Tuscan wine touring reaches its peak in Siena, where world-class vintages and historic estates await. The surrounding hills offer two main wine experiences: the legendary Brunello di Montalcino region and the medieval castle wineries dotting the countryside. Small-group tours (typically 8-12 people) work best, letting you chat with winemakers and learn proper tasting techniques without the crowds.
I’m particularly fond of tours that combine wine education with cultural stops – you’ll understand both what’s in your glass and why it matters. The best operators make wine approachable, whether you’re a beginner or an experienced sipper.
Standout choices include family-run Montalcino visits and castle tours with intimate wine-paired lunches. These smaller operations deliver more authentic experiences than large commercial wineries.
Check out these top-rated Siena wine tours for your Italian adventure:
Key Points
- The Brunello di Montalcino Trip offers a full-day tour visiting 3 wineries, including a family-run estate, with tastings of Brunello and Rosso wines.
- The Siena Sparkling Wines tasting features a one-hour session at Enoteca Perlage, showcasing 3 wines and led by an expert educator, capped at 10 participants.
- The Brunello Tour is a 6-7 hour excursion visiting 2 boutique wineries, including tours, tastings, and a 3-course lunch, with a 98% recommendation rate.
- The Chianti and Castle Tour is a half-day experience visiting 2 wineries, sampling 7 wines and local snacks, and includes free time in Monteriggioni.
- The Wine Experience at an Organic Chianti Winery offers a 1.5-hour tour, tasting of four organic wines, and is wheelchair accessible with free cancellation.
Small-Group Brunello Di Montalcino Wine-Tasting Trip From Siena
Departing from Siena, this small-group Brunello di Montalcino wine-tasting trip offers an immersive exploration of the renowned wine region.
Over the full-day excursion, travelers will visit three wineries, including a family-run estate, and enjoy tastings of the area’s legendary Brunello di Montalcino and Rosso wines.
The itinerary also includes a Tuscan lunch at one of the wineries, as well as a visit to the historic Abbey of Sant’Antimo.
With a maximum of 8 travelers, the tour provides a personalized experience, allowing guests to interact directly with winemakers and gain insights into the winemaking process.
Consistently praised for its knowledgeable guides, delectable food and wine pairings, and stunning Tuscan scenery, this trip is a must for oenophiles and culture enthusiasts alike.
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Siena: Wine Tasting Experience With Tuscan Sparkling Wines
At the Enoteca Perlage in Siena, travelers can embark on a captivating one-hour wine tasting experience that showcases the region’s renowned Tuscan sparkling wines.
Priced from $36.85 per person, the tasting features three distinct sparkling wines produced using Champenoise, Ancestral, and Charmat methods. Guests will savor the flavors of Sangiovese, Trebbiano, and Vermentino grapes, paired with local delicacies to enhance the experience.
Led by an expert wine educator, the tasting provides insights into Tuscan viticulture and winemaking. Limited to 10 participants, the experience is wheelchair accessible and offered in English, French, and Spanish.
With a 5/5 rating from traveler reviews, this personalized tasting is a must for any wine enthusiast visiting Siena.
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Siena: A Wine Tour and Tasting Experience
For wine enthusiasts visiting Siena, a captivating wine tour and tasting experience awaits.
Siena wine tour offers a personalized exploration of Tuscany’s renowned wine region, with small group sizes ensuring intimate attention. The tour includes visiting organic vineyards, historical cellars, and sampling at least four organic wines typical of the area.
A light Tuscan lunch featuring fresh seasonal ingredients is also provided. With a 5.0 rating from 292 reviews, the tour is highly praised for its knowledgeable guides, beautiful properties, and delicious offerings.
Confirmation is received at booking, and free cancellation is available up to 24 hours before the experience.
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Siena: Tour and Wine Tasting in a Tuscan Private Castle
Travelers frequently embark on a captivating tour and wine tasting experience at a Tuscan private castle, situated in the serene Val di Merse region just outside Siena.
This 2-hour private group activity costs $45.27 per person and is available in Italian, English, and French. Guests can explore the castle’s gardens, Renaissance chapel, and organic winery, while learning about the property’s history from a knowledgeable guide.
