Tuscany from Rome: What to See in Tuscany

May 19, 2026

Whether you have a week to explore or just one unforgettable day to take a trip to Tuscany from Rome, few places capture the imagination quite like the Val d’Orcia. With its rolling vineyards, medieval hill towns, cypress-lined roads, and world-famous food and wine, this iconic region offers everything travellers dream about when they picture Italy.

But Tuscany is much more than postcard-perfect landscapes. It’s a region of historic cities, Renaissance treasures, unforgettable culinary traditions, and charming villages where life still moves at a slower pace. So, here are some of the very best things to do on your travels to Tuscany from Rome.

Two people stand and look at the hilltop town of Piazza San Pietro, Tuscany, Italy, with red rooftops and green hills.

The rolling green hills are dotted with little towns and villages, the perfect places to stop and explore

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Take a Tour of the Best Things to Do in Tuscany

Exploring Tuscany without a car can be a challenge, especially if you’d rather sip and savor the region’s world-famous wines. That’s why our latest tour is the perfect solution: a seamless, all-inclusive day trip to Tuscany from Rome that combines comfort, indulgence, and iconic sights.

While seeing all of Tuscany from Rome in a single day isn’t possible, we’ve handpicked the most breathtaking corner – the Val d’Orcia valley, a UNESCO World Heritage Site known for its rolling hills, storybook villages, and award-winning wines.

On this carefully curated journey to Tuscany from Rome, you’ll stroll through charming hilltop towns, feast on a traditional lunch and wine tasting at an organic farmhouse, and even climb a medieval castle tower for panoramic views. And yes, there will be plenty of wine!

Sit back, relax, and let us take you on the ultimate Tuscan adventure – Tuscany from Rome has never been so effortless or so delicious.Getting to Tuscany from Rome is easy. Figuring out where to go first is what’s difficult!

Explore Tuscany’s Famous Hill Towns

No trip to Tuscany is complete without visiting its legendary hill towns. Perched on ridges and surrounded by vineyards and olive groves, these medieval villages are among the region’s greatest treasures.

Monticchiello

As you travel through the scenic landscapes of Tuscany from Rome, the breathtaking countryside gives you a taste of what’s to come—culminating in the enchanting hilltop town of Monticchiello. Tucked away in the Val d’Orcia region, this medieval gem with fewer than 250 residents captures the very essence of Tuscany: rolling green hills, cypress-lined roads, and panoramic views that feel like stepping into a painting.

Monticchiello is a quiet, storybook village that invites you to slow down and truly take in your surroundings. While the sweeping views will leave you awestruck, be sure to take a walk through the village itself. Though small, it’s rich in character and history.

One highlight not to miss is the Chiesa dei Santi Leonardo e Cristoforo, home to beautifully preserved frescoes dating back to the 14th and 15th centuries—an artistic treasure in this peaceful, rural setting.

Whether you’re a history buff, a photography lover, or simply searching for authentic charm on your Tuscany from Rome journey, Monticchiello offers a memorable stop that perfectly captures the heart of the region.

Monticchiello on our Tuscany from Rome Tour

Pienza

A hightlight of any trip to Tuscany from Rome is Pienza – one of the top towns in Tuscany! A UNESCO World Heritage Site since 1996, this town was completely rebuilt as an ideal Renaissance town in 1458 by Pope Pius II.

The main attractions here are situated in Piazza Pio II, where you’ll find the cathedral dedicated to Santa Maria Assunta, the town hall, Piccolomini Palace, and Borgia Palace.

Enjoy a lovely stroll in this town and as you walk along the Via del Casello, you will have yet another spectacular view of Val d’Orcia.

Some notable festivals that take place in Pienza include the Festival of Flowers (second Saturday and Sunday in May), where the town will be decorated with splendid floral scenes, and the Cheese Fair in September.

On the topic of cheese, Pienza, also known as the “capital” of Pecorino cheese, is the place for cheese-lovers! And we won’t leave Pienza without tasting a variety of its famous pecorino cheese and the opportunity for you to buy some to take home.

A storefront with crackers, pasta, wine, and olive oil on shelves in Tuscany.

Step inside local shops in Pienza to pick up local bites and artesan products from the region.

Montalcino

Renowned for its celebrated red wine, Montalcino, situated on top of a hill boast splendid views of the countryside. Here we will visit La Fortezza and climb up to the walls and lookout towers.

La Fortezza is pentagonal shape building reconstructed by the Sienese in 1361 and from its walls, you’ll have a birds’ eye-view of the gorgeous Tuscan countryside.

Walk along the walls of Montalcino Castle on our day trip from Tuscany to Rome

Enjoy a Farm-to-table Tuscan Lunch

One of the highlights of our day trip from Tuscany to Rome is a hidden gem, an organic farmhouse tucked away from the main road and completely immersed in the Tuscan countryside. The narrow road leading up to the farmhouse means that you won’t find huge buses here (if you find any other visitors at all!), making it a wonderful place to fully enjoy the intimate and tranquil atmosphere.

