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Plan Your Tour

The difference between a good trip to Italy and a great one is almost always in the planning. Not the hotels and the flights — those are easy. The harder questions: which week in October is worth the journey to Umbria, how to navigate the Italian rail system without losing half a day, what the seasons actually mean for the places you want to visit. This is where those questions get answered.

October in Italy: the definitive guide

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A top-down view of a rustic basket filled with fresh, whole black truffles, symbolizing the autumn gastronomic harvest in Italy.

September in Italy: the definitive guide

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A wicker basket overflowing with ripe red grapes sits between rows of vines during the September grape harvest, or vendemmia, in Tuscany, Italy.