Considered the green heart of Italy, Umbria and Tuscany span the Italian countryside north of Rome. Umbria, in particular, is a relaxing (and lamentably skipped over) stop when you travel between Italy’s capital and more famous Tuscan towns like Montepulciano and Siena. Umbria and Tuscany’s natural beauty will immerse you in the soul of Central Italy. But what is there to do and see when traveling between Rome and Florence?
Historic vineyards and rolling hills typify the Umbrian and Tuscan countryside. In other words, these Italian regions are pure paradiso (paradise) for nature lovers. Some of the best things to do in Umbria and Tuscany are outdoors – whether it’s hunting for truffles near Spoleto (Umbria) or taking a "wine ride" bike tour through Chianti (Tuscany). Open-air travel activities abound in Central Italy – so, whether you’re a food-loving gourmand or avid hiker, Italy’s green core boasts an experience for every traveler
So, you’re probably asking yourself: “how should I spend one week in Tuscany and Umbria?” For a perfect week in Italy, we recommend the day-by-day itinerary below ((we can always customize it further to suit your interests or passions)). This Italy itinerary includes some of Italy’s best wine regions, Italian Renaissance art and plenty of time to connect with the local Italians who call these lovely lands home.
Departing from Rome in the morning, you’ll be driven in style by an English-speaking driver through the bellissimo countryside of Lazio and Umbria. Along the way, you’ll pass rolling hillsides, verdant vineyards and millennia-old towns. Before entering Umbria, your friendly driver will bring you to the striking Italian town of Civita di Bagnoregio – arriving here is like traveling back in time. Teetering on a stone crest high above a deep green gorge, Civita is accessible only by a footbridge. In fact, the only way to enter the town is via a stone corridor carved by the Etruscans 2,500 years ago. After strolling Civita’s foot-smoothed cobblestones, you’ll enjoy a prosciutto-filled panino – served on oven-fresh focaccia.
Following lunch, your local driver will transport you in comfort to the ancient city of Spoleto – one of Umbria’s most historically significant (and visually eye-popping) settlements. Before arriving at hillside Spoleto, you’ll stop for a guided Italian wine tasting at an Umbrian vineyard that first made wine in 1212AD. Today, it is one of the few wineries in Italy to craft Champagne-style bubbly using the hand-turned methode traditionelle (“metodo classico” in Italian). Indeed, the vineyard’s elegant sparkling wines are aged inside a sandstone cave—where temperatures stay a constant 13° C. As part of your guided Italian wine tasting, you’ll enjoy a behind-the-scenes tour through the vineyard’s stone cellars.
After your private tasting with a sommelier-guide, your driver will bring you to Spoleto. Here, you’ll slumber in elegance at a boutique hotel housed inside a 600-year-old noble mansion. Overlooking Renaissance gardens and Umbria’s green hills, your luxurious lodging occupies a meticulously restored 13th-century palace – just a 5-minute walk from Spoleto’s historic Duomo (cathedral).
As one of Italy’s most ancient towns (with artifacts found here dating back to the Bronze Age), Spoleto is a patchwork of competing histories – from an ancient Roman theater to the city’s stately bridge, which was built in 1350 and rises a whopping 264 feet into the air. Crowned in the 14th-century Rocca Albornoziana fortress, Spoleto is an unparalleled hilltop jewel framed by the verdant Apennine Mountains. You’ll discover the high-points of Spoleto in the company of a guide born and raised in the area – exploring major sights and the hidden gems loved by locals. Tour highlights include Piazza del Duomo, the city’s medieval walls, and the Arco di Druso.
In the afternoon, you’ll have time to enjoy a leisurely lunch and to explore Spoleto’s meandering stone streets at your own pace. For dinner, you’ll be treated to a feast of Umbrian flavors and true Italian hospitality – savoring a hands-on cooking class inside a Spoleto chef’s actual home. Together, you’ll learn to make pasta from scratch (grandma’s recipe) – paired with local wines and appetizers like norcini (salami) and pecorino umbro (sheep’s milk cheese). Slumber overnight then in your elegant palace-hotel in the heart of historic Spoleto.
Prized equally by Italian cooks and global gourmands, black gold grows under Umbria’s glens. Wild truffles are a food specialty in Umbria – vaunting an aromatic and nutty flavor. Chefs here use these fragrant fungi to level up pasta, crusty bread and steaks. Umbria’s wooded hills are the ideal habitat for truffles, which are harvested between November and March. Since truffles mature underground, people need an extra nose to dig them up — a dog trained to sniff out these tasty tartufi.
