Tuscan Treasures: A Three-Day Itinerary

Tuscany is best enjoyed when you’ve got the time to slow down and make things up as you go along – lazily driving from village to village, poking your head into old churches, speaking with the locals and sampling local delicacies. However, if your time in Tuscany is brief, it helps to have an outline of where to go and what to see and do, so we’ve put together a three-day itinerary that covers some of the delights that this gorgeous region has to offer.

Day One – Fabulous Florence 

Best Tuscany Guide : Florence

We begin by heading to Florence, the birthplace of the renaissance and jewel of Tuscany. In all honesty, we would never advise you to try to ‘do’ Florence in a single day. However, if your time is limited, or you are just looking to get a small taste of what the city has to offer, we suggest the following highlights.

Begin your day at Il Duomo di Firenze (Piazza del Duomo), before the cathedral becomes overcrowded later in the day. There has been a church here since the 5th century, although the current building dates from the end of the 13th century. Artistic treasures include the immense dome, built by Filippo Brunelleschi, frescoes and statues by Uccello and Bruneschelli and the gorgeous fittings of the interior.

To get a feeling for Florence’s most famous ruling family, the Medicis, head over to the Basilica di San Lorenzo (Piazza di San Lorenzo 9), two or three minutes walk away. This church essentially became the private church of the Medici family after Giovanni di Medici offered to rebuild the crumbling structure in 1419. A highlight is the Medici Chapel filled with Michelangelo’s statues.

Alternately, we advise you devote a morning to Florence’s most famous gallery, the Uffizi (Piazzale degli Uffizi). Afterwards, for lunch, try ‘Ino (Via Accademia dei Georgofili) for a gourmet panini and fresh salad, accompanied by a glass of local wine.Best Tuscany Guide: Florence Cathedral

In the afternoon, wander down to the Ponte Vecchio. While it can be a bit crowed, this medieval bridge over the river Arno, built in 1345, has been a marketplace for goldsmiths and other tradesmen, and you can still find many gamely selling their wares from the shops lining the bridge. Bring your camera for the terrific views of the city from the centre of the bridge.

Now for shopping we recommend the Boutique Luisa via Roma (Via Roma, 19/21/r) for the latest fashions with an avant-garde edge. This store is a Florentine original, having opened in 1930 and catering to a very select clientele.

By this stage you’re probably gasping for an ice cream, Bar Vivoli (Via Isole delle Stinche, 7r) is the subject of intense debate – is it the best gelato in all of Florence? You’ll have to help us decide.

For a Florentine delight that combines heritage and excellent opportunities for shopping, stop by the Farmaceutica di Santa Maria Novella (Via della Scala, 16), the world’s oldest operating pharmacy. Open since 1221, the Farmaceutica sells its famous handmade perfumes, scents and cosmetics alongside medicinal cures. The interiors are quite astonishing and you’ll fall in love with their trademark fragrances.

End the day with one of Florence’s culinary delights, the Bistecca Fiorentina. This beauty is very rare, rather large wood-grilled T-Bone steak, meant to be shared between two or three people, Try this delight at the Michelin-rated Ora d’Aria (Via Accademia dei Georgofili 9r), one of Florence’s most renowned restaurants. It’s worth noting that bookings are essential. Otherwise you might like to try Trattoria Marione (Via della Spada 27) or L’Osteria di Giovanni (Via del Moro, 22, 50123)

Piazza di Santa Maria Novella - JK Place Florence

Where to stayJK Place Florence

With a chic, contemporary design by architect Michele Bonan, JK Place has an unbeatable location on the Piazza di Santa Maria Novella, which you can admire while savouring a glass of prosecco on the hotel’s rooftop bar.

Check rates and availability for JK Place, or see all of our fantastic Florence hotels here

Day Two – Monteriggioni and San Gimignano 

San Gimignano Tuscany

Day two, we adopt a slower pace and centre on two of the walled towns that Tuscany is famed for, both within easy reach of Siena – Monteriggioni and San Gimignano.

Start your day by scaling the medieval walls of Monteriggioni. They were built in the built in the 13th century to both defend the town and provide a fortification in defence of nearby Siena. The walls span about 570 metres and very little of it – and the town itself – has changed architecturally since the 15th century. From the walls, there are terrific views in all directions.
Quench your thirst by visiting the Vinicola Bartali (Strada dell’Abate 3) as you head north, out of town. This vineyard has a store selling wine, olive oil and local delicacies, and tasting are always available.

After wine tasting, drive the rest of the way to San Gimignano. This hilltop town has a very ancient history – it was first settled in Etruscan times.

