8 Best Wine Tours from Siena & Wine Tastings

Siena sits in the middle of some of Tuscany’s most famous wine country. From here, you can reach Chianti, Montalcino, Montepulciano, and the Val d’Orcia without changing hotels every night.

I absolutely fell in love with Siena the first time I visited. The city is beautiful, but its location is also a huge part of its appeal. It works especially well on a Tuscany itinerary if you want to combine historic towns with vineyard visits.

A tour makes sense because many countryside wineries are difficult to reach without a car. More importantly, you do not need to choose between driving and tasting the wine. Some experiences include transportation from Siena, while others take place in the city or require you to reach a nearby winery independently.

To help you choose, I compared the best Siena wine tours by region, duration, transport, and group format. You’ll find everything from a 9-hour Brunello day trip to a 2-hour wine class in central Siena.

➥ Why trust me? I’m Italian, from Bologna, and I’ve spent the last 10+ years helping millions of travelers plan trips to Italy. I’ve visited Siena and traveled extensively around Tuscany. I selected these experiences by comparing their current itineraries, practical details, traveler feedback, and overall value.

I usually book tours through Viator and GetYourGuide because they offer a large choice of reliable operators and flexible cancellation policies. Most tours can be canceled up to 24 hours in advance for a full refund, but always check the conditions for your booking.

Best Wine Tours from Siena: Quick Picks

Short on time? These are the Siena wine tours I recommend most:

OUR PICK: Best Brunello Wine Tour from Siena

Duration: 9 hours
Type: Small-group wine tour with transport (max 8 people)
Best for: Travelers who want the most complete wine-focused day trip

The Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena is my top pick because it devotes the entire day to one of Tuscany’s most celebrated wines. You leave from central Siena and travel south into the Montalcino countryside with a wine expert.

The first stop is a small winery, where you’ll walk through the vineyards, visit the cellars, and taste both Rosso and Brunello di Montalcino. You’ll then continue to the medieval town of Montalcino, with free time to explore its shops and admire the views over the surrounding countryside.

Next, you’ll visit a family-run winery and meet the winemakers before sitting down for a generous Tuscan lunch paired with local wines. The menu includes cold cuts, cheeses, and bruschetta, followed by pasta or risotto and dessert such as cake with coffee or almond biscuits with dessert wine.

After lunch, the tour continues to Sant’Antimo Abbey. The final stop is a third winery, where you’ll learn more about how Brunello is produced and aged before enjoying one last tasting.

What I particularly like about this itinerary is that the three winery visits are broken up by time in Montalcino and at the abbey. The group is also capped at eight people, making it a strong choice if you want a sociable tour without the feel of a large coach excursion.

Why this is the best tour

This is the most wine-focused and complete group tour in the lineup. It combines three wineries, lunch, Montalcino, transport, and a maximum of eight guests. It also has a much longer review history than most Siena wine tours, with over 1,000 traveler reviews.

Read what the reviews say:

“If you’re looking for a wine tour from Siena, look no further, this was the best experience of our trip. Our guide was fantastic and very knowledgeable on all things Brunello wines and the surrounding area of Montalcino. We got to not only visit wineries and learn about how they make the wine, but also visited an old monastery and wandered around a small town as well. This was a top notch tour and I would recommend it to anyone who likes wine and good company.”

Jessica_B – Read more reviews

This tour includes roundtrip transportation from central Siena, a local guide, three winery visits, wine tastings, and lunch. ➥ BOOK IT HERE

Pienza and Montepulciano Small-Group Tour from Siena

Duration: 8 hours
Type: Small-group tour with transport (max 8 people)
Best for: Travelers who want Val d’Orcia scenery, Pienza, and Vino Nobile

The Pienza and Montepulciano Small-Group Tour from Siena is the best choice if the landscape and hill towns matter as much to you as the wine. You’ll leave Siena by minivan and travel through the Crete Senesi toward the Val d’Orcia.

Your first main stop is Pienza, where you can explore the compact historic center. A 3-course lunch and pecorino tasting at an organic farm are included, giving this tour a stronger food component than most wine excursions.

In Montepulciano, you’ll visit an underground cellar and taste Vino Nobile. You’ll also have time to walk through the steep historic center and around Piazza Grande independently.

This tour meets in central Siena, but hotel pickup is not included. Museum tickets and gratuities are also excluded.

