Tuscany is a magical land with so much to offer. I have been personally visiting for years and I believe I will never tire of it. This beautiful region of Italy, and the neighbouring regions of Umbria and Marche, offer endless possibilities and itineraries. And if you happen to go there in high season, as we did this summer, you can still have a wonderful time without going anywhere near the crowds of tourists visiting Florence or flooding Siena during the Palio season.

Obviously, the wonderful sites found within these bustling areas, such as the treasures of Uffizi Museum, the beauty of the Cathedral of Santa Maria del Fiore, Florence Duomo and St. John’s Baptistery and the adorned city of Siena during the Palio season, are worth fighting to see; so, if you haven’t been, I encourage you to visit them.

If the travel season is too busy, perhaps you can consider visiting these world famous locations another time. Or maybe you are lucky enough to have already been to these sites and now you simply want to do a more in-depth exploration of the Tuscan region; experience the local culture and discover some of the hidden gems. Or, perhaps, you could simply do both; check out the world famous attractions and also take some time to tour other parts of this delightful region.

Most towns and villages in this part of the Bel Paese are little jewels that take you back, in an instant, to a different time and a different way of life. To this day, mainly a farming society, the region has probably one of the most beautiful rural landscapes in the world; a place where man’s hand has gently worked with the original natural beauty of the terrain to shape it into what it is today, producing a Botticelli’s bucolic dream land.

This year we based our excursions out of Simignano; about 20 minutes outside of Siena. You need a centrally located base when you plan to visit Tuscany. A place that allows you to reach anywhere you wish to visit within an hour car ride; saving you the hassle of unpacking and packing every day to change accommodations. Driving through Tuscany is a leisurely activity and trust me, you won’t mind having to find your way home every day when the landscape you are driving through is just as much worth the trip as the place you’ve just visited. Going from place to place in Tuscany is not a chore or a means to an end; it’s part of the experience.

I firmly believe the best way to explore Tuscany is by car. Just roaming aimlessly throughout the countryside is one of my preferred activities when I am there and you always discover some hidden treasures while doing so; a little farm selling their own produce along the road, a country restaurant serving authentic and delicious food, a lovely spot that you’ll want to stay at next time, a country villa that you’ll be dreaming about for the next 12 months…

This fashion of lazy wandering also provides you the most relaxing experience you can ever have as a tourist. No maps or itineraries to follow, no check list of places to cover; just field after field of sunflowers and wheat, vineyards and olive trees, rural chapels and scattered farmhouses… And when you are done for the day, just switch on your GPS and head back home; you won’t have gone very far. The countryside roads are winding, the pace is slow. You will probably have stopped countless times just to admire the landscape, soak in the colours and the mist in the air raising from a mountain in the distance or from a field below. This is the sort of place where the change of pace in your itinerary is profound, allowing your mind to expand just as much as the vast horizon before you.

From Simignano – a lovely little village of 30 people, where the local breed of pig, Cinta Senese, is far more numerous than the local population (or anywhere nearby for that matter)  – we spent 5 days in Bagnaia, you can easily visit:

Val d’Orcia:

  • San Quirico d’Orcia

  • Montepulciano

  • Pienza

  • Montalcino

  • Borgo Bagnaia

  • Monastero Benedettino di Sant’Anna in Camprena: built in 1334 in the middle of the beautiful Val d’Orcia, only 6 kms from Pienza. This secluded monastery was chosen by Anthony Minghella as the set for some famous scenes of the movie, The English Patient, such as the scene where Juliette Binoche is shown, by candle light, the frescos in an abandoned chapel.

This area is known as Crete Senesi, literally Senese Clays, for the distinctive soil composition which provides a grey colouration that makes the landscape look almost lunar at times. Here you will find many spots where the iconic Tuscan scenery is similar to what you would see in movies or read about in books. The area is also famous for its white truffle!

All these places can’t boast world renowned art as the more famous locations can, but I promise you that admiring one of the less known frescos in a little country church (in which you are the only visitor) pays off tenfold.


Relais La Suvera

Villa la Suvera, 70

53031 Loc. Pievescola

Casole d’Elsa (SI)

Tel. +39577960300

Ex Pope Julius II summer residence; it was originally a fortress and was later acquired by the patrician Ricci Family. This place is simply stunning.

