Hidden Jewels of Italy’s Northern Route Tour

A 15 day trip to Italy 
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Come reveal the hidden jewels of Italy on this custom tailored tour that will uncover the marvels often overlooked by many. You will find majesty in historic castles and splendor along the coastline of the Italian Riviera. You can taste the celebrated flavors around Parma and witness the extraordinary tilt to the Leaning Tower of Pisa. Traverse the regions north of Rome to discover the exquisite landscapes and villages, artwork and flavors that have concealed themselves behind the celebrity of larger cities. This is a vacation where treasured memories lie and are yours for the taking. 

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General Information

Racks of Pecorino cheese inside a dairy farm.
boats in the port of portovenere cinque terre liguria
Detailed Itinerary

Places Visited 

Rome, Spoleto, Norcia and Valnerina,  Assisi, Spello, Montefalco, Bevagna, Deruta, Perugia, Urbino, San Leo And Gradara (Montefeltro Castles), Ravenna, Parma and Food Valley, Le Cinque Terre, Lucca, Pisa, Arezzo (Il Casentino), Siena and Val d’Orcia

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1 – Open Treasures

Welcome to the sparkling jewel of Rome, the “Eternal City,” filled with a mixture of ancient ruins and modern luxuries, and where neo-classical buildings are as prominent as the antique stones where politicians once used and where they continue to roam. You will be met by a private transfer at the airport and taken to the city center where your gorgeous accommodation awaits you with an arrival cocktail, a perfect welcome to the cobblestone streets and marvelous views. The city palpitates with energy from eager commuters, lively piazzas, and effervescent history. In the afternoon you will have a short, guided walk through the historical center where the heart of the city lies.

At the edge of the ancient city you will find the imposing Colosseum, the remaining titan of gladiator games that was once filled with roaring fans, gruesome battles, and mesmerizing scenes. The rotund amphitheater is no less tremendous today than it must have been thousands of years ago, rising over the open square next to the Forum. People encircle the architectural marvel that ascends into the sky with arched entryways that have held their structural integrity for almost two millennia, beginning with their construction in 70 AD. The excitement over the Colosseum has not waned, and you can feel the sensational beat of the past come to life all around you in the open city.

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

Day 2 – Within A Glistening Heart

After a delectable breakfast you will make your way into Umbria, known as the “Heart of Italy.” The hills are nothing less than splendid, rolling throughout the horizon, yet often overlooked for the more famous hills of Tuscany. However, the beauty of Umbria is not only in its landscapes but also within its lesser frequented towns, making it a perfect treasure. Once near Valnerina the green hills become craggy mountaintops filled with an immense natural majesty which mesmerizes the most ardent cynic.

The area was practically inaccessible until 1998, making the pristine scenery shine through. You can see the Marmore Waterfalls, the highest falls in Italy, tumbling down the cliff near the medieval town of Vallo di Nara. For lunch you will dine on exquisite black truffles accompanied by the traditional ham and sausages for which the region is known. Castelluccio is an Umbrian village known as the highest settlement in the Apennines. The city looks to rise off of the valley floor as if it were reaching for the mountaintop beyond. The medieval architecture gives an imposing view to the charming town which, while sometimes snow-covered, is surrounded by a sea of poppies from late May to early July. The extraordinary hues of the flowers range from shades of yellow to blue, violet and more. Umbria is a quiet, secret gem, scented with wonderful aromas and which radiates beauty for all of its visitors. 

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

Day 3 – Splendor of Hills

Start your day with a charming walk along the pink stone buildings of Spello. Although there are many medieval towns within Italy, each one is unique in its architecture and culture which has persevered through the diverse history of the region, the country, and the world. Spello’s elegance sits within its narrow streets which are often filled with vivacious flowers that blossom beside the rugged, stone architecture. The perfume from the flowers gives openness to the walkways that could seem too slender at times. For lunch you will arrive at Montefalco with the promising aroma of pecorino cheese and the famous Sagrantino wine. The village is known, not only as the only place in the world to produce Sagrantino, but also for the illustrious flavor it provides. The varied temperature creates a wine that is richly red with a full-bodied elegance and which often tastes of spice and bold fruits. 

