In this guide21 sections
- The 12 Best, Ranked
- Tuscany Wine Tours from Florence · 8 experiences
- Tuscan Safari: Villas, Vineyards, Cheese, Wine & Lunch
- Florence Vespa Tour: Tuscan Hills & Italian Cuisine
- Tuscany Bike Tour: One Day Through the Hills of Chianti
- Pizza & Gelato Cooking Class at a Tuscan Farmhouse
- Compare the Tuscany Tours
- Tuscan Wine Tour with Lunch, San Gimignano & Organic Wineries
- Self-Drive Vintage Fiat 500 Tour: Tuscan Wine Experience
- Private Tuscany Wine Tour Experience from Florence
- Horseback Ride & Poolside Day with Tuscan Lunch
- Tuscany Wine Tours from Rome · 2 experiences
- Tuscany Wine Tour from Rome with Private Driver
- Montepulciano & Pienza Tuscany Full-Day Tour from Rome
- Tuscany Wine Tours from Siena · 2 experiences
- Tuscany Hiking Tour from Siena Including Wine Tasting
- Educational Wine Tour & Tasting in Siena
- Tuscan Safari from Florence
- Tuscany Travel Logistics
- Cities, Towns & Villages within Tuscany
- Frequently Asked Questions About Wine Tours in Tuscany
Tuscany is the region wine travelers dream about — rolling Chianti hills, medieval hilltop towns, and estates where the Sangiovese in your glass was grown on the slope outside the window. The fastest way in is a guided tour, and these are the ones real travelers rate highest.
Below are the best wine tours and tasting experiences across Tuscany, organized by where you’ll set off from — Florence, Rome, or Siena — so you can match a tour to your base. Every experience is bookable through Viator, and Winetraveler readers get a reader bonus with code JULY2550.
The 12 Best, Ranked
Tuscany Wine Tours from Florence · 8 experiences
Traveler favorite1Tuscan Safari: Villas, Vineyards, Cheese, Wine & Lunch
Italy’s iconic Tuscany region is more than just a destination – it’s a feast for all your senses. This full-day Tuscany wine and food tour, departing from Florence, offers you the chance to taste the region’s finest offerings, guided by experts with in-depth local knowledge.
Navigate the enchanting Tuscan countryside in a comfortable 4×4 minibus, stopping to explore a historic wine estate and villa, and a cellar filled with delectable Chianti Classico — each stop an opportunity to taste locally-sourced cheese and other Tuscan delicacies before a traditional 3-course winery lunch.
Best on two wheels2Florence Vespa Tour: Tuscan Hills & Italian Cuisine
Venture off the beaten path and explore the heart of Tuscany on a classic Vespa scooter. This unique tour takes you on a scenic ride through the Tuscan hills, starting from the Renaissance city of Florence, with a knowledgeable local guide leading the way to hidden gems.
After exploring the countryside, head back to a welcoming country estate to indulge in a traditional Italian meal — bruschetta, pasta, and a cheese and salami board. To keep it intimate, the tour is limited to 15 travelers.
Best active day3Tuscany Bike Tour: One Day Through the Hills of Chianti
Escape the bustling city of Florence and immerse yourself in the natural splendor of the Tuscan countryside. This top-rated bike tour combines awe-inspiring scenery, centuries of history, and an authentic taste of the region’s flavors in an active way.
Pedal across fertile valleys and hilly landscapes adorned with olive trees and vineyards, stopping to explore a 12th-century villa and a traditional restaurant for a mid-day meal, with tastings of Chianti wine and local olive oil along the way.
Most booked4Pizza & Gelato Cooking Class at a Tuscan Farmhouse
Embark on a delightful culinary adventure near Florence, nestled within a picturesque Tuscan estate. Ideal for culinary enthusiasts and culture lovers, this hands-on experience teaches you the art of crafting two Italian treasures – pizza and gelato – guided by a professional Italian chef.
