Siena Tours in August 2026
Planning for a trip to Siena during August? We offer 20+ tour packages to Siena departing in August 2026 that have 200+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Siena on your August holiday.
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10 Best August 2026 Tours in Siena
Join one of these handpicked Siena August 2026 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
Imagine wandering through the rolling vineyards and sun-drenched hills of Tuscany, glass of Chianti in hand, with Renaissance cities as your backdrop. The "Tuscany Walks & Chianti Wines" trip is tailored for seasoned travelers who appreciate a balance of invigorating exploration and cultural depth. Over eight days, this guided trekking tour lets you absorb the essence of the region at a comfortable, moderate pace, taking in Chianti, Siena, San Gimignano, Florence, and more.
Your home base is the welcoming village of Pancole, where the Sabatini family’s hospitality offers a true taste of Italian life. Daily walks wind through lush vineyards and olive groves, leading to iconic sites and off-the-beaten-path treasures alike. Expert guides share Tuscany’s history and secrets as you explore Siena’s medieval streets and Florence’s Renaissance masterpieces, ensuring every moment is rich with local insight.
This tour package’s unique selling point is its combination of scenic hikes, immersive cultural experiences, and convivial wine tastings that foster genuine connections with fellow travelers. With all accommodation, transport, and meals included, your only focus is to savor Tuscany’s flavors and vistas. If you’re seeking a walking tour that weaves together fine wine, local hospitality, and historical wonders, this journey through the heart of Italy is not to be missed.
8 days
USD 2,775fromUSD 2,692
Step into the heart of Tuscany and experience its timeless beauty on the "Via Francigena: Best of Tuscany" walking tour. Over nine days, this self-guided journey leads travelers along the famed pilgrimage route from San Miniato Alto to Buonconvento, passing through San Gimignano, Monteriggioni, and Siena. Each day’s walk offers a blend of historic hamlets, fortified towers, and rolling vineyards, with achievable daily distances suited for moderately active explorers. Along the way, indulge in regional delicacies like white truffles, Siena’s pici pasta, and saffron from San Gimignano. Evenings are spent in carefully selected hotels and agriturismi, combining authentic hospitality with comfort. The unique selling point: this tour package immerses you in Tuscany’s best food, landscapes, and culture—all along an ancient pilgrimage trail.
9 days
fromUSD 1,290
Southern Tuscany’s rolling hills and medieval wonders await on the "Via Francigena: Southern Tuscany from Siena" tour. Over eight days, this self-guided trek takes you from Siena through San Quirico d’Orcia, Radicofani, and other picturesque villages, traversing a landscape of lunar-like Crete Senesi and cypress-lined backroads. The region’s historic context and stunning vistas provide a rewarding backdrop for moderately active travelers. The unique selling point: this tour package delivers an immersive journey through one of Italy’s most beautiful rural regions, where every day’s walk unveils new cultural and natural treasures along the ancient Via Francigena.
8 days
fromUSD 1,260
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
Italy’s classic wonders come alive on the "Grand Journey of Italy - 11 Days," an easy-paced tour designed for experienced travelers eager to savor the country’s highlights. Starting in Rome, this trip sweeps you through the hilltop charm of Assisi, the artistic treasures of Florence, and the iconic Leaning Tower of Pisa.
Stroll the refined streets of Bologna, glide through the romantic canals of Venice, and soak in Tuscany’s rolling landscapes. The adventure continues south to the haunting ruins of Pompeii, the coastal allure of Sorrento, and the sunlit glamour of Capri—each stop offering a fresh perspective on Italy’s rich heritage.
Throughout the journey, you’ll enjoy comfortable accommodations, seamless transport, and insightful guidance, ensuring a worry-free exploration of each destination. The tour finishes back in Rome, closing the circle on an epic Italian experience.
What makes this tour stand out? Its comprehensive itinerary brings together Italy’s most beloved cities and scenic regions in one seamless package—perfect for travelers seeking a grand, yet relaxed, immersion into Italian culture and history.
11 days
fromUSD 5,695
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
16% Off Today
Set out on a 22-day grand tour across Europe, discovering the continent’s most celebrated cities and hidden treasures. The Best of Europe tour, beginning and ending in London, is perfectly crafted for experienced travelers and seniors seeking a moderate adventure through Paris, Rome, Amsterdam, Venice, and many more. Explore castles, sip local beers, and take in the beauty of Budapest, Vienna, Prague, and Zagreb on expertly guided excursions. With built-in free days, you’ll have the flexibility to follow your own interests or simply soak up the atmosphere. The standout feature of this tour package is its comprehensive coverage of both Western and Eastern Europe, ensuring an unparalleled variety of landscapes, cultures, and experiences in a single, unforgettable journey.
22 days
USD 4,835fromUSD 4,085
Follow in the footsteps of medieval pilgrims on the "Via Francigena: Lucca to Siena" tour, an 8-day self-guided hiking trip through Northern Tuscany’s enchanting landscapes. Ideal for experienced travelers and seniors with a moderate sense of adventure, this private tour lets you traverse the flat plains of Val d’Elsa, ascend into the Tuscan hills, and explore UNESCO-listed towns such as San Gimignano and Monteriggioni. Comfortable, family-run accommodations and delicious local cuisine enhance each day’s journey. The unique selling point of this tour package is the freedom to experience Italy’s iconic countryside and historic villages at your own pace, steeped in tradition and beauty.
8 days
fromUSD 1,190
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
See all Siena August 2026 Tours
Top Siena Tour Activities for August 2026
From city sightseeing tours to art and architecture and others, here are some popular tour activities in Siena with departures in August 2026.
Siena August 2026 Tours for all Age Groups
Siena tours in August 2026 designed for all ages—families, young adventurers, seniors, and everyone in between.
Siena August 2026 Tour Types
Discover Siena August 2026 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
Get a customized trip to Siena in August 2026
Plan a multi-country or regional adventure across Siena in August 2026, 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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