10 Best Chianti Multiday Tours in May 2026

Accommodations

Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Tuscany Walks & Chianti Wines - May 2026

20% OFF TODAY

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Tuscany Walks & Chianti Wines - May 2026

4.8

(89 reviews )

No booking fees

Best price guaranteed

The trip had a really good balance of activities, with plently to do while still leaving you time to relax and chill out. Tuscany is so beautiful and Fattoria Voltrona was a great place to stay. I would definitely recommend this trip to my friends.

Trekking and HikingFood tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Siena, Tuscany, Chianti, Pancole

Siena, Tuscany, Chianti, Pancole, Florence, San Gimignano

20% OFF TODAY

Duration8 days

From

USD 2,773

USD 2,226

Saving

USD 547

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Private Gourmet Wine Tour in Tuscany - May 2026

4.5

(2 reviews )

Trip customizable

Best price guaranteed

What a beautiful time spent in Tuscany on this trip. This was a wonderful tour. Great accommodations! Fabulous wines and meals. We had a wonderful driver, Brando, who was patient and knowledgeable. This is a trip well worth it. Villa Lecchi was elegant and made us feel very special! Spectacular location in the heart of Chianti hills

Food toursWine tasting tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

22-89 yrs

Operated in

english, german

Destinations

Tuscany, Chianti, Florence, Sien

Tuscany, Chianti, Florence, Siena, Pisa

Duration4 days

From

USD 2,854

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Rome, Florence & Tuscany Family Adventure - May 2026

(3 reviews )

Trip customizable

Best price guaranteed

Hi Stefania! Sorry to take so long to write back. It has been crazy trying to get back into the swing of things at work after that trip. Italy was amazing!! We absolutely loved it! As for feedback on the trip, we really don't have anything that was negative. We loved everything that was planned! We especially loved how you planned the sites that we went and how the pattern flowed (not sure if you did it on purpose but we think so). Also, thank you for being very accessible to us during the whole planning of the trip. You helped put us at ease and it was very reassuring that we chose the right company. That is all that I can given you that might be considered constructive. The rest I could say would just be compliments on everything else. If I can think of anything else that I think is useful I will definitely email you. Hope all is well, Jane P.S. - Does your company only provide trips for Italy or other countries as well, just wondering for the future :)

Food tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Rome, Florence, Tuscany, San Gim

Rome, Florence, Tuscany, San Gimignano, Chianti, The Vatican

Duration8 days

From

USD 7,743

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The Tuscan Dream Self-Drive - May 2026

(2 reviews )

Trip customizable

Best price guaranteed

GO!!! Our first time in Italy and this package was absolutely amazing. The price, sights, hotels and people couldn’t be beat. Really, just go!

City sightseeing

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Rome, Siena, Tuscany, Chianti, Pistoia

Duration7 days

From

USD 629

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Super Sales

Tuscany to Cinque Terre: Wines, Villages & Unforgettable Walks - May 2026

(3 reviews )

No booking fees

Best price guaranteed

The "Tuscany to Cinque Terre: Wines, Villages & Unforgettable Walks" tour really lived up to its name and my expectations. In one short week we travelled to all these places to experience its beauty, nature, food and culture. We indeed had unforgettable walks with everyone, our incredible CEO Francesco and amazing fellow tour members. I highly recommend this tour!

Sightseeing Tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, Cinque Terre, Chianti

Duration7 days

From

USD 1,899

USD 1,842

Saving

USD 57

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27% OFF TODAY

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Premium Rome to Venice - May 2026

No booking fees

Best price guaranteed

Uncover the warmth and richness of Italian culture as you journey from Rome to Venice on an eight-day Premium adventure. Travel through the rustic heart of Tuscany as you seek out culinary delights and tucked-away treasures among the rolling countryside. Explore the wonders of Venice’s Piazza San Marco, Pisa’s Leaning Tower and Rome’s Colosseum – one of the Seven Wonders of the World – with an expert local leader. From ancient monuments and lively cities to sprawling vineyards and traditional Tuscan cuisine – this adventure will make memorable moments for both the Italian novice and maestro.

