Charm & Romance in Italy’s Countryside: Tuscany and Umbria Tour

In the morning, the gentle glow of the sunlight will spread over the Garden of the Oranges before you travel to Terni, the “City of Lovers.” The aroma of pinolata, macaroons made from pine nuts, and almond cookies known as tozzetti, filter through the doors of various bakeries. The modern streets blend into the ancient city center, where the beauty in the medieval roots emerges, featuring the remains of St. Valentine, the patron saint of lovers.

Stroll hand-in-hand down the cobbled lanes of the city until you step into the Basilica. The bright yellow façade was erected in the 17th century atop foundations first laid in the early 7th century. After visiting the tomb of St. Valentine to pay homage to a unique and protective symbol of love, continue to the nearby Falls of Marmore, the tallest human-made waterfall in the world.

The morning light washes over the romantic streets of Orvieto before you set out to traverse the countryside of Umbria and the medieval fortress of Spoleto.

Romans erected grand arches and an amphitheater along the plateau situated beneath the rugged peaks of the Apennines while the Dukes of Lombardy used Spoleto as their capital in the 6th century, leaving behind a stunning Romanesque Cathedral. The 14th-century papal fortress of Rocca Albornoziana maintains the history of the town in its National Museum, tracing the efforts of the Roman, Byzantine, and Carolingian settlers through artifacts such as sarcophagi and remarkable jewelry.

In the afternoon, you will meet your chef and enter the garden kitchen to learn about the local and cultural flavors of Umbria. The scent of garlic and basil fills the kitchen as jasmine blossoms in the gardens. Before you sit down to eat, the meal becomes more decadent as your chef grates black truffle over your pasta.

The morning light glints off the golden stones of the fortress of Spoleto. The scent of almond cookies returns to the air and fades beneath the herbaceous aroma of the vineyards spreading across the slopes of the Apennines. Travel to the hillside town of Assisi, home to the inspirational figure of Saint Francis.

The plains spread across the valley reaching to the rival city of Perugia. You can see the Basilica from the valley basin, rising along an outcropping with its Romanesque bell tower. The lower church was erected in the early 13th century, with the upper levels completed in the late 1200s. The scent of frankincense continues to fill the halls. The venerated stone of St. Francis’s tomb stands at the center of the High Altar. Four figures of prominent disciples face the tomb like guardians. Frescoes depicting the early life of the saint shine in the dim light of the lower Basilica.

In the morning, you will find the aroma of hazelnut and cherries drifting through the doors of a small bakery in Assisi. 

In Montefalco, you can find slopes that lead into the verdant valley decorated with oak, chestnut, and olive trees. Vineyards spread across the lowlands and the foothills with historic flavors that date back to the mid-16th century. The town stands atop a hill with golden and rosy stones while the church spires maintain Romanesque and Gothic styles that soar above the narrow cobbled lanes. Outside of town, you can visit a family-owned vineyard first mentioned in documents in the 13th century. 

Your guide will pour you the first sample as you toast with your lover to the flavors to come. The ruby hues of the wine lead to aromas of cherry and wild berries. The balanced body and freshness stem from the Sangiovese grape, while the Merlot provides the smooth aromatics.

After breakfast, your private transfer will greet you in the hotel lobby and escort you north and over the border to Tuscany. The landscape is as romantic as you pictured, with rolling hills, endless rows of vines, and cypress trees bordering the country roads like rows of spires. The herbaceous aroma emanates from the mixture of olive groves, chestnut trees, and sprawling vines that lead to the medieval hilltop towns. Wine stores are known as enoteche line the quiet cobbled lanes of Montalcino within the preserved 13th-century walls. The dramatic towers and fortified walls of Montalcino Castle embody a storybook fortress, adding a touch of fantasy to the romantic spirit of the historical town.

The town has changed little since the 16th century and will immerse you both in views to sun-drenched hills glowing with yellow and red flowers, along with idyllic olive groves and lone cypress trees rising out of the hillsides. You can step into a wine bar for a perfect example of traditional Tuscan cuisine and the wines of Val d’Orcia.

Your romantic Italian fantasy will continue in the town of Monteriggioni with its millennium of history. The slopes lead to the defensive castle walls, and two large entrances lead into the plateau, one that faces the city of Siena, and the other facing north to Florence.

In Siena, the brilliance of the city that once rivaled Florence in power and artistic vision crafts a romantic ambiance. The scent of gelato and maple drifts from the ice cream shops along the hidden cobbled avenues. The replica of the 15th-century Fonte Gaia, the Fountain of Joy, trickles on a small lane off the main Piazza del Campo, accentuating the impressive masterpiece of the Fontebranda, a fountain depicting the life and birth of Saint Catherine. For a unique and secluded perspective of Siena, you traverse a portion of the Bottini, a 15-mile system of tunnels that has brought water to the city since the 12th century.

In the morning, you will feel as though you have Siena to yourself. You can stroll down the cobbled lanes and enjoy the sunlight as it washes over the black and white marble of the nearby Cathedral before you travel to the town of Volterra.

Winding cobbled lanes twist beneath stone archways and lead to serene public piazzas. You can stand on a small terrace and bask in the view over the valley, guiding your eyes to the soaring towers of San Gimignano, a nearby hill town. Etruscan ruins pepper the town beneath the golden walls and the spacious, deserted squares. The walls on the outskirts of town were originally built in the 4th century BC, accounting for an amount of people twice the size of its current population.

In San Gimignano, you can stand beneath the 13 remaining towers out of the original 72. You can venture to the top of the Torre Grossa for a secluded, stunning view of the Tuscan countryside.

Florence is a beloved city that ushered in the splendors of the Italian Renaissance. Pass through the historical walls that frame the city center as the marvelous dome of the Cathedral crowns the heart of Florence with unreinforced brick, as designed by the architectural master Brunelleschi. The rosy hue of the brick continues to shimmer above the green, white, and pink marble that adorns the façade. The scent of marzipan and chocolate drifts out of the confectionaries and contend with the savory aromas of fresh pasta dressed in a sauce of garlic and tomatoes. The merchants around San Lorenzo display leather goods and handmade silk garments, and you can step off of the streets and into the Accademia, which houses Michelangelo’s iconic statue of David.

In the evening, continue to San Miniato, a church on the hill that overlooks the city. Monks perform Gregorian chants each evening, allowing their melodic voices to echo across the Tuscan hillside in view of the idyllic architecture of the Renaissance city.

The sunlight of the morning shines over the bell tower attached to Palazzo Vecchio, which stands at nearly 310 feet above the cobbled piazza. The palace now houses the city government, along with exquisite frescoes that adorn the paneled ceiling accentuated with gold leaf. The jewelers on the Ponte Vecchio open their doors and create elaborate window displays while artisans craft specialty books and restore antique furniture. After one last leisurely morning, your private transfer will greet you at your hotel and escort you to the airport for your flight home.