Four Days in Tuscany, Private Tour

This four days tour allows travelers to enjoy the beauties of Tuscany as well as getting a bite of the famous Italian Christian tradition. Four days through breathtaking views, ancient medieval cities, historical vineyards, religious centers of world importance.

per adult from




4 days


Hotel pickup available


Mobile ticket

Select Date and Travellers

No tour options available.

  • What's included :
    • Air-conditioned vehicle
    • WiFi on board
    • Private transportation
    • Parking Fees
    • Tolls
    What's excluded :
    • Hotel must be booked by customers at Cortona town or nearby

  • Day 1: Rome- Orvieto- Cortona

    Stop At: Orvieto, Orvieto, Province of Terni, Umbria
    In this beautiful town, travelers have the chance to visit one of the most beautiful gothic Duomo of the world of the 13th c. Moreover the undergrounds tour is very exciting and the clock-tower percfect to enjoy the panorama all around. This place is really magical and people like very very much!
    Duration: 2 hours

    Stop At: Cortona, Cortona, Province of Arezzo, Tuscany
    Cortona is a small welcoming town in the Valdichiana, in the province of Arezzo.
    The city, enclosed by a wall where Etruscan and Roman tracts are still visible, was built on a hill, which reaches about 600 meters in height. This elevated position guarantees an excellent view from different points of the city, which allows you to admire the splendid landscapes of the Valdichiana, also seeing Lake Trasimeno.

    The center of Cortona develops around the Piazza della Repubblica, which overlooks the Palazzo Comunale.
    The city is small, but offers several interesting things to visit, including the Diocesan Museum (in which a beautiful table of the Annunciation by Fra Angelico is kept) and the MAEC (Museum of the Etruscan Academy and the City of Cortona), in the which are exhibited, among other things, many finds from the different Etruscan areas of the area. At the museum you can get information on visits to the Archaeological Park of Cortona.

    Do not miss a visit to the beautiful Sanctuary of Santa Margherita, patron saint of the city, and to the Fortress of the Girifalco. Both are located on the highest point of the hill, which can be reached by walking, keeping in mind that the path is short enough, but all uphill. Following the path that runs along the city walls, you can also enjoy beautiful views of the surroundings. The Fortress of the Girifalco, built for military purposes, has undergone important changes over the centuries and is currently only partially accessible.

    Several small shops selling handicrafts and local gastronomy are located on the main streets of the center of Cortona. In the area excellent wines are produced (we are also a few kilometers from Montepulciano and Montalcino) and there is no shortage of wine bars.
    In the city there are several restaurants, mostly oriented towards traditional local and Tuscan cuisine (in the Valdichiana Chianina is bred, one of the most ancient and quality Italian cattle breeds).

    Just outside the walls of Cortona, there is the Franciscan hermitage Le Celle, the first convent built by San Francesco d 'Assisi in 1211, in which today a small community of friars lives. Over the centuries the hermitage has undergone several renovations and extensions, during which the small cell of San Francesco has been preserved, which can still be visited today.

    In summer in Cortona the Tuscan Sun Festival is organized, an exhibition dedicated to art in which international stars and artists participate every year.

    Duration: 2 hours

    No meals included on this day.
    No accommodation included on this day.

    Day 2: Cortona - San Gimignano -Siena

    Stop At: San Gimignano, San Gimignano, Tuscany
    San Gimignano, a small fortified city halfway between Florence and Siena, is famous for its architecture and for its beautiful medieval towers that make the city profile truly unique.

    In the most prosperous period, the wealthy families of San Gimignano came to build 72 towers as a symbol of their well-being and power. Of these, 14 remain today which contribute to making the town atmosphere even more fascinating.

    Declared a World Heritage Site by UNESCO in 1990, San Gimignano is one of the small pearls of the Sienese province and also offers excellent local products such as saffron and white wine called Vernaccia di San Gimignano.
    Duration: 3 hours

    Stop At: Siena, Siena, Tuscany
    It is commonly called " The Medieval Town of Tuscany"
    Siena, located in the heart of Tuscany and surrounded by hills, is one of the most beautiful medieval cities in Italy.
    The heart of the city is the famous Piazza del Campo, with its particular shell shape, in which the famous Palio is held, one of the most important events for all the Sienese. The Palio di Siena is a passionate horse race that takes place every year, in July and August and its origins seem to date back to the seventeenth century.

    According to legend, Siena was founded by Senio, son of Remo, and in the city there are several statues depicting the mythical Romulus and Remus suckled by the she-wolf. Piazza del Campo has been the central nucleus of Siena since Roman times, which had their forum here.
    The square was repaved during the Government of the Nine, a semi-democratic group in power between 1287 and 1355, with a division into nine sections in memory of the Government and symbolizes the cloak of the Madonna that protects the city.

