Siena, San Gimignano, Tuscany, Lunch and Wine Tasting
One day. Four destinations. A full taste of Tuscany's medieval soul and celebrated wine country.
This Tuscany small-group day tour is designed for travelers who want to experience the region's finest medieval towns, rolling countryside, and local culinary traditions without sacrificing depth or authenticity. Led by passionate local experts, the journey covers Monteriggioni, Siena, the Chianti region, and San Gimignano in a single well-paced day.
Traveling by 8-seat minivan keeps the experience intimate and flexible, allowing the group to move through each destination at a comfortable rhythm. Your guide brings genuine regional knowledge to every stop, framing what you see with cultural context and personal insight rather than rehearsed commentary.
The tour strikes a deliberate balance between guided discovery and independent exploration. Structured walking segments alternate with free time, giving travelers the space to browse artisan shops, sit in historic piazzas, or simply absorb the atmosphere on their own terms.
Tour Highlights
Walk the walls of Monteriggioni, Tuscany's most intact medieval fortress village and a filming location for Gladiator.
Explore Siena's UNESCO-listed historic center, including Piazza del Campo and the Gothic Siena Cathedral.
Visit a working Chianti winery for a tasting of five wines paired with extra virgin olive oil and balsamic vinegar.
Sit down to a traditional Tuscan lunch included as part of the winery experience in the heart of wine country.
Wander the medieval towers and cobblestone lanes of San Gimignano, a UNESCO World Heritage Site.
Travel through the scenic Chianti countryside aboard a comfortable 8-seat minivan with a small, like-minded group.
Itinerary
Meet your guide in Florence and board the minivan for a scenic hour-long drive into the Tuscan countryside. The first stop is Monteriggioni, a remarkably well-preserved 13th-century fortress town whose circular walls and fourteen towers remain almost entirely intact. Known to fans of cinema and gaming alike, the village offers a genuinely immersive step into medieval Italy.
Arrive in Siena for an orientation walk through its historic center, winding past Gothic palaces, artisan workshops, and narrow stone streets that have changed little over centuries. The walk culminates at Piazza del Campo, the shell-shaped square that hosts the famous Palio horse race each summer. Free time follows, with the Siena Cathedral - an extraordinary example of Italian Gothic architecture - within easy walking distance.
Journey into the Chianti region for a visit to a local family winery set among vineyards and olive groves. The tasting includes five wines alongside extra virgin olive oil and balsamic vinegar, paired with a full traditional Tuscan lunch. This is the culinary centerpiece of the tour and a genuine introduction to the flavors that define the region.
Arrive in San Gimignano, whose skyline of medieval towers rising above the Val d'Elsa earned the town its nickname as the Manhattan of the Middle Ages. Explore at your own pace, visiting the Collegiata, Torre Grossa, and the artisan shops lining the piazzas. The town's UNESCO status reflects both its architectural integrity and its cultural significance.
Board the minivan for the approximately one-hour return journey to Florence, arriving back at the starting point by early evening. The drop-off is at the original meeting location, making onward plans easy to manage.
What Is Included
Included
- Private 8-seat minivan transport throughout
- Professional local guide for the full day
- Visit to Monteriggioni fortress village
- Guided orientation walk in Siena
- Chianti winery visit with tasting of 5 wines
- Extra virgin olive oil and balsamic vinegar tasting
- Traditional Tuscan lunch at the winery
- Visit to San Gimignano UNESCO site
Not Included
- Hotel pickup and drop-off
- Entry fees to museums or monuments
- Personal travel insurance
- Gratuities for guide (discretionary)
- Personal expenses and souvenirs
Important Information
Ready to Explore Tuscany?
Secure your place in this small-group day tour and spend nine hours moving through some of the most storied landscapes and towns in central Italy. Availability is limited to eight guests per departure.
Book Now
