Cortona, Tuscany
Overview
Discover Cortona: Private Tours, Experiences & Custom Travel
The town of Cortona is a beautiful hill-top town in South-Eastern Tuscany, that has become notorious in recent years because of the film 'Under the Tuscan Sun'. It is here where the lead character purchases her property in the lush countryside which surrounds the town.
An encounter with Cortona is an encounter with art, history and mysticism. Getting to know this timeless town is a real rediscovery of our past. Within its mighty Etruscan walls Cortona jealously guards its treasures and offers testimony to the history of a most noble civilization as well as enchanting views of the landscape enclosed by Lake Trasimeno and the Appenines.
From its high perch on top of a verdant hill Cortona dominates the Val di Chiana and offers commanding views over the valley all the way to the peaks of the Monte Amiata. The medieval aspect of buildings and alleyways gives the town a charming, unspoilt air. The Basilica of Santa Margherita and the Convent of Le Celle in the upper part of town invite guests to discover Cortona from up above down a path of art and faith, only a stone’s throw away from the city centre. A walk through the Rugapiana (the only flat street in town) will take you past the Piazza della Repubblica, overlooked by the commanding medieval Palazzo Comunale (town hall) and to the Piazza Signorelli with its Palazzo Casali, the current home of the Museo dell’Accademia Etrusca e della Città di cortona (MAEC) that houses vast collections of Etruscan and Roman archaeological finds.
Located at the northern end of town just across from the Cathedral the Museo Diocesano is a real jewel-case housing works by major local artists such as Luca Signorelli as well as one of the most enchanting Annunciations by Beato Angelico. Just outside the city gates at the foot of the hill the Melone I and II at Sodo are two of the finest examples of Etruscan burial-mounds dating to the 6th century B.C. A short drive in the direction of Foiano della Chiana will take you to the Abbey of Santa Maria at Farneta, one of the finest examples of Romanesque art in the area. An event not to be missed is the CortonAntiquaria antique fair, one of the most interesting national antique fairs. The event takes place every year in the 18th century Palazzo Vagnotti from the last Saturday of August to the second Sunday of September.
Cortona in pictures
Gallery
A few frames from our own trips. The rest are in the gallery below.
Map
Get your bearings before you go
Multi-Day Holidays Tours
Whole journeys, planned end to end
Flavors of Fall in Tuscany: Olive Harvest, Truffles, Wine & Cooking
Experience Tuscany during its most delicious season, when the countryside comes alive with the annual harvest. From the grape harvest of September to the olive groves and truffle season of October and November, spend a week on a family-owned wine and...
Full day Off beaten sites discovering Tuscany & Umbria
South from Florence, north from Rome, Tuscany & Umbria are Italy's green heart & the geographic centre of the country. A long way from either coast, what is to be enjoyed in Tuscany and Umbria is the rolling sea of green..
Villas
Private homes with stories of their own
Italy,Tuscany,Cortona
Italy,Tuscany,Cortona
Italy,Tuscany,Cortona
Photo Gallery
Explore Towns and Cities in Tuscany
Every town here has its own personality. We know them by name.
Arrezzo
Bagno Vignoni
Barga
Carrara
Castiglion Fiorentino
Chianciano Terme
Chianti
Cortona
Elba Island
Fiesole
Florence
Livorno
Lucca
Maremma
Montalcino
Montecatini
Montepulciano
Monteriggioni
Monticchiello
Pienza
Pietrasanta
Pisa
Porto Santo Stefano
San Gimignano
San Miniato
Saturnia
Siena
Terme di San Filippo - San Filippo Natura Hot Springs, Tuscany
Val D'Orcia
Viareggio
Volterra
Our Featured Properties
Stays we picked one by one
Italy,Tuscany,Florence
Italy,Tuscany,Castiglion Fiorentino
Villa Stefano: Ideal Property for Artists, Families & Large Groups in Tuscany
Italy,Tuscany,Pistoia
Italy,Tuscany,Chianti,Castellina in Chianti
Italy,Tuscany,Montepulciano
Italy,Tuscany,Montepulciano
Italy,Tuscany,Florence
Italy,Tuscany,San Gimignano
Italy,Tuscany,Volterra
Italy,Tuscany,Arrezzo,Arezzo
Italy,Tuscany,Montepulciano
Italy,Tuscany,Montepulciano
Popular Transfer Routes in Cortona
The rides our guests ask for most, with a driver who knows the way.
Italy Vacation Specialists provides licensed private transfer services throughout Italy, including Cortona and surrounding areas. With over 20 years of experience, our professional English-speaking drivers offer both Business Class and Luxury Class vehicles for airport transfers, city-to-city rides, and full-day chauffeur services. All vehicles are fully insured, well-maintained, and operated by vetted local drivers who know the roads, traffic patterns, and best routes across the region.
Every journey is different. Tell us where you need to go.
Request a Transfer QuoteQuick Enquiry Form
Tell us about your dream trip and we'll craft the perfect itinerary for you.
In their words
Stories That Stay With You
Here's what our guests share about their unforgettable journeys
From the journal
IVS Magazine
Latest
14 September 2026
Italy’s Best Autumn Food Festivals: Where to Eat, Drink and Celebrate in 2026
Read the piece
Plan it with us
For customized holidays and expert advice for travel in Italy and the Mediterranean, Get in touch with your travel agent or contact us via our.
-
Direct In Italy: +39 375 823 5314
-
Toll Free: 1-866-779-2565