Tuscany and Umbria – itinerary 6 nights

A journey through art, wine, and timeless Italian beauty

Superbly enjoyable and vastly alluring, Tuscany and Umbria charm beyond belief. A never-ending appeal of ethereal landscapes, fashioned by nature and embellished by humankind, scenic borghi and glorious food in abundance, every village perched on a hill, every frescoed church and every meal you’ll enjoy here tells a story. One of hard labour and invaluable artistry, the legacy of the many brilliant minds that lived in these regions having shaped a living treasure trove. Words can barely describe the poetry that has blessed central Italy – the entire peninsula, for that matter! – over the centuries, crafting outstanding destinations that stir all senses. From remote mountains to lovely beaches, world-class masterpieces to rolling hills, ethereal lakes and local handicraft in droves, Tuscany and Umbria are delightful, unique destinations that never fail to impress.

Day 1. Marble galore

Start your journey in glitzy Forte dei Marmi on the Versilia coast and admire the contrast of the rugged Apuan Alps in the distance while walking on the beach. Northern Tuscany is rich in splendid towns like Pietrasanta – the Athens of the north – loved by countless artists who have chosen to live here: explore the town to see how contemporary artworks are set alongside the beautiful 13th c. Duomo.

From here, the gleaming white patches on the mountains call you to Carrara, home to the world’s most celebrated marble. Visit the quarries for an awe-inspiring experience inside the very heart of the mountain, where Michelangelo once chose the blocks for his masterpieces. End your day in the nearby village of Colonnata, tasting the famous Lardo di Colonnata, aged in marble basins and sliced paper-thin — a true delicacy of this land where art and flavor intertwine.

Day 2. Poetry in motion – a Tuscan love affair

Move south and touch on Lucca and its dazzling Piazza Anfiteatro, embracing the city with its medieval touch, perhaps walking along the external walls to grasp the marvel of the city or going up Torre Guinigi to see the surrounding countryside. Take the road that snakes up the hill to striking Volterra, dominating the plain from a vantage point: its medieval alleys are magnificent – as is the precious Art Gallery with fine works by Luca Signorelli, Ghirlandaio and Rosso Fiorentino. Choose a shiny piece of locally produced alabaster before travelling to epic San Gimignano, a compelling sight with its 14 medieval towers and exceptional 13th c. Palazzo Comunale. Try local Vernaccia wine and glorious food before reaching the splendid Siena countryside

Day 3. Beyond the Palio: beauties of Siena

Renowned the world over for its Palio, Siena’s unique Piazza del Campo square is simply mesmerizing. As is the rich heritage of the frescoes in the Town Hall depicting the Good and Bad Government by Ambrogio Lorenzetti and the many artworks in town, including the exceptional Duomo, containing masterpieces by Nicola and Giovanni Pisano, Michelangelo, Donatello and Bernini. You can sense how proud each contrada is as you walk around town, perhaps stepping into a local trattoria to enjoy a Tuscan delight. Find time to travel south and see the Abbey of San Galgano, its overpowering beauty a unique sight at dusk.

Day 4. Of wine and other stories

Move south and explore lovely Montalcino, home of the prestigious Brunello di Montalcino, perhaps Italy’s most famous red wine. Get lost in its medieval alleys and raise a glass to this divine region. Continue towards the serene beauty of the Romanesque Abbey of Sant’Antimo, with its glorious church, abbey and garden, before reaching Umbria and unique Orvieto. You may feel star-struck gazing at its Gothic cathedral, its façade among the most striking in Italy, with colourful frescoes, mosaics and bas-reliefs, the interior a stunning art collection with monumental frescoes by Luca Signorelli.

Day 5. Italy’s green heart

Umbria is not only artworks and delicious food, but also majestic natural treasures like Lake Trasimeno: Italy’s fourth largest lake, the area is simply stunning, with lovely Isola Polvese or Isola Maggiore restful destinations. Continue towards splendid Perugia, famous for Umbria’s finest art collection, but also its vibrant soul – thanks to its many university students and the world-famous Umbria Jazz festival. Feel its warm embrace as you meander from Piazza IV Novembre to its famous Fontana Maggiore, Umbria’s National Gallery, stopping to savour a gourmet meal, tasting Umbria’s regional sublime cuisine.