Belmond Hotel Castello di Casole

Località Querceto

53031 Casole d’Elsa


Tel. +39577961501

Set in an estate of 4200 acres, the property is comprised of the Castle which is now a hotel and the casali that you can rent or buy. This is one of the finest properties I’ve seen. Service and food are top quality and the view is just breath-taking. We had a lovely encounter with porcupines on our way out at night after a delicious meal at their terrace restaurant. Unforgettable.

La Bagnaia Golf & SPA Resort

Strada Statale, 223 km 56

53016 Siena SI

Tel. +39577813000

This is an entire medieval village converted into a hotel managed by Hilton. Lovely Spa and delightful grounds. We enjoyed the restaurants and the possibility of simply relaxing in different places. I actually spent quite some time in the SPA and walking in the woods with my dog, while my children enjoyed the pool and the grounds. Deer and hares are simply everywhere and it’s lovely to encounter them on your way to breakfast or on your evening stroll.

Agriturismo S. Anna in Camprena

Loc. S. Anna in Camprena

53026 Pienza (SI)

Tel. +39578748037

Mob. +393384079284


Taverna dei Barbi

Loc. Podernovi

53024 Moltacino (SI)

Tel. +39577841117

Budget accommodation

Agriturismo Casa al Gianni

Loc. Simignano

Piazza del Pozzo, 12

53018 Sociville (SI)

Tel. +39577311002

Lovely place and great hosts, offering self-catering accommodations on the family farm where they breed the famous Cinta Senese pig. The atmosphere and friendliness of the hosts and the village is unrivaled.


Relais La Suvera ***

Villa la Suvera, 70

53031 Loc. Pievescola

Casole d’Elsa (SI)

Tel. +39577960300

I loved the casual restaurant for a light lunch; something not easy to find in Tuscany, where the food is quite robust. The main restaurant serves a delicious gourmet dinner of several courses.


Belmond Hotel Castello di Casole ***

Ristorante Pazzia (outdoor) or Tosca (indoor)

Località Querceto

53031 Casole d’Elsa


Tel. +39577961501

My absolute favourite. It doesn’t come cheap but it’s worth every penny. If you go, a must try is the beef fillet with fois gras and truffle. Just divine! And the wines… Wonderful service and from the terrace you can admire a sunset that you will hardly forget for the rest of your life.

La Pergola (Pizza a km vero) *

Via Giuseppe Garibaldi, 22

53030 Radicondoli (SI)

Tel. +39577790717

Presidio Slow Food for pizza. Top ingredients, interesting pizzas and a stunning view of the valley below. Recommended for dinner so you can admire the sunset. Make sure you reserve a table in good time.

La Taverna di Cecco

Via Cecco Angiolieri, 19

53100 Siena

Tel. +39577288518

Compagnia dei Vinattieri

Via delle Terme, 79

Via dei Pittori, 1

53100 Siena

Tel. +39577236568

Il Grillo Moro

S.da Aeroporto di Ampugnano

53018 Sociville (SI)

Tel. +39577393533

Osteria del Borgo

Via Ricasoli, 25

Mensano (SI)

Tel. +39577963911

Mob. +393332590925

Trattoria Toscana Il Vecchio Forno **

Via della Piazzola, 8

53027 San Quirico d’Orcia (SI)

Tel. +39577897380

Loved the food, the porcini and truffle dishes, the Brunello di Montalcino served at fair prices and the ambiance. Eating out in a courtyard under a pergola is just what Italy is all about!

La Bottega di Giovannino

Wine Bar

Via Roma,

6 Radda in Chianti

53017 Siena

Mob. +393395356675

La chiocciola di La Locanda dei Nonni

Via M. Mencatelli 2/4

Pienza (SI)

Tel. +393391848208

Foresteria Villa Cerna

Loc. Casina dei Ponti, 57

53011 Castellina in Chianti (SI)

Tel. +395771510998

Mob. +393381615428

Vineyard Visits, Wine Tasting

Taverna dei Barbi

Loc. Podernovi

53024 Moltacino (SI)

Tel. +39577841117

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