For the best Tuscan wine-tasting experience, smart travelers focus on two main regions: Chianti and San Gimignano. The finest tours combine wine education with unforgettable countryside views. Half-day visits work well for sampling regional wines and learning production basics, while full-day excursions allow time to explore historic hill towns between tastings. I especially recommend tours that include family-run estates – they offer more intimate tastings and better cultural insights than large commercial wineries.
Top picks include the Chianti countryside e-bike tour (great for mixing scenery with sipping) and small-group van tours to organic wineries near San Gimignano (perfect for focusing on wine quality and tradition). Each stop typically includes 3-4 wines paired with local cheese and bread.
Let’s look at our favorite wine tours across Tuscany’s celebrated wine country.
Key Points
- Full-day wine tours from Livorno to the Tuscan countryside, including stops in San Gimignano and Volterra, with wine sampling and scenic views.
- Intimate wine and cheese tasting experiences at Ripalte Design Winery, showcasing the finest local wines and cheeses.
- Immersive wine and food tasting tours at Podere Montale Winery in Val d’Orcia, featuring Sangiovese grapes and Tuscan specialties.
- Private shore excursions from Livorno to Pisa and Florence, with a wine tasting experience and personalized attention.
- Unique wine tasting adventures, such as an e-bike tour through the Chianti region and organic farm tours with natural wine tastings.
Wine Tasting & Tuscany Countryside, San Gimignano & Volterra
On this full-day wine tour, travelers will venture out from the port of Livorno into the picturesque Tuscan countryside.
The 9-hour experience includes stops in the medieval towns of San Gimignano and Volterra, as well as a tasting at a local winery.
Highlights include panoramic views, wine sampling with snacks, and live commentary from a professional escort or English-speaking driver.
While not wheelchair accessible, the tour is stroller-friendly.
Reviewers praise the knowledgeable guides, scenic landscapes, and overall enjoyment of the experience.
Some suggestions include clearer meeting point directions and more time at the winery.
Read our full review: Wine Tasting & Tuscany Countryside, San Gimignano & Volterra Review
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Tuscany: Ripalte Design Winery Wine and Cheese Tasting Tour
Frequently, travelers venture to the picturesque Ripalte Design Winery in the heart of Tuscany for an immersive wine and cheese tasting experience.
This 2-hour tour offers a chance to sample a variety of the winery’s finest wines paired with local cheeses. Guests can explore the winery’s unique architectural design and learn about the winemaking process from knowledgeable staff.
Reviews praise the tour’s intimate setting, with a 4.9 rating from 652 travelers. At $44.22 per person, it’s a popular option for those seeking an authentic Tuscan wine tasting.
Whether a novice or connoisseur, visitors can appreciate the winery’s attention to detail and the chance to savor the flavors of the region.
Read our full review: Tuscany: Ripalte Design Winery Wine and Cheese Tasting Tour Review
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Visit to the Cellar With Wine & Food Tasting Over the Val Dorcia
Travelers seeking a deeper dive into Tuscan wine and cuisine often venture to the Podere Montale Winery in the picturesque Val d’Orcia region.
This highly-rated wine and food tasting tour boasts a 97% recommendation rate and a Badge of Excellence. Guests can learn about the region’s renowned Sangiovese grapes, explore vineyards on an extinct volcano’s slopes, and tour a Montecucco DOCG winery.
The experience also includes savoring Tuscan specialties like artisanal cured meats, regional Pecorino cheeses, and extra virgin olive oil, all while taking in scenic views from the winery’s terrace.
With a maximum group size of 32, this tour offers an intimate and informative dive into the flavors of Tuscany.
Read our full review: Visit to the Cellar With Wine & Food Tasting Over the Val Dorcia Review
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Saturnia: Tuscan Farm Tour With Wine Tasting
The Saturnia: Tuscan Farm Tour With Wine Tasting takes visitors on an immersive journey through the rolling Maremma hills.
Priced at $42.11 per person, this 1.5-hour tour offers a guided tasting of organic wines, a selection of Tuscan cheeses, cold cuts, and homemade bread, and a scenic walk with stunning views of the countryside.
Visitors can explore the wine cellar, observe the winemaking process, and capture the beauty of the Tuscan landscape.
The tour is limited to 8 participants and is available in Italian and English, with free cancellation up to 24 hours in advance.
An expert staff is on hand to guide participants through the tasting experience.
Read our full review: Saturnia: Tuscan Farm Tour With Wine Tasting Review
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Livorno Shore Excursion: Pisa, Florence and Chianti Wine Private Day Trip
This private full-day shore excursion from Livorno takes visitors on a captivating journey through the iconic cities of Pisa and Florence, culminating in a wine tasting at a renowned Tuscan winery.
With a 5.0 rating and recommended by 100% of travelers, this excursion boasts a Badge of Excellence in Tuscany. Highlights include the Leaning Tower of Pisa, the historic sites of Florence, and a delightful wine tasting.
