Disclosure: Some of the links on this site are affiliate links. If you make a purchase through one of them, I may earn a small commission at no extra cost to you. Read my full disclaimer here. Thank you for your support!
This guide covers 15 wine tours across Tuscany’s main wine regions – Chianti, Siena, Brunello di Montalcino, Montepulciano and Bolgheri – organised by area so you can find the right option based on where you’re staying and what you want to drink.
I’ve spent months in total in Tuscany’s wine country across multiple trips. I’ve stayed in Chianti, in Montepulciano, in Montalcino and in Siena. I’ve visited wineries, drunk Brunello at the source and Vino Nobile in the cellars where it’s made – and I still order from wineries I visited there.
Brunello di Montalcino is the wine I’d choose above all others in the region; Vino Nobile is the one most people underestimate; Chianti Classico, done well, is the one you end up drinking most of over the course of a week.
And Vernaccia di San Gimignano – Tuscany’s only white DOCG – is the one I’d reach for on a warm afternoon when you’ve been drinking big reds all week and want something that tastes like the opposite of them.
Each regional section gives my top picks for that area. For the full comparison of every available tour in each region, the dedicated posts are linked at the top of each section.
My Top Pick for Each Tuscany Wine Region
- Chianti – Small-Group Wine Tasting in the Tuscan Countryside: two wineries in the Chianti Classico heartland, winery owners leading the tours, maximum 25 people, departing Florence
- Siena – Educational Wine Tour & Tasting at La Lastra: organic winemaking 2km from Siena’s historic centre, four wines, light lunch, three hours
- Brunello di Montalcino – Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena: three wineries, traditional Tuscan lunch, maximum eight people, nine hours, 650+ five-star reviews
- Montepulciano – Montepulciano Wine Tasting and Cellar Tour: one hour in a historic cellar in the town centre, five wines, 4.9 stars
- San Gimignano – San Gimignano Wine & Food Tasting on an Organic Farm: eight organic wines including Vernaccia di San Gimignano Riserva on a working estate, three hours, maximum eight people, transport from San Gimignano included
- Bolgheri – Bolgheri Premium Wine Tasting with Winery Tour: monovarietal premium tastings at Terre del Marchesato, 75 minutes, five stars
Table of Contents Show
15 Best Wine Tours in Tuscany: Quick Overview
| Tour | Region | Duration | Best for |
| Small-Group Wine Tasting in the Tuscan Countryside | Chianti | 4h 45m | Authentic Chianti, small group |
| Chianti Wineries Tour with Food & Wine Tasting | Chianti | 5.5 hours | Two wineries, accessible price |
| Chianti Safari: Villas, Vineyards, Cheese & Lunch | Chianti | 9 hours | Full day, 4×4 adventure |
| Small-Group Brunello Trip from Siena | Siena/Montalcino | 9 hours | Best overall Brunello experience |
| Educational Wine Tour & Tasting at La Lastra | Siena | 3 hours | Organic winemaking, shorter format |
| Wine Class – Tuscan Classics | Siena | 2 hours | In-city, evening, beginners |
| Small-Group Brunello di Montalcino Trip from Siena | Brunello | 9 hours | Three wineries, top-rated |
| Val d’Orcia Brunello Tour from Florence | Brunello + Vino Nobile | 10.5 hours | Two wine regions in one day |
| Guided Winery Tour & Gourmet Tasting at Corte Pavone | Brunello | 2.5 hours | Biodynamic estate, six wines |
| Brunello Cooking Class at Castello Tricerchi | Brunello | 4 hours | Families, cooking + wine |
| Montepulciano Wine Tasting and Cellar Tour | Montepulciano | 1 hour | Quick, central, 4.9 stars |
| Wine Tour Ebike Experience | Montepulciano | 5 hours | Active, two wineries, private |
| Wine Tasting & Lunch in a Typical Winery | Montepulciano | 1.5 hours | Sommelier, 14th-century cellar |
| San Gimignano: Wine & Food Tasting on an Organic Farm | San Gimignano | 3 hours | Vernaccia DOCG, full estate tour, 8 wines |
| Bolgheri Premium Wine Tasting with Winery Tour | Bolgheri | 1h 15m | Premium monovarietal tasting |
| Bolgheri Classic Wine Tasting with Winery Tour | Bolgheri | 1h 15m | Value, historic estate |
15 Best Wine Tours in Tuscany
Best Chianti Wine Tours
Renowned for its ruby-red wines and picturesque landscapes, the Chianti region embodies the essence of Tuscan viticulture.
Situated between Florence and Siena, it offers a diverse array of vineyards and historic estates.
If you’re interested in taking a Chianti wine tour, you can discover the full spectrum of Chianti’s offerings in our post on the best Chianti wine tours from Florence.
Small-Group Wine Tasting Experience in the Tuscan Countryside
★ RATING: 5/5 Stars | 🕰 TOUR LENGTH: 4 hours 45 minutes | ✓ Book now
My top Chianti pick. Four hours and forty-five minutes from Florence, two wineries in the Chianti Classico heartland, six wines with olive oil tastings paired with local cheese, salami and bruschetta.
