Piazza del Campo and Torre del Mangia in Siena at sunset, a highlight of Tuscany wine tours from Chianti to Montalcino
Close-up of ripe Sangiovese grapes on the vine in a Tuscan vineyard, ideal for Chianti Classico and Brunello wine tasting
Neat rows of green vines in a rocky Tuscan vineyard near Montalcino, perfect setting for Brunello and Chianti wine tours
Sunlit vineyard rows in the Tuscan countryside near Montalcino, ideal setting for Chianti and Brunello wine tasting tours
Historic stone fortress in Montalcino, Tuscany, a scenic stop on Siena, Chianti and Brunello wine tasting day trips
Bottles of Brunello di Montalcino and Tuscan reds displayed in a local winery shop on a Siena and Chianti tasting tour
Curving trail through lush green Tuscan hills leading to iconic cypress trees near Siena on a Chianti and Brunello tour
Rolling green and yellow fields of the Val d’Orcia in Tuscany with distant farmhouses seen on a Siena and Montalcino tour
Golden wheat fields and solitary cypress grove under clear blue skies in rural Tuscany on a Brunello wine tasting day trip
Rolling Tuscan hills and vineyards near Montalcino on a Siena, Chianti and Brunello wine tasting tour in Tuscany, Italy
Neat rows of Chianti and Brunello vines in a sunlit Tuscan vineyard overlooking the scenic hills around Montalcino, Italy
Historic Piazza Salimbeni in Siena with medieval palazzo and statue, a cultural stop on the Tuscany Chianti Brunello tour
Siena Cathedral’s striped Gothic façade and bell tower glowing at sunset on a Tuscany day trip from Florence
Narrow medieval alley in Siena’s historic center with stone palaces, boutiques and locals on a Tuscany walking tour
Sunlit Piazza del Campo in Siena with medieval brick palaces, cafés and crowds on a Tuscany wine and culture tour
Torre del Mangia tower rising above Piazza del Campo in Siena, a highlight of Discover Tuscany and Chianti wine tours
Visitors relaxing in Siena’s Piazza del Campo, a lively medieval square featured on Discover Tuscany Chianti day trips
Panoramic view of Siena’s historic skyline and cathedral, a scenic stop on Discover Tuscany Chianti and Brunello tours
Panoramic view of Siena Cathedral and medieval rooftops on a clear day during a guided Discover Tuscany tour
Bronze panther fountain sculpture against rustic brick wall in Siena, visited on Discover Tuscany walking tour
Tuscany Day Trip: Siena, Chianti & Wine Tasting Tour
From € 100.00
Listing ID : 47343

Activity

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.

Book Now

Frequently Asked Questions

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
Last updated: 2025-07-15 | Product ID: TX-SIENA-BRUNELLO-001

Activity

Availability

You can book up to the start time, as long as there are places remaining. Book now to guarantee your spot.

Additional Information

Physical: Wheelchair Not accessible

Duration

9 hours

Languages

English - Speaking Guide

Spanish - Speaking Guide

French - Speaking Guide

Italian - Speaking Guide

Additional Information

Electronic. Show the voucher on your phone.

Cancellation Policy

Select Date

Meeting Point

Complete Operator information, including local telephone numbers at your destination, are included on your Confirmation Voucher. Our Product Managers select only the most experienced and reliable operators in each destination, removing the guesswork for you, and ensuring your peace of mind.

End Point

Complete Operator information, including local telephone numbers at your destination, are included on your Confirmation Voucher. Our Product Managers select only the most experienced and reliable operators in each destination, removing the guesswork for you, and ensuring your peace of mind.

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