Wine Tours
Tuscan hills and a hill town at sunset seen from Cortona, Arezzo province

Tuscany Wine Tours Beyond Chianti

Eighty tours, 25 to 776 EUR. Nine reviews in ten belong to one day-trip page; the three wine towns share the other 4,746.

Nine Tuscan reviews in ten belong to one page. Of the 44,886 reviews on the 80 Tuscany wine tours here, 40,140 sit on the twenty day trips with a winery lunch, and most of those on a single coach day from Florence. The three places where the wine is actually made and poured, Montalcino, Montepulciano and San Gimignano, share the other 4,746. This page is about Tuscany outside Chianti, and it is organised around that split: what each of the four formats costs, where it leaves from, which dates and denominations sit behind the names, what it costs at the estate door, when the harvest and the local feasts fall, and how to choose between them. Chianti has a page of its own and we only point to it. Prices are per person as listed; where a tour is private, the vehicle is usually the unit, and the text says so.

Everything below is read from the listings on the four Tuscany pages on 30 September 2026, twenty tours each, and from the sites of the consortia and estates named in the text. Where a number comes from an estate's own site or a consortium, it says so. Where it comes from a route planner, treat it as a guide and check the operator. Distances marked as straight lines are measured between town centres, so they are what a crow would fly, not what a bus will drive.

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Wine Tours Experiences in Tuscany

Private Tuscany Day Tour from Florence by Mercedes: Siena, San Gimignano, Chianti Hills
Free cancellation

Private Tuscany Day Tour from Florence by Mercedes: Siena, San Gimignano, Chianti Hills

4.7 (157) 4.7 stars out of 5, 157 reviews

A private Mercedes with hotel pickup and drop-off, photo stops wherever the views call, and an optional Chianti Classico tasting at a local wine estate.

€ 395.00
Private Vernaccia Vineyard Lunch with Wine and Olive Oil Tasting
Free cancellation

Private Vernaccia Vineyard Lunch with Wine and Olive Oil Tasting

4.8 (46) 4.8 stars out of 5, 46 reviews

A private table in one of San Gimignano's oldest Vernaccia vineyards, with organic wine, olive oil and balsamic tastings and a farm-to-table Tuscan meal.

€ 68.00
Private Walking Tour of Montepulciano from Piazza Grande with Cellar and Nobile Tasting
Selling fast

Private Walking Tour of Montepulciano from Piazza Grande with Cellar and Nobile Tasting

4.9 (17) 4.9 stars out of 5, 17 reviews

A private guide leads from Piazza Grande down the main street, through Renaissance palaces and film locations, to an underground winery and a glass of Nobile.

€ 132.36
Rome to Montepulciano and Montalcino Day Trip: 12th-Century Winery Lunch, Brunello Museum
Free cancellation

Rome to Montepulciano and Montalcino Day Trip: 12th-Century Winery Lunch, Brunello Museum

4.9 (139) 4.9 stars out of 5, 139 reviews

Winery lunch and tasting in Montepulciano, then Montalcino and the Temple of Brunello museum (entry not included). Day trip by bus from Piazza del Popolo, Rome.

€ 107.99
Rome to Siena and San Gimignano Day Trip: Tenuta Torciano Tasting of 10 Wines and Lunch
Free cancellation

Rome to Siena and San Gimignano Day Trip: Tenuta Torciano Tasting of 10 Wines and Lunch

4.8 (135) 4.8 stars out of 5, 135 reviews

Tenuta Torciano, a 13-generation winery, hosts a ten-wine tasting and a local lunch after Siena's Piazza del Campo and San Gimignano. Full-day trip from Rome.

€ 268.00
Rome to Tuscany by Train: Chianti and Vernaccia Wineries, San Gimignano
Free cancellation

Rome to Tuscany by Train: Chianti and Vernaccia Wineries, San Gimignano

4.9 (27) 4.9 stars out of 5, 27 reviews

A guided day trip to Tuscany by high-speed train from Rome, tickets included, with two wineries, a Chianti tasting, San Gimignano and free time in Florence.

