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

A 10 day trip to Italy 
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Your romantic adventure together will keep your love at the forefront and be enhanced by the lush landscapes and majestic towns of Umbria and Tuscany on your personalized romantic tour of Italy. Enjoy a passionate embrace in a stunning vineyard before sampling celebrated Brunello di Montalcino, indulge in the uninterrupted company of each other as you drift down the Tiber River dining on a selection of delectable dishes, and then climb to the top of a medieval tower for unrivaled views of Tuscany. Take the chance to sneak a kiss around every corner, and fall in love anew amidst the beauty of Italy.

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General Information

Detailed Itinerary

Places Visited 

Rome, Orvieto, Spoleto, Assisi, Montefalco, Monteriggioni, Volterra, Florence, Terni, Narni, Mamore Falls, Bevagna, Siena, Montalcino   

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Rome – Arrive in Rome and Enjoy a Romantic Cruise down the Tiber River

Rome is known as the “Eternal City,” and embodies the tenants of Italian culture, from leisure to history, artistic aesthetic to a devoted relationship with romance. Your private transfer will greet you at Rome’s Fiumicino Airport and escort you to your boutique hotel at the heart of the historic city. Ivy drapes over the façade as nearby, the water cascades beneath the empowering figure of Oceanus posing at the center of the Trevi Fountain.

Your private rooftop terrace provides a secluded view of Rome’s protruding church spires and domes that will captivate. After taking a moment to settle into the comforts of your beautiful hotel, you can make your way to the banks of the Tiber River at Saint Angelo’s Pier and board an elegant boat. The lights over the river will flicker on the water and bring an ethereal glow to Rome while your four-course meal introduces an enticing array of aromas as you bask in the romance listening to the soft strumming of a guitarist. You have an unadulterated view of the dome of St. Peter’s Basilica soaring above the city as you cruise by on a perfect first night in Rome. Italy is a region unlike other; learn more by seeing how our partner Italy honeymoon tour operators can personalize the experience for you.

What’s Included: accommodation, airport transfer, tour, dinner

Day 2: Orvieto – Visit Terni, Narni and Marmore Falls en route to the Charms of Orvieto

In the morning, the gentle glow of the sunlight will spread over the Garden of the Oranges. The stunning citrus aroma drifts along the walkways that wind through Parco Savello as couples stroll the ruins that once surrounded the Savelli Castle. After your morning walk, your private transfer will greet you after breakfast and escort you north to travel into the heart of Umbria with its luster of gold and green hills rolling beneath majestic medieval towns.

You will soon arrive in 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. The city and the Basilica teem with life around the Feast of St. Valentine on February 14th.

The two of you can 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 whitewater careens down the cliffs at nearly 300 feet tall, causing the mist to spread along the lush ferns and moss over three drops.

What’s Included: accommodation, transfer, tour, breakfast

Day 3: Spoleto – Travel to Spoleto for Romantic Ambiance and a Couple’s Cooking Class

The morning light washes over the romantic streets of Orvieto to reveal the cobbled lanes, hidden archways, and terraces that overlook the vineyards, olive groves, and oak trees most often associated with Tuscany. Set out to traverse the countryside of Umbria, leaving Orvieto behind for 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. One of the surviving frescoes in the fortress displays a romantic chivalric myth akin to an Arthurian legend, creating a romantic ambiance within the fascinating historical complex.

In the afternoon, you will meet your private 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. You can snack on a selection of pecorino and goat cheese accompanying marinated olives. The pasta dough you make will stick to your fingers, contrasting with the soft flour. Before you sit down to eat, the meal becomes more decadent as your private chef grates black truffle over your traditional stringozzi, a long, thick pasta noodle.

What’s Included: accommodation, transfer, tour, breakfast, dinner

Day 4: Assisi – Venture to the Terraced Cobblestone Streets and a Lavish Basilica of Assisi

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. After breakfast, travel to the hillside town of Assisi, home to the inspirational figure of Saint Francis. Cobblestone lanes wind along the slope until reaching the summit of Monte Subasio.

The plains spread across the valley reaching to the rival city of Perugia. In the evening, the sunlight casts the marble pillars and facades in a rosy glow, returning the sleepy, romantic ambiance to the ethereal streets. 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. After stepping into the galleries of the Basilica, you can venture to the top of the hill to reach Piazza del Comune. Fragrant strawberry and chocolate gelato decorate the ice cream shop that borders the public piazza. You may find a hidden gem in the partially excavated Roman Forum located to the piazza’s northern edges, dating back to the 1st century Temple of Minerva.

