10 romantic things to do in Siena, Italy

10 romantic things to do in Siena, Italy

Rich Italian wines, picture-perfect picnics and striking sunsets – there's plenty for loved-up couples to do on a trip to this medieval city, says Daisy Cropper

1. Seek out the city's Contrada

Each of Siena's 17 districts has its own symbol, colours, flag, church, and even a rival, forming powerful and passionate traditions that date back to medieval times. These clans are known as Contrada and make up the foundations of the city's unique, community-led and relaxed way of life.

Each district is adorned with adoration for its Contrada. Streets are lined with flags, small signs, lamps and more. See if you can discover all 17 symbols on a self-guided walk of the city. Tick them off as you find them: caterpillar, dragon, eagle, forest, giraffe, goose, owl, panther, porcupine, ram, shell, snail, tortoise, tower, unicorn, wave and wolf.

If you're lucky, in the evening you may be treated to the sight of small parades or flag-waving crowds and hear drums beating. The Contrada often practise for their annual parades at the Palio (see number 9 below).

2. Hunt the hidden battlements

Siena's past has been colourful to say the least. Fighting battles against Florence and armies from further afield (including the English) has left the city scarred and rebuilt time and time again. Different rulers had different styles, which are reflected in Siena's varied cityscape.

Across the city you'll see square-shaped Guelphic merlons or battlements. Although beady-eyed visitors will be able to spot the well-hidden Ghibelline battlements - shaped like a swallow's tail - tucked away amid the red-roofed houses. This curved design was a favourite of Florentine rulers.

It's easy to spot the imposters at the top of the Torre del Mangia (entrance in the Palazzo Pubblico) - although there's a steep entry fee (€8-13) and over 400 steps to navigate.

3. Supper on the streets

After a day packed full of sight-seeing you'll need to recharge and chill out in the evening. Siena's narrow labyrinth streets and towering buildings create a maze of little-known backstreet restaurants and bars. Coupled with the city's hilly location - outside dining has a different edge.

Staggered down the steep slopes are tables on raised platforms (a little like stages) to balance out the angles. Find yourself perched on small benches, surrounded by wall-flowers, candles and your other half for company.

Ristorante Santa Caterina (website in Italian) at Via della Galluzza, 26, is the perfect place to try out local cuisine. Themed around the city's contrada, with coats of arms and memorabilia covering the walls, this is the perfect place to experience Sienese life, with a bit of atmosphere. The menu is varied, suiting all tastes (I'd recommend the pheasant), but leave room for the delightfully sweet deserts and don't miss a glass (or two) of the region's speciality - rich-red Chianti wine.

4. Treat yourselves to something sweet

Along with conservation of the city's medieval landscape, the proud residents of Siena have conserved other aspects of ancient life. Stroll down to il Magnifico (Via dei Pellegrini, 27) - a bakery serving wonderfully more-ish biscuits, sweets and cakes similar to what would have been eaten centuries ago.

Owner Lorenzo will let you nibble away for free until you find your favourites... To keep in with tradition, pick up a box of ricciarelli - small, sweet and chewy biscuits made predominantly from almonds. Be warned: once you pick up one, you'll be wanting more.

For a sit-down treat, head to Nannini (Via Banchi di Spora, 24) - the best place in the city for coffee. Try rich, dark espressos or a creamy cappuchino for a caffeine kick, or chomp down on the cafe's huge range of tempting pastries, cakes and cookies.

5. Lap up the local specialities

It's a fact: Italians love their ice cream, and travelling is all about experiencing other cultures, right? So dive in and lick up as much of the local stuff as you can!

Head for Gelateria Brivido on Via del Pellegrini, 1, for mound upon mound of the creamy stuff. As you enter the palour you'll be greeted by a huge see-through counter filled with various flavours flamboyantly decorated: mango - dotted with flakes of the fruit, coconut - with coconut shells dug in, coffee - yep, you guessed it, with coffee beans sprinkled over - the old favourites are all there.

Adventurous couples mights try the luminous pistachio, tempting chocolate-hazelnut or the tangy very-berry flavours.

6. Bathe in a medieval font

Well you can't actually bathe in this fountain but that's what residents would have done here centuries ago. Located below the San Domenico church, the Fontebranda acted as a bathroom for thousands of city dwellers. Locals claim they'd still drink the water here so it's a refreshing stop on a city tour.

Built in 1193 the fountain proved to be an important meeting point for city dwellers - made up from three basins: one for washing, another for extracting water and one for animals - sit back and imagine what city life was like centuries ago.

The fountain also marks a major point on the city's complex network of underground tunnels, which once supplied the entire city with water. The bottini worms its way beneath the city for a staggering 25km - all of which were dug by hand using rudimentary tools hundreds of years ago.

7. Escape the hordes

Tucked away around the bustling city are rare pockets of greenery - bushy olive trees and soft green grass make for the perfect place to escape the crowds. For a place with a difference make for Orto dei Pecci - found behind the Museo Civico and main Piazza del Campo. Head around the tortoise-shell market place and towards the dusty track to the left.

Since the 16th century the land here has been cultivated with kitchen gardens and is open to the public. Scour the greenery for medieval medicinal herbs and keep an ear out for the resident dwarf donkey.

The track also leads to All'Orto dei Pecci - a restaurant serving simple, local Italian food. Push the boat out and stop for lunch: fresh tomatoes used on the crunchy bruschetta are grown in the back-garden and the super-thick spaghetti (known as pici) may look worm-like, but is a wholesome Sienese speciality.

8. Be awe-struck by San Domenico

This impressive Gothic structure stands tall on one of the city's many hill tops. Dominican monks first founded their monastery in 1125, with construction on the church beginning in 1226. Free entry to the church, a treasury of art work and frescos to explore, and tip-top views of Siena outside make this a place worth stopping by.

Head for the church in the early evening - sunsets aren't visable from here but cast a bewitching orange glow across the city's centuries-old rooftops and cathedral. The crowds tend to disperse around this time too, so it will be just the two of you.

9. Get your hearts racing at the Palio

An annual event which is sure to get your hearts racing - il palio is celebrated twice a year on 2 July and 16 August. Dubbed Italy's most spectacular festival, it is essentially a bareback horse race, where riders circle the main Piazza del Campo three frantic times. There are 17 competitors - one for each of the city's Contrada - and the race has unique importance to each and every one of them.

Top viewing spots around the square can charge up to €300. Join in with the locals and witness the race from the ground in a huddle in the Piazza for free. Local tour guide Rita Ceccarelli says the atmosphere is electric and you literally move with the crowd.

Via Giovanni Dupre is the local's favourite entrance to the Piazza on race day. Couples fearful of big crowds or small places should steer clear of the packed out event - the crowds are BIG.

10. Toast to your love in Italy's largest wine exhibition

Italy, and in particular Tuscany, is world-famous for its wine. Where better to explore the intricacies of this region's specialty than in an exhibition housing more than 1,600 bottles? Entocea Italiana is home to wines from across the country and visitors can explore the wide range on offer, and try a glass or two (for a fee).

For wine-lovers this exhibition reflects both big businesses and tiny vine-yards, painting a balanced view of the country's complex wine industry. Housed inside the bastions of the 16th century Medici Fortress, with grand arches and elaborate features, it makes for an interesting setting too.

Entocea Italiana is on the Fortezza di Santa Barbara - close to the city's main bus station - and serves lunch and dinner in a cool, cave-like restaurant.

Image credited to Daisy Cropper.

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