Before lunch, wander around this farm and you’ll likely run into goats, donkeys and pigs. You may even be lucky to see peacocks during their courtship ritual with their dazzling patterned plumage all fanned out.

By then we hope you’ve worked up an appetite for lunch as it’s going to be a feast. All the dishes served are based on seasonal ingredients from the farm, and you’ll also be sipping on wines from their vineyard, all this set within a backdrop of breathtaking views. The joys of life under the Tuscan sun!

Lunch on our on our Tuscany from Rome Day Trip

From Farm-to-table, enjoy an unforgettable lunch experience in the Tuscan hills.

Insider Tip: Tuscany’s cuisine changes dramatically from town to town, so don’t leave without trying local specialties like pici pasta, wild boar ragù, pecorino cheese, and of course, pair them with the delicious regional wines. Here’s our full guide to the best food to try in Tuscany.

Go Wine Tasting

Of course no trip is complete without doing some wine tasting in Tuscany. We’ll stop at a top Montalcino vineyard where we will visit the wine cellar and have a behind-the-scenes look at the procedures involved in producing the prestigious Brunello di Montalcino.

Of course, you will also taste the variety of wines produced at this vineyard, including their award-winning Brunello di Montalcino.

Tour guide with a glass of wine in the vineyard

If you visit Tuscany, you must enjoy at least one wine tasting experience.

Discover the beauty of Val d’Orcia

Val d’Orcia is one of the most photographed landscapes in Italy, and for good reason.

This UNESCO-listed valley is home to rolling golden hills and winding cypress roads. You will also pass vineyards and olive groves and can stop off in fairytale villages for a drink, or a spot of lunch.

Agriturismo Podere Terrapille outside of PIenza

Podere Terrapille, in the countryside of the Val d´Orcia, just outside of Pienza

If Tuscany looks like a painting in your imagination, this is probably the place you’re picturing.

Beyond the famous names, Tuscany rewards travellers who slow down and explore smaller villages. Places like: San Quirico d’Orcia, Bagno Vignoni and Montepulciano offer quieter streets, fewer crowds, and some of the region’s most memorable views.

Montepulciano, a beautiful Tuscan town known for its Vino Nobile

Insider Tip: Most visitors focus only on Tuscany’s hill towns, but the region also has a stunning coastline and beautiful Mediterranean escapes. If you have extra time, consider exploring the famous islands of Tuscany, including the spectacular Island of Elba.

How far is Tuscany from Rome?

Tuscany begins just north of Rome, but the distance depends on where you’re going.

Florence: about 1.5 hours by high-speed train from Rome
Val d’Orcia: about 2.5 to 3 hours by car
Montalcino: about 2.5 hours by car
Pienza: about 2.5 hours by car

That makes a trip from Rome to Tuscany surprisingly accessible, for a day trip or an overnight stay.

How to get from Rome to Tuscany

There are several ways to travel from Rome to Tuscany, and the best option depends on what kind of trip you want.

By train

The fastest and easiest option if you’re heading to major cities like Florence, Siena, or Arezzo. High-speed trains from Rome to Florence take as little as 1 hour 30 minutes, making it a very convenient choice. However, trains won’t take you into Tuscany’s famous countryside. To reach smaller villages like Pienza or Montalcino, you’ll usually need to rent a car or arrange additional local transport.

By rental car

Hiring a car gives you the greatest flexibility and is ideal if you want to explore Tuscany’s scenic backroads, hill towns, vineyards, and smaller villages at your own pace. Just keep in mind that driving in Italy can be challenging for first-time visitors. Expect narrow country roads, limited parking in historic centres, and restricted traffic zones (ZTLs) in many towns and cities.

By guided tour

For many travellers, this is the easiest and most enjoyable option. A guided tour removes the stress of planning, navigating, and driving, while giving you access to carefully chosen stops, local insights, and experiences like wine tastings or farmhouse lunches.

It’s especially ideal if you want to see Tuscany’s countryside rather than just its cities, and enjoy a glass of Brunello without worrying about who’s driving home.

A group of people cheering wine glasses at a long dining table.

Cheers to great company and excellent wine!

Insider Tip: Tuscany is one of the most popular escapes from the Eternal City, but it’s far from the only option. If you’re planning a longer stay in Italy, check out our guide to the best day trips from Rome for even more amazing destinations.

Want to experience Tuscany without the stress?

Exploring Tuscany independently can be wonderful, but planning transport, driving rural roads, and coordinating wineries and villages can quickly become complicated. That’s why many travellers choose a guided experience.

Our Tuscany tour from Rome takes you straight into the heart of the region, through Val d’Orcia’s rolling hills, into beautiful hill towns like Pienza and Montalcino, and to unforgettable vineyard and farmhouse experiences, all without worrying about trains, driving, or logistics.

See Tuscany the easy way—and spend your time enjoying it, not planning it.