At Chic Retreats, we believe that Tuscany is best enjoyed on an improvised basis – 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 1 – FABULOUS 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.
We advise beginning your day at Il Duomo di Firenze (Piazza del Duomo) for as the day progresses, the city’s cathedral will become crowded and you will have less time to enjoy the place. 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. Entrance is free, but we recommend you rent the €2,50 audio guide.
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. Entrance fee is € 5,00
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 3r/7r, Ph +39 055 219208) for a gourmet panini and fresh salad, accompanied by a glass of local wine.
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. Other candidates for the best gelato in town include Gelateria La Carraia (Piazza Sauro Nazario, 25/R) and Perche, No? (Via dei Tavolini 19).
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 along side 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, Ph +39 055 200 1699), one of Florence’s most renowned restaurants. Bookings for dinner are absolutely essential, however – don’t expect to just walk in! Give them a call. Otherwise you might like to try Trattoria Marione (Via della Spada 27, Ph +39 055 214756) or L’Osteria di Giovanni (Via del Moro, 22, 50123, Ph +39 055 284897)
Nearby Chic Retreats – JK Place Florence is, as the name suggests, centrally located in the city, as is Hotel Santa Maria Novella. Just outside the city, Villa Cora, Villa di Vignamaggio and Borgo i Vicelli are our picks. The charming Il Borro is approximately one hour south of Florence.
DAY 2 – MARVELLOUS MONTERIGGIONI AND SAN GIMIGNANO
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. Entrance from the ticket office at the main town gate is €3.
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, Ph +39 0577 943199) for their acclaimed degustation menu and wine pairings. It’s very highly rated, so we advise giving them a call beforehand.
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. Entrance fee is €6,00.
Spend the rest of your afternoon wandering the town and admiring its simple, medieval charms until dinner time, then hop back in the car and make the drive north, once again to Castello Fuglinano (Loc. Casaglia, Ph +39 338 164 6242) for dinner. This castle originating from the 10th century now boasts a restaurant with view over San Gimignano, and wonderful homemade Tuscan cuisine. Bookings are strongly recommended, so give them a call ahead of time.
Nearby Chic Retreats – Il Falconiere lies ninety minutes to the west of Monteriggioni, as does Il Borro. Castello di Velona and La Bandita are both just over ninety minutes south of Monteriggioni. Borgo Pignano and Barbialla Nuova are within fifteen minute’s drive of San Gimignano.
DAY 3 – SENSATIONAL 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.
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. Entrance is €12,00 and includes entrance to the cathedral museum.
Time for lunch. We love the views at Ristorante San Domenico (Via Camporegio 17, Ph +39 0577 275707). Another great spot for lunch is Taverna San Giuseppe (Via Duprè 132, Ph +39 0577 42286) 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. Entrance is €8,00 and kids under six go free. The views from the top are spectacular.
Families might enjoy spending time wandering the streets looking out for the colorful 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, Ph +39 0577 286 054 ) 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, Ph +39 0577 471 39) for lovely food and the chance to spend your evening sampling Tuscany’s finest drops.
Feel that we’ve missed out something absolutely essential? Email us and we’ll include your tips in future newsletters.