Tuscany and Umbria

Perfect for a laid-back vacation without the stresses of driving!

This itinerary includes the main sites in Florence paired with an exploration of the region of Umbria.
The sprinkling of expertly-guided visits is balanced with time for individual exploration. No great visit to Italy can forego some wine and cooking adventures in between. Spend the evening in charming, upscale accommodations that retain their Italian charm, in well-positioned locations for strolling to dinner each evening without the need for a driver.

12 nights and 13 days

Possible Hotels

  • (3 nights) Florence:  Hotel degli Orafi
  • (3 nights) Bagno Vignoni: Hotel Le Terme
  • (2 nights) Assisi : San Crespino – Historic Residence
  • (2 nights) Orvieto:  Hotel Palazzo Piccolomini
  • (1 night) Florence: Hotel degli Orafi

Day 1 - Departure

Departure from USA/Australia

Day 2 - Arrival in Italy

A private driver will collect the group for a transfer from Florence airport to the accommodation in the Florence city center. After check-in, the afternoon and evening will be at guests’ leisure for individual activities.


Day 3 - Florence Explorations

At 9:00 am, a private tour guide will be waiting in the hotel lobby for a 3-hour morning exploration of the city streets, focusing on the religious center of Florence. Guests will see the Cathedral, Baptistery and Belltower along with the governmental center with Piazza della Signoria, Palazzo Vecchio and Piazzale degli Uffizi. Depending on personal interests, the tour can also touch on Piazza della Repubblica, Palazzo Strozzi, Dante’s neighborhood and the Ponte Vecchio.

Following will be free time for lunch and an afternoon for individual explorations. During this time, guests could choose to explore the Cathedral Complex in more detail, climb to the top of the Dome or Bell Tower, discover the San Lorenzo church area, visiting the Santa Croce Basilica or Florence’s town hall – Palazzo Vecchio. Of course, there is also plenty of shopping to do along the way!

Day 4 - Florence explorations

Today’s private tour will start at 8:30 am and shall focus on the Uffizi Gallery, an amazing museum of Renaissance old master paintings. Concentrating on the highlights of the collection affords a better understanding of the evolution of art in painting, seeing masterpieces by Giotto, Cimabue, Botticelli, Leonardo da Vinci, Michelangelo and Raphael. Time permitting, there is the option to cross the river to explore the Oltrarno area, replete with artisan shops and magnificent Renaissance palaces.

The afternoon is dedicated to individual explorations, including a visit to the Accademia to see Michelangelo’s incredible masterpiece, the David (completed when the great master was only 26 years of age!), along with the 6 unfinished statues said to also be by the great master.


Day 5 - Tuscan Countryside San Gimignano and Siena

9.00 AM check out and Departure with private driver for Full day excursion
In the morning visit San Gimignano, famous in the 13th century for pilgrims on the Via Francigena route, which went from Northern Europe to Rome. The city is famous today for its majestic medieval tours. Lunch in town or at a local winery, which makes a red Chianti Colle Senese or the lovely white Vernaccia di San Gimignano.

In the afternoon visit Siena, which preserves its medieval character beautifully with a mix of Gothic and Romanesque elements. Siena flourished during the 13th and 14th century. Visit the Campo, the semicircular square famous for the Palio horse race which is held twice a year. Be sure to also take a peak inside the impressive Duomo cathedral.

In the late afternoon arrive to the quaint hamlet of Bagno Vignoni, where popes, kings and queens have been soaking in the curative waters from centuries past and their waters still work magic today. Hotel check in. Evening and Dinner on own at leisure. There are a number of charming restaurants in the village. 

Day 6 - Tuscan Countryside Montalcino and Pienza

Your driver will pick you up for a morning exploration of the area around Montalcino. Produced in the stately wine area surrounding the picturesque town of Montalcino, today there are some 200 boutique wineries creating one of Italy’s most important reds. Brunello di Montacino is made from 100% Sangiovese grapes, whose roots go back at least to the 1500s, with many arguing that its ancestors date back right through to Roman times. Perched above a hill at an elevation of 1850 feet above sea level, Montalcino is framed by the most stunning panorama. Its ancient medieval walls encase a fortress dating back to 1361, an ancient basilica, 13th century churches and convents, and museums housing collections featuring a full gamut of artworks spanning from historic to modern times. Visit a Brunello winery in the morning and enjoy a wine tasting.
Afterwards time to stroll the quaint shops around the town of Montalcino and enjoy lunch with suggestions. 
Afterwards stop in the town of Pienza, with its stately palaces and architecture that embraces the picturesque landscape in the surrounds. Originally named Corsignano, its name change coincided with Renaissance humanist and local Enea Silvio Piccolomini becoming became Pope Pius II, instructing the entire village to be rebuilt. This town is considered an “ideal Renaissance city”. Return to Bagno Vignoni, dinner and overnight.

Day 7 - Tuscan Countryside around Bagno Vignoni - PM cooking class

Day for individual explorations – no driver
In the morning enjoy a stroll in the nearby countryside or partake in some of the spa services at the hotel, including a dip in the natural curative warm waters. Lunch with suggestions in a quaint caffe in the village. In the late afternoon at 17.00, enjoy a hands on cooking class in Casa Banchetti, a nearby private home located very close to the hotel. Learn to make the local “Pici” pasta with walnut or tomato sauce, a second meat dish such as Etruscan beef fillet with lard with a side dish and dessert (for example a ricotta cheese and honey tart). The actual menu will vary with the season and available products.

Return to hotel and overnight. 

