Tuscany's capital is packed with world-class art and history. Don't miss the Duomo and its iconic dome, the Uffizi Gallery, and a walk across the Ponte Vecchio. If shopping is your thing, Via de' Tornabuoni is Florence's answer to Fifth Avenue. About 1 hour by car, or 1.5 hours by direct train from Siena.
A charming, walkable city with a completely different vibe from Florence. Go to the top of Lucca's Renaissance-era city walls that encircle the historic center. About 2 hours by car.
If you can build in extra days, Rome is unforgettable. See the Colosseum, throw a coin in the Trevi Fountain, wander the Vatican and Sistine Chapel, and shop around the Spanish Steps. About 2.5–3 hours by car or train.
Tuscany isn't just hill towns, the coast is about 1.5 hours from the estate. Castiglione della Pescaia and Follonica are close for a relaxed day by the sea.