Tuscany Winter Tours and Trip packages

Traveling to Tuscany in Winter? We offer 15+ tours, trips and vacation packages to Tuscany in Winter. Our Tuscany in Winter tour packages and trips have 590+ customer reviews. All the Tuscany Winter tour packages and trips are carried out by hand-picked, qualified local and international Tuscany tour operators.

Duration

4 days22 days

Day Tour
Multiday Tour

Departures

December 2025
January 2026
February 2026

Tour Types

Group tours
Private tours

Physical Rating

easy
moderate

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.

Guide Types

Guided Tours
Partially Guided Tours
Self Guided Tours

Start & End Location

Price

USD 694USD 9,272

Budget Tours
Luxury Tours

2 Trips in Tuscany with 26 Reviews

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

4.9

(25 reviews )

No booking fees

Best price guaranteed

Excellent trip with free time to explore on your own and plenty of included tour, interesting sights and great step on guides. Our guide, Ben was very, very good. Highly recommend this tour

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

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Via Francigena: Walk from Lucca to Siena - Winter tours

(1 review )

Trip customizable

Best price guaranteed

Discover the Tuscan countryside and culture on this 8-day self-guided walking tour. Through the extensive footpath network of the area, roughly following the traces of the Via Francigena, one of Europe’s most important ‘highways’ in medieval times, you walk from village to village and experience a full immersion in the world-famous Tuscan landscape. The tour is perfect as an introduction to the region and a great choice for people who love museums, galleries and Gothic and Romanesque architecture. You have plenty of time to visit attractions on most of the days. You will also have time to visit all the beautiful medieval villages and historic towns along the Via Francigena: starting from beautiful Lucca, you’ll pass through Fucecchio, San Miniato, Gambassi Terme, the stunning San Gimignano with its medieval skyscrapers and Monteriggioni, admired by Dante in his Divine Comedy. An optional detour can bring you to beautiful Colle Val d’Elsa and the tour ends in Siena, arguably the most perfectly preserved medieval town in Tuscany. This tour threads together some of the most attractive towns and villages in Tuscany in an eloquent procession. However, the emphasis of the tour is to enjoy the countryside, the rolling vineyards, the poppies in spring and the wild cyclamen in autumn. The area north of Siena is an amazing landscape of rolling hills, alternating vineyards and forests, while cypresses line the way leading to the distant farmhouses. Walking here is an unforgettable experience and many of the views have barely changed for hundreds of years. Accommodation and some meals are included. You spend a night in one of the best agriturismos in Tuscany, and the final night in the heart of Siena, in one of the most characteristic little hotels. This is a moderately easy tour which is suitable for those who have some experience of walking and a good general physical condition.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel, Hostel

Age Range

18-99 yrs

Operated in

English

Destinations

Siena, Tuscany, Lucca, Altopasci

Siena, Tuscany, Lucca, Altopascio, San Miniato Alto, Gambassi Terme, San Gimignano, Monteriggioni

Duration8 days

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2 Trips in Tuscany with 26 Reviews

Upcoming Departures

Dec 01

10+ seats remaining

Mar 13

10+ seats remaining

Upcoming Departures

Dec 18

Dec 19

Tours and Trip Packages to Tuscany in Winter

Get a customized trip to Tuscany in Winter

2 Trips in Tuscany with 26 Reviews

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

Via Francigena: Walk from Lucca to Siena - Winter tours

2 Trips in Tuscany with 26 Reviews

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Food, wine, events and nightlife

Adventure and sport

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Tours and Trip Packages to Tuscany in Winter

Get a customized trip to Tuscany in Winter

2 Trips in Tuscany with 26 Reviews

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

Via Francigena: Walk from Lucca to Siena - Winter tours

2 Trips in Tuscany with 26 Reviews