The tasting includes organic wines, complemented by water and a snack. With an outstanding 5/5 rating based on 9 reviews, this tour provides an educational and relaxing experience in a picturesque setting, making it a top pick for wine enthusiasts visiting Siena.
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Brunello Di Montalcino Wine Tour of 2 Wineries With Pairing Lunch
Embarking on the Brunello di Montalcino Wine Tour allows visitors to explore the renowned Tuscan wine region and its prized Brunello.
This 6-7 hour experience takes travelers to two boutique wineries, where they’ll enjoy tours, tastings, and a 3-course pairing lunch.
Pickup and drop-off service, as well as an English-speaking driver, ensure a seamless journey.
The tour’s highlight is the opportunity to learn about Brunello production and tasting techniques from knowledgeable guides.
With a 98% traveler recommendation rate and 4.9/5 overall rating, this tour offers an immersive and engaging wine experience amidst the stunning Val d’Orcia landscape.
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Excursion to Tuscany With Wine Tasting in a Winery From Rome
Those seeking to explore the renowned Tuscan wine region can embark on an immersive Excursion to Tuscany with Wine Tasting in a Winery from Rome.
Priced from $251.61 per person, this one-day tour offers a comprehensive experience, including a guided tour of Siena, free time in Monteriggioni and San Gimignano, and a tasting of Chianti red wine and local products in a winery.
The tour includes high-speed train tickets, round-trip bus transportation, and a tour escort. Comfortable attire and shoes are recommended, and instructions will be provided before the excursion.
With free cancellation up to 24 hours in advance, this tour is an excellent opportunity to discover the beauty and flavors of Tuscany.
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Walking Tour of Siena With Food & Chianti Wine
What better way to experience the historic charm of Siena than through a walking tour that showcases the city’s renowned food and wine?
This 2-hour tour takes visitors on a small-group exploration, limited to just 12 people, to sample Chianti Classico wine, Tuscan salami, prosciutto, and pecorino cheese.
The tour also includes a delightful gelato tasting and a hearty lunch of homemade pasta, pecorino, and cold cuts.
With an expert, licensed guide leading the way, travelers will discover Siena’s top sights while enjoying its culinary delights.
The tour’s impressive 97% recommendation rate and a Badge of Excellence attest to its quality and value.
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Siena – Private Dinner With Fine Wines in Etruscan Cave
Nestled in the heart of Siena, Casa Tua restaurant offers an exclusive dining experience in an ancient Etruscan cave.
For $294.77 per person, guests can enjoy a private 2-hour dinner or lunch featuring a full menu of Tuscan specialties, expertly paired with top Italian wines.
The menu includes an appetizer, first course, main course, and dessert, served in a softly lit, warm atmosphere surrounded by aged wine bottles.
A dedicated sommelier narrates and serves the wine pairings throughout the meal.
This experience is renowned for its attention to detail and welcoming atmosphere, though it’s not suitable for those with mobility issues or dietary restrictions.
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Chianti and Castle Small Group Tour From Siena With Wine Tasting
The Chianti and Castle Small Group Tour from Siena with Wine Tasting is a popular half-day excursion that allows visitors to discover the renowned wine region of Chianti and the charming medieval village of Monteriggioni.
The tour includes visits to two wineries, where guests can sample 7 types of wines, olive oil, and balsamic vinegar, along with local snacks.
The highlight is the free time to explore the well-preserved Monteriggioni castle and village.
Guests praise the knowledgeable guides and beautiful Tuscan scenery, though some note the second winery visit feels rushed, and a few experienced visits to Monteriggioni after dark.
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Wonderful Tuscan Wine Tour: Siena, Chianti and San Gimignano
Offering an immersive exploration of Tuscany’s renowned Chianti wine region, the Wonderful Tuscan Wine Tour takes travelers on an eight-hour journey from Florence to the historic cities of Siena and San Gimignano.
Priced from $484.27 per person, the tour includes transportation, a guided visit to Siena, a lunch and wine tasting at a Chianti winery, and time to explore the medieval hilltop town of San Gimignano.