The detail that sets this one apart: the owners lead the tours themselves rather than hired guides, which changes the quality of conversation you can have about the wine. Maximum 25 people.
If you want one Chianti experience from Florence, this is the one I’d book.
| Tour Highlights | Potential Drawbacks |
|---|---|
| – Intimate group size (max 25 people) | – Not suitable for wheelchair users |
| – Visits to two distinct Chianti wineries | – Minimum age requirement (12 years) |
| – Diverse wine and olive oil tastings | – May involve stairs, challenging for some |
| – Tastings paired with Tuscan delicacies | – Weather-dependent; dress appropriately |
| – Scenic Tuscan countryside views |
Reviews:
“Let’s do this one again!!!!! Love it! I highly recommend this tour! This is actually the second time we have joined this tour because my husband and I enjoyed it the last time we were visiting Florence. The hosts are kind and patient, the travel accommodations are comfortable and efficient, and the wineries were so lovely!!! The tours were given by the owners of the wineries (a real treat!) who offered answers to questions as well as sharing their experience and knowledge.” – Angela_R, Jan 2024
Read more reviews here.
Useful information:
- Location: Piazzale Montelungo, Firenze FI, Italy
- Start Times: 8:45 AM (for 9:00 AM tour), 2:15 PM (for 2:30 PM tour)
- Duration: 4 hours 45 minutes
- Size of Tour: Small group (max 25 people)
- Accessibility: Not wheelchair accessible; involves stairs
- Included: Transport by air-conditioned vehicle with Wi-Fi, English-speaking guide, visits to 2 wineries, tastings of 6 wines and olive oils, local Tuscan snack
From Florence: Chianti Wineries Tour with Food and Wine Tasting
★ RATING: 4.5/5 Stars | 🕰 TOUR LENGTH: 5.5 hours | ✓ Book now
A half-day alternative – five and a half hours, two wineries, seven wines with traditional Tuscan snacks.
Groups go up to 30, which is larger than ideal for a wine tour, but the sommeliers draw consistently strong reviews and the price point is more accessible than tour 1.
A solid option if tour 1 is full or if the GetYourGuide format suits you better.
| Tour Highlights | Potential Drawbacks |
|---|---|
| – Two diverse winery visits | – Not suitable for wheelchair users |
| – Comprehensive winemaking insights | – Commentary in two languages might be confusing |
| – Diverse range of wine tastings | – Possible split of the group for tours |
| – Beautiful scenery of the Chianti region | – Group size may be large (up to 30 people) |
| – Tastings paired with traditional Tuscan snacks |
Reviews:
“Excellent wine tour with amazing guides and very knowledgeable sommeliers. Definitely worth booking this.” – Kunal (United Kingdom)
Read more reviews here.
Useful information:
- Location: Meet at Piazzale Montelungo, Firenze FI, Italy Start
- Time: 8:30 AM / 2:30 PM
- Duration: 5.5 hours
- Size of Tour: Shared tour with up to 30 people
- Accessibility: Not suitable for wheelchair users
- Included: Return transportation, expert multilingual guide, guided wine tastings, snacks (cheese, bread, olive oil, balsamic vinegar, salumi)
Chianti Safari: Tuscan Villas with Vineyards, Cheese, Wine & Lunch from Florence
★ RATING: 5/5 Stars | 🕰 TOUR LENGTH: 9 hours | ✓ Book now
The full-day Chianti option – nine hours by 4×4 through the Chianti countryside, visiting a family-owned historic estate and a boutique vineyard, with a traditional Tuscan lunch at a winery restaurant.
Nine wines, two olive oil samples, food tastings throughout. The off-road 4×4 format genuinely adds to the experience – you’re covering ground that a minivan can’t reach. Not suitable for wheelchair users or anyone with back problems, and there are no vegetarian food options.
Best for groups who want the day to feel like an adventure as well as a wine education.
| Tour Highlights | Potential Drawbacks |
|---|---|
| – Scenic off-road 4×4 journey through Chianti | – Not suitable for wheelchair users |
| – Visits to prestigious and boutique wineries | – No vegetarian or alternative dietary options |
| – Wine, olive oil, and food tastings | – Not recommended for those with back problems |
| – Traditional Tuscan lunch with stunning views | – May be physically demanding for some |
| – Intimate group experience (max 26 travelers) |
Reviews:
“Exciting full day tour of the Chianti wine region of Tuscany. We really enjoyed learning about Tuscany and the Chianti wine-growing region. Our guide Liv and our driver Lob were excellent. Liv was very knowledgeable about the wine-making process and history. She was most engaging and a pleasure.” – Helen_C, Dec 2023
Read more reviews here.
Useful information:
- Location: Piazza dei Cavalleggeri, 50122 Firenze FI, Italy
- Start Time: 9:00 AM
- Duration: 9 hours
- Size of Tour: Maximum 26 travellers
- Accessibility: Not wheelchair accessible; not recommended for travellers with back problems or pregnant travellers
- Included: Air-conditioned 4×4 transport, professional guide, 9 wine samples, 2 olive oil samples, food tastings, lunch
Best Wine Tours in and from Siena
Delving into the heart of Tuscany from Siena opens doors to some of the region’s most esteemed vineyards and wineries – including the much admired wines of Brunello di Montalcino and Vino Nobile di Montepulciano.
