100% customisable travel idea

From Tuscany to Umbria Art cities, terroir, and charming addresses

Italy - Florence - Siena - Castiglione d'Orcia - San Martino in Campo (Perugia) - Assisi

Italy of delights

From $3400 to $4100 per person for 9 days Price depends on departure city, season, accomodation types and selected activities

Itinerary highlights

  • A road trip through iconic Italy, from vineyard-covered hills and olive groves to cities of art and history.
  • Our selection of charming accommodation and excellent restaurants, so you can experience the art of Tuscan living.
  • Skip-the-line tickets for the Uffizi in Florence, guided tours of Siena and Assisi, exploration of Pienza and Bagno Vignoni: it’s all planned!
  • Direct flights, carbon absorption, our personalised recommendations, Concierge service: travel the Voyageurs way.
Tuscany and Umbria evoke a refined, undulating and hedonistic Italy. First, there is the iconic Florence. On either side of the calm waters of the Arno, palaces, museums and streets intertwine joyfully, revealing cafés, fountains and shaded squares. Then you’ll discoverSiena its historic rival. It stands out for its essentially medieval appearance. The shell-shaped Piazza del Campo is a symbol of the city. In the days that follow, you’ll wander through the verdant hills of Tuscany and Umbria. From Castiglione d'Orcia to San Martino in Campo, nestled near Perugia, you journey not only through space but also through time, from the Middle Ages to the Renaissance. You’ll pass through Assisi, the jewel city of Umbria and birthplace of the patron saint of all Italy. You’ll get used to pushing open the doors of old churches decorated a fresco, climbing the walls of fortresses that once protected the interests of great families, and walking alongside cypress trees and vineyards. Here, you can savour the bold flavours and dense textures of these still-authentic regions - trippa and bistecca alla fiorentina, chianti riserva, pasta with white truffle, olive oils, thin slices of lardo di Colonnata and prosciutto, as well as minestrone and pappa al pomodoro… On the plate and in the glass, Italy truly knows how to delight.… 

Your journey

Italians turn out to be more disciplined on the road than legend suggests, and distances remain relatively short. So, off we go! At every stop, you’ll savour this blend of history, sophistication and tranquillity that gives Italian hotel accommodation all its charm. In Florence, you overlook the Piazza della Santissima Annunziata from an intimate and comfortable room. On the outskirts of Siena’s historic centre, you’ll settle into an elegant 18th-century villa that has been transformed into a family-run hotel, preserving its old-world charm. A small hotel set in the heart of the rolling landscapes around Castiglione d’Orcia will be your new home base. As a sweet final touch, about 10 km (6 miles) south of Perugia, you are warmly welcomed into the former summer residence of a noble 17th-century family. Every departure is tinged with the regret of not extending your stay - but if you’d like to extend it, simply let us know. To ensure you don't miss any highlights, we have arranged several private tours for you, each accompanied by a guide. Starting in Siena, the tour revolves around the highlights, of course, but also the Palio, a thrilling horse race that takes place every year. Next comes the exploration of two singular historic towns, each remarkable in its own way: Pienza, the “ideal city” designed by Pope Pius II according to the humanist principles of the Renaissance, and Bagno Vignoni, a tiny village already visited by the Romans for its thermal waters. Finally in Assisi, you’ll be captivated by the spiritual and cultural brilliance, with the Basilica of Saint Francis as the main landmark. As for your skip-the-line tickets for the Uffizi Gallery in Florence, they are already in hand! Finally, for any last-minute requests or in case of unforeseen circumstances, our on-site concierge is just a phone call away to assist you.
Florence - Italie © Faustine Poidevin
Florence - Italie © Faustine Poidevin
Castiglione d'Orcia - Italie © Droits réservés
Castiglione d'Orcia - Italie © Droits réservés
Castiglione d’Orsia - Italie © Droits réservés
Castiglione d’Orsia - Italie © Droits réservés
Castiglione d'Orcia - Italie © Droits réservés
Castiglione d'Orcia - Italie © Droits réservés
Toscane - Italie © Andreas Hub/LAIF-REA
Toscane - Italie © Andreas Hub/LAIF-REA
Castiglione d'Orcia - Italie © Droits réservés
Castiglione d'Orcia - Italie © Droits réservés
Galleria dell'Accademia - Florence - Italie © Faustine Poidevin
Galleria dell'Accademia - Florence - Italie © Faustine Poidevin
Toscane - Italie © Jérôme Galland
Toscane - Italie © Jérôme Galland
Toscane - Italie © Rhiannon Taylor
Toscane - Italie © Rhiannon Taylor
San Martino In Campo - Italie © Droits réservés
San Martino In Campo - Italie © Droits réservés
San Martino In Campo - Italie © Droits réservés
San Martino In Campo - Italie © Droits réservés
Florence - Italie © Droits réservés
Florence - Italie © Droits réservés
Florence - Italie © Wassimahmed/Pexels
Florence - Italie © Wassimahmed/Pexels
Sienne - Italie © Cecilia Renard
Sienne - Italie © Cecilia Renard
Sienne - Italie © jarre - stock.adobe.com
Sienne - Italie © jarre - stock.adobe.com
Castiglione d'Orcia - Italie © Droits réservés
Castiglione d'Orcia - Italie © Droits réservés