With the option for private groups, this wheelchair-accessible tour allows guests to discover the highlights of Tuscany while enjoying the flexibility of free cancellation up to 24 hours in advance.
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Tuscany Hiking Tour From Siena Including Wine Tasting
Departing from Siena, the Tuscany Hiking Tour takes travelers on a captivating 3-4 hour hike along the historic Via Francigena pilgrimage route.
Hikers will enjoy scenic views of rolling hills, olive groves, and vineyards as they pass through ancient villages. The tour includes a wine tasting at a local shop, showcasing the region’s renowned varietals.
With a maximum of 16 travelers, the guided experience provides an intimate and immersive exploration of Tuscany’s natural beauty and cultural heritage.
Comfortable shoes, water, and sun protection are recommended for the moderately paced hike, which isn’t suitable for those with physical disabilities or serious medical conditions.
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Wine Experience in an Organic Chianti Winery
Visitors can enjoy a captivating 1.5-hour Wine Experience at an organic Chianti winery nestled in the picturesque Tuscan hills.
The small-group tour, limited to 2-12 participants, is led by a certified sommelier and explores the historic cellar, family chapel, and ancient olive mill of the Montechiaro Estate.
Guests will taste four organic wines, including a Super Tuscan white, Chianti, Chianti Riserva, and a top-tier red Super Tuscan with rare Malvasia Nera grapes.
The wine tasting is paired with locally prepared dishes and an extra virgin olive oil tasting.
Priced from $36.85 per person, the experience is wheelchair accessible with free cancellation up to 24 hours in advance.
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Wine Class – Tuscan Classics
The Wine Class – Tuscan Classics in Siena, Italy provides an engaging and informative introduction to the renowned wines of the Tuscan region.
Hosted by expert instructors, the 2-hour class covers the history, production areas, and grape varieties of Tuscan wines, including Chianti Classico and Brunello di Montalcino.
Participants will sample 4-6 different wines paired with local cheeses, cured meats, and other delicacies.
With a maximum of 14 attendees, the class offers a personalized experience in a convenient central Siena location.
Highly rated by travelers, the class is an excellent choice for both novice and experienced wine lovers seeking to deepen their appreciation of Tuscan classics.
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Chianti: Wine and Olive Oil Tasting With Cellar Tour
This 2-hour Chianti: Wine and Olive Oil Tasting with Cellar Tour at Fattoria Santo Stefano offers an immersive experience to discover the renowned wines and extra-virgin olive oils of the Chianti region.
For $29.48 per person, guests explore the historic cellar, sample a selection of local wine varieties and olive oils, and enjoy delightful food pairings.
With an expert guide providing insights, the tour includes a visit to the farmhouse’s “Orciaia” for olive oil tasting.
Rated 4.9/5 by 35 reviewers, this tour promises exceptional value, service, and organization.
Travelers can book now and pay later, with free cancellation up to 24 hours in advance.
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Small-Group Chianti Trip With Wine Tasting From Siena
A captivating small-group journey awaits travelers seeking to enjoy the renowned Chianti region.
This 9.5-hour tour from Siena promises a delightful blend of history, culture, and world-class wines. Accompanied by a professional guide, the group will visit Castello di Brolio, a medieval castle with a rich past, and Castello di Vertine, a once-fortified medieval village.
The highlight is a lunch and wine tasting at Castello di Ama, set against the stunning Chianti landscape.
With a maximum of 8 travelers, this intimate experience earns a 5.0 rating and the coveted Badge of Excellence, ensuring personalized service and unforgettable memories.
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Siena: Food and Wine Walking Tour
Siena’s food and wine walking tour provides an immersive experience for those seeking to savor the city’s culinary delights.
The tour lasts 2.5 hours and allows participants to skip the line and explore a monastery where they can sample local products. With an optional audio guide, visitors can learn about the history and production of these specialty items.
Priced at $205.29 per person, this unique activity offers a chance to explore Siena’s gastronomic heritage in a hands-on and informative manner.
Whether you’re a foodie or simply looking to learn about Italian culture, this tour is a must-try during your time in Siena.
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San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
Travelers seeking to explore Siena, San Gimignano, and Monteriggioni in a comprehensive and immersive manner can opt for this fully escorted day trip from Florence.
