Italy Tour of the Most Beautiful Towns & Villages

A 14 day trip to Italy

The sensations of Italy come from traditions ingrained within the soil of the countryside and rising up through the towns and villages. On this 14-day tour through the north and south of the country you will find the most beautiful scenery displayed in Italy s natural majesty. Climb through medieval villages and find the hidden waterfalls of Umbria, revel in the Tuscan hills and visit the marvelous art of the Renaissance. From natural magnificence to humanity s endless striving for beatific perfection, you will find, wander, and wonder through it all.

General Information

Detailed Itinerary

Places Visited 

Rome, Montecassino (Abbey), Naples, Pompeii, Amalfi (Amalfi Coast), Spoleto and Valnerina, Assisi, Deruta, Montefalco, Urbino, San Leo and Gradara (Montefeltro Castles), Venice, Florence, Siena, Pienza, Montalcino (Val d Orcia)

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1 It Started with a City

The tremendous city of Rome spreads out before you and is filled with an endless energy that you can feel rushing around. You are met at the airport by a private transfer and taken to your stunning hotel within the city center. The surrounding history is almost unimaginable, dating back millennia. The air is rich with antiquity, bringing the classic in touch with the neo-classic, while the modern world forms itself around them. In the afternoon you will embark on a walk through the historical center that will display the marvels of the city s past while maneuvering through Rome s present.

A short distance from the Renaissance-era center you will find Palatine Hill, the oldest street in all of Rome. Once the most fashionable place to live in the entire Republic, it is also the most central hill in the city s celebrated Seven Hills due to the belief that Romulus and Remus were found there. The hill ascends over 120 feet above the Roman Forum, offering a remarkable view of the ancient plaza on one side. The plaza is filled with sensational remains of the ancient central life of the city and is a place where you can imagine the immense spectacle of markets and trials, and the epicenter of speeches and celebrations. Now what remains are pillars and pediments and the rising awe of visitors, inspired by the past, present, and presence of what remains.

What s Included: transfer, dinner, tour, accommodation

Day 2 Staring at the Ceiling

Your morning begins with a delightful breakfast filled with fresh, sweet brioches and the rich, strong espresso that the Italian s favor for a big start to the bright day. Your day begins with an in-depth tour of the city, taking you through the Colosseum, where gladiators battled, and around the Forum before arriving at majestic St. Peter s Square. The museum is filled with thousands of masterpieces, from paintings to sculptures, lining the opulent hallways and sometimes even gilding the ceilings. You can hear the echoing footsteps of inspired visitors moved by the delicate artwork and marvelous architecture.

You can find Raphael s School of Athens displayed with elegance on a large wall within one of the 54 galleries. The painting represents Athens s Golden Age, when philosophers embarked on their natural quest for enlightenment; each famous character within the piece, from Plato to Socrates, is characterized by a Renaissance Master, from da Vinci to Michelangelo. At the end of the museum you will find yourself wondering at the ceilings of the Sistine Chapel. One of, if not the most, famous ceilings in history will be hovering right above you, filled with dynamic colors and paneled with biblical history. You don t need to stop gazing into the refined portraits that Michelangelo brushed over a span of four years.

What s Included: breakfast, tour, accommodation

Day 3 Southern Marvels

Your day begins with a luscious breakfast which will have you ready for the day. Outside of Rome is Monte Cassino, a marvelous abbey that sits at the top of a summit and looks more like a castle than a monastery. The structure was built on preexisting Roman fortifications and maintained its shape since the 14th century until 1944 when it was destroyed by Axis powers. The basilica is lavishly decorated with mosaics dedicated to the relics of St. Benedict and his sister, St. Scholastica, both of whom survived the bombings of the abbey. The mosaics wrap around the archways and liven the walls, bringing effervescence to the interior.

Oftentimes you can overlook the luxuries and charm of a larger city where so much history and splendor exists, such is the case with Naples. Venture southbound from Rome to one of the largest cities in Italy, located on the Bay of Naples where the sapphire water glistens in the sunlight beside the roaring urban streets. Naples itself is brimming with fantastic sights, from historic streets to ancient artifacts, and features the most sensational pizza. In the evening you will find the delectable flavors of Neapolitan pizza at your fingertips as you indulge in a course that will teach you everything you need to know to create the perfect, traditional dough, sauce, and flavors.

