Itinerary
- Day 1
Florence to Colle Val d'Elsa
You'll arrive in Florence and your driver will pick you up for the drive to your accommodation in the Chianti Hills. The village setting gives you a chance to settle in and get oriented. After you drop your bags, there's a welcome drink waiting, and then dinner happens at a local spot that's been picked out for you.
- Start point
- Firenze, Firenze, Italy (Airport )
- Meals
- Dinner (Welcome dinner at local restaurant)
Included Activities
- Welcome drink at accommodation
- Dinner at local restaurant
Landmarks Colle Val d'Elsa San Gimignano Chianti Hills 
- Day 2
Val d'Orcia and Siena
Following breakfast, you'll spend about an hour driving to Val d'Orcia in southern Siena Province, which is a UNESCO Heritage site. At an award-winning farm, you'll walk through the vineyards and see the Brunello di Montalcino production up close, including time in the cellars. A light lunch with wine tasting comes next. The afternoon takes you to Siena where you can wander through the Renaissance architecture, check out the Dome and Piazza del Campo, then you'll head back to the hotel.
- Meals
- Breakfast, Lunch (Light lunch with Brunello di Montalcino wine tasting at farm)
Included Activities
- Vineyard walk at Brunello di Montalcino farm
- Wine cellar visit and tasting
- Light lunch with local food at farm
- Free visit of Siena
Optional Activities
- Dinner at local restaurant (not included)
Landmarks Val d'Orcia Siena Cathedral (Dome) Piazza del Campo 
- Day 3
Volterra and San Gimignano
After breakfast you're heading to Volterra, a medieval town on the edge of Chianti, where a guide shows you around and you'll have time to browse shops. From there it's on to San Gimignano for lunch on a terrace with vineyard views and a Chianti wine tasting paired with the meal. A guided tour of the town follows, and later you'll visit a nearby wine estate for vineyard and cellar tours. A tasting of local Chianti and food specialties wraps up the day before you return to your hotel.
- Meals
- Breakfast, Lunch (Lunch at traditional Tuscan restaurant with Chianti wine tasting on panoramic terrace overlooking vineyards), Dinner (Chianti wine and local food tasting at Wine Estate)
Included Activities
- Guided tour of Volterra
- Free time in Volterra for shopping
- Lunch at traditional Tuscan restaurant with panoramic terrace
- Guided tour of San Gimignano
- Vineyard visit at Wine Estate
- Wine cellar tour at Wine Estate
- Chianti wine and local food tasting
Optional Activities
- Dinner at local restaurant (not included)
Landmarks Volterra San Gimignano Chianti Region 
- Day 4
Bolgheri to Pisa
You'll check out after breakfast and take a minivan to Bolgheri, a small village known for Sassicaia wine and its famous Cypress road with over 2,400 trees lining both sides. Time to walk through the village and do a wine tasting at a local producer. Lunch at a traditional Tuscan restaurant gives you the chance to try regional dishes like truffle, mushrooms, and wild boar. After that, you're transferred to Pisa with an optional stop at Miracle Square to photograph the Leaning Tower, then on to either the airport or train station.
- End point
- Pisa, Pisa, Italy (Train Station )
- Meals
- Breakfast, Lunch (Lunch at traditional Tuscan restaurant featuring truffle, mushrooms, wild boar, and local specialties)
Included Activities
- Visit village of Bolgheri
- Wine tasting at local wine producer
- Lunch at traditional restaurant with local specialties
Optional Activities
- Photo stop at Miracle Square with Leaning Tower
Landmarks Bolgheri Cypress Road (Viale dei Cipressi) Piazza dei Miracoli (Miracle Square) Leaning Tower of Pisa 