The lesson culminates in a 3-course feast of appetizers, freshly made pizza, and gelato, all paired with a selection of fine wine and beer — plus a recipe booklet to take home.
Compare the Tuscany Tours
| Tour | Departs | Style | Rating | Reviews |
|---|---|---|---|---|
| Tuscan Safari | Florence | 4×4 wine & food | ★★★★★ 5.0 | 3,165 |
| Vespa Tour | Florence | Scooter + lunch | ★★★★★ 5.0 | 2,896 |
| Bike Tour | Florence | Cycling + tasting | ★★★★★ 5.0 | 1,158 |
| Pizza & Gelato Class | Florence | Cooking class | ★★★★★ 5.0 | 3,633 |
| Chianti & San Gimignano | Florence | Classic wine day | ★★★★★ 5.0 | 547 |
| Vintage Fiat 500 | Florence | Self-drive convoy | ★★★★★ 5.0 | 415 |
| Private Wine Tour | Florence | Private, 3 estates | ★★★★★ 5.0 | 54 |
| Horseback & Pool | Florence | Riding + resort lunch | ★★★★★ 5.0 | 15 |
| Private Driver (Rome) | Rome | Private, 3 hill towns | ★★★★★ 5.0 | 6 |
| Montepulciano & Pienza | Rome | Hill-town day trip | ★★★★★ 5.0 | 5 |
| Siena Hiking Tour | Siena | Via Francigena + tasting | ★★★★★ 5.0 | 47 |
| Siena Educational Tasting | Siena | Vineyard tasting tour | ★★★★★ 5.0 | 122 |
Best classic wine day5Tuscan Wine Tour with Lunch, San Gimignano & Organic Wineries
Take a break from the energetic pace of Florence and set off into the heart of the Tuscany wine region. This day trip includes round-trip transport from a central Florence location, making your adventure as comfortable as possible.
With a knowledgeable guide, you’ll gain insights into the winemaking process at local vineyards often overlooked by visitors — with wine tastings, an authentic Tuscan lunch, and plenty of time for photographs against Tuscany’s scenic landscapes.
Best for a photo album6Self-Drive Vintage Fiat 500 Tour: Tuscan Wine Experience
Couple a wine tasting with a classic Fiat 500 tour. Departing from Florence, step into the driver’s seat of a 1960s Fiat 500 and journey through the Tuscan hills as part of a scenic convoy, parking your vintage ride at a stunning 15th-century wine estate and villa.
Match a tour to your kind of day
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Best private tour7Private Tuscany Wine Tour Experience from Florence
Delve into Tuscany’s world-renowned flavors and stunning landscapes on a private wine tour from Florence. Journey through the hills with a knowledgeable sommelier guide, visiting three distinctive estates to sample top-notch regional wines and olive oil, with a traditional Tuscan lunch at a family-owned winery.
Best slow day8Horseback Ride & Poolside Day with Tuscan Lunch
Trade the bustling streets of Florence for a day of tranquility immersed in nature. Ride horseback through the picturesque Tuscan countryside, then wind down at an elegant country resort in the Florentine hills — with a delightful Tuscan lunch served poolside and complemented by local Chianti wine.
Tuscany Wine Tours from Rome · 2 experiences
Best from Rome9Tuscany Wine Tour from Rome with Private Driver
Make the most of your time with this private tour covering three enchanting hill towns in Tuscany and Umbria in one day. With hotel pickup in Rome and a full day’s transport, you can taste wine in Montepulciano, savor pecorino in Pienza, and admire the views from cliffside Orvieto.
Best hill-town day10Montepulciano & Pienza Tuscany Full-Day Tour from Rome
Trace the footsteps of the Etruscans as you visit the medieval towns of Montepulciano and UNESCO-listed Pienza, two of Tuscany’s most charming hilltop settlements. Starting from Rome in an air-conditioned minivan, you’ll have time to explore the historic streets and take in the panoramas over the Val d’Orcia, with round-trip hotel transport included.
