Siena Private Tour Highlights and Hidden Gems with a Local

5.0
(3 reviews)
Siena, Italy

Show all photos
2 to 6 hours (approximately)
Pickup offered
Offered in: English and 1 more

This walking tour offers a truly local take on Siena, far beyond the postcard views. With your host, you’ll explore hidden chapels, medieval backstreets, peaceful gardens, and the living traditions of the Palio and contrade. Whether you're tracing the path of a district rivalry, admiring Gothic architecture, or sipping wine in a tucked-away enoteca, this is your chance to explore like a local, not a tourist.

After booking, you’ll receive a short questionnaire to share your interests and travel style. Based on your responses, you’ll be matched with a like-minded host who will contact you directly to suggest a personalized itinerary. You’ll agree on a meeting point and time, and your route can adapt throughout the day based on what captures your interest.

What's Included

Direct communication with your host for itinerary planning and local recommendations.
Flexible durations and start times—choose your preferred time when booking
Pre-tour questionnaire to tailor the experience to your preferences
Private and personalized walking experience with insider tips from a passionate local
Food, drinks and tickets to any attractions
Transportation (primarily a walking experience, public transport may be used at an additional cost)
Gratuities (optional)

Meeting and pickup

Pickup points
You can choose a pickup location at checkout (multiple pickup locations are available).
Pickup details:

This is a private walking experience. Your host will meet you at your selected hotel, and the tour will begin on foot. If you’d prefer to meet at a central location instead, please choose the meeting point option. If your hotel isn’t on the list, simply select the central landmark option. Once you’ve booked, our Experience Planners will get in touch to confirm the meeting point and help with any final details to ensure a smooth and enjoyable start to your personalized tour. NO private vehicle is included. For longer distances, your host may suggest using public transport. Any transport costs can be settled on the day.

OR
Meeting point

This is a great central point to meet your host if your hotel is not listed.

End point
This activity ends back at the meeting point.

Itinerary

Duration: 2 to 6 hours (approximately)
  • Siena (Pass by)

    See Siena through the eyes of someone who lives and loves it—wandering quiet lanes, historic squares, neighborhood fountains, and hidden altars. This isn’t a scripted tour; it’s a flexible, personalized experience shaped around you. Before your walk, your host will reach out with a short questionnaire to understand your interests—whether you're drawn to sacred art, medieval architecture, local food, or peaceful viewpoints. Here are some places you might explore:

    Admission ticket free
  • Piazza del Campo (Pass by)

    Begin in Siena’s dramatic, shell-shaped square—home to the Palio horse race and centuries of civic life. Your host will share how this iconic space captures the spirit, rivalry, and unity of Siena’s historic districts.

    Admission ticket free
  • (Pass by)

    Pause at this ornate Renaissance fountain, where sculpted panels once celebrated abundance and innovation. In a hilltop city, Fonte Gaia is more than a monument—it’s a symbol of survival, pride, and ingenuity.

    Admission ticket free
  • (Pass by)

    One of Siena’s oldest and most atmospheric fountains. Surrounded by medieval stone and arches, it tells a story of water, survival, and the wool guild that once ruled the area.

    Admission ticket free
  • (Pass by)

    Stroll this refined historic street where artisan boutiques and daily life flow side by side. As locals linger over coffee, your host will share how the street links the city’s political and cultural heart.

    Admission ticket free
  • Basilica Cateriniana San Domenico (Pass by)

    Step into this solemn 13th-century church, where relics of Saint Catherine offer a powerful glimpse into devotion, mysticism, and Siena’s spiritual identity.

    Admission ticket free
  • (Pass by)

    Leave the cobblestones behind for this tranquil medieval garden just beyond the city walls. Chickens roam, herbs flourish, and Siena’s bustle fades into birdsong—offering a perfect place to pause and reflect.

    Admission ticket free

Additional info

  • Wheelchair accessible
  • Infants and small children can ride in a pram or stroller
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • After booking, you'll receive a short questionnaire to share your interests, preferences, and must-sees. Your guide will personally reach out to craft a fully customized itinerary that suits your style—whether you love history, food, hidden gems, or cultural experiences.
Supplied by City Unscripted

Show 2 more

Tags

Private Sightseeing Tours
Cultural Tours
Historical Tours
Walking Tours
Likely to Sell Out
Best Conversion
Low Supplier Cancellation Rate
Low Last Minute Supplier Cancellation Rate
New Product
Short term availability

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Show more

Rating

5.0 Based on 3 3 reviews
5 stars
3
4 stars
0
3 stars
0
2 stars
0
1 star
0
Likely to sell out
from per person
Was {{currencySymbol}}{{ summaryFromPriceBeforeDiscount }}
Book Now