Day 6. Italy’s sacred heart: the glory of Assisi and its surroundings

Umbria’s devotional atmosphere reaches its zenith in famous Assisi, the birthplace of Saint Francis and home to the splendid Basilica di San Francesco with fascinating frescos by Giotto. Nearby Spello is a quaint jewel, while lovely Bevagna is home to an exceptional wine production. In season, do not miss a truffle hunting experience to make this a unique adventure: Umbria is home to the prized Black Truffles of Norcia and Spoleto, a rare and exclusive treat that should not go amiss.u may decide to cycle along it and enjoy the splendid scenery; as you pedal, find a cellar and stop for a well-deserved wine and food tasting – it will all fall into place: this is Heaven, can I stay a little longer?

Vineyards of glory

Italy has no shortage of prestigious wine cellars, vineyards decorating the countryside from north to south. If you fancy checking on a state-of-the-art wine estate, however, do not miss Antinori nel Chianti Classico in San Casciano Val di Pesa. Voted the world’s best wine cellar in 2022, this architectural masterpiece blends seamlessly into the Tuscan hills. The strong heritage of the Antinori family extends beyond Tuscany into neighbouring Umbria, where rolling vineyards surround the Castello della Sala estate near Orvieto — a fairy-tale medieval castle dedicated to the production of elegant white wines.

Here, the crisp Orvieto Classico and the refined Cervaro della Sala, a Chardonnay-based blend with Grechetto, express the soul of Umbria: balanced, mineral, and deeply connected to the land. Across the region, other remarkable wines such as Sagrantino di Montefalco and Rosso di Torgiano reveal the bold, authentic character of central Italy. Each glass tells a story of passion, patience, and timeless savoir-faire — a journey through terroirs where history and innovation meet in perfect harmony.

Speak Scottish in northern Tuscany

Sitting between chestnut forests and the marble-clad Apuan Alps, Barga is a quaint hill town in the Serchio Valley in northern Tuscany: who would expect a Fish and Chips festival, Scottish flags hanging here and there, plus a typical red British phone box? In truth, local inhabitants migrated to Scotland at the beginning of the 20th c. searching for fortune and have come back to Tuscany to see where they all stemmed from, bringing their UK heritage with them. This happy marriage of Scottish friendliness and Italian vibes stirs interest and affection in a region blessed with a stunning variety of landscapes, traditions and emotions.

Mad hatters in Gubbio

A picture-postcard little town in northern Umbria, Gubbio is a medieval gem that boasts picturesque corners like scenic Piazza Grande, a vantage point on the countryside that comes alive with the May Corsa dei Ceri (Candle Race) to celebrate the patron saint, Saint Ubaldo. A maze of quaint streets and Palazzi, the town is also enjoyed from the local open-air Colle Eletto funicular and is also home to a peculiar tradition: in order to gain your “mad person” certificate (Patente da Matto), you will have to run around its Bargello Fountain three times, located opposite Palazzo Bargello, and the award will be yours. An amusing tradition indeed!

Orvieto’s underground soul

See what lies beneath splendid Orvieto, and uncover the city’s most mysterious side: a labyrinth of more than 400 tufa caves, tunnels, and cisterns carved by hand over 2,500 years. Hidden below the medieval streets lies an entire world — a “city beneath the city” — where time seems suspended.

Originally excavated by the Etruscans to extract stone and collect rainwater, the caves were later transformed into wine cellars, olive presses, pigeon coops, and safe shelters during sieges and the World Wars. Today, the Orvieto Underground guided tour (around 45 minutes) invites visitors to wander through softly lit passageways, admiring the delicate textures of volcanic rock and ancient tools still embedded in the walls.

It’s a fascinating journey through the layers of Orvieto’s history, revealing how the city’s beauty is not only visible above ground — in its soaring Duomo and noble palazzi — but also deeply rooted in the earth below.