10 Best Chianti Multiday Tours in September 2026

Tuscany Walks & Chianti Wines - September 2026

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Tuscany Walks & Chianti Wines - September 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

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Duration8 days

From

USD 2,773

USD 2,226

Saving

USD 547

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Private Gourmet Wine Tour in Tuscany - September 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 - September 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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Tuscany Escape, Self-drive - September 2026

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Tuscany Escape, Self-drive - September 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 - September 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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All Chianti Tours in September 2026

5 Trips in Chianti during September 2026 with 100 Reviews

5 Trips in Chianti during September 2026 with 100 Reviews

Tuscany Walks & Chianti Wines - September 2026

Private Gourmet Wine Tour in Tuscany - September 2026

Rome, Florence & Tuscany Family Adventure - September 2026

Tuscany Escape, Self-drive - September 2026

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

5 Trips in Chianti during September 2026 with 100 Reviews

5 Trips in Chianti during September 2026 with 100 Reviews

Tuscany Walks & Chianti Wines - September 2026

Private Gourmet Wine Tour in Tuscany - September 2026

Rome, Florence & Tuscany Family Adventure - September 2026

Tuscany Escape, Self-drive - September 2026

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