What s Included: breakfast, tour, transfer, accommodation

Day 4 Under Dust and Coastlines

Today you will travel along the Bay of Naples and come to the famous city beneath the ashes, Pompeii. Venture through the city on a guided tour, where you can see the legendary ruins that have been preserved by the very dangers that brought Pompeii to ruin. In the distance you can see the classic peak of Vesuvius creating the skyline over the bay. Pompeii was not a town or a village but an immense city whose streets seem to extend endlessly, making it easy to get lost along the ash covered buildings. Follow your guide through the grand highlights that have given archeologists an understanding of ancient life around 79AD. Much of the knowledge about the ancient life here has been based upon what has been uncovered and that which is now displayed. Archeologists have even found citizens of the city preserved in their final poses, and who are now encased in glass on exhibition. One of the most reveled buildings to find is the Brothel, composed of two floors where frescoes lined the metope, showing menu options for costumers. The ground floor contained five bedrooms while the higher floor was meant for upper classes, containing a separate balcony from which the luxuriantly furnished rooms could be reached.

Wind along the celebrated Amalfi Coast, known as much for its beauty as for its narrow, two-way street that hugs the cliffs. No matter how unnerving the drive might seem at times, you cannot help but marvel at the exquisite coastline. The water is sapphire blue and is diamond-like in its clarity as it reaches towards the horizon. Small towns climb up the limestone and down to the water below. Once you reach the city of Amalfi you can wander through the quaint streets and charming atmosphere until you find the cathedral in the town center. The air is rich with decadent food and jovial energy. The Duomo is mixture of light brown and white stone with arched windows that maintain an elegant design. It s as if the classic medieval architecture from around Italy was placed against the backdrop of an immaculate shore.

What s Included: breakfast, dinner, tour, accommodation

Day 5 Towns at the Heart

After breakfast you will find yourself outside of Naples en route to Umbria, the Heart of Italy. There is no mistaking the difference in scenery once you reach the borders of the region; the hills begin to tumble over the horizon in exquisite greenery before you reach the towering rugged mountains of Valnerina. It is like a forgotten wonderland of landscapes stretching around villages and towns, where the highest waterfalls in Italy, Marmore Waterfalls, pour over the mountainside. Settle into an exquisite lunch with black truffles and the wide-ranging local delicacies of ham and salamis.

Arrive in the charming town of Spoleto, where the medieval architecture wraps around the narrow streets adding historical wonderment to the natural beauty of the region. An exciting stone bridge takes you to the rising hills where the Rocca Albornoziana is located. The fortress was built in the mid to late 14th century and continues to be an imposing structure that watches over the lengths of the valley and the quiet walkways of the town. From a distance the structure looks slick and smooth; the only crevices that look to break the consistency of the facade are windows and doors. Fifteenth century frescos decorate the Painted Room, which is rich with spectacular frescoes whose vibrant color and storytelling remain.

What s Included: breakfast, lunch, tour, accommodation

Day 6 Overseeing History

The beauty of the landscape is seemingly endless, ever changing, and always captivating. Today you will find yourself ascending the hill of Assisi in the early afternoon. In the clear sky you can look out over the expansive valley and see the medieval architecture of the city s rival, Perugia. Assisi is paved with cobblestone, winding up and around the hilltop, and lined with quaint homes, restaurants, and shops that have remained in the city for centuries. The luxurious scent of sweet balsamic vinegar and creamy olive oil beckons you closer.

The Basilica of St. Francis has an embellished, far-reaching exterior, pristine in its color, and with a facade that is decorated with single adornment of a rose window that twinkles in the afternoon light. The interior is elegant with a shapely spirituality, lacking the gaudy nature in return for a deeper sign of dedication to its patron saint for whom the church was named. Frescoes decorate the walls and ceilings bringing biblical history to life once again within the center of piety. Beneath the cathedral you can enter the cool air of the catacombs where St. Francis was buried. The light bounces off of the stone, while an earthen air swirls with the draft. The quiet of footsteps up and down the stairwell is the only sound you can hear, even once you arrive back at the main hall, where the 800-year old basilica has always mesmerized its guests. Along the quintessential streets you will be lured by the delightful fragrance of several food stores, where the flavors of regional olive oils, balsamic vinegar, honey, and cheeses can be seen, tasted, and enjoyed.

