Itinerary
- Day 1
Florence to Siena
You'll arrive at Florence Airport and take a transfer to your 4-star hotel in Siena. After checking in and getting settled, the rest of your evening is free. This medieval town is known for its Gothic buildings and the famous Palio horse race that happens here.
- Start point
- Aeroporto di Firenze Amerigo Vespucci (FLR), Via del Termine, 11, Firenze, Florence 50127, Italy (Florence International Airport)
- Accommodation
- Hotel (4**** Hotel in Siena like Athena or similar)
Landmarks Piazza del Campo 
- Day 2
Siena
Once you finish breakfast at the hotel, you have the full day to yourself. Wander through Siena's charming streets at your own pace, and take time to soak in the historic medieval atmosphere without any scheduled activities.
- Meals
- Breakfast (Breakfast at hotel)
- Accommodation
- Hotel (4**** Hotel in Siena like Athena or similar)
- Day 3
Siena
After breakfast, head to the meeting point for a guided walking tour through Siena's medieval center. Your local guide takes you through cobblestone streets and squares, showing you the city's noble families, artistic works, and UNESCO World Heritage areas. The tour wraps up at Siena Cathedral with its Gothic design, and then you're free to explore on your own for the rest of the day.
- Meals
- Breakfast (Breakfast at hotel)
- Accommodation
- Hotel (4**** Hotel in Siena like Athena or similar)
Included Activities
- Guided walking tour through Siena's medieval center with local guide (1 hour)
- Siena Cathedral entrance and visit
Landmarks Siena Cathedral (Cattedrale di Santa Maria Assunta) Piazza del Campo - Day 4
Siena - San Gimignano - Chianti - Montalcino
You'll have breakfast and then head to the meeting point around 8:30 a.m. for a full-day Tuscany tour. First stop is San Gimignano, the medieval hilltop town famous for its towers, followed by a traditional winery in Chianti where you'll have lunch with local cheeses, salami, and wine. Then it's through scenic Val d'Orcia to Montalcino for a tour and tasting of Brunello wines at a local estate before heading back to Siena in the evening.
- Meals
- Breakfast (Breakfast at hotel), Lunch (Light lunch featuring local cheeses, salami, and specialties paired with Chianti wines at a traditional winery)
- Accommodation
- Hotel (4**** Hotel in Siena like Athena or similar)
Included Activities
- Visit to San Gimignano (UNESCO World Heritage Site) with free time to explore
- Traditional winery visit in Chianti with light lunch featuring local cheeses, salami, and Chianti wine pairings
- Wine estate visit in Montalcino with guided Brunello wine tasting and regional products
Optional Activities
- Wine tasting at local enoteche in San Gimignano
Landmarks San Gimignano Val d'Orcia Montalcino 
- Day 5
Siena - Monteriggioni - Pienza - Montepulciano
After breakfast, you'll go to the meeting point and travel through the Tuscan countryside toward Val d'Orcia. You'll pass by Monteriggioni, a medieval fortress town, then stop at Fattoria Lornano winery for a guided tasting. Next comes the Renaissance town of Pienza where you can walk around and check out the famous pecorino cheese from the area. The day finishes at hilltop Montepulciano for a Nobile di Montepulciano wine tasting at a local winery before returning to Siena.
- Meals
- Breakfast (Breakfast at hotel)
- Accommodation
- Hotel (4**** Hotel in Siena like Athena or similar)
Included Activities
- Guided visit and wine tasting at Fattoria Lornano winery with local snacks
- Visit to Pienza with free time to explore Renaissance architecture and pecorino cheese shops
- Visit to local winery in Montepulciano with Nobile di Montepulciano wine tasting
Landmarks Monteriggioni Pienza Montepulciano Val d'Orcia 
- Day 6
Siena to Florence
After breakfast at your hotel, you'll check out and arrange a transfer to Florence Airport by private or shared car. You'll head home with memories of Tuscany's timeless character and landscape.
- End point
- Aeroporto di Firenze Amerigo Vespucci (FLR), Via del Termine, 11, Firenze, Florence 50127, Italy (Florence International Airport)
- Meals
- Breakfast (Breakfast at hotel)
