Italy · WINE TOURS IN TUSCANY

Wine Tours in Tuscany: 15 We Would Put the Money On

79 tours  ·  from $29

All 15 wine tours in Tuscany below are bookable today, with the price, the running time and who each one actually suits. The first is first for a reason.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Meeting the coach near Santa Maria Novella
1-Day Tours, Day Trips in Tuscany, Tour Reviews, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

1.Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

★★★★★★★★★★5.0 · 21,634 reviews · 11 to 12 hours (approx.) · from $114Our pick

From Florence, spend a full day touring Siena, San Gimignano, Pisa, and the Chianti countryside by air-conditioned coach. Walk through Siena with a local guide, enter its striking cathedral, enjoy a farmhouse lunch and four-wine tasting at Fattoria Poggio Alloro, then explore two medieval towns and Pisa’s Square of Miracles. Tower tickets require an upgrade.

“Davide was amazing and so knowledgeable. We had a wonderful experience and laughed a lot! We would recommend to anyone”

Check availability →Read our full review

Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Pisa and the Leaning Tower
Tour Reviews, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

Florence: Pisa, Siena, San Gimignano, and Chianti Experience

2.Pisa, Siena, San Gimignano, and Chianti Experience

★★★★★★★★★★4.5 · 8,393 reviews · 12 hours · from $52Best value

Travel from Florence to Pisa, San Gimignano, Siena, and the Chianti Hills in a 12-hour coach tour. Choose the lunch and wine tasting package, add a Siena walking tour, and reserve Leaning Tower tickets. Guides such as Barbara, Anna, and Layla are praised for clear local stories, while comfortable transport gives you time to rest between stops.

“The trip was absolutely wonderful. Everything exceeded our expectations, the places we visited were beautiful, the atmosphere was amazing, and we truly enjoyed every moment. It was an experience we will remember fondly!!”

Check availability →Read our full review

Florence: Chianti Wineries Tour with Wine Tasting - Finding the bus at Piazzale Montelungo
Food & Drink, Food Tours in Tuscany, Tour Reviews, Tours, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

Florence: Chianti Wineries Tour with Wine Tasting

3.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 8,301 reviews · from $56

Meet your English-speaking guide near Florence’s Santa Maria Novella station, then ride a comfortable coach into the Chianti Hills. Visit two wineries, walk through vineyards, taste up to seven wines with cheese, salami, olive oil, and bread, and hear how weather, barrels, and local rules shape Chianti Classico.

“Such an incredible time! Cecilia was our guide and did a wonderful job. The host at the first winery was also incredibly knowledgeable and exciting when telling us about the wine and history. Highly recommend!”

Check availability →Read our full review

Small-Group Wine Tasting Experience in the Tuscan Countryside - First winery: vineyards, barrels, and three wines
Food & Drink, Food Tours in Tuscany, Tour Reviews, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

Small-Group Wine Tasting Experience in the Tuscan Countryside

4.Small-Group Wine Tasting Experience in the Tuscan Countryside

★★★★★★★★★★5.0 · 7,392 reviews · 4 hours 45 minutes (approx.) · from $107

Leave Florence from Santa Maria Novella for a 4-hour-45-minute small-group tour through Chianti. Visit two wineries, taste six regional wines with olive oil, cheese, salami, ham, and bruschetta, and hear local stories from guides such as Leo, Matteo, and Jonathan. Groups can reach 25 people, though some departures are much smaller.

“Leo was amazing. He was informative and told us all about the history of the vineyards and Chianti wine. We went to 2 vineyards which also had EVOO and Balsamic Vinegar. Delicious. I would do this again,”

Check availability →Read our full review

Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing - Siena Cathedral deserves a careful choice
1-Day Tours, Day Trips in Tuscany, Tour Reviews, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

5.Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

★★★★★★★★★★4.5 · 6,006 reviews · 12 hours (approx.) · from $78

Spend about 12 hours touring Tuscany from Florence, with guided Siena, free time in San Gimignano and Pisa, and an optional winery lunch with wine pairing. Guides such as Constantino, Sara, Jacopo, and Sebastiano have earned praise for keeping the large group informed and on schedule. Expect plenty of walking and limited time at each stop.

“You get a great overview of many places in a single day. There is not a lot of time for in depth sightseeing but you get to many places. They pull it off flawlessly.”

Check availability →Read our full review

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting - San Biagio and Renaissance Geometry
1-Day Tours, Day Trips in Tuscany, Food & Drink, Food Tours in Tuscany, Tour Reviews, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

6.Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 5,232 reviews · 12 hours (approx.) · from $83

Spend about 12 hours traveling from Rome to Tuscany by air-conditioned coach. Walk through Montepulciano, visit San Biagio, eat a three-course farm lunch with regional wines, and enjoy free time in UNESCO-listed Pienza. Guides such as Anna, Barbara, Antonino, and Flavio are known for adding useful history and Rome tips along the way.