Itinerary

100% customisable for you

Private transfer and two nights’ accommodation in the heart of Florence’s old town, opposite the Ospedale degli Innocenti on Piazza della Santissima Annunziata, which is a masterpiece of Renaissance architecture. Your hotel is set within the walls of a historic residence. The bedrooms, lounges and living areas are elegantly furnished in classic Florentine style, reflecting all the charm and comfort of 16th-century Italian hospitality. As you are in the heart of Florence, all that remains is to allow yourself to be swept away by the city's beauty.

The red rooftops and the dome of Santa Maria del Fiore of Florence rise up between the peaceful banks of the Arno and the hills of Tuscany. It was profoundly shaped by the family of Lorenzo de Medici, known as “Il Magnifico”, an evocative and flattering adjective shared with the Florentine city, which experienced its golden age under his rule. Even today, travellers delight in discovering its Renaissance palaces and churches and seek out a myriad of museums and art galleries. Food lovers, meanwhile, will not want to miss the delicious trippa alla fiorentina, the thickbistecca, or white truffle pasta, all of which are local specialities not to be missed.
Already planned: Fast-track tickets for the Uffizi Gallery. This is a world-renowned museum, and rightly so. The collections span from the Middle Ages to the Baroque era, and bring together masterpieces by the great painters of the Renaissance: Fra Angelico, Filippo Lippi, Piero della Francesca, Paolo Uccello, Sandro Botticelli, Leonardo da Vinci, Michelangelo, Raphael, Bellini, Titian, just to mention a few.
Optional:  Private guided walk in the footsteps of Michelangelo.

Collect your rental car and drive to Siena. Stay for two nights at the entrance to the city, in the bucolic setting of the Tuscan hills. Your hotel is located in a former 18th-century patrician residence. In your bedroom next to the garden, the rustic feel blends with modern amenities. The attentive service and well-chosen location make it an ideal haven for exploring beautiful Siena at your leisure. Florence’s historic rival stands out by almost being its antithesis. Unlike its neighbour, a jewel of the Italian Renaissance, Siena has preserved its medieval appearance. 

Planned: Private tour of Siena, the pink city. Clinging to three ochre-red clay hills the colour of “Terra di Siena”, the streets of the medieval city wind within surprisingly vast city walls before opening, amid the sea of tawny rooftops, onto the wondrous Piazza del Campo, a magical place that is the beating heart of Siena. It is in this square that the Palio takes place every summer, during which the city's 17 districts compete in a fast-paced horse race. Your private guide will tell you all the secrets of the city before taking you to see several highlights, such as the Basilica di San Domenico, Palazzo Salimbeni (which houses the Banca Monte dei Paschi di Siena, the oldest Italian bank, founded in 1472), Palazzo Tolomei, Palazzo Chigi Saracini, Piazza del Campo, and the cathedral.
Optional: Private guided tour of San Gimignano; Wine and regional food tasting at Castello d'Albola.