Our best wine tours in Siena blog post guides you in more detail through curated experiences that blend historical richness with the joy of wine tasting, directly from the ancient streets of Siena. They’re perfect to peruse through if you decide to stay in Siena for a night or two.
However, here are my top three picks of wine tours taking place, or being run from, the city of Siena.
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
★ RATING: 5/5 Stars | 🕰 TOUR LENGTH: 9 hours | ✓ Book now
The best half-day wine option from Siena – three hours, 2km from the historic centre, at the organic estate of La Lastra.
The tour covers the full vineyard-to-cellar process before a tasting of four organic wines with a light seasonal lunch. At 4.9 stars it’s one of the most consistently praised short-format wine experiences in the region.
The right choice if you want to understand how Tuscan wine is made rather than just drink it.
| Tour Highlights | Potential Drawbacks |
|---|---|
| Exclusive access to three renowned wineries | Full-day duration may not suit those with limited time |
| Intimate group size ensures personalised attention | Not suitable for large groups or those seeking a more social, bustling tour |
| Authentic Tuscan lunch at a family-run winery |
Reviews:
“Highly highly recommended. Mattia was so knowledgeable and full of fun stories. The wineries that we visited were all very unique. The lunch! The location was fabulous. The hosts were even more fabulous and their wines amazing.” – Nancy_C
Read more reviews here.
Useful information:
- Location: Piazza San Domenico, Siena, Italy
- Start Time: 09:30 AM
- Duration: 9 hours
- Size of Tour: Maximum 8 people
- Accessibility: Not wheelchair accessible, stroller accessible
- Included: Local guide, lunch, wine tastings, air-conditioned vehicle
Educational Wine Tour & Tasting
★ RATING: 4.9/5 Stars | 🕰 TOUR LENGTH: 3 hours | ✓ Book now
The best half-day wine option from Siena – three hours, 2km from the historic centre, at the organic estate of La Lastra.
The tour covers the full vineyard-to-cellar process before a tasting of four organic wines with a light seasonal lunch. At 4.9 stars it’s one of the most consistently praised short-format wine experiences in the region.
The right choice if you want to understand how the wine is made, not just taste it.
| Tour Highlights | Potential Drawbacks |
|---|---|
| In-depth learning experience about organic winemaking | Takes place in only one winery, which might not appeal to those wanting to visit multiple locations |
| Sensorial wine tasting of four unique, organic wines | |
| Light lunch featuring fresh Tuscan specialities |
Reviews:
“The wine tour and tasting at La Lastra was excellent. Our host spoke very informatively and passionately about their ‘terroir’. I’ve done a few wine tours over the years and expected this to be just another experience- but I genuinely learned a lot during our visit. The lunch and tastings provided were generous and delicious. Thank you so much – 5* – don’t miss it!” – GetYourGuide traveller, United Kingdom
Read more reviews here.
Useful information:
- Location: Azienda Agricola La Lastra, Strada della Befana 2/A, 53100 Siena, Italy
- Start Time: 11:30 AM
- Duration: 3 hours
- Size of tour: 12 people
- Accessibility: Check with the provider for specific accessibility details
- Included: Guided visits to the vineyards and cellars, sensory wine tasting, light lunch
Wine Class – Tuscan Classics
★ RATING: 5/5 Stars | 🕰 TOUR LENGTH: 2 hours | ✓ Book now
A two-hour in-city wine class in Siena’s historic centre, starting at 5pm – the best evening option in this section.
Four to five Tuscan wines with food pairings, led by English-speaking local sommeliers. Five stars.
The right pick if you want a convivial evening that doubles as a proper introduction to Tuscan wine appellations without leaving the city.
| Tour Highlights | Potential Drawbacks |
|---|---|
| In-depth exploration of Tuscan wines within Siena’s historic centre | Limited to the classroom setting, not offering vineyard visits |
| Hands-on learning experience with expert guidance | |
| Food pairings with local specialities enhance the tasting experience |
Reviews:
“Terrific class. Had a ton of fun. So convenient being in the city walls. Drank, laughed and learned a great deal. Manuel was a terrific teacher and good-natured person. No pressure sale. If you don’t know much about wine from Tuscany, want to learn and drink with a friendly group, this tour is for you.” – Hanan_S, May 2023
Read more reviews here.
Useful information:
- Location: Via Stalloreggi, 53100 Siena SI, Italy
- Start Time: 05:00 PM
- Duration: 2 hours
- Size of tour: 14 people
- Accessibility: Wheelchair and stroller accessible, surfaces wheelchair accessible
- Included: Alcoholic beverages, snacks
Best Brunello di Montalcino Wine Tours
With its distinguished reputation, Brunello di Montalcino encapsulates the pinnacle of Italian winemaking, offering a complex bouquet and remarkable aging potential. It’s definitely a town that should find its way onto any wine lover’s Tuscany itinerary.
In our best Brunello di Montalcino wine tours post, we unveil the finest tours that bring you closer to the artistry of this renowned wine.
Below, we spotlight our top four picks, offering a glimpse into the heart of Montalcino’s winemaking tradition. For an in-depth exploration, head over to the full article.
