10 Best Chianti Multiday Tours in September 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.

Super Sales

Premium Rome to Venice - September 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 5,395

USD 5,233

Saving

USD 162

View Tour

Super Sales

Premium Sicily and Tuscany - September 2026

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 10,960

USD 10,631

Saving

USD 329

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Super Sales

Premium Rome to Split - September 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

View Tour

All Chianti Tours in September 2026

3 Trips in Chianti during September 2026

Get a customized trip to Chianti in September 2026

3 Trips in Chianti during September 2026

Premium Rome to Venice - September 2026

Premium Sicily and Tuscany - September 2026

Premium Rome to Split - 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

3 Trips in Chianti during September 2026

Get a customized trip to Chianti in September 2026

3 Trips in Chianti during September 2026

Premium Rome to Venice - September 2026

Premium Sicily and Tuscany - September 2026

Premium Rome to Split - September 2026