Siena, Tuscany

Experience the Palio Race in Siena Italy with Italy Vacation Specialists

Discover Siena — Private Tours, Experiences & Custom Travel

Overview

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.

Gallery

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

Multi-Day Holidays Tours

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

STARTING FROM

€5,450 per person

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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

PRICING

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Private & Small Group Tours in Siena

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

PRICING

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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

PRICING

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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

STARTING FROM

€60 per person

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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

STARTING FROM

€220 per person

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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

STARTING FROM

€190 per person

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Hotels

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

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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Apartment

Italy,Tuscany,Siena (SI),Castellina in Chianti

Estate

Cottage Fienile

Air Conditioning +10 more

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Cottage Riccio apartment rental in Siena Italy

Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Riccio

Air Conditioning +7 more

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Cottage Talluri apartment rental in Siena Italy

Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Talluri

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

Our Featured Properties

Italy,Tuscany,Castiglion Fiorentino

Villa

Villa Stefano: Ideal Property for Artists, Families & Large Groups in Tuscany

7 Beds 6 Baths 16

BBQ +11 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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La Casa Fiorita featured rental property in Siena Italy

Italy,Tuscany,Florence

Apartment

La Casa Fiorita

4 Beds 4 Baths 4/8

Air Conditioning +11 more

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Italy,Tuscany,Val D'Orcia

Villa

Villa Gabriella

8 Beds 8 Baths 16

Bathroom with Shower +15 more

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Italy,Tuscany,Volterra

Villa

Luxury villa near Volterra

4 Beds 11

Air Conditioning +13 more

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Casa Divina featured rental property in Siena Italy

Italy,Tuscany,Montepulciano

Apartment

Casa Divina

2 Beds 2 Baths 4

Air Conditioning +9 more

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Italy,Tuscany,Arrezzo

Villa

Villa Vinaia

5 suite rooms and 3 apartments Beds 5 Baths 18 + 6

Air Conditioning +9 more

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Giardino Blu featured rental property in Siena Italy

Italy,Tuscany,Montepulciano

Apartment

Giardino Blu

2 Beds 1 Baths 5

Air Conditioning +8 more

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Italy,Tuscany,Siena

Villa

Villa in Siena for 7 people

4 Beds 7

BBQ +8 more

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Vista Collina featured rental property in Siena Italy

Italy,Tuscany,Montepulciano

Apartment

Vista Collina

1 Beds 1 Baths 2

Air Conditioning +8 more

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Italy,Tuscany,Livorno

Villa

Villa Bellissimo Palazzo

10 Beds Yes Baths 20

Air Conditioning +15 more

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Italy,Tuscany,San Gimignano

Villa

Villa near San Gimignano

5 Beds 10

Air Conditioning +14 more

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Private Transfer Routes in Siena

Seamless connections between key destinations across the region

Rome Florence

Private Transfer

Rome Naples

Private Transfer

Rome Venice

Private Transfer

Florence Venice

Private Transfer

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Stories That Stay With You

Here's what our guests share about their unforgettable journeys

“In September of 2018 I brought a group of 12 from Venice to Sicily and organized all of my services with the Italy Vacation Specialists. Being a travel agent and in the business, I know how complicated organizing travel arrangements can be in Italy and the IVS team took a huge burden off of me! I would like to start of by saying "THANK YO”

[Read More] Ann Brownell, KHM Travel Group

“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 high praise for the quality and efficiency of your work. BTW, Guiseppe was an absol”

[Read More] Jo Ann West

“This company really knows their stuff and recommended our family to stay longer in each location. We didn't listen to them, but wished we had in every single place we went. They recommended Sestri Levante over the Cinque Terre which was our favourite destination on our entire trip. We visited Rome where we stayed in the outstanding Hotel ”

[Read More] Sean & Veet Chapman, CGA

“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 we were exploring your great country.”

[Read More] Leon and Michele

“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 on vacation to make sure things were going well. I plan on using them again soon ”

[Read More] Tammy Joyce, All About Honeymoons

“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 can best see the country and not fall into tourist traps. I have been on 4 trips”

[Read More] Laura Chomiak, Travel Agent

“I traveled with JoAnn West through your services, guided by Giuseppe, in July of this year. What a wonderful experience; your service is really top notch! If I return to Italy for a tour, I will absolutely use your services again and recommend you to my friends!”

[Read More] Lucretia Brower

“Jesse & Giuseppe, Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever.”

[Read More] Bob & Sandy

“I went to high school with the owner of the company who organized my honeymoon for myself and my now wife from Tokyo. We spent three short weeks seeing Piedmont and experiencing wine paradise there, then heading to Nice in France with our private driver and flying to Rome where honestly 4 days is NOT enough. They keep saying to spend more”

[Read More] Robin and Kumi Bruun, Tokyo Japan

“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.”

[Read More] Carol Carson