Six reasons to choose Tuscany for a luxury holiday
Published 24 May 2026
Six reasons to choose Tuscany for your holiday
Tuscany is the answer when someone cannot decide where to go next. Not because it is safe or predictable, it is neither, but because it delivers more consistently, across more interests and more types of traveller, than almost anywhere else in Europe. We have been designing tailor-made holidays to Tuscany at Expressions Holidays for over 35 years. The reasons clients return, often several times, are not hard to identify.
This is not a list of obvious observations. Every reason here reflects something specific about what Tuscany offers that other destinations do not — and connects to the kinds of holidays we design for clients who know what they want and have travelled enough to know the difference.
Marcelle Hoff, owner of Expressions Holidays, says 'Tuscany rewards depth. The client who spends ten nights based in the Chianti hills, exploring slowly and following recommendations rather than itineraries, returns with a different experience from the one who ticks off the highlights in five days. Both are valid. Only one is extraordinary'.
The landscape is one of the most beautiful on earth — and it is completely accessible
The Tuscan landscape is not a backdrop. It is the holiday. The cypress-lined roads of the Val d'Orcia, the vine-covered hills of Chianti, the medieval towers of San Gimignano rising above a sea of wheat, the chalk-white biancane of the Crete Senesi — these are scenes that have shaped how the western world thinks about beauty, and they are not hidden behind fences or accessible only on organised tours.
A self-drive holiday in Tuscany is, for many of our clients, the purest form of the experience. The ability to turn off the main road, find a hilltop town that does not appear in the standard guides, sit in a square that belongs entirely to the people who live there — this is what the landscape offers when you have the time to receive it properly.
We design our Tuscan itineraries with the landscape as the organising principle. The hotel is chosen for its position within it, not merely its proximity to a city.
Florence is the world's greatest art city - and it repays serious attention
The case for Florence has been made so often that it risks sounding like received wisdom rather than a living truth. It is worth restating clearly: no other city of its size concentrates this much great art within walking distance. The Uffizi, the Accademia, the Bargello, the Palazzo Pitti, the churches and chapels that contain work by Botticelli, Masaccio, Filippino Lippi, Ghirlandaio — the density is extraordinary.
What Florence rewards is preparation and time. A client who has read about what they are going to see before they arrive, who has a good guide or a thoughtful local contact, and who resists the temptation to cover everything in a day, has a genuinely different experience from one following a checklist.
We brief our clients on Florence specifically — which museums to prioritise on which days, which entrances to use, which areas of the city reward wandering and which are best approached with a purpose. The city is familiar enough to feel manageable and deep enough to surprise clients who have been three times before. In fact, you can never have enough of Florence.
Explore our tailor-made holidays to Florence.
The food and wine are not merely good — they are rooted in a specific place
Tuscan food is not Italian food in general. It is the food of a particular landscape, a particular season, a particular tradition of cooking that uses the produce of the land rather than disguising it. Bistecca alla Fiorentina, ribollita, pici with wild boar, sheep's cheese from Pienza, bread made without salt, olive oil pressed in November from Frantoio olives on the slopes above Lucca — these are things you can eat in London with varying degrees of success, and things you can eat in Tuscany in a way that makes the version at home seem like a reproduction.
The wine is equally specific. Chianti Classico, Brunello di Montalcino, Vino Nobile di Montepulciano, Vernaccia di San Gimignano, the Super Tuscans of the Maremma coast — each has a distinct character that reflects where it is grown and how. A cellar visit at an estate in Montalcino where the winemaker talks about the vintage while you taste from the barrel is a different experience from a wine list, however good.
We arrange private cellar visits, market tours, cooking experiences and restaurant recommendations that reflect this specificity. The food and wine of Tuscany are not an optional extra — they are a reason for the trip.
The hill towns are among the most satisfying places to spend time in Europe
San Gimignano, Siena, Montepulciano, Pienza, Montalcino, Volterra, Cortona, Pitigliano — a list that barely scratches the surface of what Tuscany contains. Each of these towns has a distinct character, a distinct history and a distinct reason to visit. Siena's Piazza del Campo is arguably the finest medieval square in Italy. Pienza was designed as a utopian city by Pope Pius II and remains almost exactly as he left it. Pitigliano is built on a tufa cliff above a ravine and looks like something invented rather than grown.
The pleasure of these towns is not merely the architecture. It is the sense of continuity — of a place that has been lived in for centuries and still is, where the bar in the main square has been serving espresso to the same families for generations and where the view from the walls at dusk is essentially unchanged from what a traveller would have seen in the sixteenth century.
We incorporate the hill towns into our Tuscan itineraries as more than stops on a route. The overnight stay in a small town, the dinner in a restaurant that caters to locals rather than visitors, the early morning before the day-trippers arrive — these details transform the experience of a place.
The Val d'Orcia is a UNESCO World Heritage Site of almost implausible beauty
The Val d'Orcia — the valley of the Orcia river in southern Tuscany — was inscribed as a UNESCO World Heritage Landscape in 2004, recognised for a cultural landscape that has been shaped by Renaissance ideals of beauty and has remained largely unchanged for five centuries.
In practical terms, this means a landscape of rolling hills in shades of gold, ochre and green, punctuated by isolated farmhouses, lines of cypresses marking old roads and tracks, and the occasional hilltop town breaking the skyline. In late May, the wheat is still green and the wild flowers are at their peak. In September, after the harvest, the ploughed fields turn terracotta and the light becomes extraordinary.
We recommend the Val d'Orcia as the heart of any Tuscany itinerary for clients whose primary motivation is the landscape itself. The area contains some of our most selected properties, and the pace of the south is slower and quieter than the more visited north.
It is an exceptional destination for a special occasion
Tuscany has a quality that makes it particularly suited to milestone celebrations: it feels significant without feeling formal, luxurious without feeling ostentatious, and romantic without feeling contrived. An anniversary dinner on a terrace above the Chianti hills at dusk, a private tour of a wine estate for a significant birthday, a honeymoon week based in a farmhouse with a private pool in the Val d'Orcia — these are experiences that have the weight of occasion without the self-consciousness of a packaged celebration.
The quality of accommodation available across Tuscany — from intimate boutique hotels in restored historic buildings to elegant country properties on private estates — gives us exceptional scope when designing holidays around a particular occasion. We arrange the specific room, the welcome details, the restaurant reservation and the private experience that marks the trip as what it is.