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
★ RATING: 5/5 Stars (650+ reviews) | 🕰 TOUR LENGTH: 9 hours | ✓ Book now
My overall top pick for the Brunello region. Nine hours from Siena, three wineries, a traditional Tuscan lunch at a family estate, Montalcino village and the Sant’Antimo Abbey, maximum eight people throughout.
Over 650 five-star reviews across a sustained period. The small group ceiling and winery-owner access are what set this apart from every other Brunello tour on the market.
If you’re serious about Brunello and have a day to spend on it, this is the one.
| Tour Highlights | Potential Drawbacks |
|---|---|
| Intimate group size for a personalised experience | Not suitable for under 18s due to alcohol |
| Visits to three distinct wineries with tastings | Limited wheelchair accessibility |
| Authentic Tuscan lunch at a family-run winery | |
| Exploration of Montalcino and Sant’Antimo Abbey |
Reviews:
“The wine pairing lunch was phenomenal. Our hosts were exceptional. Driver, and guide–Keeko were professional and knowledgeable. Would definitely recommend this tour.” – Cindy_W, Nov 2023
Read more reviews here.
Useful information:
- Location: Departs from Piazza San Domenico, Siena
- Start Time: 9.30 am
- Duration: 9 hours
- Size of Tour: Max 8 people
- Accessibility: Not wheelchair accessible, stroller accessible
- Included: Local guide, lunch, visits to wine cellars and wine tasting, air-conditioned vehicle
Val d’Orcia Brunello Wine Tour: Montalcino & Montepulciano from Florence
★ RATING: 4.5/5 Stars (180+ reviews) | 🕰 TOUR LENGTH: 10 hours 30 minutes | ✓ Book now
The best Florence-based option for anyone wanting to cover both Brunello di Montalcino and Vino Nobile di Montepulciano in a single day.
Ten and a half hours, vineyard and cellar tours at each wine region, a superior lunch with views, and a stop in Pienza. Maximum eight travellers. The reviewer who names the Erolani winery specifically as a highlight is consistent with what I know of that route.
Best suited to Florence-based travellers who don’t want to drive themselves through the Val d’Orcia.
| Tour Highlights | Potential Drawbacks |
|---|---|
| Not one, but 2 renowned Tuscan wines; Brunello & Vino Nobile di Montepulciano | Not wheelchair accessible |
| Superior lunch with stunning views | |
| Visits to Montalcino, Montepulciano, and Pienza | |
| Intimate group of max 8 travellers |
Reviews:
“A Must For Tuscany Wine Tours. This was my favorite tour of the many I’ve taken all over Europe. Michele (Mike) was a superb host and driver, giving us a running basic history of what we were seeing throughout the drive from Florence to Montalcino, Pienza, and Montepulciano. The tour of Erolani winery was especially superb, and lunch was really tasty. Highly recommend!” – Kristin_H, Nov 2023
Read more reviews here.
Useful information:
- Location: Departs from Piazza degli Antinori in Florence
- Start Time: 8:00 am
- Duration: 10 hours 30 minutes
- Size of Tour: Max 8 people
- Accessibility: Not wheelchair accessible, stroller accessible
- Included: Premium van with A/C, English-speaking driver, superior lunch, 2 wine tastings, guided tours on vineyard and barrel cellar, local product food tasting during wine tasting in Montepulciano
Guided Winery Tour & Gourmet Tasting at Corte Pavone, Montalcino
★ RATING: 4.8/5 Stars (100+ reviews) | 🕰 TOUR LENGTH: 2.5 hours | ✓ Book now
Corte Pavone is a biodynamic estate and this is the best option for anyone staying in or near Montalcino who wants a 2.5-hour in-depth experience rather than a full day.
Vineyard to cross-vaulted cellar, six wines with six gourmet pairings. Two tasting formats are available: a single-vineyard Brunello Cru tasting, or the full Corte Pavone range.
The biodynamic approach produces wines with more distinct terroir expression – which makes the tasting more interesting if you want to understand why Brunello from one hillside differs from another.
| Tour Highlights | Potential Drawbacks |
|---|---|
| In-depth vineyard and cellar tour | Slightly larger group of 18; may be too big for some |
| Tasting of 6 Brunello wines with gourmet pairings | |
| Learning about biodynamic wine production | |
| Breathtaking views and lush landscape of Montalcino |
Reviews:
“The tour guide was amazing. Firstly, he explained in detail how the wine was produced, from the grapes to the wine we find in the bottle. We visited the grape fields and the cellars, and the tour ended in the restaurant, where we tasted six different wines.” – GetYourGuide traveler, Germany, October 20, 2023
Read more reviews here.
Useful information:
- Location: Località Corte Pavone, Montalcino
- Start Time: Options for 11:00 am or 3:00 pm
- Duration: 2.5 hours
- Size of group: max 18 travellers
- Included: Winery tour, 2 wine tasting options of 6 wines in total, 6 specially designed gourmet paired bites, food and wine pairing
- Accessibility: Information not provided
- Additional Info: Suitable for adults only, reservation required
Brunello Cooking Class with Vineyards View Winery in Montalcino
★ RATING: 4.6/5 Stars | 🕰 TOUR LENGTH: 4 hours | ✓ Book now
The only tour on this list that genuinely works for families travelling with older children.
