Itinerary
- Day 1
Siena
You'll arrive at your 4-star hotel in Siena and get settled into your room. Once you've checked in, the rest of the day is yours to spend however you'd like. Take a walk around the city on your own, get a feel for the place, and find somewhere for dinner. This first evening gives you a chance to start getting familiar with the medieval streets and historic squares that make Siena special.
- Accommodation
- Hotel (4**** Hotel Florence like B&B Hotel Pitti Palace, Una Hotels Vittoria or similar)
Landmarks Piazza del Campo 
- Day 2
Siena
After breakfast at the hotel, a local guide meets you for a walking tour through Siena's medieval center. You'll walk the narrow cobblestone streets and see the famous Piazza del Campo, where the Palio horse race happens each year. The tour covers the UNESCO World Heritage historic center and includes a visit to the Siena Cathedral. From there, the day is open and you can wander around on your own before picking a restaurant for dinner wherever appeals to you.
- Meals
- Breakfast
- Accommodation
- Hotel (4**** Hotel in Siena like Athena or similar)
Included Activities
- Guided walking tour through medieval Siena with local guide (approximately 1 hour)
- Siena Cathedral entrance and visit
Landmarks Piazza del Campo Siena Cathedral 
- Day 3
Siena - Monteriggioni - Pienza - Montepulciano
After breakfast, you'll travel by coach through the Tuscan countryside on a full-day guided tour. You'll see rolling vineyards, cypress-dotted hills, and the medieval fortress town of Monteriggioni along the way. First stop is Fattoria Lornano winery for a tasting and local snacks, then it's on to Pienza in the Val d'Orcia valley where you have free time to walk around and check out the local pecorino cheese. Your last stop is Montepulciano, a hilltop town with vineyards all around it, for a visit to a local winery and a tasting of Nobile di Montepulciano wine. You'll get back to Siena in the evening with time to grab dinner on your own.
- Meals
- Breakfast, Snack (Local snacks accompanying wine tasting at Fattoria Lornano)
- Accommodation
- Hotel (4**** Hotel in Siena like Athena or similar)
Included Activities
- Guided visit and wine tasting at Fattoria Lornano winery with local snacks
- Free time in Pienza to explore Renaissance architecture and local shops
- Wine tasting at local Montepulciano winery
- Coach or minivan transportation throughout the day
Landmarks Monteriggioni Val d'Orcia Pienza Montepulciano 
- Day 4
Siena - Departure
After breakfast, you'll check out of your hotel and head out of Siena. Your time in the city ends here, though you're leaving with memories of the medieval architecture, the wines, and those rolling Tuscan hills.
- Meals
- Breakfast
