Tuscan Essence: Siena, Val d’Orcia & Chianti
4
Days
3
Nights
- Departure Rome or Florence (airport / train station / cruise ship)
- Destinations Tuscany
Overview
Escape the crowded metropolis and immerse yourself in the quintessential landscapes of Tuscany. Designed for discerning travelers seeking an authentic connection with Italian culture, world-class winemaking, and medieval history, this 4-day escorted journey explores the legendary medieval city of Siena, the postcard-perfect rolling hills of Val d’Orcia, and the famous Chianti wine region.
Itinerary
-
1
Day 1 — Arrival in Siena & Medieval Heritage
- Arrival: Meet your private driver and full-time Tour Leader. Check into your 4-star hotel in Siena’s historical center.
- Guided tour of Siena: Piazza del Campo, the Duomo, and the historic contrade with an expert local guide.
- Welcome Tuscan dinner: Multi-course dinner at an authentic Sienese trattoria with regional wines.
- Overnight: 4-star hotel in Siena historical center.
-
2
Day 2 — The Wonders of Val d’Orcia – Montepulciano & Pienza
- Departure: Breakfast, then travel into the UNESCO Val d’Orcia.
- Montepulciano & wine tasting: Guided stroll and underground cellar tasting of Vino Nobile di Montepulciano DOCG with local cheese and cold cuts.
- Pienza & Pecorino tasting: Explore the Ideal Renaissance City and taste Pecorino di Pienza.
- Agriturismo check-in & dinner: Countryside estate and farm-to-table dinner.
- Overnight: Boutique Tuscan agriturismo / countryside estate.
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3
Day 3 — Heart of Chianti – Medieval Castles & Grand Tasting
- Chianti scenic drive: Chiantigiana road, villages such as Radda and Greve in Chianti.
- Exclusive vineyard tour & wine tasting: Prestigious Chianti estate with Chianti Classico DOCG tasting.
- Tuscan vineyard lunch: Multi-course lunch at the winery.
- Evening dinner: Traditional Tuscan dinner back at the agriturismo.
- Overnight: Boutique Tuscan agriturismo / countryside estate.
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4
Day 4 — San Gimignano & Departure
- San Gimignano visit: Guided walking tour of the walled hill town and iconic towers.
- End of services: Farewell transfer to Rome or Florence airport/train station/cruise ship.
Costs & services
What's included
- 1 night in a 4-star hotel in Siena historical center
- 2 nights in a charming boutique country estate / agriturismo
- All hotel city tourist taxes included
- Dedicated full-time professional Tour Leader (Days 1–4)
- Licensed local guides in Siena, Montepulciano, Pienza
- Deluxe private vehicle with licensed professional driver for all 4 days
- Daily farm-fresh breakfast
- 3 multi-course dinners
- 1 vineyard lunch at a winery in Chianti
- 2 premium wine tastings
- Complete logistics coordination and on-trip assistance
What's not included
- Lunch on Day 1 and Day 4
- Travel insurance, personal expenses, and tips
Request information
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