10 Best Chianti Multiday Tours in June 2026

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Tuscany Walks & Chianti Wines - June 2026

4.8

(90 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

Duration8 days

From

USD 3,000

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Private Gourmet Wine Tour in Tuscany - June 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 2,788

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Tuscany To Cinque Terre: Wines, Villages & Unforgettable Walks - June 2026

15% OFF TODAY

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

(7 reviews )

No booking fees

Best price guaranteed

I don't like planning trips and couldn't find a time that worked to travel with a friend, so decided to go on a group tour, and this trip was a great choice! I was really impressed with the organization of the trip, I loved the mix of planned activities and downtime, and I'm really glad I went.

Sightseeing Tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, Cinque Terre, Chianti

15% OFF TODAY

Duration7 days

From

USD 1,899

USD 1,614

Saving

USD 285

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Super Sales

Premium Rome to Venice - June 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

Duration8 days

From

USD 5,995

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

4.8

(14 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 - June 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 10,280

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

4.9

(28 reviews )

No booking fees

Best price guaranteed

The comprehensive immersion into the culture and family life during the truffle hunt was the absolute best! Seeing the beauty, walking in the hills with the dogs, and seeing how the community truly lives off the land was very inspiring. The hosts were so open and patient with our many questions. The food was incredible and the overall experience will forever be a special memory for us.

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

Duration11 days

From

USD 3,749

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All Chianti Tours in June 2026

7 Trips in Chianti during June 2026 with 141 Reviews

Get a customized trip to Chianti in June 2026

7 Trips in Chianti during June 2026 with 141 Reviews

Tuscany Walks & Chianti Wines - June 2026

Private Gourmet Wine Tour in Tuscany - June 2026

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

Premium Rome to Venice - June 2026

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

Premium Rome to Split - June 2026

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

7 Trips in Chianti during June 2026 with 141 Reviews

Get a customized trip to Chianti in June 2026

7 Trips in Chianti during June 2026 with 141 Reviews

Tuscany Walks & Chianti Wines - June 2026

Private Gourmet Wine Tour in Tuscany - June 2026

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

Premium Rome to Venice - June 2026

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

Premium Rome to Split - June 2026

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