To relish the real deal, you can hunt for truffles in Umbria with a local guide—he’s been unearthing for over 50 years! First, our driver will bring you to secluded stretch of the forest – located near Spoleto, Italy. In the company of your local guide and his truffle-sniffing dogs, you’ll scour the land for a whiff of wild truffles – drinking in epic views of the green valley below as you hunt. After digging up your Umbrian tartufo nero (black truffle), you’ll have worked up quite the appetite. So, to satisfy your tummy, you’ll lunch with your Umbrian guide at his friend’s family farm – enjoying homemade pasta crowned in the very truffles you just dug up! Travel to Italy doesn’t get more local than Umbria.
After your walk in Umbria's woods, you'll be driven in comfort to a castle-hotel outside of the hilltop town of Perugia. Housed inside a restored 11th-century stone palace, this elegant accommodation boasts frescoed ceilings, a rose garden and a relaxing sauna.
Today you will relish the Renaissance splendors of Central Italy – uncovering the hilltop jewels of Assisi and Perugia. Synonymous for its most famous resident, St. Francis, the town of Assisi boasts one of Italy’s best-known (and yet never overcrowded) cathedrals – the Basilica of St. Francis. In the company of your local art-historian guide, you’ll wander the stone streets of Assisi. Inside the basilica, you will stand in awe of Giotto’s glorious frescoes and view the tomb of St. Francis. From outside of the basilica, you can drink in epic vistas of vineyard-draped valleys and the hand-chiseled columns that frame the Franciscan cloisters.
Following lunch in an authentic trattoria, you will head with a private English-speaking driver to picturesque Perugia – known for its tradition of hand-crafted chocolates. In the afternoon, you’ll savor a hands-on chocolate-making class during a guided stroll through the city. Your visit includes a behind-the-scenes stop at a sweet shop that's been in the family for three generations. Not only will you learn how to temper and shape chocolate, you’ll enjoy a tasting of Perugia’s renowned cioccolato. In the evening, you will slumber once again in your regal castle-hotel – where you might enjoy a creative, chef-curated meal at the Michelin-starred Gradale restaurant
In today’s journey through Central Italy, you will head from the green hills of Umbria to the rolling wine country outside of Cortona, Tuscany. First, your English-speaking driver will bring you to the small Umbria village of Deruta – famous throughout Italy for its hand-painted ceramics. You will go behind-the-scenes with a family of local potters in Deruta, observing how clay is shaped and decorated according to generations-old techniques. Next, we will head to the scenic shores of Lake Trasimeno – Italy’s fourth largest lake. Once at Lake Trasimeno, you will savor a traditional lunch under the fortressed walls of Castiglione del Lago—built in the 12th century and expanded in the 1500s.
After dining by Lake Trasimeno’s sparkling shores, you will be driven in comfort – along scenic routes through Tuscany’s Val d’Orcia – to a 5-star boutique hotel just outside of Cortona. The landscape of Tuscany’s Cortona province is some of the most picturesque in all of Italy – brimming with terracotta-roofed farmhouses, cypress-lined streets and lush vineyards. In the evening, you might dine at the hotel’s restaurant – paired with the prized Brunello wines produced in this part of Tuscany.
A visit to southern Tuscany would be incomplete without a day savoring the fine Brunello wines grown in this region. After enjoying breakfast and cappuccino at your villa-style hotel, you will journey the postcard-perfect wine country around Montepulciano and Montalcino, Tuscany. Before enjoying a private-access visit to a small-batch vineyard, you will stop in the arstically-rich and historically-significant city of Montepulciano – perched above the Brunello vineyards. In the company of a local art-historian guide, you’ll enjoy a walking tour through Montepulciano’s rich history – as embodied in its art and architecture.
In the afternoon, after savoring the sights and colors of Montepulciano, we’ll head to a Brunello winery located just outside of Montalcino, Tuscany. Here, you’ll enjoy a private wine-tasting with the vineyard owners – without another tourist in sight. On top of your tasting in the winery’s private cellars, you’ll walk the vines where grapes ripen and observe Brunello being aged inside oak casks. After your intimate wine-tasting, you will return to the villa hotel near Cortona – stopping first in Montalcino to relish this medieval hilltop hamlet on your own.
Before saying arrivederci to Italy the next day, you'll close out your perfect week in Umbria and Tuscany with a once-in-a-lifetime feast -- enjoying dinner under rustic wooden beams and centuries-old stone walls.
Who's ready to spend a week in Umbria and Tuscany? Contact your travel agent (we're glad to work with them!) or firstname.lastname@example.org to make this dream vacation your lived reality.
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