Four hours at Castello Tricerchi: a guided winery tour, a hands-on cooking class making traditional Tuscan pasta dishes, then lunch with your creations paired with Brunello. Maximum ten people.
The review from Aimee, whose children aged 10-19 all loved it, is the clearest evidence the format delivers across age groups.
Best for families who want the wine experience to be part of a shared day rather than something the adults do separately.
| Tour Highlights | Potential Drawbacks |
|---|---|
| Great choice when travelling with tweens/teenagers | Not suitable for children under 10 |
| Tour of the winery and insights into wine-making | |
| Lunch with dishes prepared during the class | |
| Stunning vineyard views |
Reviews:
“This was one of our favorite experiences in Italy! All of our children (ages 10-19) LOVED it! The food was delicious, the scenery beautiful and the wine magnificent! Don’t miss this experience…well worth it!” – Aimee_P, Jun 2023
Read more reviews here.
Useful information:
- Location: Castello Tricerchi, Località Altesi, Montalcino
- Start Time: 10:00 am
- Duration: 4 hours
- Size of tour: max 10 travellers
- Accessibility: Wheelchair accessible
- Included: 4-hour tour and hands-on cooking class, tour of the winery, pairing lunch with Brunello, gratuities
- Not Included: Hotel Pickup/Drop-off (available as an add-on service)
Best Montepulciano Wine Tours
Montepulciano, home to the esteemed Vino Nobile, is a jewel in Tuscany’s winemaking crown, offering a blend of rich flavours and a storied heritage.
Explore this tradition further with our guide to the best wine tours and tastings in Montepulciano, highlighting top experiences for wine enthusiasts.
As a celebrated hilltop town, Montepulciano is also featured in our best towns in Tuscany post, making it an essential stop for those captivated by Tuscany’s scenic beauty and historical depth.
Here are my top three picks in terms of its wine tours.
Montepulciano Wine Tasting and Cellar Tour
★ RATING: 4.9/5 Stars | 🕰 TOUR LENGTH: 1 hour | ✓ Book now
My top Montepulciano pick for anyone who wants a focused, time-efficient cellar experience.
One hour in Via Ricci – one of the main streets of the historic centre – five wines DOC and DOCG with Slavonian oak barrel views, pecorino, bruschetta and crostini.
At 4.9 stars it’s the highest-rated Montepulciano tour on the list. I’d slot this into a morning or afternoon without restructuring the day around it.
| Tour Highlights | Potential Drawbacks |
|---|---|
| – Exquisite wine tasting of DOC and DOCG Montepulciano wines | – Limited to an hour, which might feel brief for some |
| – Insightful guide sharing rich history and traditions | – Accessible only by foot in a no-car zone |
| – Marvel at impressive barrels in an ancient cellar | |
| – Tasteful pairings with local Tuscan produce |
Reviews:
“Splendid tour. The wine cellar was spectacular with so many various sizes of barrels. This ancient cellar was amazing. The wine tasting and exploration of each by our guide was excellent. Lasted 1.5 hours to 2 hours start to finish. Excellent local wine.” – GetYourGuide traveler
Read more reviews here.
Useful information:
- Location: Via Ricci, 13, 53045 Montepulciano SI, Italy
- Start Time: 10:30 AM, 3:00 PM
- Duration: 1 hour
- Size of Tour: Small group
- Accessibility: Accessible only by foot; parking available at “Parking S. Donato” or “Parking P8.”
- Included: Guide, selection of pecorino cheeses, bruschetta with extra-virgin olive oil, typical crostini, five wines DOC and DOCG di Montepulciano.
Wine Tour Ebike Experience
★ RATING: 5/5 Stars | 🕰 TOUR LENGTH: 5 hours | ✓ Book now
Five hours on an ebike through the Nobile wine route, two winery stops with tastings, lunch included, private group.
The ebike takes the sting out of Montepulciano’s hills so you can actually enjoy the ride. The Val d’Orcia from above, on a clear day, is one of the more cinematically beautiful things you can do in Tuscany.
Best for active travellers who want the wine experience to feel like it was earned.
| Tour Highlights | Potential Drawbacks |
|---|---|
| – Scenic ebike ride through Montepulciano’s vineyards | – Requires ability to ride a bike on hilly terrain |
| – Two exquisite wine tastings included | – Not suitable for those with back problems or pregnant travellers |
| – Personal guide to enhance the experience | – Not wheelchair accessible |
| – Breath-taking views of the Tuscan landscape |
Reviews:
“Amazing. Rolling hills, small bed-and-breakfasts, wineries, mountains with endless vines… it was out of a movie set. Both of our wine tasting experiences were phenomenal. Our guide Pierre was outstanding. Worth every penny.” – Georgina_M, Oct 2023
Read more reviews here.
Useful information:
- Location: Urban Bikery, Via Ricci, 2, 53045 Montepulciano SI, Italy
- Start Time: 10:30 AM – 06:30 PM
- Duration: 5 hours
- Size of Tour: Private group
- Accessibility: Not wheelchair accessible, not recommended for travellers with back problems or pregnant travellers
- Included: Alcoholic Beverages, ebike, helmet, raincoat, lunch, guide.
