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Explore Siena’s Medieval Alleys and Flavors: A 2.5-Hour Guided Cultural Tour - Siena

Explore Siena’s Medieval Alleys and Flavors: A 2.5-Hour Guided Cultural Tour

Sienaeasy

Difficulty

easy

Duration

2–3 hours

Fitness Level

Suitable for most fitness levels as the pace is relaxed with several stops

Overview

Discover Siena’s medieval streets and savory traditions on a 2.5-hour guided tour that blends historic landmarks with authentic local tastings. Perfect for travelers eager to taste and explore Tuscany’s iconic city.

Siena, Tuscany

Siena Treasures & Tastes Shared Tour

For all ages! • 2.5 hours • discover Siena!

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About This Adventure

Embark on an unforgettable sightseeing tour of Siena, where you'll explore medieval alleys, iconic landmarks, and hidden gems. Discover the city's rich history, indulge in traditional Senese treats, and learn about the thrilling Palio horse race. With a local guide by your side, experience Siena's culture through its delicious food and captivating stories.

Intro

Get the ultimate introduction to Siena on a sightseeing tour that includes the main attractions as well as some of the beaten path hidden gems. Learn about the Medieval history of the city and taste some of her many treasures.

Highlights

• Discover the history, traditions and food of Siena • Visit San Domenico Church (exterior), Piazza del Campo, Duomo Square and the Cathedral (optional entry at the end of your tour) • Learn about the world famous Palio horse race and get an understanding of the meaning it has to the local community • Explore ancient alleys, dazzling squares and Renaissance (better Medieval) palaces with a local by your side • Taste traditional Senese treats such as almond cookies, stuffed panino and gelato

Inclusions: Local English-speaking guide, food samples (including sweets biscuits, and a local sandwich), and a glass of wine or beer. Exclusions: Additional food and drink, souvenirs and items of a personal nature, tips and gratuities for the guide.

Full description

Your introduction to Siena will start at the main entrance to San Domenico church, the most important landmark in Siena. This is where the relics of Santa Caterina, Italy’s patron saint, are stored, and the church also plays a significant role in Palio traditions.

We’ll stroll around Siena’s medieval centre and talk about the ‘‘Contrades’ (the name for the famous, original houses of Siena), which still compete in the 400-year-old tradition of the Palio horse race, an event that is central to the lives of the Senese. Each contrada has its own motto, flag and symbol, such as an owl, wolf or dragon. As we walk, your guide will tell you about the fierce rivalries between the houses that go back hundreds of years.

At Piazza del Campo, one of the world’s most spectacular squares, we will let you in on some of Siena’s darkest secrets and tell you stories about the city’s glorious past and its most intense and infamous conflicts. We will talk more about the Palio horse race, which takes place here twice a year. This legendary event, and the colourful pageant that proceeds it, attracts visitors from all over the world.

We will stop at a food shop to taste local sweet treats such as ricciarelli biscuits or panforte, and then just around the corner we will reach a local Vineria, where we’ll raise a glass of Senese wine, paired with a delicious panino (Italian sandwich). Our foodie stops are designed to give you a greater understanding of the culture and traditions of Siena; there’s no better way to discover a culture, in our opinion, than by eating it!

We will then head towards the hill that hosts the exquisite Gothic Cathedral and we’ll stop to talk about the nearby ancient pilgrimage hospital and hear stories about the pilgrims that passed through its doors.

Finally, we’ll explore medieval alleys until we stumble across our final stop at a artesan Gelateria, where we’ll taste the best Gelato made daily with seasonal fruits. This will be our way to end the tour and say: Arrivederci!

Additional information

Dress standard: Please wear casual dress and comfortable shoes for walking. Bring a waterproof jacket or an umbrella in case of rain. Accessibility: Yes Physical rating: Low Confirmation of booking: If you have your voucher, your booking is confirmed. We’ll see you at the start point. Get in touch if you have any concerns or require more information via the email address or phone number (business hours only) on your voucher. Child Policy: This is a child-friendly tour. Children between the ages of 4 and 11 inclusively are permitted on this tour at the rate listed above. Please select ‘child’ above when booking. Children under the age of 4 are permitted to join this tour free of charge. Please inform us at the time of booking if you’ll be bringing a child under the age of 4. You can do so in the special request box on the checkout page.

Adventure Tips

Wear Comfortable Shoes

The tour covers cobblestone streets and narrow alleys, so sturdy, comfortable footwear is essential.

Bring a Light Jacket

Siena’s weather can be breezy, especially in spring and fall, so layering helps you stay comfortable.

Stay Hydrated

Carry a small water bottle to stay refreshed during the walking portions of the tour.

Book in Advance

Small group tours fill quickly, especially in peak season—reserve your spot early to avoid disappointment.

Local Insights

Wildlife

  • Pigeons commonly seen in the Piazza del Campo
  • Occasional sightings of kestrels soaring above the city rooftops

History

Siena's historic center dates back to the Middle Ages and its Palio horse race tradition has been running since 1633.

Conservation

The city promotes sustainable tourism by encouraging walking tours and limiting vehicle access in sensitive historic zones.

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Adventure Hotspots in Siena

Frequently Asked Questions

Recommended Gear

Comfortable Walking Shoes

Essential

Essential for navigating cobbled streets and stairways comfortably.

Sun Hat

Protect yourself from strong Tuscan sun during summer months.

summer specific

Light Jacket or Sweater

Helpful for cooler mornings or evenings in spring and fall.

spring specific

Reusable Water Bottle

Essential

Stay hydrated throughout the walking tour.