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Best Tuscany Wine Tours

Best Tuscany Wine Tours

When we think of Italy’s food, there are a few things that come immediately to mind. Fresh pasta, hand-made and served al dente…  the sun-dried tomatoes and delicious cheese… there’s fresh herbs and cured meat… and of course, there’s wine! Because what Italian meal would be complete without a helping of red wine?

Producer of some of Italy’s best wines, Tuscany is also one of the world’s best wine regions. It is a place that grows the important Sangiovese grapes. They are primarily used for such wines as Brunello di Montalcino, Vino Nobile di Montepulciano, and Chianti.

When you’re in Tuscany, your experience would not be complete without getting to know some of the wineries more intimately. Hence, this list of the best Tuscan wine tours that allow you to indulge in the taste and culture of the Italian regions!

Siena Wine Tours : Chianti and San Gimignano 5-Hour Tour

Town square of Sam Gamignano with pedestrians leisurely walking along
San Gamignano town square

Siena is second only to Florence when it comes to tourism in the Tuscan region, what with its extensive collection of art, history, and architecture. It’s also from here where you could strike out to the Chianti vineyards and the magnificent landscapes that surround them. In this wine tour, your guide will lead you beyond the beaten path and onto the place where the ruby fragrance of Chianti wine is born.

Lovely alley in Sienna with potted plants and ivy growing
Siena alleyway

Your tastebuds will enjoy this product in one of the best cellars of the area, complete with a platter of cheeses, bruschetta, salami and meats — perfect companions for this drink.

After enjoying the sights, sounds, and tastes of the Chianti countryside, the tour will lead you to the UNESCO World Heritage Site that is San Gimignano. This medieval town has perhaps one of the first tower-lined skylines in the world, long before the skyscrapers of the modern day.

It is also home to the famous Vernaccia di San Gimignano wine, which you will also taste. The experience goes perfectly with a tour that spans the whole of the town, with its many squares, churches, alleys, and more.

Book Siena wine tours here.

Florence Wine Tours: Small Group Wine Tasting Tour to Tuscany

The attraction-dense Florence is also a great starting point for a wine tour! Take your time to walk around this treasure-laden city on your own. Then join your guide and a small group as you travel to the historic Chianti Classico area.

There’s just something special in this part of the world that produces some of the best wines known to man. It’s more than the beautiful sights. You will learn more about the secrets of the earth as your first stop, a wine estate, tours you around the wine’s production process.

Wine barrels in a Florence wine cellar
Wine barrels in the cellar

This particular estate has three special wines for you to sample, together with some fresh olive oil. A second wine estate tour allows you to compare and contrast not just the taste but also the production methods of the various wines. As a plus, you’ll get a firsthand experience of just how well the wines pair with famous local meats such as ham, salami, bruschetta, and more!

Book this wine tour Tuscany here.

Poggibonsi: 4-Course Cooking Class with Wine Tasting

A good wine is best savored with a good meal, and fortunately Italy is all about both. This tour takes place within the picturesque confines of San Gimignano. It is a bottega that is as authentic an Italian kitchen as you can get.

After taking your own time to absorb the town’s treasures, a chef will give you and expert-level cooking class. Feel like an expert yourself as you make some of Tuscany’s classic kitchen specialties, such as pasta, chicken stew, and some dessert.

People around a table, chopping vegetables with wine glasses
People cooking and drinking wine

Join 14 other students as you master the traditions and techniques of the Tuscan kitchen. After this, take time to appreciate how well your meal pairs with a few fine glasses of local wine.

Don’t worry — a bit later on you’d be able to go on a proper local wine tasting session where you’ll learn to appreciate the finer flavors of the red nectar. Other wine tours shift your focus to the sights around you. But this one focuses on the stimulation of your palate.

Book this Poggibonsi wine tour here.

San Gimignano: Vineyard Walk and Lunch with Wine Tasting

Lately, vineyards are no longer simply revered places that produce wine grapes. They have also been turned into aesthetic marvels, especially with the introduction of “spiral vineyards” — grape vines arranged in a spiral pattern, with a vantage point at the center from which to view the marvel.

People toasting with red wine in an Italian vineyard
People drinking red wine

Visit one such spiral vineyard in this tour, owned by the Giachi family. Here you’ll learn not just about the vines but also about the history and context of almost every structure in sight. Of course, you will also get ataste and context of the estate’s wines. You’ll be able to trace their interesting history.

The tour is capped with a sumptuous Italian lunch, with such Tuscan food as Truffle lasagna, Tuscan ribollita, cantuccini, and more.

Book the San Gimignano wine tour here.

Table set in an outdoor dining area just a few feet from the vineyard
San Gimignano vineyard meal

Montalcino, Pienza, and Montepulciano Food Tour from Siena

It says food tour on the label, but the real highlights here are the wine cellars you would be visiting. There’s one in Montalcino, which on its own is famous for its IG-worthy rolling hills and fresh produce. Its streets and fortress are typical of the Tuscan region, and its wines are as excellent.

The Pienza leg of the tour explores the area’s architectural treasures, especially the Val d’Orcia whose lanes overlook beautiful landscapes. The last leg, at Montepulciano, explores the stately buildings hand-in-hand with the area’s own ancient wine-making tradition. Finally, a bus drives you back down to Siena. Your exploration of the finer points of wine and history may continue there.

Wine barrels in front a picturesque italian town view
Montalcino Pienza and Montepulciano view

This is just a small cross-section of what Tuscany has to offer in terms of wine and all the fun that surrounds it. Wine production and wine-tasting is as much an art as is the region’s paintings and architecture. It is as much a product of nature as the unrivaled landscape that makes Tuscany such a draw for tourists the world over.

Book this multi-town Tuscany wine tasting tour here.

Red wine grapes plump and ready to be picked
Wine grapes on the vine

Of course, since the place is such a draw. You’ll want to have a way to avoid the crowds and jump the lines. This is why pre-booking, especially with a reputable tour company as Get Your Guide, is highly recommended!

Best Tuscany Wine Tours was written and photographed by Karla Ramos

Best Tuscany Wine Tours – Pin for Later


Monday 17th of February 2020

Great suggestions for wine tours. Thanks for sharing!

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