10 Best Chianti Multiday Tours in Fall

Get a customized trip to Chianti in Fall

Plan a multi-country or regional adventure across Chianti in Fall, 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.

Super Sales

Premium Rome to Venice - Fall tours

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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Super Sales

Premium Sicily and Tuscany - Fall tours

No booking fees

Best price guaranteed

Make your way to the Mediterranean to discover all the natural beauty, warm hospitality and cuisine Italy and Sicily have to offer. On this 17-day adventure, you’ll travel from Rome to postcard-perfect Venice. From visiting one of the Seven Wonders of the World – the Colosseum – to driving up the flank of Mount Etna, Europe’s largest active volcano, this trip goes the extra mile to deliver experiences that go beyond the guidebooks. Visit the famous spots like the Spanish Steps and Trevi Fountain, then go off the path to a local’s favourite restaurant. Get ready to tuck into local eats, explore iconic sites and brush up on your ancient history, all with an experienced local by your side.

Sightseeing ToursWalking tours

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Palermo, Rome, Chianti, San Gimi

Palermo, Rome, Chianti, San Gimignano, Florence, Venice, Marsala, Agrigento, Siracusa, Catania

Duration17 days

From

USD 12,175

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Super Sales

Premium Rome to Split - Fall tours

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 - Fall tours

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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Super Sales

Tuscany Escape: 7 Days Through Art, Wine & Hills, Self-drive - Fall tours

Trip customizable

Best price guaranteed

Experience the magic of Tuscany on this 7-day self-drive tour, exploring rolling hills, medieval villages, and charming towns steeped in history. Wander through Renaissance Florence, admire Pisa’s iconic Leaning Tower, and soak in Siena’s Gothic splendor. Discover the world-famous Chianti wine region with its scenic vineyards, olive groves, and hilltop villages, and wander the cobbled streets of San Gimignano, a UNESCO World Heritage Site renowned for its towers and gelato. Enjoy a journey that blends culture, gastronomy, and breathtaking landscapes at your own pace.

Self-drive or vehicle rental

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Florence, Chianti

Duration7 days

From

USD 1,034

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All Chianti Tours in Fall

5 Trips in Chianti with 28 Reviews

Get a customized trip to Chianti in Fall

5 Trips in Chianti with 28 Reviews

Premium Rome to Venice - Fall tours

Premium Sicily and Tuscany - Fall tours

Premium Rome to Split - Fall tours

Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns - Fall tours

Tuscany Escape: 7 Days Through Art, Wine & Hills, Self-drive - Fall tours

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 Fall

5 Trips in Chianti with 28 Reviews

Get a customized trip to Chianti in Fall

5 Trips in Chianti with 28 Reviews

Premium Rome to Venice - Fall tours

Premium Sicily and Tuscany - Fall tours

Premium Rome to Split - Fall tours

Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns - Fall tours

Tuscany Escape: 7 Days Through Art, Wine & Hills, Self-drive - Fall tours