Tuscany vs Umbria - which is right for your Italian holiday

1. The landscape — rolling hills versus river valleys

The Tuscan landscape is one of the most painted and photographed in the world, and arriving in the Val d’Orcia or the Chianti hills for the first time can feel like stepping into a painting you already know. The geometry of the landscape — the ridgelines, the isolated farmhouses, the silver-green of olive groves against terracotta — has an almost unreal quality. Siena, San Gimignano and Montepulciano sit on their hilltops with the composure of places that have known exactly what they are for eight centuries.
Umbria’s landscape is less immediately dramatic but rewards closer attention. The Tiber valley runs through its centre; the hills are greener and more heavily wooded than Tuscany’s, with a quality of light that differs through the seasons. Assisi on its hillside above the plain of Santa Maria degli Angeli is one of the most extraordinary townscapes in Italy. The countryside around Spoleto, the Valnerina, and the shores of Lake Trasimeno offer landscapes of genuine beauty that see a fraction of Tuscany’s visitors.
If the iconic Tuscan image is your reference point, Tuscany will not disappoint. If you are drawn to a more contemplative kind of Italian scenery — one that rewards a walk rather than a photograph — Umbria may suit you better.

2. The towns — familiar names versus private discoveries

Tuscany’s great towns — Florence, Siena, Lucca, San Gimignano, Cortona, Montepulciano — are among the finest in Italy. Florence alone justifies a visit of several days, and Siena’s Campo is one of the great urban spaces in Europe. These are towns that have been receiving visitors for centuries, and they are accomplished at it. The museums, the restaurants, the hotels are all calibrated to a high standard.
The consequence is that in high season, particularly in Florence and San Gimignano, the volume of visitors can be considerable. Clients who come to Tuscany for the first time are occasionally surprised by how busy the most celebrated towns become in July and August. Our answer is to arrange accommodation in smaller towns and to build itineraries that use the early morning and late afternoon, when the crowds thin and the light is better.
Umbria’s towns are less famous and all the more interesting for it. Perugia, the regional capital, has a genuinely lived-in quality — it is a university city with a serious food culture and a medieval centre built across a ridge above the surrounding plain. Assisi is one of the most spiritually charged towns in Italy, with the Basilica of San Francesco an extraordinary achievement of medieval art. Orvieto, sitting on its volcanic tufa cliff above the plain of the Paglia, has one of the finest Gothic cathedrals in Italy and a complex of underground Etruscan tunnels below the town. Spello, Spoleto, Montefalco and Todi are each worth a half-day at minimum.
Clients who want a sense of discovery — of finding places that feel genuinely Italian rather than internationally curated — consistently find this more readily in Umbria.

3. Food and wine — Chianti country versus the truffle heartland

Tuscan food is among the most celebrated in Italy, and deservedly so. The tradition — pici, ribollita, bistecca alla fiorentina, the wines of Chianti Classico, Brunello di Montalcino and Vino Nobile di Montepulciano — is deep-rooted and consistent. A holiday in the Chianti hills or the Val d’Orcia offers some of the finest food and wine in Italy, and the region’s wine estates, many of which offer tasting and accommodation in converted farmhouses, have been a fixture of the tailor-made holiday market for decades.
Umbria is less celebrated at the table but should not be underestimated. It is one of the two great truffle regions of Italy — the black truffle of Norcia and Spoleto is used throughout the Umbrian kitchen with a frequency and confidence found nowhere else — and the region also produces some of Italy’s finest olive oil, with the groves around Trevi and Montefalco yielding an oil that is among the most prized in the country. The wines of Montefalco, led by the Sagrantino grape, have attracted serious critical attention in recent years and remain significantly less expensive than their Tuscan equivalents.
The Umbrian kitchen uses truffles, lentils from Castelluccio, hand-rolled pasta and cured meats from Norcia with a directness that reflects the region’s character. Norcia itself, despite suffering serious damage in the 2016 earthquake and still in the process of rebuilding, remains the centre of a food culture — the norcineria tradition of pork butchery — that is unique in Italy.
Neither region disappoints at the table. The difference is that eating well in Tuscany can feel like participating in a refined tradition; eating well in Umbria can feel like a private discovery.

4. Our Tuscany holidays — the product range

Our Tuscany programme is built around hotel stays in carefully selected towns and countryside properties, and we offer single-centre, two-centre and three-centre itineraries depending on how much of the region clients want to cover.
A single-centre Tuscany holiday works well for clients who want depth rather than breadth. Florence is our most popular base, with a range of hotels from elegant city-centre properties close to the historic core to quieter addresses on the Oltrarno side of the Arno. Siena is a compelling alternative to Florence as a single base — smaller, more intimate, and better placed for exploring the Val d’Orcia and the Crete Senesi. For clients who specifically want the Chianti countryside experience without the complexity of a touring itinerary, we can place them in a small hotel in the hills between Florence and Siena, from which the vineyards and hill towns are within straightforward reach.
Two-centre Tuscany is our most frequently booked format, and the most natural split is Florence with Siena, or Florence with a countryside property in the Chianti or Val d’Orcia. Three-centre itineraries typically add a coastal element — Porto Ercole or the Maremma — or extend south to Montepulciano or Pienza. All our Tuscany holidays are arranged around hotel accommodation, allowing clients to settle properly into each base.