Browse every Tuscany wine tour
See live availability and prices across all Tuscany experiences on Viator — and don’t forget code JULY2550 for 15% off.
Tuscany Wine Tours from Siena · 2 experiences
Best for walkers11Tuscany Hiking Tour from Siena Including Wine Tasting
Step back in time, tracing the footsteps of ancient pilgrims along the Via Francigena, the historic route that connected Canterbury to Rome. The path winds through villages, vineyards, and some of Tuscany’s most picturesque landscapes, concluding in the medieval village of Monteriggioni with a curated wine tasting — and a train ticket back to Siena.
Best for wine geeks12Educational Wine Tour & Tasting in Siena
Tuscany is famed worldwide for its exceptional wines. Get an insider’s view into this illustrious industry with a tasting tour in the vineyards close to Siena — guided, unhurried, and built around the wines the region is known for.
Our top overall dayTuscan Safari from Florence
If you only have one day and want the complete Tuscany: a 4×4 run through Chianti estates, a cellar of Chianti Classico, cheese and olive-oil tastings, and a 3-course winery lunch under the vines. With 3,165 five-star reviews, it’s the most reliable single day in the region.
Tuscany Travel Logistics
Getting to Tuscany
Major Airports in Tuscany
Florence Airport, Peretola (FLR): Known as Amerigo Vespucci Airport, it’s the closest airport to the heart of Florence and Tuscany. It’s relatively small and offers fewer international connections, but it’s a popular choice due to its proximity to Tuscany’s major cities.
Pisa International Airport (PSA): Also known as Galileo Galilei Airport, this is the largest airport in Tuscany with more international flight connections. Pisa airport is well-connected to Florence and other Tuscan cities by both train and bus services.
Bologna Guglielmo Marconi Airport (BLQ): Although not located within Tuscany, it’s another good option to consider as it has strong flight connections, both domestic and international. It’s roughly an hour and a half’s train ride to Florence.
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Arriving from Other Parts of Italy
Tuscany is well-served by Italy’s extensive train network. The high-speed trains from cities like Rome, Milan, and Venice make getting to Tuscany both quick and convenient. Florence’s main station, Firenze Santa Maria Novella, is a major hub connecting Tuscany to the rest of Italy.
Getting Around Tuscany
Public Transportation
Trains: The train network in Tuscany is quite extensive, connecting not only the major cities but also smaller towns. They are generally punctual, affordable, and efficient.
Buses: For some of the smaller towns and villages, bus is the only public transport available. Although they can be less predictable than trains, buses can get you to places trains can’t reach.
Car Rental
Renting a car can be an excellent option if you wish to explore the countryside or visit vineyards at your own pace. Do remember that driving in Italy requires an International Driving Permit along with your regular driver’s license for non-EU citizens. Also, many city centers in Tuscany are limited traffic zones (ZTLs) and are camera-controlled — driving into these zones without a permit will result in a fine.
Taxis and Rideshares
Taxis are readily available in cities and larger towns. Uber operates in Florence and is another convenient option for getting around.
Other Things to Know
Best Time to Visit: Tuscany is a year-round destination, but the ideal times to visit are between April and June, and September and October when the weather is comfortable and the countryside is at its most vibrant.
Language: Italian is the official language. However, English is widely spoken in tourist areas, hotels, and restaurants.
Currency: Euro (€) is the official currency of Italy.
Safety: Tuscany is generally safe for tourists, but like any other tourist destination, be aware of your surroundings, particularly in crowded places.
Electricity: Italy operates on a 220V supply voltage and 50Hz. The power plugs and sockets are of type F and L.
