When it comes to wine and olive oil, a bigger price tag doesn’t necessarily mean better: with so much of both produced in Tuscany, you’ll often find that the house wine—served straight-up in a jug or unlabeled bottle—is more than good. If you’re visiting in November or soon after, ask for the “new” olive oil in restaurants, to enjoy the latest post-harvest releases. Skip eating in the main piazzas, which are generally lined with overpriced tourist traps. And if you’re in one of the smaller towns before dinner, join locals for la passiagata, or the evening stroll, when everyone is out to see and be seen.