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Tales from Tuscany: Our Travel Guide to Italy’s Most Iconic Region

Whether sipping a glass of Chianti’s finest as you gaze out over the heavenly Val d’Orcia or indulging in the culture and cuisine of Europe’s iconic Renaissance city, a trip to Tuscany truly tastes la dolce vita.

Welcome to our Tuscany travel guide, where we explore the best of this iconic region, including its diverse locations, excellent driving roads, and what we love to do when we tour this wonderful destination.

Ultimate Driving Tours’ guests chatting with drinks on a rooftop in Florence

Image: Ultimate Driving Tours

How to tour Tuscany at its best: when and what to visit

Tuscany is a treasure for the luxury traveller. Italy’s most celebrated region is home to iconic cities like Florence and Siena, enchanting hilltop towns such as San Gimignano and Cortona, and surrounded by countryside that’s beyond beautiful. The most difficult part of planning an itinerary is not deciding where to visit in Tuscany, but where you must leave out!

Truth be told, there is no bad time to visit Tuscany, yet some months bring out the best of the region. We find the ideal times to visit are between May and early June, then towards the end of September or early October – although anywhere between April and November will be splendid. Tuscany’s peak tourism season is June to September.

This is why we run our tours of Tuscany around the end of September and into early October. The crowds of summer have dispersed and the peak heat has mellowed, giving us ample opportunity to enjoy glorious weather. The days are warm and sunny, with nights a little cooler, allowing us to take full advantage of al fresco dining.

A man is served a bowl of filled pasta in broth at a table with white table cloth and wine glasses

Image: Ultimate Driving Tours

5 reasons why we love to tour Tuscany

Exploring historic villages, tasting world-class wines, and taking in the exceptional country roads – there are endless reasons to fall in love with Tuscany, but here are five of our favourites.

1. The incredible food and wine

The food alone makes Tuscany a bucket-list holiday destination. There are countless incredible Michelin-starred restaurants and fine-dining experiences alongside the humble trattorias and street food vendors. Wherever you dine, the standard of food and wine in Tuscany is exceptional.

Regional dishes centre around traditional peasant cuisine, where the most basic ingredients shine together. For example, ribollita is a creamy, nourishing and satisfying vegetable soup made with stale bread. On paper, it may not sound like much, but a bowlful is simply divine.

Tuscany is known for delicious cheeses, such as Pecorino Tuscano and Pecorino di Pienza, while creamy sheep’s milk Ricotta is another treat. Tuscany is also famed for producing some of the world’s finest olives, olive oil, cured meats, and truffles. You can enjoy many of these delicacies at the source as part of a truffle hunting tour, or olive oil tasting at an oil mill.

Tuscany is also an illustrious wine destination. The native Sangiovese grape dominates production in the Chianti region, but there’s a growing range of Super Tuscans made with a blend of non-indigenous grapes such as Cabernet Sauvignon and Merlot. Tuscany is where you’ll find esteemed wine towns producing Brunello di Montalcino and Vino Nobile di Montepulciano, and renowned wineries such as Antinori, Avignonesi, and Vignamaggio.

A red Lamborghini Huracan Spyder rounds a corner in the Tuscan hills surrounded by vineyards.

Image: Ultimate Driving Tours

2. The fantastic driving roads

Wondering how to tour Tuscany? The simple answer is by road – whether you’re on a vintage Vespa or cruising in an eye-catching Lamborghini, Tuscany is motoring nirvana. From the dramatic coastal routes to the serene roads of the Tuscan hills, there’s a journey to satisfy every driver.

For example, you could take a stunning tour of the Tuscan countryside by immersing yourself in the magic of the Val d’Orcia, driving from San Quirico d’Orcia to Montepulciano via Pienza. Or there’s the epic Futa and Raticosa mountain passes, which take you from Bologna in the Emilia-Romagna region to Florence in Tuscany. A testing ground for Bologna’s Ducati motorbikes, these passes offer fast sweeping corners, tight hairpins and chicanes among stunning landscapes.

The quality of Tuscan roads more than live up to the beautiful location. Generally, Italy has a reputation for poor road surfaces, but this is far from the case in Tuscany. It’s a wealthy part of the country and the roads are very well maintained and on par with those in other affluent places such as Switzerland, and Champagne and Burgundy in France.