Day 8 - Tuscan villages and arrival to the green heart of Italy

Full day excursion with private driver, travelling to Umbria.
Hotel check out and meet your driver. Head to nearby Montepulciano- a Renaissance-styled town. Montepulciano towers above the surrounding valley from a hill made of tufa rock along the hill ridge between Valdichiana and Val d’Orcia. A long main street, which is 1 mile long, leads to the main square where you find the Cathedral, the Town Hall and a number of Renaissance Palaces. The temple of San Biagio, located on the outskirts of town, is a real Renaissance masterpiece designed by Antonio da San Gallo il Vecchio. Visit a local winery that makes the historic Vin Nobile di Montepulciano.

After a short drive you will arrive the charming village town of Cortona in time for lunch. Stroll along the cobblestone streets and explore the boutiques or perhaps visit the Etruscan Museum that harks back to the origins of this historic village.

In the afternoon, upon passing Lake Trasimeno, you enter into the green heart of Italy, Umbria, arriving to Assisi in the late afternoon. Assisi is one of the most spiritual, artistic and historic towns in Italy. Inhabited since a population of Umbrians arrived around 1000 B.C., Assisi passed through Etruscan, Roman and Lombard rule, to name a few. One of the most significant sites to visit during your time here is the Basilica of Saint. Francis, begun in 1228 in celebration of Assisi’s most famed local becoming canonized. Brimming with historical, cultural and spiritual significance, it is also home to many important artistic dedications to Italy’s Patron Saint, including by artists Cimabue and Giotto. 
Arrival and hotel check-in, evening free for individual activities.

Day 9 - Umbrian Hill Towns and Wine

Full day excursion with private driver, Spello, Montefalco & Sagrantino winery
In the morning, meet with your private driver and first head to Spello, ” Splendidissima Colonia Julia “. Time to explore this town on own. Start your visit in the lower part, still surrounded by the well-preserved Roman walls, in which you will see three gates. Enter into Spello and walk the picturesque alleys, arriving to the Church of Santa Maria Maggiore with its famous Cappella Baglioni that has a ceramic Deruta’s floor and frescoes by Pinturicchio frescoes (considered his best production- look for his self-portrait).

Spello is famous for the Infiorata, a Flower Festival of Corpus Christi held between May and June. Every year the streets of Spello turn into a wonderful, spectacular, huge carpet of flowers. The downtown streets are decorated with paintings of sacred art made with flower petals.

Afterwards a short drive will take you to Montefalco, “the falcon’s mount”, located in a dominating position on the valleys of the Topino and the Clitunno rivers, and offers the viewer a sweeping panorama of the Umbrian countryside. Enjoy lunch in a delightful local restaurant. The Town Hall, dates back to the 13th century, as does the church of St. Augustine, the Romanic church of St. Bartholomew with the Portal of Frederick II (1244). In the afternoon visit a Sagrantino winery, which is one of the great full bodied Umbrian red wines of the area.

Return to Assisi and evening at leisure.

Day 10 - Orvieto

Full day excursion with private driver at disposal
Morning check out from the hotel. Time to visit Assisi a bit more, entering the ominous Basilica, the spiritual home of the great Saint.

Then depart with your driver to the Eremo delle Carceri, where Francis took spiritual refuge as a hermit during his life or else visit a local olive oil mill.

After lunch, departure to Orvieto, with time on own to explore this fascinating city in the afternoon, perched on a cliff of tufa rock of Etruscan origins. Its very famous Cathedral stands out, dating back to 1263, undoubtedly the most important architectural landmark of the city, with an elaborate, decorative Gothic façade. Inside there is a special chapel decorated by Signorelli which Michelangelo certainly studied and inspired some of his later works.

Hotel check-in and afternoon and evening for leisurely activities.

Day 11 - Civita di Bagnoregio and Bomarzo

Full day exploration with private driver at disposal
Meet your driver and visit the most unique Saint Patrizio well, built in 1527 on the edge of town, based on a plan of Antonio da Sangallo il Giovane. Afterwards head west and explore the area around Civita di Bagnoregio. This town acquired importance in the 11th and 12th centuries and was built along the ridge of a hill which was protected on three sides by deep ravines. The hill rests on layers of clay which over time tended to slip downwards. This caused the collapse of sections of the tufa rock above them. Landslides and in particular damage after an earthquake in 1695 have isolated Bagnoregio from the plateau to which it was once united and makes this almost “ghost like city” a very suggestive and interesting place to visit.

After lunch to your tastings, in the afternoon visit Bomarzo, the “Monster Park”. This Sacred Woodland today is known as Parco dei Mostri, because of its gigantic sculptures portraying heads of monsters which house benches in their open mouths where in the past the great Orsini Counts and their guests rested during the hottest hours of the day. The meaning of these works is unclear, although short sentences were carved nearby. In general there is consensus that they celebrate the Orsini’s chivalric view of the world in addition to the glory of the family. 

Return to Orvieto in late afternoon. Evening for leisurely activities, dinner and overnight.

Day 12 - Travel to Florence by way of the picturesque Chianti Classico wine area

Full day exploration with private driver at disposal
Hotel Check out. Meet your driver in the morning and transfer to Florence. Along the way stop in the Chianti Classico wine region between Siena and Florence and enjoy some small villages such as Castellina in Chianti or  San Donato in Poggio, where a countryside lunch can be enjoyed.

Chianti is one of the most beautiful hill areas in Tuscany and maybe in Italy. The landscape is characterized by vineyards, olive groves, fortresses, parish churches, and castles dominating splendid surroundings. Return to Florence taking the SS222, also known as the Via Chiantigiana, a twisting, turning and picturesque road which will eventually lead you back to Florence.

Hotel check in afternoon and evening free for individual activities. Overnight.

Day 13 - Final Transfers to Airport

In the morning hotel check out.
Private transfer to Florence airport (or other destination upon request) to conclude the holiday of a lifetime.