Siena, Tuscany

Experience the Palio Race in Siena Italy with Italy Vacation Specialists

Overview

Discover Siena: Private Tours, Experiences & Custom Travel

Siena is reknowned, both nationally and internationally, for the Palio horse race contested by the 17 contrada which divide this small city. But Siena is also unique thanks to its maze of narrow streets, its numerous towers and elegant town houses, the immense Piazza del Campo and the Cathedral which dominate the heart of the Medieval city encircled by impressive walls.

Those living in Siena enjoy an incredibly high quality of life. It is also the first city in Italy to close its center to traffic. As far as culture is concerned, Siena has been a city of great artistic significance since ancient times with internationally acclaimed institutions such as theChigiana Musical Academy, the Accademia dei Fisiocritici and Accademia degli Intronati, as well as the University for Foreigners.

Sites not to be missed: the Church of St Domenico, the Church of St Francesco, theDiocesan Museum of Sacred Art and Palazzo Salimbeni which houses important frescoes. The surrounding countryside is superbly peaceful with vineyards, olive groves,medieval hamlets and castles. The gastronomic traditions have gained international fame with the sweet Panpepato, Ricciarelli and Cavallucci being exported throughout the world.

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Explore Siena

Siena in pictures

Gallery

A few frames from our own trips. The rest are in the gallery below.

Magnificent Palio Experience, Siena

Siena Town hall, Italy

Beautiful Siena, italy

Historic marketplace in Siena, Tuscany, Italy, 07-10-2018

Night view of Siena Cathedral Santa Maria Assunta (Duomo di Siena) in Siena, Tuscany, italy. Italian

Map

Get your bearings before you go

Multi-Day Holidays Tours

Whole journeys, planned end to end

Florence, Tuscany and the Italian Riviera

A classic introduction to the must-see sites of Tuscany and Cinque Terre. From the wine-growing lands of Chianti and Val d'Orcia to the Renaissance splendour and the museums of Florence, the tour ends in the incredible natural beauty of the Italian...

Private

10 Days / 9 Nights

Tuscany Mini-Stay

A brief retreat to Tuscany promises a delightful blend of Renaissance art, rolling vineyards, and charming medieval towns. This mini holiday in Tuscany provides a perfect taste of the region's art, culture, and culinary delights in just a few memorab...

Private

3 Days / 2 Nights

Private & Small Group Tours in Siena

Days out with people who know the way

Tuscany: Siena & San Gimignano from Florence or Livorno

This tour of Tuscany begins in either Livorno or Florence and includes a visit to two of Tuscany's most beautiful towns Siena and San Gimignano which are right in the heart of the beautiful Tuscan countryside inside the Chianti wine territory. Over t...

Private

8 Hours

San Gimignano Morning Tour with Full Tuscan Lunch and Multiple Wine Tastings

North west of Siena, on the hills of Val d'Elsa, stands the medieval town of San Gimignano. Defined as the town "with a hundred towers", owing to the presence of these impressive buildings symbolising power and wealth, till the thirteenth century the...

Small Group

8 Hours

Private Tour of Tuscany's Chianti Region, including Siena

Chianti, located in Tuscany, is famous for its medieval towns and red wines. A private tour allows you to customize your itinerary for a unique experience. Explore the region's beauty whether you're a wine connoisseur, history buff or just want to se...

Private

7 Hours

Truffle Hunting & Cooking Class in the Heart of Tuscany

If you're spending your holidays in Tuscany, or even just passing through, do not miss the opportunity to learn more about one of the most mysterious ingredients of Italian cuisine: The Truffle! Have fun hunting in the woods with the truffle-dogs, t...

Semi-Private

5 Hours

Private Tour of Siena

Explore the art and history of one of Tuscany's most charming towns with the help of a knowledgeable local guide who will bring the medieval streets to life.

Private

3 Hours

Hotels

Rooms we would happily sleep in again

Italy,Tuscany,Siena

Hotel

Hotel Santa Caterina

★ ★ ★

Santa Caterina Hotel in Siena, housed in a renovated 18th-century patrician villa, is a small and co...