Montepulciano: Wine Tasting & Lunch in a Typical Winery
★ RATING: 4.4/5 Stars | 🕰 TOUR LENGTH: 1.5 hours | ✓ Book now
One and a half hours in a 14th-century cellar, four wines including Rosso di Montepulciano DOCG and Vino Nobile DOCG, with a choice of two lunch formats.
The sommelier-led format and ancient cellar setting make this the most atmospheric of the shorter Montepulciano options.
The right pick for anyone who wants wine and food together in a historic setting without committing to a full afternoon.
| Tour Highlights | Potential Drawbacks |
|---|---|
| – Historic wine cellar tour and professional sommelier guidance | – Not suitable for those with mobility impairments |
| – Tasting of four renowned local wines | – Not accessible for wheelchair users |
| – Option for a full typical Tuscan lunch with one or two courses | – Not suitable for children under 18 years |
| – Scenic setting in Montepulciano |
Reviews:
“A really pleasant and interesting experience. In addition to the lunch and the tasting made with excellent products and wines, it was very interesting to learn about the history of the cellar and the winemaking characteristics. Congratulations to the whole team.” – GetYourGuide traveler – Italy, March 22, 2023
Read more reviews here.
Useful information:
- Location: Via Talosa, 8, 53045 Montepulciano SI, Italy
- Start Time: 1:00 PM
- Duration: 1.5 hours
- Size of Tour: Group
- Accessibility: Not suitable for people with mobility impairments or wheelchair users
- Included: Winery tour, sommelier, snacks, wine tasting, lunch (optional gratuities and hotel pickup/drop-off not included)
Best San Gimignano Wine Tour
Vernaccia di San Gimignano is Tuscany’s only white DOCG wine and one of Italy’s oldest.
It predates Chianti as a classified wine and has a distinctly different character to everything else in the region: dry, mineral, with a slightly bitter almond finish that makes it one of the more interesting whites in Italy.
I’ve drunk it in San Gimignano itself and it does exactly what a good white wine should do in that context – cuts through the heat of a Tuscan afternoon and gives you a clean, refreshing counterpoint to the big reds the region is better known for.
For the wines of the Val d’Orcia and Chianti you need red wine days; San Gimignano is the one white wine day worth building in.
San Gimignano: Wine & Food Tasting on an Organic Farm
★ RATING: 5/5 Stars (100% of English-speaking travellers gave a perfect score) | 🕰 TOUR LENGTH: 3 hours | ✓ Book now
I chose this one because it does something most San Gimignano wine experiences don’t – it takes you out of the town and onto a working organic estate, Casa Lucii, where the family has been producing Vernaccia and other wines for generations.
Three hours, eight organic wines including two different vintages of the Vernaccia di San Gimignano Riserva, and a tasting spread that runs from estate cold cuts and cheeses through to the IGT Sangiovese paired with hand-made artisanal chocolate pralines and finishing with Vin Santo and cantuccini.
The full estate tour takes in the vegetable garden, olive grove, vinsantaia and a historical cellar alongside an agricultural tools collection – context that makes the tasting considerably more interesting than a standard pour-and-describe.
Transport from San Gimignano or Certaldo is included, which removes the logistical headache of reaching an out-of-town estate without a car. Limited to eight people.
100% recommendation rate from English-speaking travellers. The most complete San Gimignano wine experience I found, in a sublime garden setting with views of the towers of San Gimignano.
| Tour Highlights | Potential Drawbacks |
|---|---|
| Eight organic wines including two Vernaccia di San Gimignano vintages | Out-of-town location – transport included from San Gimignano/Certaldo |
| Full estate tour: vineyard, olive grove, vinsantaia, historical cellar | Runs at 12pm only – check availability early |
| Tasting includes Vin Santo, olive oil, artisanal chocolate pairings | Limited to 8 participants – books up quickly |
| Transport from San Gimignano or Certaldo included | |
| Wheelchair accessible | |
Reviews:
“It was the taste of Tuscany. We were so pleased to experience such nice organic wine and food! We had a small tour of their vineyard, wine storage, and their 13th-century home as well, amazing Tuscany history in the family home! Thank you for your great services and perfect quality of wine!” – Jiyoung_S, Aug 2025
Read more reviews here.
Useful information:
- Location: Casa Lucii, Località Santa Maria 49/C, San Gimignano – transport included from San Gimignano or Certaldo
- Start Time: 12:00 pm
- Duration: 3 hours
- Size of Tour: Maximum 8 participants
- Accessibility: Wheelchair accessible
- Language: English and Italian
- Included: Guided estate tour (vegetable garden, orchard, vineyard, olive grove, vinsantaia, historical cellar), tasting of 8 organic wines, cold cuts and cheeses from local farms, estate garden produce, extra virgin olive oil with bakery products, IGT Sangiovese with artisanal chocolate pralines, Vin Santo with Tuscan cantuccini, transport from San Gimignano or Certaldo
Best Bolgheri Wine Tours
Located along the Tuscan coast, Bolgheri wine, renowned for its Bordeaux-style blends, has gained prominence for its rich, full-bodied reds.
