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Tuscany & Umbria

May 7, 2025

Discover the beauty of Tuscany & Umbria – this famed part of Italy that doesn’t disappoint. Tuscany & Umbria have so much to offer and so many reasons to visit for a driving holiday. There’s the unparalleled artistic legacy with fine art and stunning architecture, fabulous cities, intriguing towns, hilltop villages and extraordinary countryside. Gourmet and wine buffs will enjoy the wonderful cuisine and wines. And with the fabled rolling countryside, great roads and plenty to do and see, it’s a delight for all, especially when you settle into the wonderful hotels we have chosen for this tour.

The tour visits the beautiful cities of Florence for its Renaissance art, Siena with its striking cathedral and central Piazza del Campo, Pisa’s famous leaning tower, Lucca’s well-maintained medieval walls encircling the historic centre, Etruscan frescoes at Arezzo, and the many towers of San Gimignano, as well as exploring the many idyllic towns and villages, vineyards, castles and cathedrals. This really is a tour not to be missed.

Provisional Dates

Click here to pre-register for this tour, or be kept informed when more information is available

Tour Highlights

  • Stay in just four beautiful, unique and fabulous hotels
  • Explore the incredible city of Florence (Firenze), the Duomo and Baptistry
  • Visit the famous galleries of the Uffizi and Accademia
  • Discover the beautiful towns such as Siena, San Gimignano, Perugia, Orvieto, Gubbio, Assisi & Lucca
  • Explore the Chianti wine-growing region
  • Drive through the wonderful Tuscan & Umbrian countryside
  • Visit the Leaning Tower of Pisa

Tour Map


Day 1:  Arrive in Florence

Arrive in the fabulous city of Florence. Stay for 3 nights in a truly stunning, five-star, historic hotel in Florence, overlooking the Boboli Gardens, just south of the river Arno. The public rooms and bedrooms are exquisite and the attention to detail is second to none.

Day 2:  Explore Florence at leisure

Spend two days in Florence, seeing the sights. Florence’s museums, palaces, and churches house some of the greatest artistic treasures in the world.

The most popular and important sites in Florence include the Cathedral, the Baptistery, the Uffizi, the Bargello, and the Accademia. The churches of Santa Maria Novella and Santa Croce are veritable art galleries, and the library of San Lorenzo is a magnificent exhibition of Michelangelo’s architectural genius. Wander some of the oldest streets in the city until you reach the Arno River, cross the Ponte Vecchio, and experience the “newest” area of Florence, the Oltrarno. Be sure to set aside time to see the vast and varied art collection housed in the Pitti Palace.

Day 3:  Another day to visit Florence

When you grow weary of museums and monuments, head outdoors. Spend a day at the Boboli Gardens or climb the hill to the church of San Miniato al Monte to experience an enchanting view of Florence. Florence and its magnificent treasures await your visit! A Firenze Card is available and includes visits to all the main museums and galleries, including the Uffizi and Accademia Galleries.

Day 4:  Visit San Gimignano

85 Miles

Leave Florence and head south, visiting the breath-taking medieval towers of San Gimignano on the way. Stay for 4 nights in a beautiful five-star hotel in the Chianti hills near Siena.

Day 5:  Explore Siena

20 Miles

Spend the day exploring the beautiful medieval city of Siena, crammed with rich treasures. For many it is infinitely more appealing than Florence. Wander around the Piazza del Campo, the main square, also renowned for the Palio (horse race). The duomo (cathedral) is simply exquisite.

Day 6:  Discover the Sienese Crete

114 Miles

A  day to discover the gently undulating Sienese Crete, meaning ‘craters’ – one of Tuscany’s great landscapes. Today’s drive winds past fortified towns, castles, abbeys, country churches, farms, storehouses, magnificent Renaissance cities of art and delightful spas, offering a journey through the Sienese Middle Ages.

Day 7:  Drive around the Chianti region

97 Miles

Enjoy a wonderful drive around the Chianti hills, dotted with woods, wheat fields, olive trees, and vines on the hillsides, and punctuated with slender cypress trees around villas, castles, farmhouses and churches. Perhaps enjoy a lunch along with a cellar tour and wine and olive-oil tasting at a beautiful villa, whose wonderful gardens were used as the setting in the film, Much Ado About Nothing.

Day 8:  Drive into Umbria

98 Miles

Drive south to Monte Amiata, a majestic, extinct volcano surrounded by hot springs. Continue westwards past Benedictine monasteries, Romanesque churches, medieval villages and unchanged landscapes with splendid views. Head into Umbria and stay the next 4 nights at a lovely hotel near Perugia.

Day 9:  Assisi & Via Flaminina

112 Miles

Explore the Umbrian valley and the historic route of the Via Flaminina. Stop to visit Assisi, inextricably bound with its most famous son, St Francis.

Day 10:  Visit Orvieto

124 Miles

Head south to the spectacular town of Orvieto with its magnificent duomo perched high on a rocky outcrop. This is the heartland of the mysterious, ancient civilization of the Etruscans, whose legacy can be seen in the many towns they founded and in their enigmatic burial complexes or necropoli. The journey then returns via the ancient town of Todi, back to Torgiano. 

Day 11:  Visit the town of Gubbio

90 Miles

Spend the day wandering around north east Umbria to the truly lovely town of Gubbio, and then drive through some spectacular gorges and fabulous scenery, before looping back to Torgiano. 

Day 12:  Drive to Lucca via Arezzo

174 Miles

Head north to Lucca, via the wonderful town of Arezzo, packed with houses and mansions in pure Renaissance style. Spend final three nights in a wonderful four-star hotel in the centre of Lucca, within the walls.

Day 13:  Drive around northern Tuscany

135 Miles

Enjoy a wonderful day’s drive around the north of Tuscany, visiting Pistoia and then to the ski resort of Abetone, before heading across to the delightful town of Barga and then back to Lucca. There is also an optional loop south to visit Pisa with its famous leaning tower.

Day 14:  A relaxing day to explore Lucca

Spend the day in Lucca. It is one of the few towns in Italy to have preserved its surrounding walls intact. These massive 16th century brick walls not only keep out the noise and traffic, but also add to the tranquil atmosphere. There is a lovely tree-lined promenade on top of the walls, which are 12 metres high. The town’s roman legacy is still evident with the grid pattern streets and it’s a very easy town to explore on foot. Depart for home.

Where we'll stay

We have hand-picked some beautiful, quality, character hotels with great charm, in superb locations across Tuscany and Umbria. We are staying in just four hotels (three to four nights in each), so there is plenty of time to relax. You will be delighted with the quality and service of each hotel – all four or five star quality. All, of course, have suitable parking for our cars, and have been personally visited and inspected by us. We have checked the parking arrangement, the rooms, the available facilities and chosen hotels in lovely areas that we’re sure you will enjoy.

What's included


  • All passports must be valid for six months after the end of the tour. You will also need your vehicle registration documents, driving licence (a photo-card licence or international permit is best), and international/European insurance cover.
  • Please check with your travel and motor insurers that you are covered for travel in Italy and Europe.
  • You are also required to carry a warning triangle, first-aid kit, two fluorescent jackets, set of replacement bulbs and a national identification sticker. You will also need 2 breathalyser kits if you travel through France.
  • However, the most important requirement is that you take pleasure in motoring through fabulous scenery and relish individual, character hotels.


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