There are so many great Tuscany wine tours to try depending on whether you want to try Chianti or Brunello di Montalcino or your pickup point, that we’ve put together this handy guide. Looking for the best winery tours in Tuscany? Keep reading for our top picks of wine tours Tuscany in 2024.

What to expect on a wine tour in Tuscany?

If you’ve been on a winery tour in Australia or the States, you should know that Tuscan wine tours are likely a little different. Besides the incredibly unique countryside, the main differences include:

  • Number of wineries: Most tours will visit two wineries max with a stop for lunch.
  • Appointments: If you’re organizing a self-guided wine tour, you’ll need to make reservations in advance rather than simply showing up on the day.
  • There’s a focus on seeing the whole estate and understanding the winemaking process rather than just tasting
  • They’re super fun, but the focus is not on it being a winery crawl/all you can drink
sangiovese vineyard

Why join a Tuscan wine tour?

 Because who wants to be designated driver?! Seriously though, if you’re interested in wine tasting Tuscany, then visiting some of the incredible wineries here is such an amazing experience. There are literally hundreds of wineries in the Tuscany wine region and it can get overwhelming quickly, so joining a wine tour is a great idea as you know you’re visiting a tried and trusted place that is used to hosting visitors.

It will probably come as no surprise that you can’t get public transport out to these places, so if you’re not confident driving in Italy or want to enjoy a few glasses of wine without worrying if you’re over the limit, winery tours in Tuscany is the way to go. If you’re a solo traveler, it’s also a great way to meet friends and enjoy a fun experience in a group setting.

wine tasting in tuscany

The Best Tuscany Winery Tours – the complete list

For a quick snapshot of some of the best vineyard tours in Tuscany, refer to this handy table weve put together. You can easily filter for the best tour for you based on price, region and other inclusions. For more details, just scroll down to see each of the tours below.


Tour Name Price Region # Wineries Lunch? Pickup from Towns Visited Tour Length
Chianti wine tour from Florence
with Devour Tours
€114 Chianti 2 Light tastings Florence Greve
Castellina in Chianti
5.5 hours
Chianti Morning Tour with Lunch €199 Chianti 2 Lunch Florence San Gimignano 8.5 hours
Private Chianti Wine Tour
with Liv Tours
for 2 people
Chianti 2 Lunch Florence Castello di Verrazzano 6 hours
Wine tour Greve in Chianti €225 Chianti 1 No Florence Greve
5 hours
Wine Tasting San Gimignano
with Grape Tours
€275 San Gimignano
2 Lunch Florence San Gimignano
Castle in Chianti
9 hours
Brunello wine tour
with Grape Tours
€275 Montalcino 3 Lunch Florence Montalcino 9 hours
Brunello Wine Tasting and lunch in a Tuscan castle €58.9 Montalcino 1 Lunch Montalcino na 1.5 hours
Montepulciano wine tour with Grape Tours €275 Montepulciano 2 Lunch Florence Montepulciano 9 hours
Wine tasting Montepulciano with lunch €55 Montepulciano 1 Lunch Montepulciano na 1.5 hours
Tuscany wine tours from Siena €76.5 Val dOrcia 2 No Siena Pienza
10 hours
Tuscany Day Trip
with Walks of Italy
€213 Chianti 1 Yes Florence Siena
San Gimignano
10 hours
Super Tuscan wine tours from Florence €449
for 2 people
Bolgheri 2 Yes Florence Bolgheri 10 hours
Rome to Tuscany tour with Walks of Italy €180 Val DOrcia 1 Yes Rome Pienza
13 hours
Tuscany Vespa Wine Tour €200 Chianti 1 Yes Florence San Gimignano 8 hours
Chianti Countryside e-bike Tour €160 Chianti 1 Yes Siena Monteriggioni 6 hours
Untold Italy Tuscany Tour From $US 4,990 Chianti 2 all meals Florence varies depending on Spring-Fall itinerary 8 days


The best Tuscany wine tours from Florence

Even if you’re not staying out in the Tuscan countryside, you can still have your Under the Tucan Sun moment by joining wine tours in Tuscany from Florence. Choose from a half day or a full day experience and away you go! Here are our tips for the best Tuscany wine tours from Florence to try in 2024:

Devour Tours knows seriously good food and wine which is why they’re our first suggestion. They offer a half-day tour with pickup from Florence and take you to two favorite family-run wineries in Chianti. You’ll also have the opportunity to explore some scenic hilltop towns accompanied by your guide!

What’s Included:

  • Guided tasting of 5 DOCG Chianti wines paired with light bites
  • Guided stroll through picturesque towns of Greve in Chianti and Castellina in Chianti

This wonderful tour includes two wine tastings, a Tuscan lunch and even time to explore San Gimignano (aka medieval Manhattan or so they say!) You’ll be picked up in Florence and then driven to the gorgeous medieval town of San Gimignano in the morning before your wine adventures start. 