Drive to Castiglione d'Orcia. Stay for two nights near the small medieval village, in the heart of the Val d'Orcia hills. Your intimate accommodation is run by a couple from Milan. The secluded location, surrounded by picturesque scenery, creates a relaxing atmosphere. The interiors are a harmonious blend of contemporary and traditional design. Your room looks out onto the delightful garden. The courtyard restaurant, next to the pool, serves Tuscan cuisine with a tasteful modern twist, paired with carefully selected local wines.

The timeless little village of Castiglione d'Orcia is set in the heart of the peaceful landscapes of the Val d'Orcia, which has been designated as a UNESCO World Heritage site. It blends in harmoniously among the hills, ravines and iconic cypress trees, creating a picture postcard Tuscan scene. The Rocca Aldobrandesca, an ancient and imposing fortress,, overlooks the village, silently guarding its medieval fortifications.
Planned:  Private tour of the medieval towns of Pienza and Bagno Vignoni. The guided tour begins in one of the best-preserved medieval villages in the whole of Tuscany. Pienza is also an ideal Renaissance town, with its famous Piazza Pio II, the cathedral and the Palazzo Piccolomini, and fully deserves its UNESCO designation. Next, you will head to the tiny hamlet of Bagno Vignoni, one of the region’s best-kept secrets, located 9 miles (15km) to the south-west. Far from the crowds, the guide will lead you to the main square and share the local history. The thermal waters that flow here have been known since Roman times, and the village is arranged around this ancient pool of steaming water. 

Drive to San Martino in Campo, in the heart of Umbria. You will be staying for two nights in the summer residence of a prominent family, which was built in the 17th century and has been regularly renovated since. Beautiful features such as frescoed ceilings, exposed beams and four-poster beds give the place a great sense of prestige. The bedrooms reflect the Italian art of harmonising eras with requirements. At the table, the focus is on highlighting local produce. The chef’s creations skilfully combine creativity,, seasonality, quality and tradition. The wine cellar offers a wide selection of regional and Italian wines, while the spa offers you all the benefits of organic wellness with state-of-the-art facilities and skilled practitioners. In short, this is the ultimate countryside accommodation for a stay in Perugia.

On the west bank of the Tiber, Perugia, the capital of Umbria, stands out as a genuine alternative to Tuscany and Florence. It easily holds its own as a major city of the Italian Renaissance. You can stroll at your own pace through its narrow streets enclosed by the city walls, dotted with art museums, palazzi, boutiques, and trendy bars and cafes. 
In the diary: Private tour of Assisi (Basilica di San Francesco and other Franciscan sites). The artistic wonders that you can admire in the city’s basilicas illustrate the remarkable and enduring religious work of Giovanni di Pietro Bernardone, Francis of Assisi (1182-1226). Led by a guide, the tour begins at the Basilica di Santa Chiara, which houses the shrine of the poverello’s disciple and founder of the Order of the Poor Clares (1212); it also contains the Crucifix of San Damiano, from which Francis is said to have received the command to rebuild the Church. Next are a few buildings from the old town, including the Roman Temple of Minerva, now the church of Santa Maria sopra Minerva. Finally, you head up to the Basilica di San Francesco. The damage caused by the 1997 earthquake has been repaired, as far as possible. The tomb of the saint is in the crypt of the lower basilica. The frescoes by Giotto and Cimabue are in the upper basilica, and they are not the only ones worth seeing! Here you are in a major centre of European civilisation.
Optional:  Historic Perugia.

Drive to Florence airport, return your vehicle and take your international flight home.

À la carte

This suggested itinerary can be customisable down to the smallest detail, including duration, stops and content. An à la carte menu of experiences is also available to create a journey that reflects who you are.