This region is attracting global attention, due to both its unique microclimate and innovative winemaking – marking Bolgheri as a rising star in Italy’s viticultural scene.
Bolgheri: Premium Wine Tasting with Winery Tour
★ RATING: 5/5 Stars | 🕰 TOUR LENGTH: 1 hour 15 minutes | ✓ Book now
At Terre del Marchesato, 5km from Bolgheri’s village centre – 75 minutes focused on premium monovarietal wines: TARABUSO (Cabernet Sauvignon) and MAURIZIO FUSELLI (Petit Verdot), each paired with bruschetta and extra virgin olive oil.
The monovarietal format is the point: you’re tasting single grape expressions rather than blends, which makes the differences between varieties legible in a way that mixed tastings rarely are.
Five stars. Wheelchair accessible. Multiple start times daily from 10am to 5.30pm.
| Tour Highlights | Potential Drawbacks |
|---|---|
| Focus on premium, monovarietal wines | May require advance booking due to popularity |
| Intimate exploration of vineyards and cellar | Specific focus on single-varietal wines may not suit all palates |
| Tastings paired with traditional Tuscan snacks |
Reviews:
“Must Visit This Winery! This was a truly amazing experience. We had a very informative tour of the winery with the arborist who showed such passion for his work. The wines were fantastic and we had a food pairing as well that was delicious! Very worth the visit.” – Stacey_K, Oct 2023
Read more reviews here.
Useful information:
- Location: Farm Lands of the Marquis, Via Località Sant’Uberto, 164, 57022 Bolgheri LI, Italy
- Start Time: Multiple options from 10:00 AM to 5:30 PM
- Duration: 1 hour 15 minutes
- Size of Tour: Maximum of 16 travelers
- Accessibility: Wheelchair accessible, stroller accessible, transportation is wheelchair accessible
- Included: Professional guide, wine tasting, alcoholic beverages
Bolgheri: Classic Wine Tasting with Winery Tour
★ RATING: 4.5/5 Stars | 🕰 TOUR LENGTH: 1 hour 15 minutes | ✓ Book now
The more accessible entry point at the same Terre del Marchesato estate – 75 minutes, three Bolgheri wines from the PAPEO Bolgheri Bianco through to the MARCHESALE Bolgheri Superiore, with traditional Tuscan bread and olive oil.
At 4.5 stars with reviews noting good value but that more detailed tasting commentary would have been welcome, this is a solid option for anyone wanting to try Bolgheri’s wines without the premium price point of tour 14.
| Tour Highlights | Potential Drawbacks |
|---|---|
| Visit to one of Bolgheri’s oldest wineries | More detailed wine production explanations desired |
| Tasting of three distinct Bolgheri wines | Limited to 1 hour 15 minutes, may feel brief |
| Includes traditional Tuscan snacks |
Reviews:
“We booked this wine tour spontaneously; great value for money, nice winery, more detailed explanations of the production process and the aromas of the wines while tasting would have been appreciated.” – AshleyLivia_H
Read more reviews here.
Useful information:
- Location: Farm Lands of the Marquis, Via Località Sant’Uberto, 164, 57022 Bolgheri LI, Italy
- Start Time: Multiple options from 10:00 AM to 5:30 PM
- Duration: 1 hour 15 minutes
- Size of Tour: Maximum of 16 travellers
- Accessibility: Wheelchair accessible, stroller accessible, transportation is wheelchair accessible
- Included: Wine tasting, professional guide, alcoholic beverages
The Cultured Voyages Edit
The hardest part of travel planning is deciding what to leave out.
That is what the Edit is for. Every second Wednesday, the thinking behind the choices – where to go, what to skip, how to spend the time once you are there. You’ll receive The Art of Understanding Places when you join, seven shifts that came out of years of trips and changed how I travel.
The Cultured Voyages Edit
The hardest part of travel planning is deciding what to leave out.
That is what the Edit is for. Every second Wednesday, the thinking behind the choices – where to go, what to skip, how to spend the time once you are there. You’ll receive The Art of Understanding Places when you join, seven shifts that came out of years of trips and changed how I travel.
What To Keep in Mind When Choosing a Winery Tour in Tuscany
Tuscany offers quite the mosaic of wine experiences, with each region presenting its signature varietals and winemaking traditions.
Whether you're drawn to the robust Brunello di Montalcino, the classic Chianti, the noble Vino Nobile di Montepulciano, or the emerging Bolgheri wines, there are several key considerations to keep in mind that can help ensure your wine tour is both memorable and enlightening.
Understanding Regional Wine Profiles
- Brunello di Montalcino: Esteemed for its full-bodied, bold flavours with notes of dark cherry and leather, originating from the vineyards around the picturesque town of Montalcino.
- Chianti: Known for its Sangiovese-based wines, offering robust flavours, high acidity, and a tannic nature, embodying the 'heart' of Tuscany.
- Vernaccia di San Gimignano: Tuscany's only white DOCG wine - dry, mineral and slightly bitter on the finish. A refreshing counterpoint to the region's big reds, and Italy's first wine to receive DOC status back in 1966.