What s Included: breakfast, lunch, tour, accommodation

Day 7 Amidst Decadent Fare

When the new day comes you will find yourself travelling through the center of Italy, arriving in Sant Angelo in Vado in the late morning. The city is bordered by the gentle trickle of a river that doubles as a moat which wraps around the city as a protectorate from would-be invaders. The low arching bridges that lead over the waterway and into the city bring you to a small expanse of medieval architecture in a city that takes you back in time to a quiet hillside. All the while, the lovely perfume of shaved truffles comes drifting through the streets. Sant Angelo in Vado is the capital of the white truffle and is home to the National Center of Truffle Cultivation where you can gain some practical experience in the truffle hunt. The sounds of barking dogs and the scent of pine and forestry often come along with the search.

In the afternoon you will come to the rising city of Urbino, home to Raphael and the persistent beauty of its seasoned architecture. On the summit of the steep hill is a fabulous statue of the famed painter looking out over the town as the panorama spreads out over the rolling countryside. The Oratorio di S. Giovanni Battista is a fantastic church decorated in the early 15th century. Frescoes drape the wall from floor to ceiling in opulent representation of the vision of the life of St John the Baptist. The vibrant colors shimmer in the graceful light as the legacy of the painters endures.

What s Included: breakfast, lunch, tour, accommodation

Day 8 Standing Over the Township ?

The splendid Montefeltro Castles bring more than just a sense of history but one of fantasy as well. Age-old stones created places of myth and legend, no more so than that of Paolo and Francesca at the castle Gradara, known to the world through the words of Dante Alighieri in the Inferno. Soon you will be in San Leo, where the village sits beneath an imposing fortress built on a jutting rock with walls that hang over the valley. Originally founded by the Romans, the current fortress came about in the Middle Ages and is divided into two main parts, the keep and the residential wing. The square turrets and gothic entrance of the keep is known to be the older section of the structure, while the towers and large corbelled wall are newer. The vivacious cliffs tower over the valley, remnants of an ancient shifting sea, giving the view from below a magnificent sail structure, billowing into the sky. In the evening you will delight in one of the finest restaurants which serves elegant, classic fare and makes you feel at home.

What s Included: breakfast, dinner, tour, accommodation

Day 9 A Most Beautiful Venice

The late morning shows you the one of a kind city of Venice, where the canals wind their way through the city like sidewalks, creating the unique atmosphere of seclusion, Orient-Travel, and romance all at the same time. You will settle into your gorgeous accommodations in the heart of the city giving you the chance to venture out into the iconic scenery. Saint Mark s Square opens up to you with enthusiasm, being one of the many places that fill endless post cards with opulence and beauty.

The basilica s earliest construction began in the 9th century and towers over the square in Byzantine prominence, with an angled dome and Moorish arches. As you step closer to the cathedral you find the glistening charm of the gilded frescoes telling stories of the New Testament within the shelter of the arches. The Rialto Bridge is also nearby, built in the 16th century and overlooking the Grand Canal in all its glory. The bridge itself is magnificent, structured in beautiful stone arching over the waterway where you can watch gondolas sweep beneath. Some say you would be hard pressed to find a more romantic spot overlooking the canal than the Rialto Bridge; however, there are always secret luxuries to be discovered within the most beautiful towns and villages.

What s Included: breakfast, dinner, accommodation

Day 10 Made for Casanova

Today you will find the secret side of Venice, away from the squares and streets crowded with visitors, and into the crowds of locals. The cobblestone streets carry people home and to local markets and you will find yourself happily lost within the quiet buildings and luxurious walkways. Through the Rialto Market you will come to Chiesa dei Frari, a large church that, from the outside, could be one like any other. However, when you take the time to enter the church you will find the stunning sophistication of the Renaissance withheld behind the soft facade. Completed in the 14th century, the church now contains works by Tiziano, along with Donatello s sculpture of St. John the Baptist, his first documented work inside the Venetian principality. As the day wears on you will climb aboard a gondola and enjoy the gentle and sweet view of Venice from its most celebrate highway, the canals. Few things are more quintessential to Venice than drifting through the city, along private docks, with the quiet breeze the new music to the city. In the evening you will enjoy a lovely baroque music concert following dinner, giving you more grandeur to add to the beautiful day.

What s Included: breakfast, dinner, accommodation

Day 11 Symbols Outside

The afternoon finds you in Florence, taken away from Venice s darling canals, and instead sitting within the heart of Renaissance beside the Arno River. From Piazzale Michelangelo you can see the entire cityscape below, stretching out from the Ponte Vecchio, the Old Bridge, to the towering dome of the cathedral. Within the Piazza del Duomo you can see the elegant cathedral up close. It s massive with white and dark green marble, and encompassed by the city itself. The dome continues to be the largest brick dome ever built.