Overlooking the vast valley to Perugia, you will come to Assisi, where the majestic hillside is filled with opulent architecture, views, and flavors. The earthy aroma of olive groves spirals through the air as you come to the home of one of the most well known religious figures in Christendom, St. Francis. Step inside the Basilica and find a quiet and simple demonstration of piety, in tune with St. Francis, yet also imbued with soft beauty from frescoes by Giotto. The essence of myrrh drifts away as you enter the catacombs where lesser light gives a forbidden feeling to your exploration and where you can find the resting place of St. Francis himself.

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

Day 4 – Ancient University Town

Perguia is the city known for the Griffin and its luxurious chocolate, along with being home to one of the oldest universities in Europe. The university was founded in the 14th century and continues to give the city an influx of cultural curiosities from around the world. The city is a medieval jewel situated across the valley from Assisi. The main square is bordered by large square stone buildings, including the Palazzo dei Priori, and decorated with a fountain at its center. The streets around it narrow and widen, and rise and fall along the hillside.

Walking through Perugia is like venturing into the past, each step taking you along a hidden route into a different time. You can almost taste the chocolate as rumors spread about the annual chocolate festival that takes place during October. Just south of the city center you can find the Porta di San Pietro, a 10th century church that remains a pillar of sensational architecture and history with an interior combining gilt and marble. You can also find a revered Pietá by Perugino. Why not meander through the Orto Medieval Gardens for a stroll through history and see what the bushes, flowers, and tranquil fountains would have been like centuries ago?

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

Day 5 – Containing the Renaissance

Urbino is a city of the Renaissance, holding the treasures of the past like an open trunk displaying them to the world. The city was the birthplace of Raphael and continues to shine in wonderment. You can see the opulent palace rising over the cityscape from the surrounding hills. The russet hue adds an earthy complexion to the skyline. The latter half of the 15th century gave rise to a renowned sovereignty. The triangle of Piazza della Repubblica sits in a depression between the twin bulges of a hill. You will easily find Palazzo Ducale at the top of the hill overlooking the landscape and the town below.

The opulent arches and pillars of the courtyard continue to shimmer in a pink light. Today the palace rooms contain the Galleria Nazionale delle Marche, displaying an eclectic array of paintings including Piero della Francesca’s Flagellation of Christ. The work is a stunning representation of distance and detail from a time when perspective was still making its way into the art world.  The city is blessed with magnificent panoramas and the decadent flavors of truffle within the countryside. It is natural to want to hoard the treasures found in Urbino, especially when they seem to be such secrets.

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

Day 6 – Wandering Adored Castles

Within the undulating hills and greenery, tucked away in the northern corner of Marche, you will come to Montefeltro. Like many hilltop towns, Montefeltro looks out over the green pastures and lush Monte Carpegna forest; you can practically catch the scent of prosciutto di Carpegna surrounded by truffles. One of the major draws of the area is the Gradara Castle, protected by two walls, one of which reaches over 2,400 feet in length.  In the evening, there is an undeniable view of the glowing medieval village below.

While touring through the castle you will not only have the marvelous scenery of the hills and forest pressing up against the colorful village, but you will stroll through literary jewels as well. Gradara Castle is said to be home to one of the most tragic love stories of all, between Paolo and Francesca, as told by Dante Alighieri in the Inferno. The room is gilded around the frame and the curtains around the bed are drawn. There is an endless romance to the atmosphere that seems to burst forth from the window and the artistry, reflected in the tile and glinting in the gilded chandelier, bringing a new kind of gem to the day. In the afternoon you will find yourself in the impressive village of San Leo settling in to an elegant Italian dinner.

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

Day 7 – Luxurious Parts Unknown

Cross the hills of Tuscany and enter the stunning region of Emilia Romagna, coming to the valley of Casentino. The forested land is filled with castles and monasteries, bringing you into the treasured world seemingly made of fairytales and storybooks. In the early morning a great mist can sweep across the lush hills, finding towers and treetops sticking through the top of the hazy wave. The Franciscan Sanctuary of La Verna is set over the cave where St. Francis received his stigmata. If you were just passing by you might miss the monastery altogether, somewhat camouflaged by the surrounding limestone protruding from the trees. The building was constructed in the 13th century and mesmerizes visitors, not just for its location but also for its tranquil ambiance. The stone roofs give way to oddly shaped chimneys built by the local friars. Lunch will be served in the company of the monks and pilgrims alike, a unique experience that brings you closer to the culture of the surreal landscape, the generous locals, and the beauty of your surroundings. In the evening you will find yourself in marveled city of Ravenna, ready for to settle in for the evening.