- Siena and Montepulciano: These areas offer a spectrum of experiences, from the structured elegance of Vino Nobile to more approachable Rosso di Montepulciano wines, characterised by their fruitier and softer profiles.
- Bolgheri: A newer region on the Tuscan wine map, gaining recognition for its high-quality Bordeaux-style blends, showcasing the versatility of the Tuscan terroir.
Tour Origin Points and Transportation
- Consider starting your tour from urban centres like Florence or Siena for convenience, especially if you prefer not to drive. Note that tours from Florence to regions like Montalcino require a full-day commitment due to the distance.
- Most of the tours that start in cities will also include transport; and for pretty much any tour that includes a multiple number of wineries the same can be said.
- Tours to individual wineries, you will likely need to find your own transport to and from.
Exclusivity and Group Size
- Tours vary from intimate, small-group settings offering a personalised experience to larger, more social group tours.
- Brunello tours, for example, cater to a more exclusive market, reflecting the prestige and price point of Brunello wines. You can expect these tours to be either small-group, or private in nature.
Food Pairings and Local Cuisine
- Many tours incorporate food pairings or meals, highlighting the synergy between Tuscan wines and the region's rustic cuisine. Look for tours that celebrate this culinary harmony, and knock off two birds with one stone!
Physical Accessibility
- Assess the physical demands of each tour, especially if mobility is a concern. Some tours involve walking through vineyards or navigating historical cellars.
Customisation and Seasonal Considerations
- Customisation options can enhance your tour, especially if you have specific wineries or wine types in mind. Also, consider the season of your visit, as the landscape and tour offerings can vary throughout the year.
Some Common Questions to Have
Are wine tours in Tuscany suitable for beginners?
Absolutely, wine tours in Tuscany cater to everyone, from beginners to connoisseurs - so don't let this put you off. If you're new to wine, a tour can be a fantastic introduction. You'll learn heaps about tasting techniques, grape varieties, and winemaking processes.
Plus, the guides are usually passionate about making wine accessible to all, so don't be shy to ask any questions you have – no matter how basic they might seem.
Can I join a wine tour without a car?
Yes, you can - in fact wine tours in Tuscany seem to cater very well to this market! Many tours offer pickup services from major cities like Florence and Siena.
For those starting in more remote locations, some companies provide transport options as well. It's always worth checking the tour details for transportation options, or you could reach out directly to the tour provider to arrange something that works for you.
What should I wear on a wine tour in Tuscany?
Comfort is key! You'll likely be walking through vineyards and cellars, so wear comfortable shoes suitable for uneven terrain. The weather can be quite variable, too – hot during the day and cooler in the evenings – so layers are your friend. And don't forget a hat and sunscreen if you're visiting in the summer!
Is it possible to accommodate dietary restrictions on wine tours?
This typically shouldn't be a problem. Many tours that include food are more than willing to accommodate different dietary needs. Just make sure to mention your requirements when you book to give them the heads up in advance and to make necessary preparations for you.
Whether you're vegetarian, vegan, or have specific allergies, they can usually tailor the food to suit your needs. The local cuisine is delicious, and it's worth experiencing alongside the fantastic wines.
How much wine will I be tasting?
This varies by tour, but generally, you can expect to taste anywhere from 3 to 6 different wines. It's all about quality over quantity; you'll be savouring each sip and learning about the characteristics of each wine.
Are children allowed on wine tours?
This depends on the tour operator. Some tours are more family-friendly and can accommodate children with non-alcoholic beverages and even have activities for them. However, others might be more focused on the wine experience and set an age limit for participants. It's best to check the tour details or contact the provider directly if you're planning to bring along younger family members.
Can I buy wine directly from the vineyards?
Yes, and the wineries will love you for it - for them, tours are a great showcase of what they have to offer! Visiting the vineyards is a great opportunity to purchase wines directly from the source, often including limited editions or special vintages not widely available elsewhere. Plus, it's a wonderful way to support the local winemakers.
Many wineries can even arrange shipping for you if you're worried about luggage space. I've been ordering small shipments of Vino Nobile di Montepulciano from a winery I visited many years ago each year at Christmas - it's great to have that connection into the future.
What's the best time of year to go on a wine tour in Tuscany?
Tuscany is beautiful year-round, but each season offers a different experience. Spring (April to June) and autumn (September to November) are particularly magical times to visit, with comfortable temperatures and the landscape either blooming or harvest-ready.
Summer can be quite hot but vibrant with tourists and full of life. Winter is quieter, which can be perfect if you're looking for a more intimate experience, though some wineries may have reduced hours or tours.
Planning Your Tuscany Wine Trip
If I were planning a Tuscany wine trip from scratch, I'd start with Chianti - it's accessible from Florence, the landscape is exactly what you picture when you imagine Tuscany, and the Classico wines are consistent enough that a day there gives you a solid baseline. Then I'd spend a night or two in Montepulciano or Montalcino and taste the wines at source. The difference between Brunello in a restaurant glass and Brunello at the estate where it's made is significant enough to be worth planning around.
For the full tour comparison in each region:
Related reading for Tuscany
Like this post? Please share or save for later…
