10 Best Chianti Multiday Tours in June 2026

Get a customized trip to Chianti in June 2026

Plan a multi-country or regional adventure across Chianti in June 2026, with help from a local expert.

Alessandra GalassiTravel Expert in Italy
Danilo CataniaTravel Expert in Italy
Enrico Maria MalacarneTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
Simon H.Travel Expert in Belgium, France, Italy & Switzerland

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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.

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 2,793

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

18% OFF TODAY

Super Sales

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

18% OFF TODAY

Duration7 days

From

USD 1,899

USD 1,566

Saving

USD 333

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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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All Chianti Tours in June 2026

3 Trips in Chianti during June 2026 with 23 Reviews

Get a customized trip to Chianti in June 2026

Private Gourmet Wine Tour in Tuscany - June 2026

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

3 Trips in Chianti during June 2026 with 23 Reviews

A Taste of Tuscany - Hilltop Towns and Vineyards - 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

3 Trips in Chianti during June 2026 with 23 Reviews

Get a customized trip to Chianti in June 2026

Private Gourmet Wine Tour in Tuscany - June 2026

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

3 Trips in Chianti during June 2026 with 23 Reviews

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