The 8 Best Tuscan Wine Tours of 2023

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Rolling hills of Tuscan vineyards in the Chianti wine region tour

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The Rundown

Best from Florence: Private Tuscany Wine Tour

Private Tuscany Wine Tour Experience from Florence
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Florence is Tuscany’s capital, but to get the real Tuscan wine experience, you’ll want to get out of town. This private tour begins with your professional sommelier guide picking you up at your Florence hotel and whisking you away to the countryside. Your guide will carefully select three wineries, all very different but each producing top-quality wines. The first will be a traditional grand wine estate, where you’ll tour the cellars and enjoy the opportunity to ask questions of the winemaker.

The next will be an estate that grows its grapes organically, and the last will be at a small family-owned winery. At all three, you’ll have ample opportunity to learn, ask questions and, of course, taste! At the final stop, your tasting will be accompanied by a spread of local cuisine, including homemade pasta, fresh bruschetta, meats, cheeses, and dessert. The sommelier who guides this tour is deeply knowledgeable about both the winemaking and wine-tasting processes, as well as the lay of the land in the Tuscan wine scene, so it’s an ideal tour for those who really want to dig in and learn more.

As a private tour, it also offers some flexibility—take the time you need to ask the questions you want to ask and savor every sip.

Best from Rome: Montepulciano Noble Wine Tours

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If your Italian vacation is headquartered in Rome, or if Rome is just the closest you’ll otherwise get to Tuscany, consider this tour, which allows you to escape Rome’s busy cityscape for a day and get out to the beautiful rolling hills of Tuscany. Your guide will pick you up at your hotel in a comfortable Wi-Fi-equipped Mercedes and begin your two-hour drive out to the handsome Tuscan town of Montepulciano, home of the famous wine which bears its name, Vino Nobile de Montepulciano.

You’ll visit one of the town’s finest wineries and get a private cellar tour with one of its winemakers, who’ll teach you about the history of the wine, as well as tasting and pairing advice. Then you’ll head upstairs for a tasting of both organic wine and organic olive oil from the estate. After your wine tasting, you’ll have lunch in Montepulciano and then head for an afternoon stroll in Pienza, home of the world-famous Pecorino di Pienza cheese, made in the same way in this tiny commune for thousands of years. After taking your time exploring this historic town, you’ll head back to Rome in comfort.

Best for Small Groups: Wine and Food Tour in Chianti

Wine and Food Tour in Chianti Wine Region (Tuscany)
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Ride in comfort in a climate-controlled minivan from Florence into the surrounding countryside for a wine tasting at two separate world-class wineries on this small-group tour. Your English-speaking guides will accompany you throughout the day, explaining the history of the Chianti wine region, the process of viticulture, and offer tasting tips and notes to help you get the most out of each sip.

Beyond the Chianti Classico that made the region’s name famous, you’ll also get to try some “Super Tuscans,” the newest style of Tuscan wine, developed just within the last century (“new” is relative in these parts) using grapes grown locally from grape varietals that are not traditional to this region (mainly the famous grapes of Bordeaux: cabernet sauvignon and merlot).

After your tastings, you’ll have a chance to explore the medieval hill town of San Gimignano, famous for its tower. The tour, flexible due to the small size of the group, will have a number of opportunities to stop for photo ops throughout the day.

Best Value: Wine Experience in Tuscany

San Gimignano
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You’re not really likely to find a cheap high-quality wine tour in Tuscany, but this one is fairly priced and offers a lot of bang for your buck. The small-group tour, which offers hotel pick-ups in central Florence, includes tastings and tours of both wineries and other local producers, as well as visits to at least one of Tuscany’s charming tiny hillside towns, in a full day of events.

You’ll tour two wineries and enjoy two tastings of wine and artisanal olive oil. You’ll also have opportunities to taste other local delicacies, including balsamic vinegar, cheese, olives, and gelato. A full lunch, featuring local ingredients, is included at one of the vineyards. Along with a small-town visit, your driver will make stops at some particularly stunning groups of cypress trees and olive groves for photo ops, as well as an end-of-the-day stop at Michelangelo Square, which offers perhaps the most beautiful panoramic view of Florence.

Best Express: Flavors of Maremma

Tuscan vineyard
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Not ready to sign on for a big bus tour? No worries — this single-location tour might be the right choice for you. You’ll simply head to a winery in Maremma, a micro-region of Tuscany that has only recently made it into the oenophile’s standard lexicon but has done so with a splash. You’ll tour the estate, learning about the wines made in the region and the process of becoming a DCOG (an official Italian governmental designation for wines, obtained by Maremma in only 2007).

And then, the fun part: a tasting! The wine bar here offers a variety of wines for tasting, and this tour specifically includes tastings of two fine wines, each carefully paired with a house-made bruschetta.

Best Organic Wine: Organic Bio Wine and Food Tour

Chianti wine
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Some people might scoff at the idea of organic wine as some sort of new age, newfangled thing, but as locals will tell you, it’s really non-organic wine that’s the newfangled thing—organic is the way that Tuscan wines have been produced for millennia. This full-day tour includes a pickup and drop-off at your lodgings anywhere in Tuscany (yes, really) and includes tours at two different organic wineries in Chianti, as well as complete tastings of both wine and other locally made products (olive oil, vinegar, cheese, produce, and more).

San Gimignano is on the docket for this tour, too, and you’ll have plenty of time to explore this sweet and ancient little town and its excellent architecture (and food markets).

Best Vegetarian-Friendly: Tour for Vegetarians in Tuscany

Piazzale Michelangelo
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Most Italian wine tastings include snacks, but these snacks often include traditional Italian meats and cheeses. If you’re a vegetarian, you might consider this private tour, which makes a point of keeping things veg-friendly. You’ll visit two different wineries in Chianti, both of which produce organic wines, and enjoy your wine tastings alongside nibbles that are crafted with vegetarians in mind, which is to say you won’t just get stuck with a stack of plain crackers and a couple of olives.

This full-day tour, as with so many in Chianti, stops at San Gimignano (it’s just so perfectly sweet and medieval, people can’t stay away. Plus, the world champion gelato shop is there, what’s not to like?), as well as at Michelangelo Square on the way back into the city.

Best Tasting Lesson: The Best of Tuscan Wines in Chianti

Best of Tuscan Wines in Chianti
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Vineyard visits and wine tastings are a whole lot more fun when you actually know how to taste wine. Which, as we’ve all learned from the true wine-lovers in our lives (or in the movies), is a more complicated process than just taking a swig. This class, located in the heart of the small Chianti town of Greve, introduces students both to the history and culture of Tuscany (and how that influenced the wine and other agricultural products of the region) and the basics of how to pour, swirl, sniff, and sip. You'll also learn how to know what you’re looking for, what people mean when they say “finish” and “fruity” and “heavy tannins” and all of those other fancy-schmancy wine words that may not make a whole lot of sense to those of us who may only barely know our reds from our whites. The class includes tastes of at least three separate top-quality Tuscan wines, as well as accompanying snacks.

Our Process 

Our writers spent 2 hours researching the most popular Tuscan wine tours on the market. Before making their final recommendations, they considered 25 different tours overall, screened options from 25 different brands and manufacturers, and read over 40 user reviews (both positive and negative). All of this research adds up to recommendations you can trust.

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