With planning comes shopping. Luggage, raingear, and walking shoes have been my main purchases so far.
I originally bought this bag at REI:
But I returned it and bought this Rick Steves bag instead:
Both bags convert to backpacks, but the Rick Steves bag is carry-on compliant (though it expands in case I need more space to carry things I buy), and the REI bag is bigger than the official allowed carry-on size. Also, the Rick Steves bag has a waist strap, which will make it much more comfortable if I have to carry it on my back much.
I showed it to my friend Cathy, and she said she doesn't believe I can get two weeks' worth of stuff into it. So that made me a little nervous, and I decided to do a dry run. I packed one pair of pants, one pair of shorts, five shirts, five t-shirts, five pairs of underwear, five pairs of socks, one sweatshirt, my CPAP, and my toiletry bag, and zipped it up. And it was loose. And not very heavy when I slung it onto my back. I'll be able to fit lots more if I have to. So take that, Cathy!
Rick Steves says to pack the same whether you're going for five days or five weeks. I got a little bottle of travel wash and a spray odor eliminator at his store in Edmonds, so I'm all set to wash and wear. And I bought travel t-shirts and underwear from ExOfficio.
I spent a lot of time shopping around for the right rain jacket, and finally settled on the Marmot PreCip. It only weighs 13 ounces, it packs into a very small amount of space, and it seems to be very breathable.
Everything I've read indicates that the American tourists are most recognizable because they wear sneakers, so I wanted to find something nicer. I read a lot of reviews, and I decided on Merrell Psychics. I've been breaking them in, and they're very comfortable, plus they're a nice attractive shoe I can wear out and about.
And I think I'm going to rent a car for one day so I can get off the beaten path a little and explore the Tuscan hill towns that are harder to reach by bus. I will probably do that on one of the days I'm in Siena.