Italy Vacations in Siena Italy

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Farmhouse Accommodation Tuscany

When planning your Italy vacations, Tuscany is one of the most picturesque regions of central Italy. Whether you visit the ancient cities, towns and villages or tour the picture perfect countryside, your senses will be delighted by the overwhelming beauty.

While you are in Tuscany, consider staying in a villa or farmhouse and exploring the stunning villages and vineyards in the region.

Visit the wineries of Chianti Classico, Brunello di Montalcino, Nobile di Montepulciano, the Chianti Supertuscan Wine tours and San Gimignano wine tours.

Italy Vacations in Siena Italy Il Campo Square
View of Piazzo del Campo and Palazzo Pubblico Town Hall in Siena Italy

Siena Italy, a glorious walled city with narrow streets and alleyways, magnificent museums and churches, charming hotels, romantic restaurants and great designer stores and boutique shops is a spectacular destination to include in your Tuscany Italy vacations.

Getting to Siena is an adventure in itself, and wandering around inside its ancient walls is like being in a fairytale story book.

On one of my trips to Siena, I discovered an electronic store and bought a compact hair blow-dryer kit. That was one of my best souvenier purchases as I use that hair dryer on all of my travels.

Italy Vacations in Siena Italy Piazza del Campo
The Il Campo Square in Siena Italy where the Palio Horse Race is Held Annually

Siena’s central square, Piazza del Campo (Il Campo), is one of Italy’s most beautiful and dramatic piazzas.

The town square, Il Campo, houses the Palazzo Pubblico, the Torre del Mangia, and other exquisite architectural treasures.

Italy Vacations the Duomo in Siena Italy
Stunning Black and White Marble Inside the Cathedral of Siena (Duomo di Siena)

Siena has maintained its medieval Gothic appearance.

The Siena Duomo is a fabulous Gothic cathedral made of black and white marble with an exquisite inlaid marble floor.

Italy Vacations in Siena Italy View of the Duomo
The Duomo and Cypress Trees in Siena Italy

The Duomo is located in the center of the medieval walled city and can be seen from many points around Siena.

Italy Vacations Cobblestone Streets in Siena Italy
Exploring the Streets of Siena Italy – the Palazzo Pubblico Bell Tower in the Background

Siena Italy has so many wonderful winding streets and alleys and be prepared to climb up some steep cobblestone pathways.

Italy Vacations in Siena Italy Side Street
Wander Around the Beautiful Streets of Siena Italy

Take a walk up to the Duomo or Il Campo square and you will see the constricted stairways, delicate arches, sleepy squares, and red clay houses.

Siena Events for Your Italy Vacations

Siena is famous for hosting the Palio horse race. This event is held twice each year on July 2nd and August 16th at the Il Campo square.

The race hosts ten horses and riders, bareback and dressed in the appropriate colours, representing ten of the seventeen Contrade (city wards).

A spectacular pageant, the Corteo Storico, precedes the race and attracts visitors from around the world and you will want to include this event during your Italy vacations.

Siena Italy Dining Ideas

One of my favourite places to stay in Siena or to have a meal is at the Palazzo Ravizza.

The views of the Tuscany valley are magical.

Italy Vacations at Palazzo Ravizza in Siena Italy
The Beautiful Palazzo Ravizza Hotel in Siena Italy

Palazzo Ravizza has an exquisite restaurant inside and a wonderfully romantic garden patio with views of Tuscany. A wonderful setting to include in your Tuscany vacation ideas.

Italy Vacations in Siena Italy Outdoor Dining in Tuscany
The Gorgeous Terrace and Gardens of Palazzo Ravizza in Siena Italy

The first time I came to Siena was late one July evening when I met up with a friend who was taking summer courses in art history and architecture.

I was greeted with a salad made with fresh local ingredients and local wine from Siena. What a treat!

Italy Vacations A View of the Tuscany Valley
For Your Siena Italy Vacation Ideas Discover Romantic Pathways

The next morning I awoke to the sound of a singing rooster.

I opened up the wooden shutters to a fairy tale view of the Tuscan valley with a fog hovering over the vineyards, olive groves and majestic cypress trees.

Italy Vacations Views of Tuscany in Siena Italy
Magical Views of Tuscany around Siena Italy

The backyard, surrounded by a 3 foot stone wall, had many old olive and fig trees, a terraced garden, and an ancient well in the center of the yard. I will never forget the surreal feeling.

Include Shopping in Your Siena Italy Vacations

You will be delighted when you discover all the delightful boutiques and great shops of all kinds in Siena Italy.

I actually bought some fantastic European hair appliances in Siena which I use whenever I travel anywhere in the world.

Italy Vacations Shopping in Siena Italy
Great Vacation Ideas – Go Shopping in Siena Italy

Siena offers the best in Italian fashions and you can also find bargains. There a wonderful grocery stores, bakeries, pharmacies, enotecas, or whatever you may need.

