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13 BEST Wine Tastings & Wine Tours from Siena [2024]

In search of wine tastings & wine tours from Siena? You will find a comprehensive list of the very best options in this article. Check it out!

In the beautiful region of Tuscany, Siena is a special place. The city oozes charm, history, and impressive architecture. It’s also within easy reach of the most enchanting Tuscan towns and, more importantly, wineries. 

Siena is a fantastic place to stay during your Tuscany itinerary. The Chianti countryside is merely 24 miles (40 km) away, after all. This makes it extremely easy to visit Tuscan wineries and cellars on a day.

What’s more, there are plenty of excursions providing a memorable wine trip into the countryside. In this article, I’ve compiled the very best wine tastings & wine tours from Siena.

From indulging in wine flights in the city’s taverns to heading into the countryside for a winery visit, the options are varied. 

Read on to discover the most amazing Siena winery tours. They combine tradition and innovation and will allow you to taste delicious Italian vino.

Why can you trust my picks? Hailing from Bologna and having spent a significant time exploring Italy in-depth, I’ve developed a keen palate for Tuscan wines.

With a decade of experience recommending the best activities in Italy, I’ve handpicked Siena wine experiences that offer authenticity and great value.

I usually use Viator and Get Your Guide to book activities around the world. I especially recommend them for their fantastic cancellation policy. If your travel plans change, you can cancel most tours up to 24 hours in advance for a full refund. 

In a rush? These are the best tours

THE BEST TOURBrunello di Montalcino Wine-Tasting Trip from Siena
WINE TASTING Siena: A Wine Tour and Tasting Experience
PRIVATE TOURPrivate Tour: Montalcino Wine Tasting Experience
COOKING CLASS WITH WINE A Brunello Cooking Class with Vineyards View Winery
VESPA WINE TOUR Vespa Tour with Lunch & Chianti Winery from Siena

OUR PICK: The BEST Wine Tour from Siena 

Our top pick is this Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena. You’ll get to explore the famed Brunello di Montalcino wine region, immersing yourself in the countryside with an expert.

Visit three remarkable wineries in the area, in each of which you’ll enjoy a comprehensive tour. This will allow you to delve into the wine-making process and savor the famous wines. A delicious Tuscan lunch at a family-run winery is also included.

Finally, wander around the enchanting Montalcino village. The group is capped at 8 participants, so you’ll enjoy your guide’s personalized attention.

Why is this the best tour? With over six hundred raving reviews, this excursion provides a superb introduction to the world of wine-making. You’ll discover the production process in not one but three different wineries, gaining an in-depth knowledge of the craft.

Plus, generous and informative tastings are included, and the group is small and intimate.

Read what the reviews say

“We had an outstanding day tasting Brunello di Montalcino! Mattia was the absolute best guide; he is so knowledgeable not only about wine but also about history. You will have a blast on this tour; highly, highly recommend as it was one of our favorite days of our trip!”

Alex_L – Read more reviews

This tour includes: A local guide, lunch, wine tastings, and winery visits. ➥ BOOK IT HERE

Other Great Winery Tours from Siena

▶️ Embark on a Chianti and Castle Small Group Tour from Siena with Wine Tasting for a half-day of explorations and wine discoveries.

Relax in an air-conditioned vehicle as you head to Fattoria Lornano, a delightful winery in the Chianti countryside. There you’ll catch a glimpse into the process of winemaking, and savor delicious local wines and olive oils. 

Next up is Monteriggioni, a medieval town with an incredible castle worth exploring. After some free time to wander around its alleys, head to a second winery. There you’ll indulge in more wine tasting and samples of Balsamic Vinegar. 

This Siena winery tour includes: Roundtrip transportation, wine, vinegar, and oil tastings, and a guide. ➥ BOOK IT HERE


▶️ Get ready to soak in the stunning Tuscan vistas on this Pienza and Montepulciano Small-Group Tour from Siena.