In the footsteps of Michelangelo 

What’s on the schedule: a private guided tour of the neighbourhood where Florence’s most eminent sculptor—and probably the most eminent of the Renaissance—grew up. Transformed into a museum, Casa Buonarroti houses family mementos and collections assembled by the master's great-nephew. Here you learn anecdotes about his life, his early works, and his connection with the powerful Medici family. An immersion into the intimacy of a genius artist.

San Gimignano decoded

San Gimignano was once an essential stopover for pilgrims travelling to Rome or returning via the Via Francigena. The noble families, masters of the city, erected seventy-two tower houses there, emblems of their opulence and power. Although only fourteen of them remain today, San Gimignano has preserved the essence of its mediaeval atmosphere. During the tour, the private guide will unveil the secrets of the San Giovanni Gate, Piazza della Cisterna, Piazza del Duomo with its collegiate church, the Palazzo del Popolo and its majestic Torre Grossa - the last and tallest of the city's towers - as well as the Church of Sant'Agostino and its 15th-century frescoes by Benozzo Gozzoli, revealing the city's captivating heritage.

Tasting of local wines and regional dishes

In the heart of Chianti Classico, Tuscany, stands Castello d'Albola, built in the 15th century and transformed in the Renaissance. It is a lovely wine estate, now the property of the Zonin family. Located on the hills of Radda near Siena, it is one of the highest vineyards in Tuscany (at around 400 metres above sea level), rooted in clay marl soils, the famous terroir Albarese. What’s planned: tours of the historic cellars, followed by a lunch-wine tasting of four wines paired with four typical dishes from the Tuscan culinary tradition.

Historic Perugia

Perugia has preserved Etruscan walls from its past that bear witness to its ancient grandeur, alongside numerous remains from the Middle Ages and the Renaissance. An industrial and commercial centre and a lively university town, it is also distinguished as the birthplace of the Umbrian school of painting. Accompanied by a private guide, you will discover the fascinating Rocca Paolina and its underground remains, the Porta Marzia, the lively Corso Vannucci, the San Lorenzo Cathedral, the Fontana Maggiore - an undisputed jewel of Italian Gothic sculpture - and finally Porta Sole.

Why visit Italy with Voyageurs du monde?

Every day, our travel specialists craft bespoke experiences shaped around each traveller's profile, desires and budget. These passionate experts design experiences delivered on the ground by a local network of Concierges and trusted contacts. These fully customisable, made-to-measure trips are complemented by a wide range of high-end services (lounges, 24/7 assistance, travel booklet, app, Wi-Fi, restaurant booking, etc.)

Let us create your trip

A few of the advantages of travelling with us to Italy

  • Globally unique concierge service
  • Gourmet Voyageurs
  • Adjust your trip while travelling
  • 24-hour assistance
  • CO2 absorption

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Estimated budget

Price depends on departure city, season, accomodation types and selected activities

The estimated budget for this trip is $3,400 to $4,100 per person.

A fixed price is rarely applicable to a bespoke journey. The final cost depends on various factors, such as the level of service, travel dates, and booking lead times. The only definitive price will be the one provided in your personalized proposal.

The average price for this trip is $3,700 per person


Included in this suggestion

  • The direct international flight with a scheduled airline
  • Airport taxes and fuel surcharges
  • Carbon absorption contribution for your trip's CO2 emissions through reforestation projects (via our Philippe Romero Insolite Bâtisseur Foundation)
  • Private transfer on arrival in Florence
  • Seven days of car rental
  • Two nights in Florence, in a superior double room with breakfast.
  • Two nights in Siena, in a double room with breakfast.
  • Two nights in Castiglione d'Orcia, in a double room with garden view, with breakfast.
  • Two nights in San Martino in Campo (Perugia), in a double room with breakfast
  • Skip-the-line tickets for the Uffizi Gallery in Florence
  • A private guided tour of Siena.
  • A tour of the villages of Pienza and Bagno Vignoni with a private guide.
  • A private guided tour of Assisi
  • Our on-site Concierge service
  • A travel booklet with useful information (your day-by-day itinerary, hotel contact details, a personalized selection of our recommendations, etc.)
  • Our recommendations and reservations at selected restaurants
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