Cities, Towns & Villages within Tuscany
Florence
As the capital of Tuscany, Florence is an incredible mix of art, history, and culture. It’s the birthplace of the Renaissance, and home to world-class museums such as the Uffizi Gallery and the Accademia Gallery, where you can admire Michelangelo’s David. The city also has a rich culinary scene, with countless trattorias serving classic Tuscan cuisine. Florence is an ideal base for day trips throughout the region, thanks to its central location and excellent transportation links.
Siena
Famous for its medieval cityscape and the historic Palio horse race, Siena is a must-visit. The city’s heart is the Piazza del Campo, a shell-shaped square that hosts the Palio twice every summer. The Siena Cathedral (Duomo di Siena) is another highlight, featuring intricate Gothic architecture. Siena’s historical center has been declared a UNESCO World Heritage Site for its preserved medieval city planning and architectural splendor.
Pisa
Known worldwide for its leaning tower, Pisa has much more to offer. The city hosts a wealth of historic sites, including the Piazza dei Miracoli, where you’ll find the Leaning Tower, the Pisa Cathedral, and the Baptistery. For an authentic Tuscan experience, visit during June when the city celebrates the Luminara di San Ranieri festival with thousands of candles lighting up the riverside.
Lucca
Enclosed by well-preserved Renaissance walls, Lucca is a charming town ideal for leisurely exploration. Its cobblestone streets, beautiful piazzas, and numerous churches, including the Lucca Cathedral, offer a snapshot of its rich history. One fun fact is that the town’s intact city walls have been transformed into a pedestrian promenade, perfect for biking or a leisurely walk.
San Gimignano
Known as the “Town of Fine Towers”, San Gimignano is famed for its 14 medieval towers that dominate the skyline. This UNESCO World Heritage Site offers fantastic art, great dining, and world-class gelato at the Gelateria Dondoli, a two-time champion of the Gelato World Cup. Its proximity to Chianti makes it an excellent stop on a Tuscan wine tour.
Montepulciano
This medieval and Renaissance hill town is known for its Vino Nobile wines. Stroll along the Corso, a grand avenue packed with Renaissance palazzi and churches, or visit the impressive Tempio di San Biagio. The town also offers panoramic views over the surrounding vineyards and Val d’Orcia.
Montalcino
Best known for its Brunello di Montalcino wines, this hilltop town is a favorite among wine lovers. Besides its wine, the town boasts a stunning fortress offering panoramic views, a charming historical center, and the beautiful Romanesque Abbey of Sant’Antimo.
Volterra
A true hidden gem, Volterra offers Etruscan, Roman, and medieval sites, including the Roman Theatre and the Etruscan Acropolis. Volterra is also renowned for its alabaster craftsmanship, a tradition that dates back to the Etruscan period.
Cortona
Set on a hill overlooking Lake Trasimeno, Cortona is one of Tuscany’s oldest towns with a history dating back to the Etruscans. Visit the Museo dell’Accademia Etrusca, or explore the town’s charming narrow streets and squares. The town is also known from the book and movie “Under the Tuscan Sun.”
Frequently Asked Questions About Wine Tours in Tuscany
What kinds of Tuscany wine tours and wine tasting experiences are there?
Plenty — and this list shows the range. You can ride a Vespa or cycle through the Chianti hills, self-drive a vintage Fiat 500, take a classic 4×4 wine-and-food safari, join a hands-on pizza and gelato class, or book a private sommelier-led tour to three estates. Most depart from Florence, with strong options from Rome and Siena too.
When is the best time of year for a wine tour in Tuscany?
Late spring (May–June) and early autumn (September–October) are ideal — comfortable temperatures, green-to-golden vineyards, and, if you time it right, the September harvest. Summer is hot and busy; winter is quiet but many estates run reduced schedules.
What is the main wine region in Tuscany?
Chianti — and specifically Chianti Classico between Florence and Siena — is the heartland most tours visit, built on the Sangiovese grape. Montepulciano (Vino Nobile) and Montalcino (Brunello) further south are the other headline appellations, reachable on the day trips from Rome and Siena above.