Explore the charming medieval town of Pienza, and savor a delectable lunch at a local dairy farm. Then, dive into the art of making Italy’s famous pecorino cheese.

The next stop is Montepulciano, a hill town steeped in history and renowned for its wine. Roam the noble palaces and charming alleys of the village at your leisure. Then, tour the local underground wineries, and sip on the finest Vino Nobile.

You’ll also get to immerse yourself in the legacy of the noble families that once inhabited this town. The tour is limited to eight participants.

This tour includes: Roundtrip transfers, a 3-course lunch, pecorino cheese tasting, a cellar tour, and wine tasting. ➥ BOOK IT HERE


▶️ Indulge in a luscious day of vino exploration with the Chianti and San Gimignano – 2 Wineries with Pairing Lunch Tour.

You’ll be taken to three handpicked wineries near Monteriggioni. There, sip and swirl delicious varietals, including the beloved Chianti Classico. 

At the winery in San Gimignano, you’ll get to pair your wines with a gourmet lunch. You’ll also have the chance to stroll the town’s historic streets and admire the rolling landscape that surrounds it! 

This tour includes: Hotel pick-up and drop-off, a winery tour with tastings, a driver/guide, lunch, and bottled water. ➥ BOOK IT HERE

The BEST Wine Tasting in Siena

▶️ This Siena: A Wine Tour and Tasting Experience is the perfect activity to relish the regional wines without going far. An expert sommelier will teach you how to discern subtle flavors of the different wines as they conduct a guided wine tasting.

In the vineyards, delve into the agronomic cycle of organic grapes, from genetics to harvesting. This will be followed by a cellar tour in which you’ll gain insights into the winemaking process.

Indulge in a sensorial wine tasting of four organic wines, and cap off the experience with a delectable light lunch. 

The seasonal menu will be paired with exquisite wines and organic extra-virgin olive oil. This tour is for small groups of up to 12 participants, and you can choose between morning and afternoon departures.

This Siena wine tasting tour includes: A guided visit to the vineyards and cellars, a wine-tasting session, lunch, and bottled water. ➥ BOOK IT HERE


▶️ Uncork the secrets of Tuscan wines with this entertaining Wine Class – Tuscan Classics.

Led by a local expert, you’ll explore the region’s best wine areas and get to taste up to 5 iconic varietals. Learn to swirl, smell, and savor the different wines. 

Prepare to discover the history and legends behind each sip, and learn about the perfect food pairings for each type of wine. Cheers to a fun-filled and very educational class that’ll turn you into an authentic Tuscan wine connoisseur!

This tour includes: Wines and snacks. ➥ BOOK IT HERE

Limited Time? Check These Half-Day Tours

▶️ Unveil the charm of Chianti on this Afternoon Semi Private Chianti tour from Siena. It kicks off with a fascinating walking tour outside Siena’s Fortress.

You’ll then travel back in time as you step foot in Monteriggioni, an enchanting medieval town nestled amidst the Tuscan Hills. 

Along the way you’ll hear riveting tales of the epic battles between Siena and Florence from your friendly guide. During your visit to an organic family-owned winery, enjoy a taste of four delightful Chianti Classico wines.

The tastings will be paired with Pecorino cheese, bruschetta, and other regional delicacies. 

This half-day wine tasting tour from Siena includes: Roundtrip transfers, a tour of the cellars, wine tastings, and snacks. ➥ BOOK IT HERE


▶️ This Dinner & Drinks in the Chianti Vineyards from Siena/Chianti allows you to uncover the enchantment of Tuscany in the best possible way. Eating and drinking, of course!

Tour around the winery and its cellars, and discover all the magic that goes on behind the winemaking process.  

As the sun dips below the horizon, relish a vineyard aperitivo followed by a four-course feast. You’ll also sip on a variety of exquisite wines to go along with your dinner.

