Hiking in Tuscany is wonderful! It's such a grand way to enjoy the countryside & doing it with an organized group sounds more than civilized: sag wagon, no wrong turns, definite place to lay your head at day's end & assured dining.

For boots, you'll no doubt get lots of advice. I'm a 30-mile/weekly kind of walker & a confirmed backpacker as well, but I don't take or wear hiking boots on my travels. They're too heavy & bulky! I wear leather made-for-walking shoes, preferring the lightest weight possible. My latest are an absurdly expensive but heavenly pair of Arcopedico boots; these I wear for all but the roughest terrain & they look nice enough for urban wear. It's much less trouble to purchase a can of shoe wax when at my destination to keep them looking nice than to haul too many shoes. When I know we'll be tramping in the wet for a couple of weeks, I wear a pair of goretex ankle-high trailrunners. I've not encountered a footpath yet in Tuscany that would require heavy-duty hiking boots, but you'll see other folks wearing them.

Take my advice with a grain of salt if you like; I'm firm about not carrying anything more than necessary on my person while hiking. I've been known to remove the back pockets of hiking pants (who puts anything of value in those pockets when hiking!), the buttons on shirts (just sew the plackets shut), so why would I ever wear clunky heavy boots?

Gail In Eugene...