WINE COUNTRY · TUSCANY WINE TOURS

Tuscan Wine Tours: 15 to Book Between Florence and Siena

31 tours  ·  from $34 a head

One hill, two famous appellations and a lot of cypress. These 15 take in Chianti, Montalcino and the Val d’Orcia, priced per head, with the driving time from each city spelled out.

Private Self-Guided E-Bike Ride in Tuscany with Vineyard Visit - Fiesole brings the first big view
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Private Self-Guided E-Bike Ride in Tuscany with Vineyard Visit

1.Private Self-Guided E-Bike Ride in Tuscany with Vineyard Visit

★★★★★★★★★★5.0 · 775 reviews · 4 to 7 hours (approx.) · from $96Our pick

John and the E-Bikes Florence team set you up with a pedal-assist bike, helmet, phone holder, and GPS route. You ride independently from Florence through Fiesole and Tuscan hills to Poggiopiano vineyard, where wine, olive oil, cheese, meats, and bread are available to buy. The route returns via Piazzale Michelangelo.

“This was exhausting but really fun. It took us 6 hours to complete the trip, but we did stop twice for beers and wine. The views were gorgeous and the self -guided map was great.”

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Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region - San Gimignano: towers, gelato, and a short walk
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Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region

2.Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region

★★★★★★★★★★4.5 · 128 reviews · 8 hours (approx.) · from $520

Travel from Florence by private Mercedes with a driver such as Placido, Christian, Julian, or Valentine. Explore Siena and San Gimignano at your own pace, then follow the Chiantigiana wine road. Add a winery tasting and farmhouse lunch if you want. Hotel pickup, WiFi, and return transport are included.

“Wonderful guide and friend. He was the most charming gentleman who made us so comfortable. Would really recommend him.”

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Tasting in a Tuscan Vineyard with transfer from Lucca - Walking among the vines
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Tasting in a Tuscan Vineyard with transfer from Lucca

3.Tasting in a Tuscan Vineyard with transfer from Lucca

★★★★★★★★★★5.0 · 104 reviews · 3 hours (approx.) · from $107

Meet at Lucca’s Porta San Donato for a short afternoon transfer into the countryside. Guides such as Tommaso, Raffaele, and Marco introduce you to Lucca and local wine before a family-run vineyard visit, cellar tour, and tasting of several wines with Tuscan meats, cheese, bread, and other small bites. Groups are capped at 15.

“This was a wonderful tour - our guide Raffaele was very knowledgeable. We were a group of 9 people (this was a private tour) and staying in a Villa in the countryside outside of Lucca, and the tour operators went out of their way to collect us directly from our Villa in a minibus, even though it was in the complete opposite direction from Lucca to the vineyard. The vineyard itself was a beautifully run family business and we experienced sunset in the vines sipping wine and snacking on homegrown produce.”

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Tour through the vineyards and wine and olive oil tasting in Tuscany - Four wines with a proper Tuscan tasting plate
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Tour through the vineyards and wine and olive oil tasting in Tuscany

4.Tour through the vineyards and wine and olive oil tasting in Tuscany

★★★★★★★★★★5.0 · 97 reviews · 1 hour 30 minutes (approx.) · from $45

At Villa La Ripa near Arezzo, you’ll visit the winery, walk through the vineyards when weather allows, and taste four estate wines with Tuscan bread, cured meats, cheeses, and award-winning extra virgin olive oil. English-language guides such as Anita, Claudia, Marius, and Virginia explain the villa, grapes, wine-making, and oil production.

“The wine tour was amazing and the estate is beautiful. But that goes without saying, what needs to be said is how hospitable and kind their staff was. Livia truly made us feel at home and although we came with a party of 17 people, she gave each of us a unique and valuable experience.”

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Montalcino: Vineyard Picnic with a Bottle of Wine - Choosing the tour option at Corte Pavone
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Montalcino: Vineyard Picnic with a Bottle of Wine

5.Vineyard Picnic with a Bottle of Wine

★★★★★★★★★★4.9 · 87 reviews · 1.5 - 2.5 hours · from $47

At Corte Pavone Winery near Montalcino, you can pair homemade Tuscan specialties with a bottle of red, white, or rosé wine. Choose the version with a one-hour vineyard and cellar tour to learn about the winery’s Brunello Cru path, then settle into a private picnic with valley views. Vegetarian and vegan food is available by request.

“bellissima esperienza , personale molto gentile e cibo di ottima di qualità . grazie mille ❤️”

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Montalcino: Castle and Vineyards Tour with Tasting - The castle route is short but full of details
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Montalcino: Castle and Vineyards Tour with Tasting

6.Castle and Vineyards Tour with Tasting

★★★★★★★★★★4.2 · 55 reviews · 1 hour · from $41Best value

You’ll tour a 600-year-old castle estate in Montalcino with an English- or Italian-speaking host, walking past vineyards, the Peruzzi bridge, a historic chapel, and old cellars. The one-hour visit ends with three Brunello-area wines and local snacks. Expect a small group of no more than 10 people, though the castle visit is brief.

