Siena walking tour with lunch & Chianti wine

If you’re dreaming of wandering through the charming streets of Siena, soaking up its history, tasting regional goodies, and enjoying some local wines, this tour might catch your eye. We’ve looked into one highly-rated experience that promises all of that—an immersive small-group walking tour that combines Siena’s secrets, delicious Tuscan fare, and regional wines in just a few hours.

What really stands out about this tour? First, the knowledgeable guides who bring Siena’s stories to life. Second, the well-curated food and wine tastings that give you a taste of the region in a relaxed, friendly setting. But, like any experience, it’s not perfect—one thing to consider is that the tour runs for about two and a half hours, so it’s a fair amount of walking, which could be tiring if you’re not used to it. It’s ideal for those who love history, food, and wine, and want an authentic, small-group experience that’s more personal than a larger bus tour.

Key Points

• Small group size (max 12) fosters a more intimate, engaging experience.
• Includes food and wine tastings—from gelato to prosecco, plus a hearty Tuscan lunch.
• Rich in Siena’s history and secrets, with stops at lesser-known spots.
• Ideal for food lovers and history buffs who want a relaxed, educational outing.
• Offers vegetarian options and is suitable for most travelers.
• Price reflects a full experience with guide, tastings, and meals, making it a good value.

What to Expect from This Siena Walking Tour

This tour is designed to give you a genuine feel for Siena, beyond the typical tourist spots. It’s a well-balanced mix of culture, food, and wine, all wrapped in a small-group setting. You’ll meet your guide at the Hotel NH Siena, ready to start your adventure around 10:30 am, and the experience wraps up in Piazza del Campo, the city’s iconic square.

The Itinerary Breakdown

Piazza san Domenico & Gelato Tasting

Your first stop is near the Basilica of San Domenico, where you’ll get a chance to sample award-winning organic gelato—three flavors that highlight regional ingredients. This is a sweet, refreshing way to start the tour and get a taste of local craftsmanship. Guests have raved about the gelato, with one reviewer calling it “one of the best tours I’ve been on,” citing the interesting stories and delicious treats as highlights. At just 15 minutes, it’s a quick but memorable introduction.

Hidden Underground & Medieval Cave

Next, you’ll venture underground to explore a medieval cave dating back to 600 BC—a secret spot not open to the public usually. This is a fascinating peek into Siena’s ancient past, and the guide will share stories that aren’t found in guidebooks. It’s also where you’ll see a collection of red wines, adding to the mystique. This stop is free of charge but offers a rare glimpse into Siena’s underground history—definitely a highlight for those intrigued by the city’s layers.

Views Over Siena’s Oldest Bank

One of the most unique parts of this tour is learning about Siena’s oldest bank, still in operation since 1472. The guide will point out the building and explain its significance, offering insight into Siena’s longstanding financial history. Seeing a bank that’s centuries old, still functioning today, is a little reminder of the city’s enduring traditions.

Piazza Tolomei & Local Secrets

Moving to Piazza Tolomei, you’ll get to admire medieval buildings, historic cafés, and hidden alleys. Here, the guide shares local stories and anecdotes—a chance to see Siena’s everyday life beyond the tourist spots. This part of the tour is particularly appreciated for giving you a more personal connection to the city, with reviews mentioning the “interesting information about the city and local traditions.”

Piazza del Campo & Wine Tasting

Of course, no trip to Siena is complete without standing in Piazza del Campo, the heart of Siena’s famous Palio horse race. Here, you’ll enjoy a 30-minute sparkling wine tasting, featuring regional Prosecco and local wines. This tasting isn’t just about drinking; it’s an educational moment where your guide explains regional wine-making traditions, which many guests found both enjoyable and informative.

Tuscan Lunch in Via Pantaneto

The grand finale is a full-fledged Tuscan lunch in a traditional Osteria. Think homemade Pici pasta, Pecorino cheese, bruschetta with extra virgin olive oil, and Ricciarelli biscuits—paired with Chianti or white wine. The meal lasts about an hour, giving you plenty of time to relax and chat with your group. Reviewers have consistently loved the quality of the food, with comments highlighting the “delicious” dishes and the hospitable atmosphere.