€ 199.00
Rome to Tuscany Day Trip by Coach: Montepulciano, Pienza, Vineyard Lunch and Wine Tasting
Free cancellation

Rome to Tuscany Day Trip by Coach: Montepulciano, Pienza, Vineyard Lunch and Wine Tasting

4.7 (5,671) 4.7 stars out of 5, 5,671 reviews

A three-course vineyard lunch with Brunello di Montalcino, a guided walk in Montepulciano and free time in Pienza, all by air-conditioned coach from Rome.

€ 99.00
Rome to Tuscany Day Trip: Tenuta Il Quinto Tasting, Countryside Lunch and Big Bench #300
Free cancellation

Rome to Tuscany Day Trip: Tenuta Il Quinto Tasting, Countryside Lunch and Big Bench #300

5.0 (96) 5.0 stars out of 5, 96 reviews

Two tastings, at Tenuta Il Quinto and Enoteca Scansanese, plus a countryside lunch and a stop at Big Bench #300, with hotel pickup in Rome and return.

€ 280.00
Siena Province Day Trip: Monteriggioni, Pienza, Montepulciano and Two Wine Tastings
Free cancellation

Siena Province Day Trip: Monteriggioni, Pienza, Montepulciano and Two Wine Tastings

4.1 (166) 4.1 stars out of 5, 166 reviews

An 11.5-hour circuit with a vineyard tasting, a pasta lunch with Tuscan ragù and a Montepulciano winery tasting of four wines, leaving from Villa Costanza.

€ 119.00
Siena Station Minivan Wine Tour: Montepulciano, Pienza, Val d'Orcia and Brunello Lunch
Free cancellation

Siena Station Minivan Wine Tour: Montepulciano, Pienza, Val d'Orcia and Brunello Lunch

4.1 (123) 4.1 stars out of 5, 123 reviews

Staff in green shirts meet the group at Siena station for a minivan day of cellar visits, with Nobile in Montepulciano and Brunello to finish in Montalcino.

Discounted price€ 109.65Regular price€ 129.00
Small Family Vineyard at Sovestro near San Gimignano: Cellar Visit, Lunch, Four Wines
Free cancellation

Small Family Vineyard at Sovestro near San Gimignano: Cellar Visit, Lunch, Four Wines

4.9 (88) 4.9 stars out of 5, 88 reviews

A talk on Italian wine rules precedes a local-products lunch, four estate wines and a dessert wine, a short walk or drive from the walls of San Gimignano.

€ 65.00
Small-Group Brunello and Montepulciano Wine Day from Cortona in a 9-Seat Minivan
Selling fast

Small-Group Brunello and Montepulciano Wine Day from Cortona in a 9-Seat Minivan

4.7 (26) 4.7 stars out of 5, 26 reviews

A small group in a 9-seat minivan meets the owners of a boutique Montalcino winery, then tastes at an old Brunello cellar, with pick-up in Cortona or Siena.

€ 499.00
Small Group Day Trip from Montecatini Terme: Siena, San Gimignano and Chianti Estate
Free cancellation

Small Group Day Trip from Montecatini Terme: Siena, San Gimignano and Chianti Estate

4.8 (58) 4.8 stars out of 5, 58 reviews

Small group from Montecatini Terme with a winemaker-led Vernaccia and Chianti DOCG tasting between San Gimignano and Siena, a Siena guide paid on the day.

€ 169.00
Small-Group Horseback Ride with Winery Lunch and San Gimignano Visit
Free cancellation

Small-Group Horseback Ride with Winery Lunch and San Gimignano Visit

4.9 (67) 4.9 stars out of 5, 67 reviews

Riders of any level are matched to a gentle horse, then a winery farm serves a Tuscan lunch with guided tastings before a stroll through San Gimignano.

€ 190.00
Small-Group Tour: Chianti Winery, San Gimignano and Vernaccia Lunch Tasting

Small-Group Tour: Chianti Winery, San Gimignano and Vernaccia Lunch Tasting

4.8 (22) 4.8 stars out of 5, 22 reviews

Two Tuscan wine regions in one small-group day: a Chianti winery known for Riserva and a Supertuscan, free time in San Gimignano and a Vernaccia lunch tasting.