“A visita ao castelo é bem rápida. Mas o guia fala da propriedade e produção do vinho no local, responde as perguntas. A degustação é perfeita! Servem com uns petiscos, incluindo queijo pecorino de diferentes maturações. Achamos q no final faltou mostrar onde compra o vinho, foi finalizado meio solto, e acabamos nem comprando no local. Vale muito a experiência!”

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Small Group Wine Tasting in Tuscany with Vineyard Visit - Walking the vines at Fattoria San Pancrazio
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Small Group Wine Tasting in Tuscany with Vineyard Visit

7.Small Group Wine Tasting in Tuscany with Vineyard Visit

★★★★★★★★★★5.0 · 54 reviews · 5 hours (approx.) · from $161

Leave Florence with a small group of up to 10 and reach Fattoria San Pancrazio in about 25 minutes. A sommelier such as Luca or Iris explains the grapes and winemaking, followed by on-site tastings, a cellar visit, and a traditional Tuscan lunch. You return to Florence after about five hours.

“We had an amazing time with our guide Luca! He was so knowledgeable and he made us feel comfortable. The winery was beautiful, the wine was so good and the charcuterie and lunch were delicious! We were very happy with how personal the experience was, we were not expecting it to be just the two of us, thank you so much Luca!”

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San Gimignano: Tuscan Vineyard Lunch with Wine Tasting - Arriving at Tenuta Torciano in San Gimignano
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San Gimignano: Tuscan Vineyard Lunch with Wine Tasting

8.San Gimignano: Tuscan Vineyard Lunch with Wine Tasting

★★★★★★★★★★4.8 · 52 reviews · from $141

Meet your English or Italian-speaking wine expert at Tenuta Torciano in San Gimignano for a two-hour Tuscan lunch with local wines and extra virgin olive oil. You’ll taste regional dishes, hear about wine and oil production, then have time to stroll the gardens and vineyards. Parking is free, but transportation is not included.

“The wine tasting and lunch was incredible. The place was beautiful and the host was super friendly and knew a lot about wines. We loved the wines and the food. We recommend this 100%”

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Tasting in a Tuscan Vineyard with transfer from Pisa - From Porta a Lucca into the Tuscan hills
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Tasting in a Tuscan Vineyard with transfer from Pisa

9.Tasting in a Tuscan Vineyard with transfer from Pisa

★★★★★★★★★★4.8 · 44 reviews · 4 hours · from $105

Meet at Porta a Lucca for a four-hour van trip into the Tuscan countryside. With guides such as Tommaso and Raffaele, you’ll walk among the vines, tour a family-run cellar, hear the farmer’s story, and taste organic wines with garden produce, Tuscan salami, and pecorino.

“Tomasso was a superb host. A highly personal tour to local vineyard, with insightful Lucca knowledge. If you’re looking for a local, small group tour and to have an authentic wine experience look no further!”

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Montepulciano: Winery Tour, Tasting, and Vineyard Picnic - The 30-minute winery and cellar visit
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Montepulciano: Winery Tour, Tasting, and Vineyard Picnic

10.Montepulciano: Winery Tour, Tasting, and Vineyard Picnic

★★★★★★★★★★4.8 · 43 reviews · 4 hours · from $105

Spend four hours at Podere Casanova Montepulciano with an English- or Italian-speaking guide. Tour the winery, cellar, and vineyard, then enjoy a picnic of meats, cheeses, bread, dessert, and a bottle of red or brut wine. Guides such as Mirko, Emanuele, and Alessandro bring winemaking to life.

“Fantastic! Tour guide was informative and personable, and the picnic baskets were full of cheese, meat, your chosen wine, water, and a dessert. Plus you can picnic wherever you’d like!”

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Private Tuscany Wine Country Day Trip from Rome with Lunch - Montepulciano and its underground wine cellars
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Private Tuscany Wine Country Day Trip from Rome with Lunch

11.Private Tuscany Wine Country Day Trip from Rome with Lunch

★★★★★★★★★★4.5 · 36 reviews · 11 hours (approx.) · from $1,067

Leave Rome early in a Mercedes with an English-speaking driver-guide and spend the day among Tuscany’s hill towns and vineyards. Visit Montepulciano, Bagno Vignoni, Montalcino, and Pienza, with wine tastings and a Tuscan lunch of cold cuts, cheeses, and bruschetta. Guides may include Max, Roberto, Giancarlo, or Khan.

