than a bucket or creating a memory. It would celebrating a living life.
I came across this documentary film of the Mille Miglia. It takes you through the wonderful event, it's history, the places, the people, and the cars. Enjoy
This video is a more upbeat from the down to earth funny guy, Jay Leno.