Siena Tours in December 2025
Planning for a trip to Siena during December? We offer 10+ tour packages to Siena departing in December 2025 that have 70+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Siena on your December holiday.
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10 Best December 2025 Tours in Siena
Join one of these handpicked Siena December 2025 tour packages, tailored to the season.
Craving a taste of Italy’s most iconic UNESCO sites in just five days? The "Italy City Break" is your passport to a whirlwind of art, history, and vibrant culture. Starting from Rome, you’ll journey to the medieval town of Assisi—birthplace of St Francis—before heading to Florence, the city where the Renaissance began.
Wander through Florence’s architectural marvels, then continue north to explore the artistic treasures of Bologna, Padua, and the canals of Venice. The adventure doesn’t stop there; Tuscany’s world-renowned vineyards invite you for a final taste of la dolce vita before a return to Rome.
Tailored for young adults and seasoned travelers who appreciate efficient yet immersive sightseeing, this trip ensures you soak up Italy’s best in record time. The guided tour package includes essential highlights, expert insights, and a seamless travel experience.
USP: A curated route through Italy’s cultural heartlands, blending world heritage sites, culinary delights, and breathtaking scenery—making it a perfect short escape for those who want to experience Italy’s essence without compromise.
5 days
fromUSD 1,780
3% Off Today
Italy’s finest cities await on the 'Treasures of Italy' tour, a 13-day sightseeing journey designed especially for seniors who appreciate comfort and culture. Starting and ending in Rome, you’ll travel through Florence, Milan, Siena, and more, enjoying curated experiences and rich history at every turn. All hotels, transportation, and meals are included, letting you focus on the scenery and stories. The true highlight of this trip is its comprehensive itinerary, offering seniors an easy-paced yet thorough exploration of Italy’s artistic and architectural masterpieces.
13 days
USD 1,901fromUSD 1,844
From the medieval charm of Assisi to the artistic grandeur of Florence, the Discovery of Italy: 8 Days tour offers an easy-paced journey for young adults and seasoned travelers alike. Explore the Leaning Tower of Pisa, wander Bologna’s elegant streets, and soak in Venice’s romantic canals. The itinerary captures Tuscany’s rolling hills and Montepulciano’s beauty, with Rome bookending your adventure. The unique selling point: a curated blend of Italy’s top attractions and cultural encounters, ideal for those eager to uncover the best of Italy in a single trip.
8 days
fromUSD 2,750
Picture yourself winding through the Chianti hills, glass in hand, as you embark on the "Private Gourmet Wine Tour in Tuscany." This four-day easy-paced trip is designed for experienced travelers who appreciate the finer things in life. Savor world-renowned wines like Brunello di Montalcino and Chianti DOC, indulge in local delicacies, and explore the storybook villages of Volterra and San Gimignano. With private guidance and a flexible itinerary, this tour package blends scenic landscapes, culinary delights, and personalized attention. The USP? Exclusive access to authentic Tuscan experiences—perfect for those seeking both indulgence and cultural depth in their Italian getaway.
4 days
fromUSD 2,840
3% Off Today
From the cobbled streets of Rome to the breathtaking vistas of Salerno, 'Golden Italy' is a 15-day sightseeing adventure crafted for seniors. This group tour brings you through Perugia and five additional Italian gems, with all hotels, transport, and meals arranged for a seamless experience. The USP is its extensive coverage—providing a comprehensive, easy-paced exploration of Italy’s most beloved cities and regions, perfect for travelers seeking a longer, more immersive Italian journey.
15 days
USD 2,412fromUSD 2,340
3% Off Today
Indulge in the romance of Rome, Siena, and Florence on the 'Roman Holiday' tour—a relaxed 8-day group sightseeing trip designed with seniors in mind. With all hotels, transport, and meals included, you can enjoy the journey with peace of mind. This tour’s unique appeal lies in its carefully curated experiences, combining iconic sights with comfortable travel and plenty of time for leisure. It’s the perfect tour package for those who wish to savor Italy’s beauty without any rush.
8 days
USD 1,055fromUSD 1,023
3% Off Today
From the grandeur of Rome to the elegance of Milan, 'The Essential of Italy end Milan' offers a 9-day sightseeing tour tailored for seniors. This group trip connects you with Italy’s most iconic cities, all while ensuring your comfort through included accommodation, transport, and meals. Designed for those who want to discover Italian art, cuisine, and history at an easygoing pace, the standout feature here is the seamless blend of must-see sights and relaxed travel—making it an ideal tour package for mature explorers.
9 days
USD 1,248fromUSD 1,211
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.
8 days
fromUSD 691
Step into a world of art, history, and romance on the "Explore Italy - 4 Days" tour—an ideal short getaway for young adults and experienced travelers. Beginning with a convenient pick-up in Rome, your journey takes you through the medieval charm of Assisi, the UNESCO-listed beauty of Siena, and the Renaissance masterpieces of Florence.
Wander the elegant streets of Bologna, marvel at the grandeur of Padova’s Sant’Antonio Basilica, and let the magic of Venice’s canals and bridges capture your imagination. Every stop is packed with iconic sights and authentic local flavor, making this adventure as enriching as it is efficient.
The unique selling point of this tour package is its expertly curated route—allowing travelers to experience the very best of Italy’s culture, architecture, and cuisine in just four days. For those seeking a memorable Italian escape, this trip delivers history, beauty, and inspiration at every turn.
4 days
fromUSD 1,630
3% Off Today
Venice and Rome form the bookends of 'The Essential of Italy,' an 11-day guided group tour crafted for the senior traveler. This trip allows you to experience Italy’s cultural heart with thoughtfully arranged accommodation, transport, and meals. The sightseeing itinerary balances famous landmarks with local flavor, ensuring you enjoy Italy’s charm without overexertion. The USP is the stress-free structure—providing seniors with a worry-free way to see Italy’s highlights and hidden gems, all at a gentle, enjoyable tempo.
11 days
USD 1,577fromUSD 1,530
See all Siena December 2025 Tours
Top Siena Tour Activities for December 2025
From city sightseeing tours to cultural, religious and historic sites and others, here are some popular tour activities in Siena with departures in December 2025.
Siena December 2025 Tours for all Age Groups
Siena tours in December 2025 designed for all ages—families, young adventurers, seniors, and everyone in between.
Siena December 2025 Tour Types
Discover Siena December 2025 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
Get a customized trip to Siena in December 2025
Plan a multi-country or regional adventure across Siena in December 2025, 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
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