“Wonderful scenic tour. Thoroughly enjoyed the Tuscan countryside. Enjoyed the winery! Nice to be in a small group throughout the day, gives more individual attention. Just one of the stops had a very steep climb to meet the Guide. Just needed more of a warning about the steepness for people who may have health conditions that a climb like this can affect.”

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Montalcino: Castle and Vineyards Tour with Tasting - The castle route is short but full of details
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Montalcino Castle and Vineyards tour with tasting

12.Montalcino Castle and Vineyards tour with tasting

★★★★★★★★★★4.0 · 35 reviews · 1 hour (approx.) · from $46

At Castello Tricerchi, you’ll explore a 15th-century estate, its courtyards, vineyard setting, medieval cellars, chapel, and historic rooms. An English-speaking guide such as Alice or Alessandro explains the castle and winemaking before you taste three red wines with water and breadsticks. The group is capped at 15.

“Interesting castle history although tour was short due to pouring rain. Wine tasting was great. The castle dog Nana was cute and got a lot of attention off everyone.”

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Visit Cuenca and a Vineyard in Spanish Tuscany from Madrid - The cathedral and the city’s best-known houses
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Visit Cuenca and a Vineyard in Spanish Tuscany from Madrid

13.Visit Cuenca and a Vineyard in Spanish Tuscany from Madrid

★★★★★★★★★★4.5 · 33 reviews · 11 hours (approx.) · from $156

Travel from Madrid in a small group of up to eight, walking Cuenca’s steep lanes, visiting its cathedral and Hanging Houses, then meeting winemaker Enrique Moreno for a sunset tasting with local snacks. Guide Andrés is often assigned, though guides may speak Spanish, English, or Portuguese. Lunch is not included.

“Must do! Cuenca is beautiful and tranquil. The hosts were super nice and knowledgeable. Answered questions and took pictures with no rush. Going to the vineyard and sharing charcuterie and wine with the winemaker was amazing.”

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Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence - San Gimignano and its medieval towers
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Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

14.Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

★★★★★★★★★★5.0 · 28 reviews · 8 hours (approx.) · from $430

Spend about eight hours with a private driver exploring San Gimignano and the Chianti wine region from Florence. Marco, Lorenzo, Sam, or Tomasso may tailor the day to your interests, with possible winery visits, countryside viewpoints, Volterra, or the Florence American Cemetery. Pickup and drop-off are included.

“Our private tour was customized by Marco, the owner, through email correspondence. We left all the details to him and we weren't disappointed.”

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Tasting in a Tuscan Vineyard with transfer from Pisa - From Porta a Lucca into the Tuscan hills
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Tasting in a Tuscan Vineyard with transfer from Pisa

15.Tasting in a Tuscan Vineyard with transfer from Pisa

★★★★★★★★★★5.0 · 28 reviews · 4 hours (approx.) · from $107

Meet at Porta a Lucca in Pisa at 3:30 pm, then ride into the Tuscan countryside near Lucca for a family-run winery visit. You’ll tour the cellar, learn how wine and olive oil are made, and taste several wines with local meats, cheeses, bread, honey, and cake. Guides such as Tommaso, Marco, and Rafael also share stories about the area.

“We were driven to the vineyard by our driver Tommi, who was very knowledgeable of the area. Excellent tour of this beautiful family vineyard in Tuscany. We met the family, and were shown around by a very knowledgeable guide. We learnt the whole process from growing the grapes, through to bottling. We tried several wines accompanied by local meats, cheeses and bread, followed by local honey and cake. We would highly recommend this tour. We visited in January, but the sun shone and we ate inside, in front of a lovely fire.”

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New in Tuscany Wine Tours

★ 5.0Wine Tasting in Montepulciano with Visit to the Vineyards Private TourFrom $9482 reviews
★ 4.5from Rome Montepulciano and Montalcino, the Wine RoutesFrom $1359 reviews
★ 4.5Livorno port to Bolgheri wine region and Etruscan castle2 reviews
★ 5.0Discovering the Bolgheri vineyards and tasting local productsFrom $3310 reviews
★ 5.0Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from FlorenceFrom $41310 reviews
★ 5.0Private Tuscany Day Tour: Siena and Chianti Wine Region from Florence2 reviews
★ 5.0E-bike Tuscany and Chianti Self-Guided Tour with Vineyard VisitFrom $428 reviews
★ 5.0Semi-Private Chianti Wine Tour with Dinner in Tuscany VineyardFrom $2273 reviews
★ 5.0From Roma: Montepulciano and Montalcino, on the Wine Routes8 reviews
★ 5.0Visit Cuenca and a vineyard in the Spanish TuscanyFrom $1534 reviews

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