€ 285.00
Sunset Terrace Dinner with Eight-Wine Tasting Overlooking San Gimignano
New

Sunset Terrace Dinner with Eight-Wine Tasting Overlooking San Gimignano

4.9 (11) 4.9 stars out of 5, 11 reviews

Dinner on an exclusive sunset terrace over San Gimignano, with eight wines, olive oils and balsamics, homemade lasagna, a meat course and Vin Santo dessert.

€ 63.00
Talosa Cantina Storica, Montepulciano: Cellar Visit, Etruscan Tomb and Four-Wine Tasting
Free cancellation

Talosa Cantina Storica, Montepulciano: Cellar Visit, Etruscan Tomb and Four-Wine Tasting

4.6 (141) 4.6 stars out of 5, 141 reviews

A sommelier guides you through a 16th-century cellar with Etruscan-attributed tunnels and a tomb, then pours four local wines with bread and regional products.

€ 34.90
The Tour Guy Rome to Tuscany: Civita di Bagnoregio, Montepulciano Winery Lunch and Pienza
New

The Tour Guy Rome to Tuscany: Civita di Bagnoregio, Montepulciano Winery Lunch and Pienza

4.8 (180) 4.8 stars out of 5, 180 reviews

Civita entry and shuttle are included, plus four wine tastings, olive oil and a pici lunch at a family winery. Round-trip coach from Rome with an expert guide.

€ 90.30
The Tour Guy Tuscany Day Trip from Florence: Siena, Six-Wine Chianti Lunch, San Gimignano
Free cancellation

The Tour Guy Tuscany Day Trip from Florence: Siena, Six-Wine Chianti Lunch, San Gimignano

4.8 (298) 4.8 stars out of 5, 298 reviews

Six wines with artisanal olive oil and a three-course lunch at a family Chianti winery, between a walking tour of Siena and free time in San Gimignano.

€ 99.83
Towns of Italy Afternoon Tour from Florence: Siena, San Gimignano and Winery Dinner
Free cancellation

Towns of Italy Afternoon Tour from Florence: Siena, San Gimignano and Winery Dinner

4.7 (351) 4.7 stars out of 5, 351 reviews

A Tuscan dinner and wine tasting at a boutique Chianti winery follows a guided Siena walk and free time in San Gimignano. Minivan departure from Florence.

€ 105.82
Tuscany Day Tour from Florence: Pisa, Chianti Winery Lunch, San Gimignano and Siena
Free cancellation

Tuscany Day Tour from Florence: Pisa, Chianti Winery Lunch, San Gimignano and Siena

4.6 (694) 4.6 stars out of 5, 694 reviews

A light lunch with a three-wine tasting at a Chianti winery sits between Pisa's Piazza dei Miracoli and a guided walk in Siena. Tower tickets are optional.

Discounted price€ 44.20Regular price€ 52.00
Tuscany Horseback Ride with Winery Lunch, from Florence or San Gimignano
New

Tuscany Horseback Ride with Winery Lunch, from Florence or San Gimignano

5.0 (41) 5.0 stars out of 5, 41 reviews

A small-group horseback ride for beginners and intermediate riders crosses vineyards and olive groves, then a multi-course estate lunch with wine tasting.

€ 120.00
Two-Winery Walking Tour from Piazza Grande, Montepulciano: Oak-Barrel Cellars, 2.5 Hours
Free cancellation

Two-Winery Walking Tour from Piazza Grande, Montepulciano: Oak-Barrel Cellars, 2.5 Hours

4.4 (20) 4.4 stars out of 5, 20 reviews

Oak barrels, brick-walled chambers under Renaissance palaces and two wineries, the second on classifications and grape varieties, each ending in a tasting.

€ 55.00
Val d'Orcia by Coach from Florence: Montalcino, Pienza, Montepulciano and Pecorino
Free cancellation

Val d'Orcia by Coach from Florence: Montalcino, Pienza, Montepulciano and Pecorino

4.6 (55) 4.6 stars out of 5, 55 reviews

The second tasting happens in a historic underground cellar in Montepulciano, after Brunello in Montalcino and pecorino in Pienza, on a full day by coach.

€ 92.00

Ratings collected by Viator, Tripadvisor and Civitatis