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Discover Siena's highlights in 1.5 hours with this guided walking tour featuring panoramic views, iconic landmarks, and tasting local gelato and Tuscan wines.

This Siena wine tasting and gelato tasting tour offers a delightful way to see one of Italy’s most beautiful medieval towns. Priced at $63.05 per person, the tour spans approximately 1 hour and 30 minutes and includes visits to key landmarks, stunning vistas, and tastings of three artisan gelato flavors and Tuscan wines. The tour departs from Hotel NH Siena at 10:30 am, making it an ideal morning activity, especially for those wanting a relaxed yet insightful introduction to Siena.
Led by a certified local guide who has lived and worked in Siena for many years, this experience provides an authentic perspective on the city’s traditions, myths, and secrets. The small group size—limited to 12 travelers—ensures a more personalized and engaging experience. While the tour is suitable for most, it’s perfect for those interested in combining sightseeing with culinary delights. A key highlight is the opportunity to enjoy unique panoramic views, explore historic neighborhoods, and taste some of the best local gelato and wines Siena has to offer.
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The tour begins at Fortezza Medicea, a fortress offering some of Siena’s best panoramic vistas. From here, you’ll see the city walls and get a sweeping view of Siena’s colorful rooftops and medieval streets. The 30-minute stop is free of charge and provides perfect photo opportunities, along with a chance to hear stories about Siena’s history and mysteries from your guide.
This vantage point is not only beautiful but also historically significant, giving insight into Siena’s defensive architecture. Visitors can appreciate the distant rolling Tuscan hills while learning about the town’s strategic importance in the past.

Next, the tour takes you to Basilica Cateriniana di San Domenico, where a magnificent view of Siena’s towers and the Duomo unfolds. Here, the guide explains the importance of this basilica, built in honor of Saint Catherine of Siena. During this 15-minute stop, the group enjoys three delicious gelato flavors from an award-winning shop, showcasing the city’s renowned artisan craftsmanship.
The gelato tasting is a highlight, especially for those who appreciate authentic Italian desserts. The guide’s insights help deepen the experience, emphasizing Siena’s local flavors and traditions.

A quick 5-minute walk leads to Via della Sapienza, where a hidden medieval cave dating back to 600 BC awaits discovery. This underground site offers a glimpse into Siena’s ancient past and the history of local wine production. The guide shares stories about important wines of the world, connecting Siena’s historical wine culture with broader Mediterranean traditions.
This stop adds a fascinating layer to the tour, blending archaeology, history, and enology in a compact visit.

Next, the tour moves to Piazza Salimbeni, home to the world’s oldest bank founded in 1472. While the exterior can be admired in 20 minutes, the tour emphasizes Siena’s long-standing financial history and architecture.
Finally, the group arrives at Piazza del Campo, Siena’s most famous square and the site of the ancient Palio horse race. The 15-minute stop here allows visitors to soak in the lively atmosphere, admire the Palazzo Pubblico, and enjoy some local wines. This spot encapsulates Siena’s vibrant civic life and medieval charm, making it an ideal endpoint for the tour.
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The tour begins at Hotel NH Siena, located at Via La Lizza, 1, and ends in Piazza del Campo. The small group of up to 12 travelers ensures a relaxed pace and personalized interaction. The service animals are allowed, and the tour operates rain or shine, making it adaptable to weather conditions.
Booking typically requires advance reservation, with most travelers scheduling about 36 days in advance. The mobile ticket system simplifies check-in, and the tour includes free cancellation up to 24 hours before the start.

What truly distinguishes this experience is the combination of local expertise, culinary tastings, and stunning viewpoints. The guide’s local background and friendly approach receive high praise, making the visit more than just sightseeing. The gelato and wine tastings bring a delightful flavor to the tour, allowing participants to enjoy Siena’s best culinary products in context.
The duration and pace are well balanced, providing a comprehensive look at Siena’s highlights without feeling rushed. The focus on iconic landmarks and hidden gems like the medieval cave gives a well-rounded picture of the city.

This tour is ideal for travelers seeking a short but rich introduction to Siena. It suits those interested in history, architecture, and local culinary traditions. The small group size and personalized guide provide an intimate experience, perfect for first-time visitors or those wanting a taste of Siena’s authenticity.
While not designed for extensive walking or demanding physical activity, the stops involve some gentle strolling and standing, so comfortable shoes are recommended. The tour’s weather-dependent nature suggests checking the forecast for optimal enjoyment.
This guided walking tour offers a fantastic way to see Siena’s top sights, enjoy breathtaking views, and indulge in local foods and wines. The expert guide brings Siena’s stories alive, sharing insights into its history, legends, and secrets. The tastings of gelato and Tuscan wines add a delicious dimension, making this an especially memorable experience.
While the tour covers several landmarks, it remains manageable and engaging, perfect for those who want a compact, authentic taste of Siena in a relaxed setting. The free cancellation policy adds peace of mind, allowing flexible planning. This tour delivers genuine value for history enthusiasts, food lovers, and curious travelers alike.
“The guide was amazing! Kind, personable and grew up there! He gave great insights and introduced us to the best gelato of our entire European trip….”
How long is the Siena wine and gelato tour?
The tour lasts approximately 1 hour and 30 minutes, making it a perfect morning activity.
What is included in the price of $63.05?
Participants enjoy guided visits to key landmarks, three artisan gelato flavors, and Tuscan wines.
Where does the tour start and end?
It begins at Hotel NH Siena and ends at Piazza del Campo.
Is the tour suitable for all weather conditions?
Yes, the tour runs rain or shine. Weather may affect some outdoor stops but generally does not impede the entire experience.
Can I cancel the tour if my plans change?
Yes, free cancellation is available up to 24 hours before the start.
Is a large group involved?
No, the group is limited to 12 travelers, ensuring a more personalized experience.
Are service animals allowed?
Yes, service animals are permitted on this tour.
Will I get insider tips on Siena’s best restaurants?
Yes, the guide can provide recommendations for restaurants and activities upon request.
Do I need to reserve in advance?
Yes, most travelers book about 36 days in advance to secure a spot.
What makes this tour stand apart?
The combination of local expertise, scenic views, and culinary tastings creates a well-rounded and authentic Siena experience.