Chianti’s picturesque hills, located between Florence and Siena, offer Italy’s most accessible wine experiences. For top value, head to Terre di Perseto Winery, where English-speaking guides walk you through the winemaking process and finish with generous tastings. Local family-run estates provide intimate tours where you’ll learn centuries-old traditions firsthand. For adventure seekers, Vespa tours combine wine tasting with scenic rides through cypress-lined roads and medieval villages. Back-roads explorations let you discover hidden wineries while sampling regional specialties like pecorino cheese and fresh-pressed olive oil. Let’s check out the best Chianti wine tours worth your time and money.
Key Points
- The Terre di Perseto Winery & Farm offers a 2-hour guided tour with a tasting of 4 Chianti wines and an olive oil tasting, starting at $39.63 per person.
- The Chianti Colli Fiorentini Winery Tour is a 5-hour small-group experience that explores renowned vineyards and includes a guided tasting and light lunch.
- The Chianti Half-Day Vespa Tour from San Gimignano allows you to explore the Chianti Hills on a Vespa, with a guided orientation, authentic Tuscan lunch, and wine tasting.
- The Chianti Wine Tour from Florence visits two historic wineries, offering a tasting of over 10 award-winning Chianti wines, a full Tuscan lunch, and an olive oil tasting.
- The Chianti, Montalcino & Montepulciano Private Tour from Florence is a 12-hour private tour that includes guided wine tastings, a typical Tuscan lunch, and visits to picturesque towns in the region.
Chianti: 4 Wines +1 Oil Guided Tasting & Tour
For those seeking an immersive Chianti experience, the “Chianti: 4 Wines +1 Oil Guided Tasting & Tour” at Terre di Perseto Winery & Farm is a must-try. This 2-hour guided tour takes visitors on a journey through the winery’s history and production processes, led by a knowledgeable live guide in English or Italian.
The highlight of the experience is the wine and oil tasting, where guests can sample 4 exceptional wines – 2 IGT Tuscan, 1 Chianti Classico, and 1 Chianti Classico RISERVA – along with the winery’s own extra virgin olive oil. The tour also includes 2 bruschettas per person, providing the perfect complement to the tasting.
Depending on the season and weather, visitors may even have the opportunity to take a short walk through the vineyards.
With a price starting at $39.63 per person, this tour offers excellent value for money. Guests can skip the line through a separate entrance and take advantage of the reserve now, pay later option.
Read our full review: Chianti: 4 Wines +1 Oil Guided Tasting & Tour Review
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Chianti Colli Fiorentini Winery Tour 18KM From Florence
Nestled just 18 kilometers from the heart of Florence, the Chianti Colli Fiorentini Winery Tour offers a captivating glimpse into the rich winemaking heritage of the Chianti Hills.
This 5-hour small-group experience allows you to explore the region’s renowned vineyards and sample the renowned Chianti wines.
The tour starts with a visit to a family-owned winery, where you’ll learn about the centuries-old traditions and modern techniques used to produce the Chianti Colli Fiorentini.
You’ll then enjoy a guided tasting of their finest wines, accompanied by a light lunch featuring local delicacies.
Next, you’ll visit a second winery, where you’ll delve deeper into the art of winemaking and savor more exceptional vintages.
Throughout the tour, you’ll be captivated by the stunning Tuscan countryside, with its rolling hills, cypress trees, and picturesque villages.
Whether you’re a wine enthusiast or simply seeking an authentic taste of the region, the Chianti Colli Fiorentini Winery Tour is an unforgettable experience.
Read our full review: Chianti Colli Fiorentini Winery Tour 18KM From Florence Review
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From San Gimignano: Chianti Half-Day Vespa Tour With Lunch
Departing from the iconic town of San Gimignano, this Chianti Half-Day Vespa Tour with Lunch offers an exhilarating way to explore the picturesque Tuscan countryside.
Priced at $166.87 per person, the 4.5-hour tour takes you on a scenic ride through Chianti’s hills, vineyards, and rural houses, with a small group limited to 8 participants.
