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Renaissance and Romantic Italy - 10 days in Nov?

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We're planning a 25th anniversary trip to Italy for November. Will be husband's first trip there. My last trip to Italy was nearly 30 yrs ago. We've both traveled extensively in other parts of Europe, US & Asia, but keep missing Italy. We have 10 days/9 nites.

High points should be romance, Renaissance history & art, great food & wine, and a bit of wandering (our travel style). We've already cut out Rome - will have to plan another trip!

Does the following itinerary look doable for a Nov trip? Any recommendations on where to stay longer vs shorter?

Venice – 2 or 3 nites
Train to Florence – 2 or 3 nites
Car to Val d’Orcia, Tuscany – 2 or 3 nites (see Sienna as daytrip or on way)
Car to Ravenna (possibly via San Marino) – 1 nite (DH really wants to see the mosaics)
Train to Milan – 1 nite (for flight home; or better to fly out of Venice? Can likely get direct flight to DC from Milan).

Thanks!

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