Siena Tours in November 2025
Planning for a trip to Siena during November? We offer 10+ tour packages to Siena departing in November 2025 that have 80+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Siena on your November holiday.
See all Siena November 2025 Tours
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10 Best November 2025 Tours in Siena
Join one of these handpicked Siena November 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
3% Off Today
For a truly immersive escape into the Tuscan lifestyle, "Local Living Italy—Tuscany San Gimignano" offers a week-long adventure centered in the medieval gem of San Gimignano. This guided wildlife trip invites you to settle into shared accommodations with fellow travelers and a knowledgeable CEO, all while having Rome and Florence at your fingertips.
Venture into the heart of Tuscany: stroll vineyard-laced hills, discover medieval treasures, and embrace your creative spirit amid the region’s rolling countryside. Optional day trips to Siena and Florence add depth for those who want to experience Italy’s cities, while ample free time lets you savor local wines or wander rustic farmsteads.
The unique selling point of this tour package is its focus on forging meaningful connections—with the land, local traditions, and your travel companions. Whether you’re a solo explorer or seeking a communal travel vibe, this trip provides a rare opportunity to live and breathe the authentic Tuscan way of life.
7 days
USD 1,749fromUSD 1,697
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
fromUSD 2,729
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 2,847
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
This self-drive tour offers you the opportunity to discover one of the most beautiful areas in Italy: Tuscany. Visit at your own pace and choose how you want to spend your days. Begin your Tuscan adventure in Montecatini Terme, a charming spa town nestled in the Province of Pistoia, ideal for relaxing amidst thermal waters and elegant architecture. Next, you may decide to visit Lucca, just 30 minutes away, where ancient walls and Roman streets lead to San Michele’s majestic piazza. Then, continue to Pisa and marvel at the iconic Leaning Tower, Baptistery and Duomo in the stunning Piazza dei Miracoli. Later, explore Florence, home to Renaissance treasures like the Duomo, Michelangelo’s David, and the Uffizi Gallery. The following day, immerse yourself in the rolling vineyards of Chianti, savoring wines in Radda and Greve, with a detour to picturesque Montefioralle. Onward to Siena, wander medieval lanes to Piazza del Campo, then step back in time in San Gimignano, famed for its towers and timeless views. Conclude your stay with panoramic scenes from Montecatini’s historic funicular before heading south toward Rome. In Rome, explore iconic landmarks such as the Colosseum, Pantheon, and Trevi Fountain. Stroll historic streets, savor authentic Italian cuisine and reflect on a journey filled with culture, beauty and timeless charm. This route is perfect for those seeking Scenic tours of Italy, blending culture, relaxation and breathtaking countryside.
7 days
fromUSD 629
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
See all Siena November 2025 Tours
Top Siena Tour Activities for November 2025
From city sightseeing tours to cultural, religious and historic sites and others, here are some popular tour activities in Siena with departures in November 2025.
Siena November 2025 Tours for all Age Groups
Siena tours in November 2025 designed for all ages—families, young adventurers, seniors, and everyone in between.
Siena November 2025 Tour Types
Discover Siena November 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 November 2025
Plan a multi-country or regional adventure across Siena in November 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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