Hello, Below is our close to final itinerary for mid may 2027. This is our first trip as a family (4 adults) and prefer a relaxed pace. Is there a way to organize this to replace one of the 3 nights in Tuscany areas to 4 nights? Is the Florence, Siena and Val d’orcio too much overlap? As a family we like to feel immersed in an area as much as possible and prefer being able to walk to town/village whenever possible. We will book a wine tour and a cooking class at some point. For those wondering about a car we will have a car after Florence and will ditch it in Chiusu before heading to Rome for a family wedding. One thought I had was collapsing Siena and Val d’Orcia into one 4 night and add 2 nights in Orvieto and ditching the car there. Or some other variation of that. I have made reservations but all refundable at this point. Also would love to hear your thoughts on my lodging choices and must see or do. Thank you!
Dates Nights Base Status
May 15–18 3 Varenna — Villa Monti, Violet Suite ✅
May 18–21 3 Florence — Oltrarno Borgo San Frediano ✅
May 21–24 3 Siena — Palazzo di Valli ✅
May 24–27 3 Val d’Orcia / Pienza area? 🔎
May 27–31 4 Rome — Via Germanico, Prati District ✅