Things to Do in Siena: The Very Best Tours & Experiences to Book Right Now

Siena is one of Tuscany’s most captivating gems—a place where time seems to have stood still since the Middle Ages. If you are currently planning your itinerary, you are likely wondering about the absolute best things to do in Siena to experience its authentic charm, maximize your time, and bypass the notorious crowds, especially during peak travel seasons.

This guide is specifically crafted for savvy travelers who want a stress-free planning experience. Below, you will find the top-rated Siena tours, up-to-date pricing, direct booking links, and incredible perks like flexible payment options.

Top Tours in Siena and Beyond: Which One is Right for You?

To truly appreciate the city and its postcard-perfect surroundings, booking an expert-led tour or securing priority entrance is the ultimate smart move. Whether you are looking for a cultural walk through the historic Contrade (neighborhoods), an outdoor equestrian adventure, or an immersive wine tasting among rolling vineyards, Siena has something for every travel style.

Securing your tickets online ahead of time doesn’t just keep your trip organized; it saves you precious hours that would otherwise be wasted waiting in lines under the Tuscan sun. Best of all, every single experience selected below features free cancellation up to 24 hours in advance, meaning you can lock in your spot today with zero risk and adjust your plans if things change.

Here is a quick comparison table to help you review prices and key features at a glance before diving into the details:

Horseback Riding Tour in the Stunning Sienese Countryside

If you want to step away from the bustling city streets and immerse yourself in nature, this is the perfect Siena tour for you. Hosted by Colle Pinzuto Horseriding, this excursion invites you to ride through rolling hills, silver-green olive groves, rivers, and those iconic cypress-lined roads that have made Tuscany world-famous.

Your expert guide will lead the way, pointing out local flora and fauna while sharing fascinating medieval history, stories, and legends of the region. The trail ride is fully accessible to everyone—even if you have never ridden a horse before—as the horses are exceptionally well-trained and gentle. All safety gear and an introductory lesson are included. For a truly special touch, you can opt to add a riverside picnic or a local wine tasting.

• Price: From €62 per person.

• Please note: This activity is not suitable for children under 14, pregnant guests, or individuals over 113 kg (250 lbs).

👉 Check available dates and book your horseback riding tour on GetYourGuide

Priority Entrance to the Siena Cathedral & Piccolomini Library

When deciding how to best visit Siena, the Cathedral (Duomo) is an absolute non-negotiable masterpiece. This fast-track ticket allows you to completely bypass the exhausting ticket office lines and walk straight into one of Europe’s most acclaimed artistic treasures.

Once inside, you can marvel at the breathtaking inlaid marble mosaic floor, along with intricate sculptures by Michelangelo, Donatello, and Nicola Pisano. The ticket also grants you access to the spectacular Piccolomini Library, renowned for its vibrant, floor-to-ceiling frescoes painted by Pinturicchio. An official digital audio guide is included, which you can easily access on your smartphone via a QR code upon arrival.

• Price: Just €12 per person for an invaluable cultural experience.

👉 Get your skip-the-line Siena Cathedral tickets on GetYourGuide now

Guided Tour of Siena and the Duomo (Italian Language)

For those planning a quick Siena day trip and looking to maximize their time, this 1-hour walking tour is a fantastic choice. Led by an expert local guide from the Associazione Centro Guide Siena, you will stroll through the historic via di Città straight into the majestic Piazza del Campo—the beating heart of the city and the home of the legendary Palio horse race.

From there, your guide will escort you inside the Cathedral to uncover the history behind monumental works by Bernini, Michelangelo, and Donatello. A great bonus: if the cathedral is temporarily closed for extraordinary religious services, the tour seamlessly redirects to the fascinating Santa Maria della Scala museum complex, ensuring you still get a rich, uninterrupted cultural experience.

• Price: From €35 per person (entrance tickets included).

• Note: This specific tour is conducted in Italian.

👉 Check availability and book this Guided City Tour on GetYourGuide

Organic Wine Tasting at a Private Tuscan Castle

For wine lovers, this stands out as one of the most exclusive escursioni Siena (Siena excursions) has to offer. Tucked away in the peaceful Merse Valley just a short drive from the city center, the medieval Castello Poggiarello opens its private gates for a literal step back in time.

The experience includes a guided walk through the castle’s Renaissance gardens, a private 16th-century chapel, and the estate’s charming organic winery. After exploring the history of the grounds, you can sit back and relax while tasting premium organic wines—featuring both traditional Sangiovese and surprising international varieties—paired with delicious local Tuscan snacks. On-site private parking is completely free for guests.

• Price: From €43 per person.

• Accessibility: This property is fully wheelchair accessible.

👉 Secure your spot for this exclusive Castle Wine Tasting on GetYourGuide

Medieval Walking Tour & Priority Duomo Entrance (English)

Want an in-depth look at the city from an insider’s perspective? This 2-hour walking tour—fully conducted by a certified, English-speaking local guide—takes you off the beaten path to discover the authentic soul of medieval Siena.

Starting at Piazza San Domenico, you will visit the historic Basilica dedicated to St. Catherine of Italy, admire Palazzo Salimbeni (the oldest surviving bank in the world), and learn all about the fierce rivalries of the city’s Contrade. The tour concludes beautifully with skip-the-line priority entrance into the Siena Cathedral, where your guide will lead you through the awe-inspiring, art-packed chapels.

• Price: From €40 per person.

• Dress Code: Because you will be entering an active place of worship, modest dress is strictly required (shoulders and knees must be covered).

👉 Book your English-guided walking tour and Duomo experience on GetYourGuide

The Perfect Finish to Your Tuscan Adventure: Where to Stay

After a memorable day spent riding through rolling vineyards or admiring Renaissance frescoes, there is truly nothing better than retreating to the luxury and tranquility of your own private estate.

If you want to experience the true magic of this region, elevate your holiday by booking an exclusive historic villa with TuscanMansions. Perfectly situated in the most scenic, panoramic corners of the surrounding countryside, our curated luxury properties feature private swimming pools, breathtaking views of the Tuscan hills, and an unmatched level of privacy and comfort.

Don’t settle for a generic hotel room. Treat yourself and your loved ones to a holiday of a lifetime. Visit the TuscanMansions website today to find the perfect luxury villa for your next dream escape to Tuscany!