Chill out

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Chianti, Florence

27% OFF TODAY

Duration8 days

From

USD 5,245

USD 3,816

Saving

USD 1,429

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7% OFF TODAY

Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns - May 2026

No booking fees

Best price guaranteed

On a journey through the less-traveled country roads of Umbria and Tuscany, discover another side to the Italy you love. Stroll Assisi’s old city, and explore the Umbrian hill town of Spoleto, where the gilded façade of the cathedral rivals with the silvery sheen of the olive trees. Visit Florence, the “Cradle of the Renaissance.” In Siena, stand inside one of Tuscany’s most ancient piazzas. Admire the famous towers of San Gimignano and hunt for truffles in the Umbrian countryside. Delight in regional specialties and Italian wine with every dinner. Feel like a local as you discover the marvels of wine, cuisine, culture, and history.

Countryside and village visits

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Tuscany, Chianti, Umbria

Rome, Tuscany, Chianti, Umbria, Pienza

7% OFF TODAY

Duration11 days

From

USD 3,749

USD 3,499

Saving

USD 250

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15% OFF TODAY

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Tuscany Escape, Self-drive - May 2026

Trip customizable

Best price guaranteed

Tuscany is brimming with secluded valleys, magnificent rolling hills and majestic medieval villages boasting bustling restaurants, piazzas and ancient narrow cobble-stoned streets. Its rich landascape is complemented by towns overflowing with Reinassance art and architecture. Proud of its olive oil, there’s acclaimed gastronomy and, perhaps the best-know wine area, Chianti, is stunningly beautiful with gentle hills clocked by olive groves and vineyards and ancient castles and grand palazzi which have been magnificently restored as impressive hotels.

Self-drive or vehicle rental

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Florence, Chianti

15% OFF TODAY

Duration7 days

From

USD 1,053

USD 895

Saving

USD 158

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A Taste of Tuscany - Hilltop Towns and Vineyards - May 2026

4.5

(6 reviews )

No booking fees

Best price guaranteed

Trip was excellent. Tour Guide, Gus, was fantastic, very knowledgeable, great communicator, and made sure all of our needs were met. Food and wine tour could not have been better. Never really liked many wines but the tastings proved me wrong. The agricultural farms were great and the food fresh and abundant. Villages were quaint. Castle was very interesting - 34 generations living in it and continuously running a vineyard and producing wine since 1141 is unbelievable! Looking into another food tour in another country. Gave accommodations less rating because hotels were in old buildings and they made due with space available: 1) First 2 nights in Hotel Bologna, the room was very, very small and had 2 twin beds aligned in tandem against one wall - would not have fit any other way, 2) Hotel Le Cisterna, last 3 nights, walls were so thin we could hear every word people next door said.

Wine tasting toursFood tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Pisa, Pienza, Siena, Chianti, Vo

Pisa, Pienza, Siena, Chianti, Volterra, San Gimignano

Duration8 days

From

USD 3,040

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Super Sales

Premium Rome to Split - May 2026

No booking fees

Best price guaranteed

Embrace the cultural, culinary and natural delights of Italy, Slovenia and Croatia on a 16-day Premium adventure. Travel through the rustic heart of Tuscany, explore the wonders of Venice’s Piazza San Marco and Pisa’s Leaning Tower and visit the home of a Nobleman in Rome with an expert local leader. Discover the waters of Lake Bled and the underground world of the Postojna Caves. Ride the cable car up Mt Vogel for views over Lake Bohinj and appreciate the caves and waterfalls in Plitvice Lakes National Park. Coloured by sunshine and flavoured with local wine, this pocket of Europe is a joy to explore.

Culture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Split, Rome, Bled, Rovinj, Plitv

Split, Rome, Bled, Rovinj, Plitvice Lakes National Park, Zadar, Chianti, San Gimignano, Florence, Venice

Duration16 days

From

USD 8,980

USD 8,711

Saving

USD 269

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All Chianti Tours in May 2026

10 Trips in Chianti during May 2026 with 105 Reviews

10 Trips in Chianti during May 2026 with 105 Reviews

Tuscany Walks & Chianti Wines - May 2026

Private Gourmet Wine Tour in Tuscany - May 2026

Rome, Florence & Tuscany Family Adventure - May 2026

The Tuscan Dream Self-Drive - May 2026

Tuscany to Cinque Terre: Wines, Villages & Unforgettable Walks - May 2026

Premium Rome to Venice - May 2026

Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns - May 2026

Tuscany Escape, Self-drive - May 2026

A Taste of Tuscany - Hilltop Towns and Vineyards - May 2026

Premium Rome to Split - May 2026

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All Chianti Tours in May 2026

10 Trips in Chianti during May 2026 with 105 Reviews

10 Trips in Chianti during May 2026 with 105 Reviews