The Value of the Experience

At $100.72 per person, this tour offers a lot. It’s not just about ticking sights off a list; it’s about feeling immersed in Siena’s culture through conversations, food, and wine. The guide’s local knowledge shines through, making each stop meaningful. Plus, with vegetarian options available, it’s accommodating for different dietary needs.

The tour’s inclusion of guide, tastings, and lunch makes it a good value, especially given the small group size that ensures more personal attention. The maximum of 12 travelers means you’ll get to ask questions and interact, which many reviews note as a plus.

What Travelers Say

Most reviews are glowing—many call it one of the best tours they’ve taken, praising the friendly guides, interesting stories, and delicious food and wine. One reviewer noted that the tour was longer than expected, which they saw as a plus, since it meant more time to enjoy Siena’s sights and flavors.

There are a few less positive comments—one reviewer claimed the lunch was “a disaster,” but they clarified it was not with this tour provider, implying they might have been confused about which experience they booked. The majority of feedback highlights knowledgeable guides, great food, and authentic local experiences.

Practical Details and Tips

This is a walking tour, so wear comfortable shoes. The group size is small, which makes it suitable for those who prefer a more intimate experience and less waiting around. The tour starts at 10:30 am, fitting nicely into a morning itinerary, and ends in the heart of Siena. Be sure to check the weather forecast, as the tour runs rain or shine—most travelers find Siena’s streets charming, even in less ideal weather.

The tour is suitable for most people, but keep in mind it involves quite a bit of walking around Siena’s historic streets. The lunch menu may vary seasonally, but you’ll always get regional Tuscan favorites.

If you’re traveling with dietary restrictions, vegetarian options are available. The tour does not include entry to Siena’s Duomo, which costs €12 if you decide to visit afterward.

Is This Tour Right for You?

This experience is ideal if you love history, want a personalized look at Siena, and enjoy tasting regional food and wine. It’s perfect for curious travelers who want a relaxed, engaging day with a small group, avoiding busloads of travelers. If your goal is to see Siena’s famous sights with a knowledgeable guide and taste a bit of Tuscany along the way, this tour hits the mark.

It might not be the best fit if you prefer a more structured sightseeing schedule with less walking or if you’re traveling on a tight budget. Similarly, if you’re after a comprehensive guided tour through Siena’s interior sites like the Duomo, you’ll need to pair this with other experiences.

FAQs

Is this tour suitable for vegetarians?
Yes, vegetarian options are available, especially during the meal portion, and the guide will accommodate dietary preferences.

How long does the tour last?
The walking part runs for approximately 2 hours and 30 minutes, including stops, with the meal lasting about an hour.

What’s included in the price?
You get a licensed guide, gelato tasting, a full Tuscan lunch, wine and Prosecco tastings, and access to special stops like the underground cave and historic bank.

Where does the tour start and end?
It begins at Hotel NH Siena and finishes in Piazza del Campo.

Are there any additional costs?
Entry to Siena’s Duomo costs €12 if you choose to visit separately; otherwise, the tour price covers everything else.

Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours in advance, which offers flexibility if your plans shift.

If you’re seeking an authentic, small-group experience that blends Siena’s history, architecture, delicious food, and regional wines, this tour is worth considering. It’s especially good for those who want to learn from friendly guides and enjoy a relaxed, immersive day. The combination of engaging stories, tasty tastings, and a hearty Tuscan lunch makes it a memorable way to experience Siena beyond just sightseeing.

While it’s not perfect for everyone—particularly if you’re not a fan of walking or are looking for a more structured, indoor-focused experience—most reviews suggest it’s a well-rounded, value-packed tour for anyone eager to experience Siena’s charm and flavors.

Enjoy your trip, and if you do choose this tour, I hope it becomes a highlight of your visit!