The tour includes round-trip transportation, a licensed guide, and independent exploration of each charming historic town. Highlights include a guided tour of Siena’s cathedral, a visit to a Chianti winery for a wine tasting and lunch, and free time to discover the iconic landmarks and medieval architecture.
With a maximum group size of 45, and some small groups of up to 8 travelers, the experience offers a balance of structured guidance and independent discovery.
The tour receives positive reviews for the quality of the wine tasting and the knowledge of the tour leaders.
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Organic Winery Tour and Wine Tasting in Siena
Nestled amidst the rolling Tuscan hills just 2 kilometers from Siena’s historic center, an organic winery beckons travelers to explore its sustainable viniculture.
For $78.96 per person, the 2.5-hour Organic Winery Tour and Wine Tasting promises an immersive experience. Guests will tour the vineyards and cellars, learning about organic winemaking techniques, then sample five organic wines paired with seasonal Tuscan cuisine.
With a 5/5 rating based on 63 reviews, the tour offers excellent value, highlighted by a knowledgeable guide whose passion for organic viticulture is contagious.
This is a must-do experience for oenophiles visiting Siena, with convenient cancellation and payment policies.
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Vespa Tour With Lunch&Chianti Winery From Siena
Offering a thrilling way to experience Tuscany’s renowned Chianti region, the Vespa Tour with Lunch & Chianti Winery from Siena promises an unforgettable adventure.
This 6-hour tour whisks travelers through the picturesque countryside, stopping at the medieval town of Monteriggioni and a celebrated Chianti winery.
After a safety briefing and helmet fitting, guests can navigate the winding roads on their own Vespa scooters or share the experience with a companion.
The tour includes a winery visit, tastings, and a light lunch showcasing local flavors.
While the tour generally receives positive reviews, guests note the importance of scooter experience and caution regarding safety and communication from guides.
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Siena: Educational Wine Tour & Tasting
For those seeking a more educational and immersive wine experience in Siena, the Siena: Educational Wine Tour & Tasting offers a unique opportunity.
This 3-hour tour takes visitors to an organic winery just 2 km from Siena, where they’ll explore the vineyards, learn about organic winemaking, and enjoy a sensory tasting of 4 local wines.
The tour also includes a light lunch featuring fresh Tuscan specialties.
With an overall rating of 5/5 and exceptional guide reviews, this tour provides an in-depth understanding of the winemaking process and the vineyard ecosystem.
Booking flexibility and a convenient location make it an excellent choice for wine enthusiasts visiting Siena.
Read our full review: Siena: Educational Wine Tour & Tasting Review
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Frequently Asked Questions
Can I Bring My Own Wine on the Tour?
Generally, it’s not recommended to bring your own wine on a wine tour. Most tour providers supply a curated selection of local wines for tasting, and allow you to purchase bottles to take home. It’s best to follow the tour’s guidelines.
Do the Tours Accommodate Dietary Restrictions?
Many wine tour companies accommodate dietary restrictions, offering vegetarian, vegan, and gluten-free options. Guests should let the tour operator know in advance so they can make the necessary arrangements.
How Much Walking Is Involved in the Tours?
The amount of walking varies across different wine tours, but participants can expect to do some moderate walking. Many tours provide transportation between wineries, limiting the overall walking. It’s best to inquire about specific details for each tour.
Are There Any Age Restrictions for the Tours?
Most wine tours don’t have age restrictions, but children may need to be accompanied by an adult. It’s best to check with the tour operator about their policies regarding minors to ensure a safe and enjoyable experience for all participants.
Can I Purchase Wine Directly From the Wineries?
Yes, you can typically purchase wine directly from the wineries visited on wine tours. Many offer tastings and sales of their products, so visitors can bring home their favorite bottles.
The Sum Up
Siena offers a variety of engaging wine tours that cater to different preferences. From small-group Brunello tastings to organic winery visits, travelers can enjoy the region’s renowned winemaking traditions. Whether seeking an educational experience or a leisurely Vespa adventure, Siena provides ample opportunities to savor the flavors of Tuscany’s celebrated wines.