Itinerary
- Day 1
Florence
After arriving in Florence, you can set up a private transfer to get to your hotel. From there, you have the day to wander through the city at your own pace, taking in the history and energy of the streets around you.
- Meals
- Breakfast
Optional Activities
- Private transfer to hotel
- Day 2
Florence
Join a small group walking tour that hits Florence's main sights. You'll skip the lines at the Accademia Gallery to see Michelangelo's David, then head to the Florence Duomo with its famous dome. Next comes the Baptistery's Gates of Paradise. Along the way, you'll walk past Piazza della Signoria, Palazzo Vecchio, and Ponte Vecchio while your guide shares stories and local knowledge about what you're seeing.
- Meals
- Breakfast
Included Activities
- Small group walking tour of Florence highlights
- Skip-the-line entrance to Accademia Gallery to view Michelangelo's David
- Visit Florence Duomo
- Visit Baptistery to view Ghiberti's Gates of Paradise
- Walk through Piazza della Signoria, Palazzo Vecchio, and Ponte Vecchio
Landmarks Accademia Gallery Michelangelo's David Florence Duomo Baptistery of Florence Piazza della Signoria Palazzo Vecchio Ponte Vecchio - Day 3
Siena - San Gimignano
A full day through Tuscany with a guide and driver takes you through several stops. Start at Florence's panoramic viewpoint, then move to Siena for a walking tour of its central square and cathedral. Lunch happens at a family vineyard in Chianti with traditional homemade food and wine tastings. After that, head to San Gimignano to wander the medieval streets and check out local shops.
- Meals
- Breakfast, Lunch (Traditional homemade lunch with wine tastings at a family vineyard in Chianti)
Included Activities
- Scenic stop at Florence's panoramic viewpoint
- Guided walking tour of Siena
- Visit Siena's central square and cathedral
- Traditional homemade lunch in Chianti with wine tastings at family vineyard
- Visit medieval town of San Gimignano with time to wander and explore
Optional Activities
- Shopping for souvenirs in San Gimignano
Landmarks Siena Central Square Siena Cathedral San Gimignano Chianti Wine Region - Day 4
Florence to Montepulciano
Your private transfer from Florence kicks off with a stop in Arezzo, where you'll walk through the historic center and see the Basilica of San Francesco up close. After that, head to Cortona and wander around the charming alleys while taking in the views over Val di Chiana. Find a spot for lunch whenever works for you in either town, then continue on to Montepulciano. Once there, check in to your farmhouse or hotel and settle in. The day wraps up with a Tuscan dinner to get you started on the right note.
- Meals
- Breakfast, Dinner (Tuscan dinner at the property or in city center)
Included Activities
- Private transfer from Florence to Montepulciano with stops in Arezzo and Cortona
- Explore historic center and Piazza Grande in Arezzo
- Visit Basilica of San Francesco in Arezzo
- Stroll through alleys in Cortona
- Visit Piazza della Repubblica in Cortona
- View Val di Chiana from Cortona
Optional Activities
- Lunch at leisure in Arezzo or Cortona
Landmarks Piazza Grande Basilica of San Francesco Piazza della Repubblica Val di Chiana 
- Day 5
Montepulciano
Your morning in Montepulciano starts at Piazza Grande, then moves through local shops and a traditional restaurant. Visit an underground wine cellar to taste Pecorino cheese from Pienza, Tuscan salami, handmade pici pasta, bruschetta with Tuscan olive oil, and Vino Nobile di Montepulciano DOCG and Vino Rosso di Montepulciano DOC. In the afternoon, you can explore on your own or join an optional hands-on cooking class to learn how to make pici pasta.
- Meals
- Breakfast
Included Activities
- Guided tour of Montepulciano starting at Piazza Grande
- Visit local shops in Montepulciano
- Visit traditional restaurant and underground wine cellar
- Taste Pecorino cheese from Pienza, Tuscan salami, and handmade pici pasta
- Taste bruschetta with Tuscan olive oil
- Wine tasting of Vino Nobile di Montepulciano DOCG and Vino Rosso di Montepulciano DOC
Optional Activities
- Hands-on cooking class to learn pici pasta making
Landmarks Piazza Grande, Montepulciano Pienza - Day 6
Val d'Orcia Region
Full-day private tour through Val d'Orcia starts in the morning with Pienza and San Quirico, two Renaissance towns where you can see the architecture and scenic landscapes. Grab lunch at your own pace in either town for local Tuscan dishes. The afternoon takes you to Montalcino to learn about and taste Brunello wine. Later, you're free to relax or explore more of Montepulciano before heading back for the night.
- Meals
- Breakfast
Included Activities
- Private full-day tour of Val d'Orcia region
- Explore Pienza
- Explore San Quirico
- Visit Montalcino
- Wine tasting of Brunello wine in Montalcino
Optional Activities
- Lunch at leisure in Pienza or San Quirico with local Tuscan dishes
Landmarks Pienza San Quirico d'Orcia Montalcino Val d'Orcia - Day 7
Montepulciano
Have breakfast before you head out from Montepulciano. If you need a private transfer to continue on, just let them know and they can arrange that for you.
- Meals
- Breakfast
Optional Activities
- Private transfer from Montepulciano to next destination (available upon request)