Pros

• Maximum of eight participants
• Combines Pienza, Montepulciano, food, and wine
• Lunch and roundtrip transportation are included

Cons

• Only one dedicated cellar visit
• Hotel pickup is not included

This tour includes roundtrip transportation from central Siena, a guide, a 3-course lunch, pecorino tasting, a cellar tour, and wine tasting. ➥ BOOK IT HERE

Chianti Wine Tours from Siena

Small-Group Chianti Trip: Best Full-Day Chianti Tour

Duration: 8 hours
Type: Small-group wine tour with transport (max 8 people)
Best for: Travelers who want a complete day in Chianti Classico

The Small-Group Chianti Wine-Tasting and Castles Trip from Siena is the strongest option if Chianti is your priority. You’ll leave from central Siena in a small group of no more than eight people and travel into the Chianti countryside.

The itinerary includes visits to three wineries with guided tastings, where you’ll learn about Chianti Classico production and taste the local wines. A Tuscan lunch is also included, so this is a more complete food-and-wine day than the shorter budget tour.

You’ll also visit Castello di Brolio and travel through the villages and vineyard-covered landscapes of the region. The smaller vehicle allows for a more intimate experience than a standard coach excursion.

This tour costs considerably more than the 5-hour Chianti option, but it includes a longer itinerary, lunch, and a maximum group size of eight.

Pros

• Maximum of eight participants
• Transportation from central Siena is included
• Includes winery visits, wine tastings, Castello di Brolio, and lunch

Cons

• More expensive than the shorter Chianti tour
• Requires most of the day

This tour includes transportation from central Siena, a guide, three winery visits and wine tastings, visit to Castello di Brolio, and lunch. ➥ BOOK IT HERE

Hidden Castles & Chianti: Best Budget Wine Tour

Duration: 5 hours
Type: Group wine tour with transport
Best for: Travelers seeking an affordable Chianti tour from Siena

The Hidden Castles & Chianti Wine Experience is the best budget choice because it includes transport and two winery visits without taking up the entire day. It departs from the area around Siena train station.

You’ll travel through the Chianti countryside and taste seven wines across two wineries. The experience also includes local olive oil and balsamic vinegar tastings.

Between the wineries, the route includes Castellina in Chianti and the medieval village of Monteriggioni. This adds some sightseeing, but the schedule is shorter and of course less in-depth than the Brunello top pick.

A full lunch is not included, so do not book it expecting the long winery meal offered by the more expensive day tours.

Pros

• More affordable than the 8- and 9-hour tours
• Transportation and two winery visits are included
• Leaves part of the day free in Siena

Cons

• Lunch is not included

This tour includes transportation from Siena, a guide, two winery visits, seven wine tastings, and samples of local products. ➥ BOOK IT HERE

Chianti Sunset Tour: Best Evening Wine Experience

Duration: 3 hours
Type: Winery tour, tasting, and dinner without transport
Best for: Travelers who want to keep the daytime free for sightseeing

The Chianti Sunset Tour with Dinner & Wine Tasting is an appealing alternative to a daytime excursion. The experience starts with a guided visit through the vineyard and cellar, followed by a tasting of four wines.

You’ll then sit down for a full Tuscan dinner paired with the estate’s wines. The sample menu includes strawberry gazpacho with burrata, ricotta and pecorino agnolotti, and homemade chocolate cake with vanilla ice cream. It is a more substantial evening than a simple tasting class and works well if you want wine to be the focus of dinner.

The important catch is that transportation from Siena is not included. You need to arrange your own trip to and from the winery, and you should plan the return before tasting.

Pros

• Keeps the daytime free for Siena
• Includes a vineyard and cellar visit, four wines, and dinner
• Shorter than a countryside day tour

Cons

• Transportation is not included
• Not ideal if you prefer to stay within walking distance of central Siena

This experience includes a vineyard and cellar tour, four wine tastings, and a Tuscan dinner. Transportation is not included. ➥ BOOK IT HERE

Wine Tastings in and near Siena

Winery Tour and Wine Tasting near Siena

Duration: 3 hours
Type: Small-group winery experience without transport (max 12 people)
Best for: Travelers who want a real vineyard visit without an 8- or 9-hour tour

The Siena: A Wine Tour and Tasting Experience takes place at an organic winery just outside Siena. It is not a tasting room in the historic center, so you still get to walk through the vineyard and visit the cellar.