You’ll get to ride a stylish 50cc Vespa, with a guided orientation and test drive to ensure safety. The tour includes an authentic Tuscan lunch and wine tasting at a local winery, along with a guided tour of the cellar.
Throughout the experience, you’ll discover off-the-beaten-track locations and enjoy the expertise of your English-speaking guide.
Please note that previous scooter or motorcycle driving experience is required, and you’ll need to bring your original driving license, a credit card for a deposit, and a passport or ID.
The tour isn’t suitable for pregnant women, those with mobility issues, or children under 18.
Read our full review: From San Gimignano: Chianti Half-Day Vespa Tour With Lunch Review
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From Florence: Chianti Wine Tour at 2 Estates W/Lunch&Snacks
Although departing from Florence, this 5-hour Chianti wine tour immerses visitors in the heart of the renowned Tuscan wine region. Priced at $354.59 per person, the tour offers a private group experience led by a live English-speaking guide.
Guests will visit two historic wineries, tasting over 10 award-winning Chianti wines, including rare rosé, sparkling rosé, and unique white Chianti varieties. The tour also includes snacks and a full Tuscan lunch, as well as a tasting of extra virgin olive oil.
Roundtrip transportation is provided from the Florence city center, with the meeting point conveniently located in front of the Florence Central National Library. The tour operates rain or shine and features free cancellation up to 24 hours in advance.
While not suitable for pregnant women and children under 18, the flexible booking option allows guests to reserve their spot without upfront payment. This Chianti wine tour promises an immersive and authentic taste of the region’s winemaking traditions.
Read our full review: From Florence: Chianti Wine Tour at 2 Estates W/Lunch&Snacks Review
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Tuscany: Chianti Wine Paradise Tour
What better way to discover the heart of Tuscany than the Chianti Wine Paradise Tour? Priced from $406.74 per person, this 7-hour experience takes you on a journey through the picturesque Chianti hills.
You’ll get to taste local wines and savor typical Tuscan appetizers, all while taking in the scenic views of centuries-old roads and the medieval town of San Gimignano.
The tour includes pickup from your hotel or apartment in a comfortable Mercedes Minivan or Car, and it’s led by a professional driver and guide.
While reviews are generally positive, with praise for the driver’s knowledge and the San Gimignano visit, some note the lack of an actual winery tour with wine production experience.
To ensure a more authentic experience, consider visiting smaller family wineries.
With free cancellation and the option to reserve and pay later, the Chianti Wine Paradise Tour offers a convenient way to explore the Tuscan countryside.
Read our full review: Tuscany: Chianti Wine Paradise Tour Review
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Florence: Chianti, Montalcino & Montepulciano Private Tour
If you’re seeking a more comprehensive exploration of Tuscany’s renowned wine regions, the Florence: Chianti, Montalcino & Montepulciano Private Tour is an excellent choice. Priced at $587.16 per person, this 12-hour private tour provides a deep dive into the winemaking traditions of Chianti, Montalcino, and Montepulciano.
You’ll be picked up from your centrally located Florence hotel at 8:00 AM and driven in a deluxe air-conditioned vehicle with Wi-Fi.
The tour includes guided wine tastings, a typical Tuscan lunch, and a visit to a centuries-old cellar for tastings of Chianti wines and olive oil.
You’ll also explore the picturesque towns of Greve, Castellina, Monteriggioni, Montalcino, and Montepulciano, enjoying the region’s scenic landscapes, including the UNESCO-listed Val d’Orcia.
While the driver provides general introductory information, they aren’t licensed guides, so you won’t receive in-depth guided visits inside city centers, museums, or churches.
Read our full review: Florence: Chianti, Montalcino & Montepulciano Private Tour Review
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Sum Up
The Chianti Hills offer a range of guided tours that allow visitors to explore the region’s renowned wineries, sample its acclaimed wines, and enjoy the stunning Tuscan countryside. Whether you prefer a leisurely tasting and tour, a Vespa adventure, or a private excursion, there’s an option to suit every traveler’s interests and preferences in this renowned Italian wine country.