The streets are energetic and lively, filled with locals bringing home groceries, and people relaxing in the local cafes enjoying an afternoon espresso and who seem to lend vibrancy to the day. The Baptistery holds large golden doors, mentioned most recently in Dan Brown s novel Inferno; the doors themselves are called The Gates of Paradise, containing impeccably carved scenes from the bible that took Ghiberti 27 years to complete. The best of Florence can be experienced by walking through its storied streets. However, no matter how gracious a city can be, some things can only be housed in a museum.

Later in the afternoon you will come to the Galleria dell Accademia to discover the legendary statue of Michelangelo s David, an indisputable masterpiece. Even if the work were not placed on a literal pedestal it would tower over you with its height of nearly 14 feet. The incredible detail arises not only from the musculature but within the facial structure and inspiring story. The work has endured as a classic piece of art throughout time that now stands before you, a work that has the power to literally take your breath away.

What s Included: breakfast, dinner, tour, accommodation

Day 12 Within Lavish Facades

Today is dedicated to capturing the magnificence of Florence s artistic past with a visit to Oltrarno. You will venture across the Ponte Vecchio into the neighborhoods that lie outside of the city center. Artisanal wood carvers and mosaic ateliers, goldsmiths and engravers continue their craft which has been passed down through generations. The sounds of tinkering and tools clinking can be heard all around you before you finally arrive in the marbled halls of the exquisite Uffizi Gallery. The long walkways are lined with opulence, from the polished floors to the gleaming wooden arches that overlook the Piazza outside. The galleries contain the works of Italian masters, from Michelangelo to Tiziano, along with the unparalleled work by Botticelli, The Birth of Venus. The painting s size is enough to move you, but the brushstrokes and colors are unmatched, bringing the Goddess Venus to life with sensuality and a form of vulnerability as she gives a slight smile to all those who pass by.

What s Included: breakfast, tour, accommodation

Day 13 Within the Tuscan Hills

Outside of Florence are the famed rolling hills of Tuscany. Beneath the shimmering sun lies the stunning greenery that has captured imaginations and hearts for centuries. En route to Rome you will stop at the darling city of Siena, known for its several hills and the famous annual horse race, il Palio, on July 2nd and August 16th. The cobblestone streets meander through town and up and down the hillside. The famous Duomo is marbled with black and white coloration and an intricately carved facade. Designed in the early 13th century and taking almost 50 years to complete, the rose window shines brightly in the sunlight; however, it is the interior that is truly ravishing. The lofted arched ceilings give an open atmosphere to the central cathedral and the air is mixed with frankincense and myrrh.

The true beauty of the Duomo is not in its ceilings or ornately decorated walls, but it is in the floor. Several mosaics are carved into the marbled floor depicting scenes from the Old Testament. It was designed and created by 40 different artists over the course of almost 200 years. One of the most iconic images is that of the She-Wolf of Siena, the emblem of the once great city-state, and also one of the oldest pieces in the church. As the day moves forward you will make your way through the hills arriving in Rome in time for a delicious and heartfelt dinner.

What s Included: breakfast, lunch, dinner, transfer, accommodation

Day 14 Towns and Villages Continue

Today you wake to another buttery brioche filled with chocolate or jam, accompanied by a cappuccino that lifts your spirit and senses. It is always hard to say goodbye to the stunning towns and villages that now feel fabulously familiar, and which welcomed you in with open arms and smiling faces. You will make your way to the airport filled with the exquisite memories of your time in Italy, from medieval villages to the wonderful canals of Venice. As the plane begins its ascend, there is no doubting the magnificence of your time within the Eternal City and beyond and your memories of your time in Italy will urge you to come back soon.

What s Included: breakfast, transfer

You may want to customize this trip further and add other countries in Europe. For ideas, please visit the page for European Orient-Travel tour operators.



orient recommends the following guidelines for customized, Orient-Travel trips to Italy, excluding international flights:

  • 5-star: USD $450 - $1,000+ per person per day
  • 4-star: Minimum USD $350 per person per day
  • 3-star: Minimum USD $300 per person per day

The customized package will include hotels, airport transfers and other transportation within Italy, guided tours or activities, unique experiences, trip planning, and 24X7 support during your trip.

Please inquire for a custom quote. The price is customized based on final hotel choices, travel dates, and other custom preferences.

Be sure to browse the section for European tours if you want other itinerary options.