Our top 5 towns to visit in Tuscany

1. San Gimignano

The walled town of San Gimignano is perched on top of a stereotypical Tuscan hill and is famous for its medieval towers, which you will find spread through the villages creating an beautiful skyline.  San Gimignano is located between Florence and Siena which makes it the perfect base for exploring the Tuscan countryside - and away from the worst of the Tuscan crowds! 

There are 14 towers that remain in San Gimignano (there was once 72) that were built from about the year 1200 onwards by various families living in San Gimignano.  The higher the tower, the greater the wealth of the family that built it.  

Climb Torre Grossa for stunning panoramic views of the Tuscan countryside and of San Gimignano itself.

San Gimignano - View of the Tuscan Countryside from Torre Grossa

2. Siena

The medieval renaissance town of Siena sits on three hills in the heart of Tuscany.  The centrepiece of the town is the Romanesque-gothic Siena Cathedral which has a stunning facade that dates back to 1380.

Piazza del Campo, in an almost perfect shell-shape, is home of the Palio Horse Race which happens on 2 July and 16 August every year and is well worth the visit if you can handle the crowds.  The Siena bell tower, Torre del Magia, looks down imposingly over Piazza del Camp and is well worth the walk up for great views over the Tuscan Countryside.  

Siena Cathedral with a side of Alana

Siena - Piazza del Campo

View of the Tuscan Countryside from Siena

3. Lucca

Lucca does not necessarily have the same wow factor as its big brothers Siena and Florence but is beautiful in its own way nonetheless.  Unlike the majority of 'old towns' in Tuscany and Umbria, Lucca is not situated on a hill.  As a result the town had to build seriously thick walls; so thick that now there are whole parks the size of city blocks situated on top the wall which the locals now enjoy.  This is what we loved most about Lucca; being able to hire bikes and ride the 4km circuit on top of the wall which encircles the town - the ride takes you through gardens, parks and viewing spots giving you a great views of Lucca's historic centre. 

Add to Lucca great restaurants, churches dating back to the 12th century and a friendly atmosphere and it quickly becomes one of our favourite places in Italy.

Riding Bikes on the walls of Lucca


4. Florence

The birthplace of the Renaissance is the epicentre of art and culture within Tuscany and Italy.  The Statue of David in the Galleria dell'Accademia and the Uffizi Gallery are at the top of any artist's must see list.  Add to this the beautiful and unique Il Duomo in the heart of Florence and it is no wonder that Florence sees over 10 million tourists a year. 

To get away from the somewhat suffocating crowds make your way to the Boboli Gardens, via the Ponte Vecchio, and experience the Medici wealth that ran Florence when it was one of the richest places in the world in the 16th century. Keep going up the hill to Piazza Michelangelo for stunning views over Florence at sunset.

In terms of the amount of things to see, Florence is unrivalled in Tuscany. 

Florence - The view from Piazza Michelangelo

Florence - The view from Piazza Michelangelo

5. Monteriggioni

We ran into Monteriggioni driving down the freeway from Florence to Siena and decided to stop on a bit of a whim. Monterigginoi is a beautiful walled castle village which sits on a small hill overlooking vineyards - virtually turning the mental image you get when you imagine Tuscany into reality.  

The castle town has beautiful small streets and is perfect to wander through on a stop to either Siena or Florence.  If you are lucky enough to be traveling through here at the first weekend of July, Monteriggioni has its version of Siena's Il Palio with the locals dressing up in medieval clothing - the cost of 10 Euros is well worth it.

There are many country houses (Agriturismos) located near here that would make a great base!


Other things to do in Tuscany

1. Chianti

Lying between Florence and Siena in the heart of Tuscany is the Chianti Classico wine region.  Beautiful vineyards on rolling hills and interesting, old wineries, Chianti is a great place to start exploring Tuscany.  There are many places where you can hire bikes and ride through the vineyards.  We would recommend you start at Barone Riscasoli Winery which is located at the hilltop Castle of Brolio. 

2. Pisa

Pisa as a town, in our opinion, is pretty bloody ugly!  But... we understand the need to get the obligatory 'holding up' the Leaning Tower of Pisa photo.  Pisa is only a 25 minute drive from Lucca or an hour from Florence so its not too bad to drop in for a few hours and checkout - just not one of our favourite places.

Leaning Tower of Pisa