What’s included:

  • Visit San Gimignano
  • Wine tasting and Tuscan lunch at San Casciano in Val di Pesa
  • Wine tasting in San Michele a Torri 


sangiovese wine

Try these Chianti wine tours

Chianti is one of the most famous wine regions in all of Italy if not the whole world, so it comes as no surprise that Chianti Italy wine tours are so sought after! If you’ve never visited the Chianti area before, it’s a must-do! Here are our tips for some of the best Tuscany wine tours in Chianti.

Private Chianti Wine Tour Tuscany with Liv Tours

If you’re looking for a romantic private wine tour, or simply a private group experience, this is it. Your driver will take you to one of the oldest Chianti producers for a tasting and the chance to explore the grounds. Afterward enjoy a visit to a small, traditional family-owned winery and enjoy a light lunch of traditional Tuscan foods paired with the estate’s wines. Pickup and dropoff in Florence too!

What’s included:

  • 1/2 day tour with a bilingual chauffeur
  • Visit an Etruscan castle and taste their classic Chianti wines
  • Light Tuscan lunch
  • 2 winery visits

If you’re specifically looking for a tour that takes in wine-obsessed Greve in Chianti, book this tour! You’ll get to explore the market town of Greve in Chianti and the Castle of Montefioralle with a local guide and your group before wine tasting at a local winery.

What’s included

  • Wine tasting at a winery
  • Round-trip private transportation from Florence
  • Half-day tour of the Tuscan Chianti region from Florence
  • Visit to Montefioralle and Greve in Chianti

San Gimignano Wine Tour

Gorgeous San Gimignano is not only famous for their medieval towers but is also Tuscany’s only well-known white wine region. Get a little off the Chianti track with a San Gimignano wine tour from Florence.

Wine Tasting San Gimignano with Grape Tours

This tour includes pickup and dropoff in Florence before whisking you away to San Gimignano. There, you get to visit an organic winery that produces some of the finest whites in the region paired with delicious appetizers. You have the chance to explore the town of San Gimignano before heading to Chianti Classico with a stop at an old hamlet winery for lunch. Sit back and enjoy a Tuscan lunch paired with the winery’s wines before heading to the final winery for the day. Nestled inside a castle, this family-owned winery is completely organic and you’ll have the opportunity to taste their wines and visit the historical cellars.

What’s included

  • Guided tour led by sommelier
  • Visits and tastings at 3 wineries
  • Tuscan lunch
  • Pickup and dropoff in Florence
san gimignano

Montalcino Wine Tours

Move over Chianti, because Montalcino is even more exclusive and one of the most prominent wine regions in the country. Just like in Chianti, the Sangiovese grape is used here but undergoes 5 years of aging before turning into delicious Brunello wine.

Brunello wine tour Tuscany with Grape Tours Florence

This is a full-day tour with wine experts from Grape Tours. You’ll get to visit 3 top family-run wineries in Montalcino on this Brunello wine tour from Florence. The first winery visit includes visiting their historic cellars and even tasting inside the castle! At the second winery, enjoy an impressive view of 10th-century Sant’Antimo Abbey before sitting down to a 4 course home-cooked Tuscan lunch paired with 4 different wines including a Riserva. You have time for a wander around the village of Montalcino before a visit to the final, smallest winery for a tasting of their elegant organic Brunello.

What’s included

  • Semi-private wine tour with private visits to 3 exceptional wineries.
  • Taste around 4 wines at each winery including a white and a rose.
  • 4-course traditional Tuscan lunch.
  • Short stop in Montalcino.

Wine tours in Montalcino Italy don’t get much better than this one! It starts and ends in Montalcino, so you’ll need to be able to get yourself there. Enjoy a walk in the vineyards with a sommelier and learn about traditional wine-making. You’ll have the chance to taste 3 different local wines before sitting down for a delicious 3-course lunch.

What’s included

  • Winery and castle visit
  • Taste 3 wines
  • 3-course Tuscan lunch


brunello wine tasting

Montepulciano Tour

In the Val dOrcia or Southern part of Tuscany, the two most important wine villages are Montalcino and Montepulciano. Majestic Montepulciano sits on top of a hill and is where the famous Vino Nobile is made.

This wonderful tour in Montepulciano includes a visit to two different wineries in the village where you’ll learn about the winemaking process and enjoy tastings at each. There’s a stop for a 3-course Tuscan lunch at a family restaurant in a medieval hamlet and time to explore the village itself.

What’s included

  • 2 winery visits with tastings
  • 3-course Tuscan lunch
  • Free time in Montepulciano

If you don’t need a transfer from Florence, this is a great tour that starts and ends directly in Montepulciano. You will enjoy a wine tasting of four different local wines led by a sommelier inside a centuries-old underground wine cellar. It concludes with a two-course Tuscan lunch!