The guide explains the growing cycle of the grapes and the production process before leading a tasting of at least four organic wines. A seasonal light lunch with fresh pasta, vegetables and dessert is included.

This is a good middle ground between a quick city class and an 8- or 9-hour day trip. However, you must reach the winery independently (it’s easily reachable by car, taxi or the winery can help arrange transportation), so check the logistics before booking.

Pros

• Includes both a vineyard and cellar visit
• Light lunch and at least four wines are included
• Maximum of 12 participants

Cons

• Transportation is not included
• The winery is outside the historic center

This experience includes a guided vineyard and cellar visit, at least four wine tastings, a light lunch, olive oil, and bottled water. Transportation is not included. ➥ BOOK IT HERE

Wine Class: Tuscan Classics in Central Siena

Duration: 2 hours
Type: Guided wine class in central Siena
Best for: Travelers who want a short, walkable tasting

The Wine Class: Tuscan Classics is the easiest option if you do not want to leave Siena. It takes place in the city center and lasts only two hours.

A local wine expert guides you through four to five Tuscan wines with accompanying snacks such as local cheese and cold cuts. The class covers the major regional wine areas, tasting techniques, and useful food pairings.

This is an educational tasting rather than a winery tour. Choose it for convenience and variety, but pick the nearby winery experience if seeing vines and a working cellar is important to you.

Pros

• Convenient central Siena location
• Four to five wines from different Tuscan areas
• Easy to fit around sightseeing

Cons

• Does not include a vineyard or cellar visit
• Snacks are included, but not a full meal

This class includes Tuscan wine tastings, guidance from a local wine expert, and snacks. ➥ BOOK IT HERE

Private Montalcino Wine Tour from Siena

Duration: 8 hours
Type: Private wine tour with pickup
Best for: Couples, families, or friends who want a flexible Brunello day

The Private Montalcino Wine Tasting Experience offers pickup from Siena and a day focused on Brunello. Because the tour is private, the route and pace can be adapted more easily than on a fixed group excursion.

The day includes winery visits, guided tastings, and food pairings with local cheeses and cured meats. Lunch at a winery is also included, making this a complete experience rather than a private transfer between tastings.

Depending on the route agreed for your date, you can also spend time in Montalcino or visit Sant’Antimo Abbey. This is the best option if privacy and flexibility matter more than price.

Pros

• Private and customizable itinerary
• Pickup from Siena is included
• Includes winery visits, tastings, lunch, and snacks

Cons

• More expensive than the group tours
• The precise winery lineup can vary

This tour includes private pickup and transportation, a tour escort, winery visits, wine tastings, lunch, and snacks. ➥ BOOK IT HERE

Is It Worth Taking a Wine Tour from Siena?

Yes, especially if you want to visit countryside wineries without driving. Many estates are not conveniently connected by public transportation, and a transported tour lets everyone in your group enjoy the tastings.

A tour also helps you understand what you are drinking. The Brunello and Val d’Orcia excursions combine wine with the landscapes and towns that shape it, while the shorter Siena experiences focus more closely on tasting and production.

The key is choosing the right format. Book a transported day trip for the countryside, the city-center class for maximum convenience, or one of the no-transfer winery experiences only if you are comfortable arranging the journey yourself.

FAQ: Wine Tours from Siena

Which wine region should you visit from Siena?

Choose Chianti for the closest classic wine-country experience, Montalcino for Brunello, or Montepulciano and the Val d’Orcia for Vino Nobile, Pienza, and famous Tuscan scenery. For the deepest wine-focused day, I recommend the small-group Brunello tour.

How long are wine tours from Siena?

The options in this guide range from two to nine hours. The central Siena wine class takes two hours, the winery and sunset experiences take three hours, the budget Chianti tour takes five hours, and the transported countryside day trips take eight to nine hours.

Do wine tours from Siena include transportation?

Some do, but not all. The Brunello, Pienza and Montepulciano, full-day Chianti, budget Chianti, and private Montalcino tours include transportation from Siena. The winery tasting near Siena and the sunset dinner do not. The Tuscan wine class takes place in central Siena and is the easiest option without a vehicle.

Can you take a Siena wine tour from Florence?

Yes. If you are staying in Florence, several day trips combine Siena with Chianti wineries, San Gimignano, or Monteriggioni. Compare the different routes in my guide to the best Siena tours from Florence.