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

Day 8 – Opening New Hidings

Ravenna is a sensational city that houses over a millennium of history and which is overrun with Byzantine mosaics. In the 6th century it was a pillar of the westernmost point to the empire. Piazza del Popolo is an open square that dates back to the 16th century when the city was under Venetian rule; the buildings are colorful and vibrant while the atmosphere brings you into a jovial mood. The Basilica di San Vitale is almost as old as the city itself, filled with the reveled mosaics that twinkle in the light. From the apostles to a beardless Jesus standing across from a sensational blue earth, it is hard to gaze at the ancient artwork and not be somehow moved. If you are more of a fan of literature than art, you can visit the tomb of Dante Alighieri, buried in Ravenna due to his exile from his beloved city of Florence.

In the afternoon you will find yourself in Parma, a small city with a big, fabulous attitude. Its immaculate architecture brings quintessence to the quiet city, filled with colorful hues and the locals’ joyful personalities. The Teatro Regio di Parma is one of the grandest opera houses in Italy, constructed in the 19th century and continuously bringing peace of mind to the local ardent opera fans. The lavish interior is the exact image you would think a European opera house would look like, gilded balconies encircling a lavish stage with a bulbous dome giving pristine acoustics to the singers. They say you can always tell if a performance is good based upon the top row, a space for standing room only, mostly designated to students unable to afford the more decadent seating below. If you close your eyes you can hear the classical sounds of Guiseppe Verdi reverberating through the historic walls.

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

Day 9 – Finding Delicacies

Treasures are indeed found within the art and architecture of the region, but the art of food has also become a gem within the countryside. The area around Parma is known as “Food Valley” due to the delicious flavors of the Parmesan cheese and Parma ham. You shouldn’t pass up the opportunity to venture into the local cheese shops where you can taste the rich, and crisp cheese taken straight from the wheel, or perhaps have a picnic with the cured Parma ham while sitting along the lush countryside. In afternoon you will arrive in Lucca, located in the grandeur of Tuscany.

The city is known for its lush medieval walls that continue to wrap around the city. Once constructed for protection, the walls have become one of the most popular walkways in the area, a place where couples stroll, people bike ride, and others just sit and let the day pass them by. The colors range from green to orange, dipping up and around the fortified walls that are lined with delicate trees while a great tower hovers in the distance. Enjoy a caffé in Amphitheatre Square, where the buildings are pressed together in a curvature creating an echoing, bilious effect around the open stones at its center. 

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

Day 10 – A Trail of Precious Stones

Hidden along the coastline Liguria is the Italian Riviera where you can find Cinque Terre: the Five Lands. Today you will venture through the various towns finding the views and the coastline extraordinary, especially within the city of Vernazza. The small houses and alleyways wind up and down the cliff, adorned at the jutting rocks by the remains of a guardian castle. You can see basil plants rising up the mountainside, some of the largest you have ever seen, which makes this the region of unparalleled pesto. Vernazza is known for its beauty due to its colorful homes which can be seen from a distant sea, and its natural harbor with calm waves lapping on the small stretch of beach beside grand boulders where people lounge in the sun. Whether overlooking the water on the cliff of Manarola, or at beaches of Monterosso, Cinque Terre will give you the opulent landscape of a coastline that is nothing less than breathtaking.

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

Day 11 – Collecting Miracles

Today you will venture out to visit the illustrious Pisa. One of the oldest cities in Italy, and best known for its tower, you will come to the Campo dei Miracoli, the Field of Miracles. The magnificent white and gray marbled cathedral shines brighter and more prominently than the tower. Often overlooked, but no less majestic, the cathedral’s grandeur is in its magnitude and its fabulous façade, where the pillars and arches climb up the narrowing structure creating a marvelous effect. The tower tends to be a most sought after image, listing to the right with a similar design as the cathedral’s façade. Although construction began in the late 12th century, the tower wasn’t completed until the 14th century, while bells were installed up until the mid 1600s. No matter how close you come to the tower it is a work of intense enterprise, from its design to its structural integrity. There is no end to the awe that it inspires in those who visit, whether by viewing the city from the top or attempting to hold the tower in the palm of your hand from a distance. In the evening you will be welcomed in the quaint city of Siena, located in the heart of Tuscany.