    The Campo is dominated by the red Palazzo Pubblico and its tower, called Torre del Mangia. The Palazzo Pubblico, as well as the Cathedral of Siena, was built during the Government of the Nine, which was the period of maximum economic and cultural splendor of Siena. The Palazzo still houses the offices of the Municipality, similarly to Palazzo Vecchio in Florence. From the internal courtyard of the Palace you enter the Civic Museum and the Torre del Mangia, on top of which, climbing the 500 steps, you can enjoy a splendid view of the city.

    The Civic Museum houses some of the most beautiful paintings of the Sienese school. The Sala del Concistoro offers one of the most beautiful works by Domenico Beccafumi, who frescoed the ceilings by painting the cycle of public virtues. In the Sala del Mappamonto and in the Sala della Pace (or Sala dei Nove) then there are real masterpieces: the great Majesty and the equestrian portrait of Guidoriccio da Fogliano at the siege of Montemassi by Simone Martini and the Allegories of Good and Bad Government by Ambrogio Lorenzetti, considered one of the major pictorial cycles of the Middle Ages.
    Duration: 3 hours

    No meals included on this day.
    No accommodation included on this day.

    Day 3: Cortona- Assisi- Santa Maria degli Angeli Church

    Stop At: Assisi, Assisi, Province of Perugia, Umbria
    The city of Assisi is a fairly small village, surrounded by a fantastic countyside, special for having a relaxed day, away from the crowds of our common noisy cities. As you approach the city you could be overwhelmed by the sense of peace it conveys. The city was founded in roman time, but its fame and importance date back to the middle age of Comuns and , when in the 13th century the basilica of St. Francis was built outside the city centre, the town of Assisi had already been built by using the pink and white local stones from the Subasio mountain.

    Duration: 3 minutes

    Stop At: Santa Maria degli Angeli, Santa Maria degli Angeli, Assisi, Province of Perugia, Umbria
    It was one of the most significative places in the life of San Francis. Built at the end of 16th century, the church, the 7th world’s largest building and, was conceived to house and unify the structures of the famous convent called Porziuncola, where the Saint choose to live , where he founded his Religious Order, and where he died October 3th, 1226.
    Duration: 1 hour

    No meals included on this day.
    No accommodation included on this day.

    Day 4: Cortona- Pienza- Montepulciano- Rome

    Stop At: Pienza, Pienza, Tuscany
    Pienza is a small village in southern Tuscany, in the famous Val d'Orcia, absolouting to be visited!
    It is located about 20 km east of Montalcino and a few miles west of Montepulciano in the beautiful region of Val d'Orcia south of Siena, among soft and poetic hills and fabulous views. Pienza enjoys a truly strategic position perched on the top of a hill, overlooking the entire Orcia valley with a breathtaking view.
    This charming village is widely known as the "ideal" city of the Renaissance, created by the great humanist Enea Silvio Piccolomini, who later became Pope Pius II. Piccolomini had the economic possibilities and influence to be able to transform his humble native village, Corsignano, into what he believed should be a utopian city, which should have embodied the principles and philosophy of the classical age and of the great Italian Renaissance.

    Duration: 2 hours

    Stop At: Montepulciano, Montepulciano, Tuscany
    The city rises on the crest of a tufa hill between two valleys, in a very suggestive panoramic place; it is a charming, typically Renaissance town. According to tradition, the city was founded in the 6th century by the inhabitants of Chiusi following the barbarian invasions and called by these Mons Politianus, as recalled by the name of the same citizens (poliziani)
    The "vino nobile" of Montepulciano, of the color of ruby, has even been celebrated by poets.

    Duration: 2 hours

    No meals included on this day.
    No accommodation included on this day.
  • Departure Point :
    Traveler pickup is offered
    Please, provide correct information regarding pick up place.Airports
    • Fiumicino Airport, Via dell' Aeroporto di Fiumicino, 320, 54, Fiumicino Italy
    • Ciampino Airport, Rome Italy
    • Civitavecchia Port, Piazza Vittorio Emanuele, 19, 00053 Civitavecchia RM, Italy
    Departure Time :
    9:00 AM
    Return Detail :
    Hotel Pickup :
    • Confirmation will be received at time of booking
    • Wheelchair accessible
    • Stroller accessible
    • Infant seats available
    • Transportation is wheelchair accessible
    • Most travelers can participate
    • This is a private tour/activity. Only your group will participate
  • You can present either a paper or an electronic voucher for this activity.
  • If you cancel at least 4 day(s) in advance of the scheduled departure, there is no cancellation fee.
    If you cancel within 3 day(s) of the scheduled departure, there is a 100 percent cancellation fee.



Age Req.


Fitness Req.


Group Size


Organised by Rome-Limousines

Activity ID: V-59821P30

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