What’s Included: accommodation, transfer, tour, breakfast

Day 5: Montefalco – Tour a Quiet Winery in Montefalco and Olive Oil Farm Bevagna

In the morning, you will find the aroma of hazelnut and cherries drifting through the doors of a small bakery in Assisi. The morning brings an unforgettable ambiance that is steeped in romantic light and private views before you continue to the town of Montefalco. Condé Nast mentioned Montefalco as Italy’s “Best New Wine Region,” in 2015, and with the snow-capped peaks of the Apennines rolling over the horizon, it is easy to see why.

The slopes that lead into the verdant valley are 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. The Church of St. Francis features elaborate works of 15th-century artists, including the Florentine painter Benozzo Gozzoli. Outside of town, you can visit a family-owned vineyard first mentioned in documents in the 13th century.  The family has owned the estate since the 19th century, spreading the vines and orchard nearly 75 acres.

Walk alongside your guide throughout the vineyards, touching your fingers to the waxy skin of the dangling grapes. The sunlight is warm and inviting on your cheeks while the tasting room offers the aroma of oak and a view over the landscape. 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. 

What’s Included: accommodation, transfer, tour, breakfast

Day 6: Montalcino – Traverse the Pristine Val d’Orcia region of Tuscany with a Wine Tour

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. The scent of mushrooms and garlic filters into the dining room as the window frames the view to the rolling greenery making the landscape look like a painting. Your server will pour a glass of Brunello di Montalcino and the aromas of fig and carob mix with fragrant espresso and leather. You will find a flavor of aged balsamic and sour cherry, offering a distinctive, subtle profile you will want to remember.

What’s Included: accommodation, transfer, tour, breakfast

Day 7: Monteriggioni – Relish the Renaissance Atmosphere of Siena and Monteriggioni

Tuscany offers endless romance thanks to the charm and majesty of preserved medieval towns that are reminiscent of storybooks and fairy tales. 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. The town remained under the protection of Siena until the city’s fall to Florence in the 15th century. The Griccioli family has owned the castle and town walls since the early 18th century, using their prestige to preserve the rich history and culture of the town.

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. Marble archways and pillars glint white in the sun, emphasized by the black lines that streak across the facades and walls. 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. 

What’s Included: accommodation, transfer, tour, breakfast

Day 8: Volterra – Indulge in Medieval Allure in San Gimignano and Volterra

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. The beams pierce the rose window and shine over the 56 separate mosaics that decorate the floor with mythological and religious histories. After a morning wander and breakfast, you will travel to the town of Volterra, known as one of the best preserved medieval cities in the country.

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. A Roman basin use to collect rainwater rises out of the garden in the archeological park.

You can wander through the romantic aroma of jasmine fading beneath the scent of chocolates near the Porta all’Arco, a mixture of Etruscan and Roman architecture that dates back to the 7th century BC, which leads into the city center. Once in San Gimignano, you can stand beneath the 13 remaining towers out of the original 72. The towers were physical symbols of the aristocratic wealth, prestige, and power in and around the city, encouraging competition between feuding families to try and build more prominent, splendid edifices across the skyline. You can venture to the top of the Torre Grossa for a secluded, stunning view of the Tuscan countryside at over 175 feet above the cobbled streets.

What’s Included: accommodation, transfer, tour, breakfast

Day 9: Florence – Delight in the Historic Beauty and Opulence on a Private Florence Tour

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.

The allure of the marvelous sculptures leads you down the wide, long hall. Unfinished works of the master artist line the walkway, including four Prigioni, images of slaves seemingly emerging from their stone enclosures. You will soon reach the cupola beneath which stands David, and you will be awestruck. Seeing the statue in person offers insight into the subtle details absent from photos and the replicas around the city. Veins adorn the long muscles around the arms and legs. His curly hair could rustle in the breeze above his piercing, stoic eyes. 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. 

What’s Included: accommodation, transfer, tour, breakfast

Day 10: Florence – Depart for Home

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. At breakfast, you can bask in the lovely ambiance of the city as it returns to life. 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.

What’s Included: airport transfer, breakfast 


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.