The personalized attention of a private guide, air-conditioned transportation, and flexibility in the itinerary make this an exceptional experience.
Travelers praise the knowledgeable guides, local insights, and memorable moments, making this Livorno shore excursion a must-do for those seeking to enjoy the wonders of Tuscany.
Read our full review: Livorno Shore Excursion: Pisa, Florence and Chianti Wine Private Day Trip Review
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From Florence: Tuscany by E-Bike With Lunch and Wine Tasting
Tuscany’s rolling hills and picturesque vineyards come alive on this e-bike tour from Florence. Priced from $135.81 per person, the 6.5-8.5 hour experience takes riders through the Chianti region, with a stop in Castellina for a self-guided tour.
The highlight is a visit to a renowned winery, where travelers enjoy a light lunch, wine tasting, and scenic countryside views.
The tour includes transportation, e-bike rental, and insurance, though it’s not suitable for children under 14 or those with mobility issues.
With a 3.7/5 overall rating from six reviews, the tour offers good value for money, according to past participants.
Read our full review: From Florence: Tuscany by E-Bike With Lunch and Wine Tasting Review
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Visit to an Organic Farm and Tasting of Natural Wines
Nestled in the heart of Tuscany, Fattoria La Maliosa offers visitors a remarkable opportunity to explore the world of organic farming and natural wines.
This intimate experience, limited to just 10 travelers, invites guests to visit an organic farm and sample an array of natural wines. The tour includes private transportation, a selection of local cold cuts, cheeses, and organic bruschetta, as well as tastings of the farm’s natural wines and extra virgin olive oil.
While the experience isn’t wheelchair accessible, most travelers can participate.
With an impressive 4.5-star rating from 26 reviews, this tour promises an enjoyable and educational exploration of Tuscany’s agricultural heritage.
Read our full review: Visit to an Organic Farm and Tasting of Natural Wines Review
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In a Carriage Among the Vineyards, Visit of the Cellar, Tasting of Organic Wines.
Venture into the heart of Tuscany’s rolling vineyards aboard a traditional carriage for an enchanting exploration of the Casadei Estate.
Enjoy an organic wine tasting highlighted by the estate’s exceptional quality and the professionalism of the staff.
Visit the on-site cellar and sample a variety of local gastronomic products and extra virgin olive oil.
This private tour, with a 4.9-star rating from 14 reviews, is wheelchair and stroller accessible.
Conveniently located in Suvereto, the experience starts and ends at the meeting point in front of the small church of S. Rocco, with ample on-site parking available.
Secure your spot with free cancellation up to 24 hours in advance.
Read our full review: In a Carriage Among the Vineyards, Visit of the Cellar, Tasting of Organic Wines. Review
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Wine Tasting in Maremma With Priority Access
Setting out on a wine tasting expedition in the Maremma region of Tuscany, visitors are granted priority access to the Podere Montale Winery.
The experience includes sampling a selection of Tuscan red wines, starting with a light, scented blend, followed by a 12-month aged Sangiovese, and culminating in an elegant, round Sangiovese Montecucco DOCG.
The winery offers free parking with electric car charging, and the experience is wheelchair and stroller accessible.
Confirmation is provided upon booking, with a 24-hour free cancellation policy.
Priced at €15.00 per person, this wine tasting tour has earned a 5.0 rating from previous travelers.
Read our full review: Wine Tasting in Maremma With Priority Access Review
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Frequently Asked Questions
Are There Specific Dress Codes for Wine Tours in Tuscany?
There aren’t any strict dress codes for wine tours in Tuscany. However, it’s generally best to wear comfortable, casual clothing that’s suitable for walking and potentially getting a bit dirty. Avoid overly formal attire, as the focus is on the wine tasting experience.
Can I Bring My Own Snacks or Picnic on the Tours?
Most wine tours in Tuscany allow visitors to bring their own snacks or picnics. However, it’s best to check with the tour operator beforehand, as some may have restrictions or offer on-site dining options.
What Is the Minimum Age Requirement for Wine Tastings?
The minimum age requirement for wine tastings is typically 18 years old, but some tour operators may allow younger participants with parental supervision. It’s best to check with the specific tour company for their age policies.
Are There Any Discounts Available for Group Bookings?
Many wine tour operators offer group discounts for bookings of 4 or more people. Discounts typically range from 5-15% off the per-person rate. It’s best to inquire about group pricing when making a reservation.
Can I Customize the Itinerary of the Wine Tours?
Many wine tour providers offer customizable itineraries, allowing you to tailor the experience to your preferences. This flexible approach ensures you get the most out of your Tuscan wine-tasting adventure.
The Sum Up
Tuscany offers an array of exceptional wine tours for visitors. From exploring historic wineries and tasting local vintages to cycling through picturic countryside, there are plenty of options to suit diverse interests and budgets. Whether you’re a wine enthusiast or simply looking to learn about the region’s rich culture, Tuscany’s wine tours provide an unforgettable experience.