Montepulciano Tours in September 2026
Planning for a trip to Montepulciano during September? We offer 10+ tour packages to Montepulciano departing in September 2026 that have 20+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Montepulciano on your September holiday.
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10 Best September 2026 Tours in Montepulciano
Join one of these handpicked Montepulciano September 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
Indulge in the romance and history of Italy on the Ultimate Italy trip, a two-week cultural odyssey from Rome to Venice. Wander the ancient ruins of Rome, admire the Renaissance glory of Florence, and traverse the colorful villages of Cinque Terre. Glide along Venetian canals, experience the elegance of Lake Como, and savor local wines and culinary delights in Tuscany. With expert guides and small group camaraderie, this tour package stands out for its comprehensive immersion in Italy’s art, history, and la dolce vita. The unique selling point: a seamless journey blending iconic sights with authentic local experiences.
14 days
Tuscan Adventure: Rome to Florence is a seven-day Italian escape, perfect for those looking to savor the country’s cultural richness and culinary delights. Stroll through Rome’s ancient ruins, sip wine in Montepulciano, and discover Siena’s medieval charm, all led by a knowledgeable Chief Experience Officer. With immersive city walks, local tastings, and a relaxed pace, this small group tour promises an authentic taste of Tuscany. The unique selling point? A harmonious blend of art, history, and gastronomy, making it an ideal trip for travelers seeking the soul of Italy.
7 days
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
For experienced travelers craving an authentic taste of Italy, A Taste of Tuscany Self-Guided Walking offers a moderate, immersive trekking adventure through the heart of Tuscany. Over 8 days, wander from Chianciano Terme through picturesque chestnut forests, rolling vineyards, and ancient olive groves, discovering medieval villages and Roman baths along the way. Sample world-renowned Vino Nobile, indulge in local Pecorino cheeses, and soak in the rejuvenating thermal springs of Bagno Vignoni. This tour’s unique appeal lies in its blend of self-guided freedom and deep local interaction, allowing walkers to savor Tuscany’s culinary and cultural riches at their own pace.
8 days
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
Let Italy’s timeless wonders sweep you away on the "Highlights of Italy" tour, a nine-day journey from Rome to Venice. This adventure immerses you in the heart of Italy’s history, art, and flavors—stand in awe of Rome’s ancient ruins, get lost in Florence’s Renaissance masterpieces, and soak up the romance of Venice’s canals. Indulge your senses in Montepulciano, savoring regional wines and culinary delights. With a perfect mix of guided sightseeing and free time, this trip is ideal for those who want to experience Italy’s highlights at a comfortable pace. The unique selling point is the tour’s comprehensive blend of iconic sites and gastronomic pleasures—delivering the essence of Italy in one unforgettable package.
9 days
Set off on a 13-day journey from Rome through Italy’s most captivating regions. Begin at Montecassino and moving WWII sites, then continue into Apulia with stops in Trani, Polignano a Mare, and the UNESCO-listed trulli of Alberobello. Discover Baroque Lecce, coastal Otranto, and Gallipoli before exploring Matera’s cave dwellings and Castelmezzano’s dramatic peaks. From Salerno, sail the Amalfi Coast to Sorrento, Positano, and Amalfi. Hike Mount Vesuvius, uncover Pompeii, and pause for a day in Rome. Continue to medieval Orvieto, discover Florence's history, and see the thermal baths of Bagno Vignoni. Discover the towns of Sovana and Capodimonte before ending back in Rome.
13 days
Uncover the beauty of central Italy on a 6-day tour from Rome through Tuscany and beyond. Explore the cliff-top city of Orvieto, admire Siena’s Gothic splendour, and enjoy the Renaissance treasures of Florence. Visit the colourful villages of Cinque Terre, marvel at the Leaning Tower of Pisa, and wander the medieval streets of Lucca and Volterra. Journey through the rolling landscapes of Montepulciano and the Val d’Orcia before discovering the Etruscan heritage of Sovana and the tranquil shores of Lake Bolsena.
6 days
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Top Montepulciano Tour Activities for September 2026
From explorer tours to cultural, religious and historic sites and others, here are some popular tour activities in Montepulciano with departures in September 2026.
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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
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
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
Set off on a 13-day journey from Rome through Italy’s most captivating regions. Begin at Montecassino and moving WWII sites, then continue into Apulia with stops in Trani, Polignano a Mare, and the UNESCO-listed trulli of Alberobello. Discover Baroque Lecce, coastal Otranto, and Gallipoli before exploring Matera’s cave dwellings and Castelmezzano’s dramatic peaks. From Salerno, sail the Amalfi Coast to Sorrento, Positano, and Amalfi. Hike Mount Vesuvius, uncover Pompeii, and pause for a day in Rome. Continue to medieval Orvieto, discover Florence's history, and see the thermal baths of Bagno Vignoni. Discover the towns of Sovana and Capodimonte before ending back in Rome.
13 days
Uncover the beauty of central Italy on a 6-day tour from Rome through Tuscany and beyond. Explore the cliff-top city of Orvieto, admire Siena’s Gothic splendour, and enjoy the Renaissance treasures of Florence. Visit the colourful villages of Cinque Terre, marvel at the Leaning Tower of Pisa, and wander the medieval streets of Lucca and Volterra. Journey through the rolling landscapes of Montepulciano and the Val d’Orcia before discovering the Etruscan heritage of Sovana and the tranquil shores of Lake Bolsena.
6 days
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