Province of Siena Holidays
At a glance
Photograph fascinating medieval architecture and local products in the small, walled village of San Gimignano.
Sip on famous local wines on a vineyard tour in the Chianti hills.
Take a day trip to the lovely city of Siena and climb the Torre del Mangia or admire the famous Duomo.
Destinations in Province of Siena
Top things to See and Do in Province of Siena
The city of Siena, as well as the province's villages and hamlets, hold regular markets selling everything from food to hand-crafted products made by local craftsmen. The Fortress Market takes place every Wednesday in Siena, located close to the Piazza Gramsci, with clothes, shoes, bags and even jewellery. Make your money go further and take a trip in July – this is when the sales are held, with reductions of up to 75%.
Via Banchi di Sopra is the main shopping street in Siena. Here you'll find an array of clothes shops and bag boutiques. If you're more into local produce and Italian souvenirs, the Via di Citta is the place to head. Just outside of the city in Castellina in Chianti, the town's shopping hall is located in the former fortress tunnels. This underground maze - which is also an alluring way to experience this historic hamlet - has art shops and even a vendor selling handmade shoes.
High-end shops can be found in Siena's shopping district, where you'll come across world-renowned names and top Italian labels. If you want the name but don't want to pay the price tag, then Valdichiana Outlet Village - located on the border of the Siena and Arezzo provinces - houses 140 shops including big names like Replay, Puma and Enrico Coveri.
Quiet evenings by the hotel bar are the norm when staying in the hamlets and villages nestled in the Tuscan hills. Though there's no harm in taking a stroll at night - you may even find yourself a small, local tavern and get chatting to the locals, or discover a secret viewpoint to enjoy the dusky scenery.
With many of the hotels found in tiny villages dotted around the province, lively nightlife isn't really in abundance unless you visit during a festival. However, if you choose to stay in the city of Siena until after dark, you'll get to enjoy the hustle and bustle of a city evening. The Cacio & Pere bar on the Via del Termini is not only known for its cocktails, but for hosting various art and photography exhibitions, local theatre and music concerts throughout the year.
Tuscan dishes, particularly from Siena, are based on natural flavours and aromas, and make full use of powerful flavours like garlic, fennel and tarragon. One of the most traditional is Pici, a thick, handmade spaghetti made from flour and water rather than the typical flour and eggs. As for sweets, Panforte is a must-try - a spicy cake of nuts and candied fruits. Also look out for Ricciarelli - they're cookies that were largely favoured by Siena's past nobility, flavoured with orange peel, candied citron and almonds.
The province of Siena is famous for its excellent local wine production, with five labels officially certified by the Denominazione di Origine Controllate e Garantita (DOCG). On top of this, it's home to one of the most widely known wine regions in the world, Chianti. With multiple vineyards to visit, you'll be able to try, buy and take home as many wines as you like - including Chianti Colli Senesi and Chianti Classico. The smaller and lesser-known Montalcino is also worth a visit, prominent for its large-scale production of Brunello.
Where to eat in Siena
Just outside the rural village of Castellina in Chianti is the Ristorante Osteria di Casa Frassi. This exclusive setting serves up typical Tuscan dishes accompanied by excellent wines from the Fattoria Casafrassi and other nearby farms. Over in the village of Casole d'Elsa is the L'orti di Casole, where you can opt to have lunch on the veranda and enjoy panoramic views of the rolling landscape. If you're in need of a sugar rush, stop by Siena's Manganelli. This authentic treasure chest is filled with smells and colours that take you back to medieval life - from candied fruit and chocolate, to milk and mint sweets.
Tuscany is known for its fairly hilly landscape, so keep in mind that some of the roads and pavements may have steep inclines and declines. The villages that surround the city of Siena are quite spread out, so you won't be able to walk between them, but walking around the village centres is pretty easy. Many are pedestrianised - this includes Siena city too - with paved streets (no cobbles in sight) making it as easy as possible to enjoy the sights on foot.
Car hire is included on Lakes & Mountains holidays to Tuscany, giving you the freedom to visit as many of the pretty medieval villages, array of cantinas and historic cities in and around the Province of Siena as you like. For example, from most accommodations in Siena, you can drive to Florence in around an hour. If you want a change of scenery, take a day trip to one of Tuscany's sandy beaches - it'll take up to two hours each way, but gives you more than enough time to catch some rays and splash about in the sea.
If you head into Siena for the day, you'll have to park on the outskirts the city and get the bus to the centre. A small bus, named Pollicino, can be picked up from many of the car parks dotted around Siena and will take you inside the city walls. Lines 51, 52 and 54 depart every 15 minutes.
On two wheels
Bikes and e-bikes are becoming increasingly popular was to explore the Tuscan region. If you're staying in Casole d'Elsa, you can hire an e-bike for the day and ride out to the rolling hills and medieval castles of the region. Tuscany is also known for its hills, so e-bikes are great for giving you a helping hand up the steepest parts.