What’s included

  • 1 winery visit with tasting of 4 wines
  • 2-course Tuscan lunch
wine tasting tuscany

Siena Wine Tour

If you’re specifically looking for a tour that starts and ends in Siena, this is it! This tour starts in Siena where you are whisked away to a local winery for a Brunello wine tasting. Next, enjoy some free time in pretty Pienza and Montepulciano followed with a wine tasting of Montepulciano wine.

Whats included

  • Visits to Montalcino, Pienza, and Montepulciano
  • Visit wine cellars and sample local wines in both Montalcino and Montepulciano
  • Free time in Montalcino and UNESCO-listed Pienza

Tuscany Day Trip with Walks of Italy

If you’re looking for wine tours in Tuscany Siena, why not join this tour that leaves from Florence and includes a visit to Siena, San Gimignano and a nearby winery? You’ll enjoy a seasonal lunch and wine tastings at a family-run farm in the Chianti region, plus guided walking tours of both towns.

What’s included

  • Guided walking tour in Siena
  • Guided walking tour in San Gimignano
  • Farm-to-table lunch with wine tastings
  • Pickup and dropoff in Florence
siena wine tour

Tuscany bike wine tours

One of the best ways to explore is on an e-bike or a vespa for a completely different perspective of the region! Have a look at these Tuscany Italy wine tours by bike now.

Ever dreamed of riding a vespa with the wind running through your hair in the Tuscan countryside? Then this all day tour is for you! It includes a visit at the gorgeous farm Fattoria Poggio Alloro and a guided stroll through San Gimignano, with free time to explore. Youll also sit down for a three-course lunch paired with a tasting of nine local wines at Tenuta Torciano.

This is one of the best wine tours of Italy Tuscany. This three hour ride takes you through vineyards, picturesque olive groves, dense forests, and sleepy villages. You will visit Monteriggioni, a beautifully restored fortress dating back to the 13th century and have some time to explore. Then sit down at a local farm for a delicious lunch with local wine and tastings of extra virgin olive oil. The tour starts and ends at the Siena train station.

vin santo

Maremma Wine Tours

The coastal area of the Maremma is much less known for wine, but a really fantastic wine region to explore. In fact, they make some of Italy’s most costly wines including Ornellaia, Sassicaia, and Masseto. The most important area for winemaking here is the Bolgheri wine zone. The wine here is a red blend of Cabernet Franc, Cabernet Sauvignon, and Merlot, aka a Super Tuscan. If you’re looking for Livorno wine tours consider one of these wine tours in Bolgheri.

This is a full-day tour with a private chauffeur who will take you along the famous Via Bolgherese to the Tuscan Coast. You get to visit two diverse wineries and enjoy tastings at both before sitting down to a traditional Tuscan meal. Pickup and drop-off from Florence!

What’s included

  • Private chauffeur
  • Pickup and dropoff from hotel in Florence
  • 2 winery visits with tastings
  • Tuscan lunch

Tuscany Wine Tours from Rome

Not enough time to spend a few days or longer in Florence or Tuscany? That doesn’t mean you have to miss out on living out your Tuscan dreams! The best thing to do is join wine tours from Rome to Tuscany for the day, and sit back and relax as all the details are taken care of! We recommend going with Walks of Italy on their Rome to Tuscany tour.

With pickup in Rome, the tour starts in cheese-crazy Pienza where you have some free time to explore before visiting a local farm for a delicious farm-to-table lunch. Next up, you get to explore the Montalcino Fortress before your first winery visit with a tasting of Montepulciano wine.

If you’ve only got a day free, this is one of the best Italy wine tours in Tuscany you can join.

rome to tuscany wine tour

Tuscany food and wine tour

If you’re looking for more of an experience that takes in wineries, local food, Tuscan culture and traditions, plus visits to some of the most charming and off-the-beaten-path towns in the region, then why not join an extended week-long tour?

Untold Italy run food and wine tours in Italy Tuscany a few times a year so you can choose between Spring and Fall or Autumn, which is probably the best time to visit the wine regions.

The tours run for 8 days and are all-inclusive with accommodation in a gorgeous stone farmhouse in the countryside, visits to family-run wineries, guided tours in towns like San Gimignano, Siena, Volterra, Pienza and more, plus even artisan visits to local ceramicists, basket weavers and Alabaster workshops. The tours include all meals and a bilingual host (normally Liv herself) will be with you the entire time.

Inspired to join one of these best wine tours in Tuscany? Whether youre a wine enthusiast or just like a nice glass of red, this is one of the most memorable experiences you can add to your trip to Italy. It will leave you dreaming of the rolling hills and with a newfound love of Tuscan wine forever.