Tuscany Day Trip: Siena, Chianti & Wine Tasting Tour
9hDuration
English, Spanish, French, ItalianSpeaking Guide
Mobile ticketAccepted
About this experience
Duration9 Hours
Group SizeSmall Group
Starts AtFlorence
LanguagesEnglish, Spanish, French, Italian
Tuscany Day Trip from Florence
Discover Tuscany: Siena, Chianti & Brunello Tasting in Montalcino
A full-day journey through medieval Siena, rolling Chianti hills, and the legendary vineyards of Montalcino.
This Tuscany day trip from Florence combines the art of living well with centuries of winemaking tradition, taking you from a UNESCO-listed medieval city to one of Italy's most storied wine estates in a single, unhurried day.
The route winds through some of the most recognizable landscapes in Italy: terraced vineyards, silver-green olive groves, and the signature rows of cypress trees that line the ridgelines of the Sienese countryside. Each stretch of road offers a new composition of the Tuscan hills before you even step out of the vehicle.
At midday, a farmhouse lunch brings the region's flavors together in one sitting, with a carefully selected flight of Chianti wines accompanying a traditional meal. The afternoon then shifts to Montalcino, where a multi-generational family estate opens its cellar for a guided tasting of five wines, including two expressions of Brunello DOCG.
Tour Highlights
Walk the medieval streets of Siena, a UNESCO World Heritage Site, and visit the iconic Piazza del Campo.
Enjoy a traditional Tuscan farmhouse lunch paired with five selected Chianti wines.
Visit a prestigious multi-generational Brunello estate in Montalcino and tour its historic cellar.
Taste five wines at the Montalcino estate, including Rosso di Montalcino, two Brunello DOCG, a Super Tuscan, and a Rosé.
Travel one of Tuscany's most scenic wine roads through the postcard-perfect Chianti and Val d'Orcia landscapes.
Discover the history of Siena's Duomo, Baptistery, and the atmospheric lanes of Via di Città.
Itinerary
1
Departure from Florence
The tour begins in Florence with a scenic drive south through the Chianti countryside. Vineyards, olive groves, and cypress-lined roads set the tone for the day ahead.
2
Arrival in Siena — Free Exploration
Siena is the capital of its namesake province and one of Italy's best-preserved medieval cities. Free time allows you to explore Piazza del Campo, the Duomo, the Baptistery, and the winding lanes of Via di Città at your own pace.
3
Farmhouse Lunch with Chianti Wine Tasting
Lunch is served at a traditional Tuscan farmhouse, where five Chianti wines accompany a regional meal. This is a relaxed, convivial stop that reflects the local culture of eating and drinking well.
4
Scenic Drive to Montalcino
After lunch, the route continues along one of Tuscany's celebrated wine roads, crossing rolling hills and vine-covered slopes toward the hilltop town of Montalcino.
5
Cellar Visit and Brunello Tasting in Montalcino
A family-owned estate that was among the first producers of Brunello di Montalcino opens its cellar for a guided tour and explanation of the wine's production. The tasting covers five wines: Rosso di Montalcino, two Brunello DOCG, a Super Tuscan, and a Rosé.
6
Return to Florence
The group departs Montalcino and returns to Florence, with an estimated arrival around 5 PM.
What's Included & Excluded
Included
Professional guide for the full day
Round-trip transportation from Florence
Farmhouse lunch with 5 Chianti wines
Cellar visit and guided wine explanation in Montalcino
Tasting of 5 wines at the Brunello estate
Free time to explore Siena independently
Not Included
Entrance fees to Siena monuments (Duomo, Baptistery, etc.)
Personal expenses and souvenirs
Gratuities for guide and driver
Travel insurance
Important Information
Please read the following details carefully before booking to ensure this tour is the right fit for your travel plans and physical needs.
Duration
The full tour lasts approximately 9 hours, departing from Florence and returning around 5 PM.
Meeting Point
The tour departs from a central location in Florence. Exact meeting point details are provided after booking confirmation.
What to Bring
Comfortable walking shoes are recommended for Siena's cobblestone streets. A light jacket is advisable during cooler months. Sun protection is recommended in summer.
Cancellation
Cancellation policies are outlined at the time of booking. Please review terms before confirming your reservation.
Accessibility
Siena's historic center involves uneven cobblestone surfaces and inclines. This tour is rated easy but may present challenges for guests with limited mobility.
Age Range
The wine tasting is reserved for guests of legal drinking age. The tour is otherwise suitable for adults and older children accompanied by an adult.
Ready to Explore Tuscany?
Secure your place on this full-day journey through Siena, Chianti, and Montalcino. Availability is limited and fills quickly during the high season.
Is this tour suitable for people who do not drink alcohol?▼
The wine tastings are a central part of the experience, but guests who prefer not to drink can still participate in the cellar visit, the farmhouse lunch, and all sightseeing stops in Siena.
How much walking is involved in Siena?▼
Siena's historic center is explored on foot and features cobblestone streets and some inclines. The difficulty level is rated easy, but guests should be comfortable with moderate walking on uneven surfaces.
What wines are included in the Montalcino tasting?▼
The tasting at the Brunello estate includes five wines: Rosso di Montalcino, two expressions of Brunello DOCG, a Super Tuscan, and a Rosé.
Are entrance fees to Siena's monuments included in the tour price?▼
No. Entrance fees to sites such as the Duomo and Baptistery are not included. Guests wishing to visit these monuments should budget for admission costs separately.
What is Brunello di Montalcino and why is it significant?▼
Brunello di Montalcino is one of Italy's most prestigious DOCG-classified red wines, produced exclusively from Sangiovese Grosso grapes grown around the hilltop town of Montalcino in Tuscany. It is widely regarded as one of the world's great age-worthy reds.
Does the tour return to Florence at the end of the day?▼
Yes. The tour concludes with a return drive to Florence, with an estimated arrival time of approximately 5 PM.
Tuscany Day TripSiena TourBrunello TastingChianti WineMontalcinoWine Tour ItalyFlorence ExcursionUNESCO HeritageFarmhouse LunchCellar VisitTuscan CountrysideItalian Wine Experience
This tour operates out of Florence, the regional capital of Tuscany in central Italy, and travels south through the Chianti Classico zone into the Sienese hills. The first major stop is Siena (Province of Siena, Tuscany), a walled medieval city located approximately 75 km south of Florence, recognized as a UNESCO World Heritage Site for its intact historic center. The route then continues to Montalcino, a hilltop town in the Val d'Orcia area of southern Tuscany, renowned internationally as the production zone of Brunello di Montalcino DOCG, one of Italy's most prestigious red wines. The entire circuit is set within the Tuscan wine country corridor, one of the most visited agritourism regions in Europe, drawing travelers interested in Italian gastronomy, wine culture, medieval history, and scenic landscapes.
Category: Wine Tours & Tastings | Destination: Tuscany, Italy | Departure City: Florence | Sub-destinations: Siena, Chianti, Montalcino | Wine Region: Chianti DOCG, Brunello di Montalcino DOCG | Activity Type: Day Trip, Cultural Tour, Food & Wine | Difficulty: Easy | Duration: Full Day (9 Hours) | Traveler Type: Wine Enthusiasts, Food Lovers, Culture Travelers, Couples, Adult Groups
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