Tuscany from Rome: How to Plan the The Perfect Day Trip

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—Val d’Orcia, 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!

Hill towns

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.

Explore the beautiful town Monticchiello for some of the best views around Tuscany.

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.

Step inside shops in Pienza to pick up local bites.

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

Organic Farmhouse

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!

Cheers to good food and even better wine!

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.

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

Ready for the perfect day trip to Tuscany from Rome?

We certainly think so—and we can’t wait for you to experience it for yourself! Whether you’re dreaming of rolling hills, historic towns, or unforgettable food and wine, this tour captures the very best of Tuscany in just one day.

Curious to learn more or ready to book your spot? Visit the tour page here for all the details. And if you join us on this unforgettable journey, don’t forget to leave a comment—we’d love to hear about your favorite moments!