Tucked into the Tuscan hills, Siena is a city frozen in time. Red brick lanes, Gothic churches, and medieval towers rise from the earth like a Renaissance stage set. A private Siena tour invites you to explore it beyond the postcards—through echoing alleys, sun-drenched piazzas, and quiet courtyards rich with centuries-old secrets.

From grand cathedrals to hidden wine cellars, every stone in Siena tells a story. Your private tour lets you walk straight into the past—at your pace, on your terms.
 <h3>Top 10 Must-See Attractions in Siena</h3>
Begin with the icons. These are the places that define Siena—bold, beautiful, and steeped in history that shaped the city and all of Tuscany.

Piazza del Campo
 Siena’s fan-shaped main square, famous for the Palio horse race. A marvel of medieval urban design, it’s surrounded by cafés, palaces, and the soaring Torre del Mangia.

Duomo di Siena
 A Gothic cathedral in black and white marble. Inside, discover mosaics, sculptures, and frescoes by masters like Pisano, Donatello, and Michelangelo.

Santa Maria della Scala
 Once a medieval hospital, now a museum complex with underground chapels, frescoed halls, and archaeological treasures spanning 1,000 years.

Palazzo Pubblico
 The town hall of Siena, housing grand rooms covered in frescoes—including Lorenzetti’s Allegory of Good and Bad Government, a civic masterpiece.

Torre del Mangia
 Climb this 14th-century bell tower for sweeping views over Siena’s terracotta rooftops and the green Tuscan countryside beyond.

Pinacoteca Nazionale
 A treasure trove of Sienese art from the 13th to 17th century, including gold-leaf altarpieces and haunting devotional portraits.

Basilica of San Domenico
 A massive brick church that holds relics of St. Catherine of Siena. Inside, wide arches and painted chapels reflect the city’s spiritual heart.

Fonte Gaia
 A striking marble fountain in Piazza del Campo with mythological carvings. The current version is a 19th-century replica of the 15th-century original.

San Cristoforo Church
 A quiet Romanesque gem just off the main routes. Its understated facade and peaceful interior offer a break from the tourist buzz.

Via di Città
 One of Siena’s oldest streets, lined with noble homes, hidden archways, and boutique shops nestled in Renaissance façades.

 <h3>Explore Siena Off the Beaten Path</h3>
Beyond the landmarks, Siena reveals itself in tucked-away corners. These local favorites offer an intimate glimpse into the city’s daily rhythm and layered history.

Contrade Neighborhoods
 Each district, or contrada, has its own flag, fountain, and museum. Stroll their streets to see how deeply tradition shapes Sienese identity year-round—not just during the Palio.

Orto de' Pecci
 A hidden green space inside the old city walls. Once used for psychiatric therapy, today it’s a peaceful garden with views of the Torre del Mangia and farm animals grazing nearby.

San Pietro alle Scale
 A small, rustic church with fading frescoes and Romanesque columns—quiet, uncrowded, and full of atmosphere.

Enoteca Italiana
 Housed in a medieval fortress, this national wine library showcases Italian wines from every region. Explore cellars lined with bottles beneath vaulted stone ceilings.

Via del Porrione
 A narrow passageway known for its artisan shops and tucked-away eateries, perfect for exploring Siena’s creative and culinary roots.

Civic Museum Courtyard
 Often missed by passersby, this enclosed stone courtyard echoes with the footsteps of past rulers and visiting nobles.

Vicolo delle Carrozze
 A narrow stair-stepped lane with worn brick walls and rooftop views that capture Siena’s quiet, everyday elegance.

Baptistery of San Giovanni
 Tucked beneath the cathedral, this site features a baptismal font by Ghiberti and a dramatic cycle of Renaissance frescoes covering the vaulted ceiling.

 <h3>Day Trip Ideas from Siena</h3>
Looking to stretch your view beyond the city walls? These nearby destinations deliver unforgettable landscapes, heritage, and wine—all within a day’s reach.

<a href="https://www.toursbylocals.com/tours/italy/san-gimignano?utm_source=internallinks&utm_medium=marketingblock&utm_campaign=siena" target="_blank">San Gimignano</a>
 Known as the “Medieval Manhattan,” this hilltown is packed with towers, frescoes, and sweeping views. Its skyline is as iconic as its gelato.