Ultimate Driving Tours’ guests admire a panorama of rolling green valleys in Tuscany from a balcony

Image: Ultimate Driving Tours

3. Stunning vistas at every turn

Wherever you go, beauty is never far away in Tuscany. It’s difficult to find a bad view while driving through the countryside and its rolling hills, cypress trees and sunkissed vines. Crystallising this is the Val d’Orcia, a UNESCO World Heritage Site comparable to the Elysian Fields that stretches between Siena and Grosseto.

As stunning as a Tuscany countryside tour is, don’t overlook the cities and towns. You can spend days exploring the quaint alleyways, tiny churches and cobblestone streets of hilltop villages, while bigger cities like Florence and Siena have magnificent architecture at every turn. Enjoy a sunset stroll along the river Arno in Pisa or people-watch in the dreamy Piazza della Repubblica in Florence.

Tourists admire the views in a bustling piazza in Florence on a sunny day

Image: Ultimate Driving Tours

4. The diversity of places to go and things to do

The iconic rolling hills of Chianti are naturally gorgeous, but to limit yourself to this central area would be a shame when the region is one of Italy’s most diverse. Exactly what you choose to visit in Tuscany will depend on your tastes, but there really is something for everybody.

Lace up your hiking boots and take a journey north to get up close with the imposing marble-rich peaks of the Apuan Alps. To the west, Tuscany meets the Tyrrhenian Sea with around 250 miles of stunning coastline. You can spend a morning in the pretty seaside village of Castiglioncello, then melt away on the long sandy beaches of nearby Viareggio in the afternoon.

The Maremma region in the south of Tuscany combines the rugged hills of Monti dell’Uccellina with wild beaches and natural reserves. Each of these landscapes contributes to the rich tapestry of Tuscany’s geography.

Elsewhere, Tuscany is regarded as the birthplace of the European Renaissance, so it’s the perfect place to indulge your artistic side. You can absorb the architecture in Florence and get lost among priceless masterpieces in the Uffizi, and then delve into smaller cities and towns like Siena, Assisi and Arezzo, with narrow streets, medieval churches and delightful trattorias.

Of course, no Tuscany travel guide would be complete without recommending tourist hotspots such as the Duomo and Ponte Vecchio in Florence, and the legendary leaning tower in nearby Pisa. Plan your visits away from peak season and you’ll find fewer crowds for a considerably more pleasant experience.

Finally, you can also enjoy quality wellbeing time with a dip in the therapeutic hot water springs at Bagno Vignoni, or take in the awesome sight of Saturnia’s cascading turquoise springs – an essential Instagram shot.

A spectacular country estate in Tuscany seen from above on a sunny evening

Image: Ultimate Driving Tours

5. Castles, villas and luxury are everywhere

Visiting the best castles in Tuscany is also a must for your Tuscan itinerary. The region is awash with ancient castles and historic villas that are open to the public, offering a glimpse of Tuscan life through the centuries.

Even better than simply exploring these places is having the opportunity to stay in them. Many castles and villas have been converted into ultra-luxe five-star hotels that combine rich history and incredible scenery with the height of luxury.

The list is long, but we will highlight Borgo San Felice – an adorable ancient hamlet and winery in the heart of Chianti that’s now a private luxury estate, complete with cutting-edge wellness facilities and a Michelin-starred restaurant. Other lavish Tuscan villa experiences that we love include Castello di Casole, Il Salviatino, and Villa La Massa.

A yellow Mercedes AMG GT leads a red Ferrari 488 Spyder round a sweeping corner in Tuscany

Image: Ultimate Driving Tours

Discover Florence and the Tuscan countryside as part of a bucket-list luxury tour

If our Tuscany travel guide has inspired you to visit this magical region, do so in style by joining us on our bucket-list Tuscan supercar driving tour. Over an unforgettably luxurious week, you will eat, drink and drive your way around Florence and the scenic countryside surrounding Siena.

Prefer to go your own way? Enjoy a luxury self-drive holiday through Tuscany. Get the keys to a supercar of your choice and head off on an expertly curated route, staying in luxury properties along the way.

If you would like to learn more about any of our incredible European driving adventures, speak with our friendly travel concierge team today.


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