“Our tour guide Barbara was very entertaining and informative. We enjoyed the views. Our favorite stop was Montepulciano. It is a long day but we are glad we did it.”

Check availability →Read our full review

SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - What happens at the wineries
Food & Drink, Food Tours in Tuscany, Tour Reviews, Tours, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

7.SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

★★★★★★★★★★5.0 · 5,088 reviews · 7 to 9 hours (approx.) · from $157

Choose a 7 to 10-hour wine safari from Florence with an English-speaking sommelier, air-conditioned 4x4 transport, private estates, cellar visits, tastings, and a Tuscan meal. Options range from Chianti to Val d’Orcia, Brunello, and Montepulciano. Guides may include Ginevra, Sara, Alex, or Fabio.

“Fabio was an excellent guide! I always recommend Walkabout Tours for anyone visiting Florence/Tuscany.”

Check availability →Read our full review

From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - The Chianti winery lunch is the day’s big payoff
Tour Reviews, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

8.From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

★★★★★★★★★★4.8 · 4,538 reviews · 12 hours · from $112

Spend a full day with an English-speaking guide such as Sara, Alessandro, or Manolo, visiting Siena, San Gimignano, Pisa, and the Chianti hills. You’ll get a Siena walking tour, free time in three towns, and an optional farmhouse lunch with four regional wines at an organic winery.

“What a day! Thank you Manolo for a wonderful day full of laughs and learning about the history of the Tuscany region. This was a great way to see so much of the beautiful Tuscan landscape and hospitality, topped off with a climb up the Leaning Tower of Pisa at sunset. Such great value for money, a must do!”

Check availability →Read our full review

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano and the town of towers
1-Day Tours, Day Trips in Tuscany, Food & Drink, Food Tours in Tuscany, Tour Reviews, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

9.San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83

Leave Florence by coach for San Gimignano’s towers, Monteriggioni’s fortress walls, and Siena’s Gothic center. At a Chianti winery, taste three Tuscan wines with a three-course lunch. Choose the Siena walking tour and cathedral entry if you want more guided history. Expect hills, uneven streets, and a long day.

“Sandro was great as our guide for all our destinations today! Highly recommend and lucky to get him!”

Check availability →Read our full review

Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Meeting at Piazzale Montelungo
Tour Reviews, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

10.Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

★★★★★★★★★★4.6 · 4,354 reviews · 12 hours · from $77

Spend 12 hours touring Tuscany by air-conditioned coach, from Pisa’s Leaning Tower to San Gimignano’s medieval towers and Siena’s Piazza del Campo. Add the three-course lunch and wine tasting for a taste of local food, then join a guide such as Marta, Aaron, or Sandro for Siena’s streets and cathedral.

“This was a very enjoyable experience. Will highly recommend.”

Check availability →Read our full review

Chianti Wine Tour from Florence - The road through Sienese Chianti Classico
Tour Reviews, Tours, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

Chianti Wine Tour from Florence

11.Chianti Wine Tour from Florence

★★★★★★★★★★4.5 · 3,979 reviews · 5 hours (approx.) · from $59

Leave Florence by air-conditioned coach for two family-run Chianti wineries. Expect vineyard and cellar visits, six or seven Tuscan wines, bruschetta, cheese, salami, olive oil, and balsamic vinegar. Guides such as Aaron, Alessandra, and Maria Luisa have led lively visits, though timing and group size can vary.

“The half day tour was fun but was a bit chaotic going back and forth between Italian, English and Spanish. The group was divided into groups once we reach the wineries but was so loud at the first stop I couldn’t understand a word our guide was saying. The second stop, each group was a bit more secluded and was bit nicer. Our guide Christina was kind, full of knowledge and a talker!”

Check availability →Read our full review

From Florence: Small Group Wine Tasting Tour to Tuscany - First winery: three wines, olive oil, and the basics
Food & Drink, Food Tours in Tuscany, Tour Reviews, Tours, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

From Florence: Small Group Wine Tasting Tour to Tuscany

12.From Florence: Small Group Wine Tasting Tour to Tuscany

★★★★★★★★★★4.9 · 3,902 reviews · 4.5 hours · from $105

Leave Florence by air-conditioned minibus for two Chianti Classico wineries. Taste six wines and local olive oils with cheese, salami, cold cuts, and bruschetta, while your English-speaking guide explains Tuscan wine traditions. Guides may include Jason, Jonathan, Leo, or Rafael, but assignments vary.

“Our guide, Leo, was awesome! He transported us and gave us history and knowledge about the wines and certifications that make Tuscany unique. Very friendly and very people-oriented. Thank you!”

Check availability →Read our full review

From Florence: San Gimignano, Siena, and Chianti Wine Tour - Starting beside Florence’s Baptistery
Tour Reviews, Tours, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

From Florence: San Gimignano, Siena, and Chianti Wine Tour

13.From Florence: San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164

Leave Florence for Siena, a Chianti estate, and San Gimignano in an air-conditioned bus or minivan. You’ll have guided time, independent walks, five wine tastings, olive oils, balsamic vinegar, and an optional Tuscan lunch featuring truffle lasagna and ribollita. Guides such as Marco, Lyla, Marta, and Enrieta are praised for keeping the day lively and well organized.

