10 Best Tuscany Multiday Tours in Winter

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.

Italy City Break - 5 Days - Winter Tours

32% OFF TODAY

Halloween Super Sales

Italy City Break - 5 Days - Winter tours

4.5

(4 reviews )

Trip customizable

Best price guaranteed

Exploring Italy through this trip was an unforgettable experience! It allowed us to see all the iconic landmarks in each city we visited, offering a remarkable variety of activities that left no room for boredom. What made the journey even more exceptional were the guides - their passion for the country, combined with their extensive knowledge, made the trip truly unforgettable. They made it a priority to connect with each and every traveler, ensuring that everyone was fully immersed in the tour. With everything taken care of, this trip exceeded our expectations and more. I highly recommend it to anyone who wants to discover Italy in the best possible way!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Assisi

Rome, Florence, Venice, Assisi, Montepulciano, Siena, Tuscany, Bologna, Padua

32% OFF TODAY

Duration5 days

From

USD 1,780

USD 1,209

Saving

USD 571

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Halloween Super Sales

Discovery of Italy: 8 Days - Winter tours

(1 review )

Trip customizable

Best price guaranteed

I have had the wonderful pleasure of touring with you, the tour was well executed. The experiences are amazing and very unique. So much fun and I will tour again. I will recommend.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, The Vati

Rome, Florence, Venice, The Vatican, Assisi, Montepulciano, Siena, Tuscany, Bologna, Padua

Duration8 days

From

USD 2,750

USD 2,668

Saving

USD 83

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Halloween Super Sales

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

4.8

(30 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

USD 3,637

Saving

USD 112

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18% OFF TODAY

Halloween Super Sales

La Dolce Vita - 11 days - Winter tours

No booking fees

Best price guaranteed

COACH TOUR: Take in the best of Italy on this 11-day journey from Rome, looping through Florence, Venice, and the sun-drenched south. Explore ancient ruins in Pompeii, cruise the canals of Venice, and marvel at the Vatican’s artistic treasures. Sip Tuscan wine in Montepulciano, discover Renaissance Florence, and see Pisa’s famous Leaning Tower. In the south, enjoy a formal dinner in Sorrento and a day trip to the glamorous island of Capri. With guided tours, scenic drives and plenty of local flavours, this trip blends history, culture and coastlines—perfect for anyone wanting a deep dive into Italy’s many highlights.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Sorrento, Florence, Bologn

Rome, Sorrento, Florence, Bologna, Venice, Tuscany, Naples, Capri

18% OFF TODAY

Duration11 days

From

USD 3,435

USD 2,832

Saving

USD 603

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Italian Expresso - 5 Days - Winter Tours

18% OFF TODAY

Halloween Super Sales

Italian Expresso - 5 days - Winter tours

No booking fees

Best price guaranteed

COACH TOUR: Explore the best of central Italy on this five-day journey from Rome to Venice, with scenic stops in Florence, Bologna and the Tuscan countryside. Visit Assisi and Siena en route to Florence, where Renaissance treasures and Tuscan cuisine await. Wander Bologna’s historic streets and enjoy a street food tasting before heading to Venice for gondolas, cicchetti and grand architecture. Wrap up with wine and views in hilltop Montepulciano before returning to Rome. With guided sightseeing, regional flavours and iconic landmarks throughout, this compact adventure is perfect for travellers keen to experience Italy’s cultural heart in style.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Tuscany, Florence, Bologna

Rome, Tuscany, Florence, Bologna, Venice

18% OFF TODAY

Duration5 days

From

USD 1,465

USD 1,208

Saving

USD 257

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Europe Jewel Christmas & New Year - Winter Tours

14% OFF TODAY

Halloween Super Sales

Europe Jewel Christmas & New Year - Winter tours

4.8

(18 reviews )

No booking fees

Best price guaranteed

The overall experience was a memorable one. There are a lot of good memories to cherish.

Christmas markets

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Amsterdam, Ghent, the Swiss Alps

Amsterdam, Ghent, the Swiss Alps, Paris, Rhine, Prague, Vienna, Budapest, Ljubljana, Venice, Tuscany

14% OFF TODAY

Duration14 days

From

USD 3,320

USD 2,847

Saving

USD 473

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Halloween Super Sales

Mediterranean Coastal Journey Spain, France & Italy - Winter tours

4.5

(24 reviews )

No booking fees

Best price guaranteed

The Mediterranean Tour was wonderful and will be fondly remembered for the rest of my lifetime. A favorite experience is difficult to choose as so many were great. I was awed by the visit to the Basilica of the Holy Family in Barcelona.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

1-99 yrs

Operated in

english

Destinations

Barcelona, Tuscany, Nice, Genoa

Barcelona, Tuscany, Nice, Genoa, San Gimignano, Costa Brava, Figueres, Marseille

Duration16 days

From

USD 5,499

USD 5,334

Saving

USD 165

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Europe Highlights Christmas - Winter Tours

9% OFF TODAY

Halloween Super Sales

Europe Highlights Christmas - Winter tours

No booking fees

Best price guaranteed

It’s the most wonderful time of the year on this 10-day Europe Highlights Christmas tour! This festive journey will take you from Italy to Switzerland and back again with countless adventures in between. Discover the beauty of Venice, Munich’s famous Christmas markets, the Amsterdam canals, the twinkling lights of Paris and the snowy Swiss Alps on Christmas day. Visit mountainous Innsbruck, explore the charming Belgian city of Ghent, cruise the Rhine River and admire Florence’s masterpieces. End the tour in Rome on New Year’s Eve after making memories to last a lifetime!

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Rome, Venice, Bavaria, Rhine, Am

Rome, Venice, Bavaria, Rhine, Amsterdam, Paris, the Swiss Alps, Tuscany

9% OFF TODAY

Duration10 days

From

USD 2,675

USD 2,430

Saving

USD 245

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Classic Europe Christmas & New Year - Winter Tours

11% OFF TODAY

Halloween Super Sales

Classic Europe Christmas & New Year - Winter tours

No booking fees

Best price guaranteed

Tick off Europe’s top destinations on this Europe Christmas & New Year tour. See London's sights and cruise the Rhine River in Germany and Amsterdam's canals. Capture famous landmarks such as the Leaning Tower of Pisa and the Eiffel Tower. Spend Christmas Day in the snowy Swiss Alps and visit the medieval town of Bruges. Taste and toast your way through Europe this festive season, savouring local delights in each country. Enjoy lunch at a British pub, indulge in Bavarian delights, sample Tuscan cuisine and try traditional Belgium waffles!

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

London, Munich, Amsterdam, Paris

London, Munich, Amsterdam, Paris, Burgundy, Swiss Alps, Tuscany, Rome, Venice

11% OFF TODAY

Duration14 days

From

USD 3,810

USD 3,390

Saving

USD 420

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All Tuscany Tours in Winter

9 Trips in Tuscany with 77 Reviews

Get a customized trip to Tuscany in Winter

9 Trips in Tuscany with 77 Reviews

Italy City Break - 5 Days - Winter tours

Discovery of Italy: 8 Days - Winter tours

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

La Dolce Vita - 11 days - Winter tours

Italian Expresso - 5 days - Winter tours

Europe Jewel Christmas & New Year - Winter tours

Mediterranean Coastal Journey Spain, France & Italy - Winter tours

Europe Highlights Christmas - Winter tours

Classic Europe Christmas & New Year - Winter 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 Tuscany Tours in Winter

9 Trips in Tuscany with 77 Reviews

Get a customized trip to Tuscany in Winter

9 Trips in Tuscany with 77 Reviews