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

Day 12 – Secrets of the Church

There are many reasons why the city of Siena is a charm within the Tuscan hills. The hills themselves are famous for their remarkable beauty, rolling along the horizon in unblemished greenery. Siena is set within those very mounds, rising atop them with stone force but never surrendering its charm to its architectural prowess. Within the medieval walls you will wander through cobblestone elegance and come to the graceful façade of the Cathedral in Piazza del Duomo. The soft orange and brown coloration of the city gives way to the spectacular image of the black and white marbled church.

The rose window captures the sunlight and shines through to the interior. The cathedral was built in the 13th century and its intricate façade and famous mosaics continue to charm and delight visitors, whether local or from afar. The most peculiar and fascinating designs are along the floor, often hidden to protect their aged form; the mosaics were carved over a 200 year span and represent the Old Testament and the marveled stories of Romulus and Remus, and Sibyls. Piazza del Campo is a magnificent sight, open and circular, focusing all eyes to the prominent palace. The clock tower stands tall and proud, and each year in July and August the entire square fills with people there to witness the celebrated Palio horse race. The streets wind into random niches but somehow, no matter where you turn, you always find your way to the main street which is filled with the scent of luscious pizza and creamy gelato. In the afternoon you will enjoy an Italian cooking class, taught and guided by an expert chef.

What’s Included: breakfast, dinner, tour, cooking course, accommodation

Day 13 – Colorful Riches

Today you will immerse yourself in the tremendous scenery of the Tuscan hills, where vineyards rush along the valleys and undulating landscape. Olives add a sensual aroma to the air as you journey through Val d’Orcia. Inside Montalcino you will find the fabulous hillside town known for Brunello wine. The small town overlooks the expanse and has castle walls wrapped around it for protection. Montelpuciano rises with the hillside and contains a large piazza that features a spectacular view of the surrounding area.

One of the main jewels of the colorful region is Pienza, a Renaissance town filed with the sleepy quality of a whisper. The narrow streets and open piazzas bring you back to the Italy of famous movies, where a Sunday would find the entire town in the main square after church, the bells peeling, and the bustling dialogue of the locals twinkling like the wreaths that line the walkways. The buildings themselves are filled with charm, from the quaint balconies to the singular bikes that stand outside the doorway. The city is also home to Silvius Piccolomini, better known as Pope Pius II, reconstructed by his patronage in the 15th century to be a model of the Renaissance, and a persistent example of the artistic beauty of architecture and scenery combined.

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

Day 14 – Return to Eternal Treasures

Today you will arrive back in Rome with the day at your leisure to explore the endless jewels of history and modernity. You can spend the day relaxing in Camp de’Firoir, the oldest market in Rome, which has continued in its tradition for over 140 years. Stroll through Via Condotti near the Piazza di Spagna, considered the Beverly Hills of Rome; the window displays shine a little brighter, the cobblestones look a little more refined, and the scent of fresh espresso seems to drift out of every open door. 

For one last sight of Rome that cannot be missed, you can head to the Piazza di Santo Pietro: Saint Peter’s Square. The square was constructed in full in the 17th century and continues to enrapture visitors and locals with its elegant glow and tremendous purity. The Basilica, described as “the greatest of all churches in Christendom,” stands like a crowned jewel in the back of the square, its dome proud and prominently displayed. Whether you tour through the museum, take a moment of reflection within the church, or meander around the Egyptian obelisk in the square, there is something splendid about the mixture of architecture and history in the wide-open space of Rome. In the evening you will have a memorable dinner in downtown Rome to commemorate your time within the hidden jewels of Italy.

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

Day 15 – Found Gems

The morning rises over the expansive city brining the freshness of espresso and delicate buttery texture of morning brioche. After a delightful breakfast you will have make your way to the airport for the end of your exquisite vacation. You have travelled throughout the northern wonders of Italy picking up treasures along the way. From medieval towns to unparalleled countryside, and all the history in between, you have found gold in the hills and antiquity written on the walls, collected sapphire Renaissance beauty and delectable cuisine. You may be leaving the jewels of behind, but the treasured memories will last forever.

What’s Included: breakfast, transfer

You may want to consider adding on other countries to your 15-days in Italy and creating a luxury European vacation. For more customization ideas, browse the reviews for Europe tour operators on Zicasso.


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.