This tour includes: Roundtrip transportation, an aperitivo, dinner, and drinks. ➥ BOOK IT HERE

Private Tuscany Wine Tours from Siena

▶️ The Pienza, Val d’Orcia, Montalcino Wine and Pecorino Cheese Private Tour from Siena is a very comprehensive, full-day tour.

You’ll travel in luxury with your group of eight as your guide offers insightful commentary. Upon reaching Azienda Agricola Capanna di Cencioni, enjoy a wine tour led by an expert.

Discover everything that goes on in the production of the famous Brunello di Montalcino, and enjoy tastings. Then, make your way to Pienza, passing by the bucolic landscapes of Val d’Orcia. You’ll have free time to embark on a self-guided tour before the day is over.

This tour includes: Roundtrip transfers from your hotel, and bottled water. ➥ BOOK IT HERE


▶️ Sip and savor the best of Italy on this Private Tour: Montalcino Wine Tasting Experience. Immerse yourself in the luscious world of Brunello wines at two renowned wineries.

Get ready to learn the secrets behind world-class wine-making from expert sommeliers. Then, enjoy the perfect pairing of cured meats and local cheeses with red wine.

Stop at an authentic winery for a light lunch, and then visit either Montalcino or the Sant’Antimo Abbey to cap off your trip.  

This tour includes: Roundtrip transfers, lunch, snacks, wine tastings, and a tour escort. ➥ BOOK IT HERE

Combine Food & Wine with this Brunello Cooking Class 

Unearth the tantalizing tastes of Siena with A Brunello Cooking Class with Vineyards View Winery. Savor Tuscan wine and cheese, tour an ancient winery, and master the culinary arts of Italy. A chef will provide all the instructions to craft delicious local dishes. 

Once everything’s prepared, indulge in a four-course lunch consisting of Tuscan antipasti, pasta, meat and veggies, and dessert. Your meal will be paired with five wines. 

This Brunello wine tour from Siena includes: A tour of the winery, a cooking class, lunch, and wines. ➥ BOOK IT HERE

Vespa Tour from Siena with Chianti Winery

Experience the stunning hills of Tuscany like a true Italian on this Vespa Tour with Lunch & Chianti Winery from Siena.

Join a fun convoy and zip through picturesque medieval villages and vineyard-clad landscapes. The thrill of driving your very own Vespa scooter alongside them is incredible! 

Head into the heart of the Chianti region and make your way to a renowned winery, led by your guide.

There you’ll learn all the steps of winemaking, before indulging in a Tuscan lunch paired with an array of local wines. 

The famous Chianti Classico, Super Tuscan, and Gallo Nero varietals will be included. If you don’t feel fit to drive, you can request an experienced tour escort to do the driving for you.

This Vespa Chianti bike tour from Siena includes: Vespa scooter and helmet rentals, a winery tour, lunch, wine tastings, and a guide. ➥ BOOK IT HERE

Tuscany Hiking Tour with Wine Tasting

Step back in time on this Tuscany Hiking Tour from Siena Including Wine Tasting. You’ll be tracing the ancient pilgrimage route, Via Francigena, which spans from Canterbury (England) to the Vatican in Rome. The trail is mentioned in records dating back as far as the 8th century!  

Wander through picturesque villages and vineyards, soaking in the stunning Tuscan scenery. You’ll finally arrive in the enchanting medieval village of Monteriggioni, perched atop a hill.

There, you’ll be rewarded with a delightful wine-tasting experience and free time to explore.

This tour includes: A guide, transfers, and wine tasting. ➥ BOOK IT HERE

  • Stefania Guglielmi

    Stefania Guglielmi is the founder of Every Steph. Originally from Bologna, Italy, she's been traveling full-time since 2016 and has visited over 50 countries across 6 continents. She believes sustainable travel and luxury travel can go hand in hand and has been advocating for responsible tourism since 2014. Stefania's advice and travel experiences have been featured in important publications such as Business Insider, Refinery29, and Yahoo Money.