Siena Tours in December 2026
Planning for a trip to Siena during December? We offer 10+ tour packages to Siena departing in December 2026 that have 270+ 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 2026 Tours in Siena
Join one of these handpicked Siena December 2026 tour packages, tailored to the season.
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
Journey through Italy’s timeless wonders with the 'Amazing Italy' tour—a 15-day city sightseeing trip that brings together the country’s most celebrated destinations. Designed for travelers who crave a relaxed yet immersive experience, this guided group tour blends classic landmarks, art, and natural beauty into a seamless adventure.
Your Italian escapade launches in Rome, where ancient history and vibrant street life converge. Step back in time as you explore the iconic Colosseum, marvel at the grandeur of St. Peter’s Basilica in Vatican City, and stroll through the eternal city’s piazzas. The rolling hills and renowned wineries of Tuscany await, with stops in Monteriggioni and San Gimignano before arriving in Florence—the cradle of the Renaissance.
Continue your journey by admiring the Leaning Tower of Pisa, then take in the dramatic cliffside villages of Cinque Terre along the Italian Riviera. In Venice, glide through enchanting canals, and in Naples, discover Europe’s greatest architectural treasures. The adventure extends to the Blue Grotto of Capri before uncovering the mysteries of ancient Pompeii, preserved beneath Mount Vesuvius’s ashes.
The tour’s unique selling point lies in its artful balance: a comprehensive itinerary with ample time to savor each destination, guided by local experts. With comfortable accommodations, inclusive transport, and select meals, this trip is perfect for discerning travelers longing for a rich, leisurely exploration of Italy’s greatest marvels.
15 days
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
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
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
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
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
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
18% Off Today
Drive through some of Italy's most iconic region on this eight-day tour that takes you through Lucca, Siena and Florence. Tuscany is brimming with secluded valleys, magnificent rolling hills and majestic medieval villages boasting bustling restaurants, piazzas and ancient narrow cobble-stoned streets. Its rich landscape is complemented by towns overflowing with Renaissance art and architecture.
8 days
8% Off Today
The rolling hills and timeless charm of Tuscany await on the "Spotlight on Tuscany" tour, a 9-day art and architecture adventure through Italy’s most cherished region. Starting and ending in Montecatini Terme, this moderate-activity trip is crafted for those who revel in culture, history, and authentic flavors.
Enjoy a 7-night stay in the renowned spa town of Montecatini Terme, your base for exploring Pisa, Florence, San Gimignano, and Lucca—Italy’s best-kept secret. Learn the region’s history at WWII’s Gothic Line and the Museum of Liberation. Delight in hands-on experiences, from a Tuscan cooking class to cheese tastings at a local farm. Savor world-class wines and the region’s celebrated cuisine, and enjoy free time to wander Florence’s artistic treasures.
With accommodations, transport, and meals included, the unique selling point is the blend of immersive culinary and cultural activities, ensuring each traveler connects deeply with the heart of Tuscany in a single, thoughtfully curated tour package.
9 days
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Top Siena Tour Activities for December 2026
From city sightseeing tours to art and architecture and others, here are some popular tour activities in Siena with departures in December 2026.
Siena December 2026 Tour Types
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