Italy Vacations around Siena Discover the Nearby Charming Towns

Between Florence and Siena lies the Chianti region with hilly, wooded, and rolling hills, small hamlets, isolated farmhouses, vineyards, olive groves, and tall cypress trees.

Here are some of the world’s finest wines as well as olive oil and pecorino cheese.

Gaiole in Chianti

Gaiole in Chianti with its two small Romanesque churches worth visiting. Greve, with its lovely market square surrounded by leafy passageways.

Radda in Chianti

Radda is one of the most enchanting towns in Chianti, with olive trees encircling the medieval setting. Some of the best olive oil and Chianti wine are produced here.

San Gimignano

West of Siena is the gorgeous, well-preserved medieval town on a hill, San Gimignano, with a distinctive skyline of soaring stone towers. San Gimignano has been referred to as the “Manhattan of Tuscany” with its tall medieval towers reaching heights of 54 metres.

Italy Vacations in San Gimignano
The Views of San Gimignano are as Stunning as are the Views in the Town

The town is completely encircled by a wall and only has 5 gates to access entry into it. This is a lovely town to visit during your Italy vacations.

Crete Senesi

Southeast of Siena is the Crete Senesi (Sienese clay hills) an area which produces the pink brick typical throughout Tuscany.

Further south of Siena are the towns of Chiusi, Montalcino, Pienza, Montepulciano, and Quirico d’Orcia.


Chiusi is an ancient Etruscan town, with settlements as early as the 6th and 7th centuries B.C.

For now, the main reason I am including Chiusi in this article is because this is the transfer point if you are travelling by train from Rome to Tuscany.

You have to change trains in Chiusi.

If you are taking the last train from Roma Termini around 8 pm Rome time, you will most likely not be able to catch your transfer train in Chiusi, so ensure you catch the earlier trains for your Tuscany Italy vacations, unless of course you have booked a Chiusi farmhouse accommodation Tuscany and plan to visit the Chiusi area.

That happened to me and I had to take a taxi for the one hour ride from Chiusi to Siena because I missed my connecting train in Chiusi.

Mind you, the taxi was new and the roads are great so that is another option. If that happens to you, expect to pay around $100 US for a 1 hour taxi ride.


Montepulciano is well known to wine connoisseurs all over the world as this fortified town is located on a hilly ridge and here is the most celebrated wine in Tuscany, the Vino Nobile di Montepulciano.

Italy Vacations in Montepulciano
The Romantic Town of Montepulciano is Known for it’s Famous Wines

This stunningly beautiful medieval hill town is one of Tuscany’s highest. Its steep slopes have attracted movie directors and several scenes for Midsummer’s Night’s Dream and Under the Tuscan Sun were shot here (as well as in Cortona for Under the Tuscan Sun).


Montalcino is another exceptionally beautiful medieval town producing the fabulous world-famous red wine; the Brunello di Montalcino, which is counted among the most prestigious of Italian wines. The narrow winding streets, steep stairs, tiled rooftops, and a dramatic hilltop position make Montalcino yet another great travel idea for Italy vacations.

Italy Vacations in Siena – Medieval Architecture

Siena Italy is surrounded by exquisite medieval art and architecture.

Italy Vacations Ancient Architecture in Siena Italy
It is Exciting to Walk Around Siena Italy and Pretend You Are in the Medieval Ages. This View Features Via delle Sperandie

The buildings have been preserved so well and the interiors are creatively decorated with artistic flare and design.

The door with the arched entrance to the right hand side of the photo above is a university dorm with fantastic views of the Tuscan valley.

Italy Vacations Medieval Architecture in Siena Italy
In Siena Italy You Will See Creative Architecture

Here are a few more examples fantastic architecture to give you an idea of what you can expect to see on your Italy vacations in Siena.

It is so interesting to walk around this stunning medieval city and experience life here.

Italy Vacations Fire Truck in Siena Italy
It Took Some Effort for the Modern Fire Truck to Turn the Corner in Medieval Siena

Siena Italy has both a modern and medieval aspect to the city.

Italy Vacations Unique Art in Siena Italy
A Water Fountain on Via de Fontanella in Siena Italy

In Siena Italy, you can be transformed to an ancient world while at the same time have access to modern day conveniences.

This contrast adds fun and fantasy to your Italy vacations.

Italy Vacations Medieval Archway in Siena Italy
Majestic Arches and Architecture in Medieval Siena Italy

The train station is located outside of the medieval walled city which has 12 gates.

It is not walking distance and you would have to take a taxi or a bus to get to train station.

Italy Vacations Gates to the Walled Medieval City of Siena Italy
Porta Laterina and Porta San Marco in Siena Italy

Italy has a great bus transportation service and if you are staying in Florence, you can easily take a bus and spend the day in Siena or any other medieval town around Siena and Florence.

Another good option is to spend a few days in each location to give yourself time to more fully enjoy the wonders of Italy vacations in Siena and Tuscany.

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