Explore our holidays to Tuscany.

5. Our Umbria holidays — the product range

Our Umbria programme is smaller than our Tuscany offer, reflecting the region’s more compact size and its position as a less widely-known destination — but it is a range we know extremely well and are particularly enthusiastic about recommending to the right client.

Perugia is our most common Umbrian base, offering a central position, excellent hotel choice, and straightforward access to the key towns of the region. Assisi, half an hour to the east, works well as a single base for clients specifically drawn to the spiritual and artistic heritage of the town — the quality of hotels there is high and the experience of the town in the early morning, before the day visitors arrive, is one of the more memorable in central Italy. Orvieto, on its dramatic tufa cliff above the Paglia valley, is a compelling single or short-stay base that some clients combine with a night or two in the Val d’Orcia before or after.

For clients who want to cover more ground, we build two-centre Umbrian itineraries that typically combine Perugia or Assisi with Spoleto or Orvieto. We also offer a Spoleto-based holiday that suits clients drawn to the arts programme of the Spoleto Festival dei Due Mondi in June and July — one of the major cultural events of the Italian calendar.

Our Umbria holidays, like all our Italy programme, are based entirely in hotels rather than self-catering properties, and we select accommodation on the basis of position, character and quality of service rather than category alone.

Explore our holidays to Umbria.

6. Tuscany and Umbria combined — the multi-centre option

The most satisfying answer to the question of which region to choose is often to combine both, and this is an itinerary we recommend with some regularity to clients who have the time and the appetite for it. Tuscany and Umbria share a border, and the transition from one to the other — through Cortona, or across Lake Trasimeno — is itself one of the more rewarding drives in central Italy.
The natural structure for a combined itinerary is to begin in Tuscany — Florence, Siena, or a Chianti countryside hotel — and to cross into Umbria for the second half of the holiday. Cortona, which sits on the Tuscan side of the border above Lake Trasimeno, makes an excellent bridge: it is technically Tuscany but looks down into Umbria, and clients who spend two or three nights there before moving to Perugia or Assisi find that the transition feels entirely natural.
Alternatively, for clients with ten or more days, we build three-centre itineraries that might place them in Florence, then Siena or the Val d’Orcia, then Orvieto or Assisi — moving gradually south and east through two regions before heading home. This is a format that suits clients who want a genuine sense of Italian central Italy as a whole rather than a single fixed experience.
A combined Tuscany and Umbria holiday works best when the itinerary allows at least three nights in each main base. Anything shorter risks reducing each place to an impression rather than a stay, and one of the pleasures of this part of Italy — particularly in Umbria — is the pace at which it reveals itself.

Which is right for you?

Choose Tuscany if: you are visiting the region for the first time and want to encounter the landscape and towns that have defined the popular image of rural Italy; if Florence is a priority; if the wines of Chianti, Brunello or Vino Nobile are a particular draw; or if you want a programme where the infrastructure for visitors is highly developed and the range of hotels is at its widest.

Choose Umbria if: you have been to Tuscany before and want a region that offers comparable rewards with a fraction of the visitors; if medieval towns and sacred architecture are your particular interest; if the truffle tradition and the wines of Montefalco appeal; or if you want a holiday with a more private, less curated quality.

Choose both if: you have ten or more days; you want to move through central Italy rather than stay in one place; or you believe, as we do, that Tuscany and Umbria make considerably more sense together than either does alone.

In every case, we design the itinerary around you rather than around a fixed product. The sample holidays below give a clear indication of the options we arrange, and each is a starting point for a conversation rather than a fixed itinerary. We welcome calls from clients who are still deciding which direction suits them best.

Explore our tailormade tour Tuscany and Umbria by rail and car.

Explore our tailormade tour The Heart of Italy - Tuscany, Umbria and Latium fly-drive holiday

Planning a Tuscany or Umbria holiday with Expressions Holidays

Every Tuscany and Umbria holiday we arrange is tailor-made around the client — the towns that suit your interests, the hotels that position you well, the pace of the itinerary that fits how you travel. We do not offer villa or self-catering holidays: all our arrangements are based in hotels, chosen for character, position and the quality of what they offer rather than star category alone. Call us on 01392 441245 Monday to Friday 9am to 5.30pm, Saturday 10am to 2pm, or email info@expressionsholidays.co.uk.