Island of Ponza +4 more

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Italy,Tuscany,Siena,Montepulciano

Hotel

Villa Cicolina

★ ★ ★ ★

Located just outside the stunning medieval town of Montepulciano, Villa Cicolina it ideally situated...

Parking +2 more

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Villas

Private homes with stories of their own

Italy,Tuscany,Siena

Villa

Villa in Siena for 7 people

4 Beds 7

BBQ +8 more

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Italy,Tuscany,Siena

Villa

Villa in Siena for 8 People

4 Beds 8

Balcony +10 more

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2.5 Beds 5

Air Conditioning +9 more

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Italy,Tuscany,Siena

Apartment

La Dimora del Gazebo

3 Beds 2 Baths 6

Air Conditioning +16 more

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Photo Gallery

Panoramic view of the city in Siena in Italy, Tuscany

SIENA, ITALY - OCTOBER 27, 2018 interior of Metropolitan Cathedral of Saint Mary of the Assumption

Siena, Italy 2016-05-02 Duomo di Siena Church

Siena, Italy 2016-05-02 Siena streets. The historic centre of Siena has been declared by UNESCO a Wo

Castiglion Fiorentino

Terme di San Filippo - San Filippo Natura Hot Springs, Tuscany

Val D'Orcia

Viareggio

Volterra

Arrezzo

Bagno Vignoni

Barga

Carrara

Castiglion Fiorentino

Chianciano Terme

Chianti

Cortona

Elba Island

Fiesole

Florence

Livorno

Lucca

Maremma

Montalcino

Montecatini

Montepulciano

Monteriggioni

Monticchiello

Pienza

Pietrasanta

Pisa

Porto Santo Stefano

San Gimignano

San Miniato

Saturnia

Siena

Terme di San Filippo - San Filippo Natura Hot Springs, Tuscany

Val D'Orcia

Viareggio

Volterra

Our Featured Properties

Stays we picked one by one

La Dimora del Gazebo featured rental property in Siena

Italy,Tuscany,Siena

Apartment

La Dimora del Gazebo

3 Beds 2 Baths 6

Air Conditioning +16 more

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Italy,Tuscany,Lucca,Camaiore

Villa

Luxury villa near Lucca

Air Conditioning +12 more

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Popular Transfer Routes in Siena

The rides our guests ask for most, with a driver who knows the way.

Italy Vacation Specialists provides licensed private transfer services throughout Italy, including Siena and surrounding areas. With over 20 years of experience, our professional English-speaking drivers offer both Business Class and Luxury Class vehicles for airport transfers, city-to-city rides, and full-day chauffeur services. All vehicles are fully insured, well-maintained, and operated by vetted local drivers who know the roads, traffic patterns, and best routes across the region.

Rome Florence

Private Transfer

Rome Naples

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Rome Venice

Private Transfer

Florence Venice

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Milan Venice

Private Transfer

Naples Amalfi

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Rome Amalfi

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Milan Lake Como

Private Transfer

Florence Siena

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Naples Sorrento

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In their words

Stories That Stay With You

Here's what our guests share about their unforgettable journeys

“Dear Guiseppe and Jesse, We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future. Hotels 1. Hotel Sovestro in San Gimignano was wond…”
Ron and Deb Crosby Read their story

“Jesse, There are no words to describe the fabulous time we had in Italy. Everything went as you promised. Absolutely no problems! The venues were fabulous. The guides were punctual and helpful. It couldn't have worked out better. You and your staff deserve hig…”
Jo Ann West Read their story

“We're home now from the most amazing trip to Italy! I can't thank you enough for your efforts and coordination of what was without question the finest vacations I've been on to date”
Carol Carson Read their story

“The trip was great; we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details, in particular Giuseppe spending the time and the focus with us on the road and as w…”
Leon and Michele Read their story

“I am a travel agent with All About Honeymoons and I would highly recommend Italy Vacation Specialists. Jessica was wonderful in helping us plan in a last minute anniversary vacation during high season without any issues. She even checked on our clients while o…”
Tammy Joyce, All About Honeymoons Read their story

“As a travel agent, but also a traveler to Italy, thee is no other company I would recommend than the Italy Vacation Specialists. Not only do they really care about what they are doing, they also really know Italy and try to educate many people about ways they…”
Laura Chomiak, Travel Agent Read their story