Time again for lunch. We recommend Cum Quibus (Via S. Martino 17) for their acclaimed degustation menu and wine pairings. It’s very highly rated, so we advise giving them a call beforehand.San Gimignano Tuscany

Start your time in San Gimignano in the Piazza Duomo, where the town’s major church, the Collegiata or Collegiate Church of Santa Maria Assunta, and the Palazzo Communale can be found – the town’s premiere attractions.

The Collegiata (Piazza Duomo 2) dates from the 12th century, although there has been a house of worship on the spot since the 10th century. Check out the utterly amazing frescoes – so vivid and vibrant after hundreds of years.

The Palazzo Comunale (Piazza Duomo 2) was the seat of power in the town from the 13th century. Climbing its bell tower, you have a spectacular view of all of the other towers, most of which are unfortunately unsafe to climb. The rest of the building is filled with meeting halls (The Sala di Dante, named after the famous poet, is a highlight) and the civic museum, with artworks by a raft of renaissance masters is worth a look.

San Gimignano L'Antico Pozzo

Where to Stay – L’Antico Pozzo

Nestled in the medieval town centre, L’Antico Pozzo is a beautiful bolthole within a restored historic building. We love the original features such as the evocative wooden beams and exposed stonework.

Check rates and availability for L’Antico Pozzo

Day Three- Sensational Siena

Tuscan Treasures Siena

Our final day will be spent in the wonderful city of Siena. Once a powerful centre of trade, military power and culture, today it remains one of the most finely preserved medieval cities in Europe.

From your hotel, head into the centre of the city to find the Piazza del Campo (Il Campo), Siena’s main square. This large space, paved in 1349, used to be the city’s marketplace. It is probably best known for the Palio di Siena, a brutal, breakneck horse race, held in July and August. In this race, the city’s fiercely competitive Contrada, or neighbourhood wards, battle for glory – sometimes quite literally! Ramming and flogging other riders is not only permitted, it is encouraged! This race remains one of the city’s great cultural treasures and some hotels overlooking the square sell out years beforehand during the race period.

If you have children, the Piazza is a terrific place to wander and chase the pigeons. It is also ringed with cafes where you can enjoy a morning coffee.

Siena Piazza

A short four minute walk away is the Duomo di Siena (Piazza del Duomo 8), the city’s cathedral. First built in the 13th century, construction and modifications continued well into the 15th century. Amongst the glories of the duomo are the floor mosaic floors that date from the 14th century, statues by Donatello, Bernini and Michelangelo, and the renaissance glories of the Chigi and St John the Baptist chapels.

Time for lunch. We love the views at Ristorante San Domenico (Via Camporegio 17). Another great spot for lunch is Taverna San Giuseppe (Via Duprè 132) for its cosy interior and real Tuscan atmosphere.

Back at the Piazza del Campo, the Torre di Mangia (Piazza del Campo 1) is for the intrepid to climb its 400 steps. The tower was built entirely of brick between 1338 and 1348 and the name translates as ‘Tower of the Eater’. It turns out that the first bellringer of the tower, Giovanni di Balduccio, was a bit of a glutton. The views from the top are spectacular.

Families might enjoy spending time wandering the streets looking out for the colourful signs that mark the boundaries of each Contrada. Each of the wards has their own animal mascot – see how many you can spot.

For some afternoon shopping, try the Via Banchi di Sopra for the leathergoods that the city is renowned for, including higher-end stores selling gorgeous bags. While the name might sound fairly touristy, Toscana Lovers (Via delle Terme, 33) sells beautiful artisanal Tuscan decor and tableware.

Wine lovers will be in paradise should they visit Enoteca Italiana (Via Camollia 72). This Siena institution is part wine bar, part exhibition. There are over 1500 wines to sample and you’ll receive recommendations on which wineries to head for from the experts on hand.

Our dinner pick to end the day is Antica Osteria da Divo (Via Franciosa 25) for its great Tuscan fare and amazing location between the Duomo and the Piazza del Campo – a truly authentic Sienese experience. Otherwise, head on over to Zest Restaurant & Winebar (Costa di Sant’antonio 13) for lovely food and the chance to spend your evening sampling Tuscany’s finest drops.

Campo Regio Relais Siena Boutique Hotel

Where to stayCampo Regio Relais

Campo Regio Relais is a charming boutique hotel in Siena’s historic city centre with just 6 beautiful bedrooms. The picturesque terrace garden has wonderful views over the spires and rooftops of medieval Siena.

 Check rates and availability for Campo Regio Relais or see all of our boutique hotels in Siena here

See all of our wonderful boutique hotels in Tuscany here