“If you’re going to to ANYTHING besides stay in Florence or Rome, do this tour. You have the opportunity to spend an entire day wandering around the Tuscan country side. One of the most beautiful ways to spend the day. The wine tasting is short, if that’s not something you’re looking for but it is still a great time.”

Check availability →Read our full review

Siena, San Gimignano and Chianti Wines Day Tour from Florence - Monteriggioni gives you a quick medieval beginning
Tour Reviews, Tours, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

Siena, San Gimignano and Chianti Wines Day Tour from Florence

14.Siena, San Gimignano and Chianti Wines Day Tour from Florence

★★★★★★★★★★4.5 · 2,542 reviews · 10 hours 30 minutes (approx.) · from $78

Travel by air-conditioned coach from Florence to Monteriggioni, Siena, San Gimignano, and a Chianti wine estate. You’ll get guided time in Siena, free time in the hill towns, and a tasting of two or three wines with snacks. Expect a long day, steep walks, and limited time in each town.

“Well organised and excellent day out. Seeing all the smaller cities around Tuscany and getting to enjoy the sights”

Check availability →Read our full review

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - San Gimignano: towers, lanes, and your first free time
Food & Drink, Food Tours in Tuscany, Tour Reviews, Tuscany Tours, Wine Tours, Wine Tours in Tuscany

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

15.S. Gimignano, Siena, Chianti & Wine Tasting Lunch

★★★★★★★★★★4.6 · 2,427 reviews · from $89

Spend a full day in Tuscany with free time in San Gimignano, a stop in Monteriggioni, a Chianti winery lunch, and a guided visit to Siena. The $89.50 tour includes transport, escort, lunch, and three wines. Add Siena Cathedral entry and a guided cathedral visit when booking.

“We had a lovely time our tour. Martha and Enrico were great! For an all day tour, you do not feel like you’re on the bus for too long between destinations. Our tour leader gave us recommendations of what to do in our free time including activities and food/drink to try before we arrived. Be aware that if it is off season, many things are closed or may open later but you can always find somewhere to eat or drink and it’s nice to walk around when it’s quieter. Our guide Marco at the winery was fun. Lunch was a plate of cold meats, bread and a pasta. Dessert was…”

Check availability →Read our full review

New in Wine Tours in Tuscany

★ 5.0Wine Tasting Experience in Ponte Vecchio: Best Tuscany selection!From $36197 reviews
★ 5.0Florence Sunset Food Tour with Wine & Dine at a Tuscan farmhouseFrom $140194 reviews
★ 4.5Wine Experience In Chianti Hills from FlorenceFrom $49195 reviews
★ 4.5Val d’Orcia Brunello Wine Tour with Montalcino and MontepulcianoFrom $277359 reviews
★ 5.0Tuscany Vespa Tour from Florence with Wine TastingFrom $241425 reviews
★ 5.0Tuscany Vespa Tours Through the Hills of ChiantiFrom $193515 reviews
★ 5.0Tuscany Vespa Tour: Lunch & Wine Tasting, Countryside RoadsFrom $228614 reviews
★ 4.5Tuscany E-Bike Tour: from Florence to Chianti with lunch and tastingsFrom $138210 reviews
★ 5.0Tuscany Wine Tour: 2 Wineries & San Gimignano from FlorenceFrom $2291,007 reviews
★ 5.0Tuscany Bike Tour with Wine, Oil and Food in the Florentine HillsFrom $95209 reviews
★ 4.5Tuscany Experience: Pisa, Siena, San Gimignano & Wine TastingFrom $53653 reviews
★ 4.0Chianti Delights: A Tale Of Two Wineries With A Vineyard DinnerFrom $106324 reviews
★ 4.5From Florence: Small-Group Tuscany Wine & Oil Tour with typical Tuscan MealFrom $96638 reviews
★ 5.0Florence Day Trip: Chianti Wine Tasting, Siena, San GimignanoFrom $235263 reviews
★ 4.5Siena & San Gimignano with Dinner in a Boutique WineryFrom $126199 reviews

Keep browsing

Colosseum Tours123Vatican Tours120Uffizi Gallery Tours44Cruises & Boat Tours228Food & Drink185Wine Tours197
Scroll to Top

Explore Italy

Pick a ruin, a gallery, a cellar or a boat.

Ancient Italy

Colosseum TicketsPompeiiAncient SitesThe PantheonThe Catacombs

Galleries

Vatican MuseumsThe UffiziThe AccademiaThe Last SupperMuseums

Food and wine

Food ToursCooking ClassesWine TastingsPasta WorkshopsStreet Food

On the water

Boat TripsGondola RidesThe Blue GrottoCapri by BoatSnorkelling