When to Go: Spring

Why: Many Romans retreat to the countryside around Easter, but after those festivities die down, there's no better time to visit Tuscany's hill towns. Usually packed with tourists during the summer high season, the plazas of Siena and San Gimignano are charming and easily navigable in the spring. And you'll be surprised how green this region gets before the summer sun browns the terrain (bring an umbrella, though, as showers are more prevalent this time of year).

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