Siena was the one time biggest rival to Florence in terms of it's wealth and power prompting warfare between the two a number of times. The founding goes back supposedly to Remus, Romulus's twin brother, and you may be forgiven for seeing the famous 'wolf and children' symbol around the place. Siena's centre is car free since 1966 making the walking side more pleasant through the winding streets. The town is more Gothic looking in its architecture than Renaissance and is home to Italy's finest gothic Cathedral, completed in 1215. The Palio is Italy's most famous horse race so it pays to book accommodation ahead, but it helps there's 2 of them-2nd July and 16th August. The race is fast, lasting about 2 minutes, but there are street parties afterwards that continue on into the night.