<a href="https://www.toursbylocals.com/tours/italy/montepulciano?utm_source=internallinks&utm_medium=marketingblock&utm_campaign=siena" target="_blank">Montepulciano</a>
 A Renaissance hilltop town surrounded by vineyards. Stroll cobblestone streets, sample Vino Nobile, and admire the perfectly preserved town square.

<a href="https://www.toursbylocals.com/tours/italy/pienza?utm_source=internallinks&utm_medium=marketingblock&utm_campaign=siena" target="_blank">Pienza</a>
 Commissioned by a Renaissance pope as the “ideal city,” Pienza blends architecture, cheese shops, and views of the Val d’Orcia into one harmonious experience.

<a href="https://www.toursbylocals.com/tours/italy/chianti?utm_source=internallinks&utm_medium=marketingblock&utm_campaign=siena" target="_blank">Chianti</a>
 Vineyards, olive groves, and stone villages line the scenic drive through Chianti. Sample bold reds, explore cellar doors, and soak in quintessential Tuscan countryside.

 <h3>Travel Tips for Your Visit</h3>
Siena rewards those who slow down and stay curious. A little preparation goes a long way in making the most of its sloping streets and cultural treasures.

Best Time to Visit
 April to June and September to October offer sunny weather without the summer crowds. July and August bring the Palio and vibrant street energy.

Getting Around
 The historic center is closed to cars. Wear sturdy shoes—Siena’s steep hills and cobbled lanes make walking the best way to explore.

What to Wear
 Dress comfortably and modestly, especially when entering churches. Layers are useful in spring and fall when temperatures vary.

Local Etiquette
 Sienese pride runs deep. A warm “buongiorno” is always appreciated. Ask before photographing people or contrada flags—they carry deep cultural meaning.

 <h3>Explore Siena Your Way</h3>
Siena isn’t just a destination—it’s a living, breathing city that still beats with medieval rhythm. A private tour gives you access to that heartbeat: the layers of history, the quiet devotion, the artistry hiding behind every arch and alley.

With expert-vetted guides, flexible cancellation, and thousands of glowing reviews, every Siena private tour offers a personalized path into one of Tuscany’s most enchanting cities.

Siena

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Orvieto Private Guided Tour

Siena Highlights and Duomo half day walking tour

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Siena. In the Cathedral, Michelangelo, Donatello, Raffaello and Bernini and we will learn the Palio of Siena

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Perugia Private Guided Tour

entrance for the privately owned Oratorio Dei Nobili;

A view of he main square of Perugia with the major Fountain and the Palazzo Dei Priori

A view of Perugia from the medieval aqueduct

The symbols of Perugia, the Griffin and the Lion

A view of the northern neighborood of Perugia

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San Gimignano Highlights and wine tasting - starting from siena

Wine tasting of 3 different types and some pecorino cheese

Via San Matteo, the entrance to the town from the Via Francigena

Panoramic view from the town. Tuscan countryside as seen on paintings or movies.

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This reflects the added effort by the guide to effectively manage increasingly larger groups.....

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3 types of wine per person to taste, licght snack included

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Palio di Siena half day tour

Chiusi, Etruscan town off the beaten track

Entrance tickets to the Etruscan underground acqueduct and the Chiusi Etruscan Museum.

Hidden gem of Tuscany

The per person price includes reserving and buying for you the entrance tickets to the tower mentioned in the tour description.
For groups of five and above, radioes will be supplied at no extra charge as well.

Visit the "other" Tuscan capital

Siena - Walking tour of a magnificent city

Discovering Siena during sunset and taste our local wine!

Siena Sunset Walking tour and Wine.

Siena and the Palio's traditions half a day tour

from Piazza del Campo to Nicchio headquarters

Piazza del Campo during the Palio's horse trails

Piazza del Campo, Town Hall and Mangia Tower

Piazza del Campo during the Palio's horse trails. Nicchio's horse and jokey are the first ones from left

Piazza del Campo, waiting for the Palio horse race

jewellery with the emblem of the Nicchio neighborhood

Montepulciano tours

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Meet your local guides in Montepulciano

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Contact the Guide

Contact the Guide

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