Siena has more history, more hills and a great place to taste wine, the Enoteca Nationale. Lucca is quieter, smaller easier to get around and has a more small town feel. It does have some great medieval art, as Ruskin noted.

Choosing between Lucca and Siena depends on your preference for atmosphere and geography. Lucca is often considered "better" for those seeking a relaxed, flat, and highly walkable experience. It is famous for its intact Renaissance walls that have been converted into a 4km elevated park for walking and cycling. Lucca is elegant, less hilly, and serves as an excellent base for exploring the northern Tuscan coast or the Garfagnana mountains. Siena, on the other hand, is "better" for those seeking a dramatic, medieval hilltop experience. It is famous for the Piazza del Campo (home to the Palio horse race) and its stunning Gothic cathedral. Siena is much more physically demanding with its steep, winding brick streets, but it offers a more "powerful" sense of history and classic Tuscan views. If you want a "fairytale" medieval city with intense energy, choose Siena; if you want a sophisticated, easy-going town where you can cycle around the ramparts and enjoy quiet piazzas, Lucca is the superior choice.