Hidden Jewels of Italy s Southern Route Tour

A 15 day trip to Italy

Southern Italy is an open region steeped in history, from ancient Greece to the Ottomans, where the coastlines are as marveled as the landscapes and the people are as diverse as the cities. On this 15-day tour through the south you will find the incredible hidden jewels that go far beyond the Amalfi Coast and Pompeii, where you venture down to the heel of Italy s boot and find precious gems along the coastline and even remnants of Greek history, some hiding within the caves. The magnificence of Southern Italy goes beyond Naples and into a region that no longer needs to stay hidden.

General Information

Detailed Itinerary

Places Visited 

Rome, Orvieto, Deruta, Bevagna, Assisi, Perugia, Spoleto, Norcia (Valnerina), Ascoli Piceno, Offida, Castel Del Monte, Trani, Alberobello, Ostuni, Locorotondo (Val D'itria), Lecce, Gallipoli, Otranto (Salento), Matera, Paestum, Amalfi, Positano (Amalfi Coast), Pompeii, Caserta (Royal Palace)

Departure Dates 

Like all custom travel itineraries, dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1 Arriving Jewels

Rome is filled with the vibrant energy of a modern city and the shimmer of thousands of years worth of history, palpable in the language, the architecture, the art, and the food. You are met at the airport by a private transfer that will quickly have you at your luxurious accommodations within the heart of the city s historic center. Settle into the comforts of your hotel and the elegance of the city with a welcome cocktail as the celebrated flavors of Rome come to light.

Stride onto the cobblestone streets of the city where the history rings through the fountains and the walkways. A guided walk through the old city will take you to unimaginable beauty displayed in the open. The Trevi Fountain is a picture-perfect representation of Rome, fed by the Acqua Vergine, an aqueduct that has served the city since before the modern millennium. In the 1700s Nicolo Salvi designed the opulent Rococo fountain that features Neptune proudly standing as the pinnacle of the piece. The gentle water trickles in as people sit and enjoy the spectacle with an aromatic glass of wine, a creamy cup of gelato, or standing at the fountain s edge with their back turned throwing a coin over their shoulder and listening for the splash.

What s Included: transfer, classic Roman dinner, accommodation

Day 2 Entering Umbria

The heart of Italy is lush with green and flowering hillsides. The Umbrian region is scented with herbaceous aromas springing from the landscape as you arrive in the city of Orvieto, a town situated over a magnificent cliff. From the distance you can see streets wind up into the cliffside where the charming cathedral can be seen towering over the rest of the cityscape. The Duomo is a multitude of styles bringing together a balance of Romanesque and Gothic architecture, including a retreating archway over the central entrance. Frescoes decorate both the outer facade and the interior, including the painting of Madonna dei Raccomandati by Memmi, dating back to the 14th century. The Palazzo del Popolo is of a coloration that blends into the cliff below; the rustic-red structure was constructed in the 14th century and now holds a conference center housed within its pleasant medieval facade. In the afternoon you will venture through the stunning artistic workshops of Deruta and Bevagna, continuing to bring traditional lure to the modern world.

What s Included: breakfast, lunch, tour, accommodation

Day 3 Griffons and Saints

Perugia is known as the city of Gryphon and Bacio di Cioccolata, meaning the griffin and chocolate kisses, along with being the capital city of Umbria. Within the medieval walls is one of the oldest universities in Italy, dating back to the 14th century. The streets wind and meander along the hillside often turning into stone stairways and offering a view of the valley below. Narrow alleyways are scented with chocolate and lead to open squares where sweets are displayed in grand windows. Enter the Palazzo dei Priori, a building established in the 14th century for the magistrate of Perugia, known as the Palace of the People. The building dominates the corner of Corso Vannucci, the main artery of the old city that enters into the main square. The opulent squared architecture follows the pathway with arches at street level and ornate windowsills lining the upper floor.

Across the valley from Perugia is the city of Assisi, also built upon a hill and one of Perugia s historical nemeses. Home to the celebrated Saint Francis, the streets of Assisi feel more like a charming town than a collective city, overlooking the lush valley with a remarkable cathedral dedicated to the city s patron. Leading into the city is the stone paved square with arched colonnade that eventually brings you to the entrance of the cathedral. The immaculate structure displays a tower to the left and a delicate rose window to the facade of the upper church. The upper basilica was constructed in the 13th century evolving from the soft-spoken piety of the original church but with a more opulent design. You can find a 28-part fresco encircling the walls once attributed to Giotto and representing images from the Old and New Testament. The quiet atmosphere brings a tranquil moment to the colorful paintings which tie together biblical history and piety. In the evening you will have a serene dinner within the alluring Umbrian countryside where the creamy aroma of olive oil is never far away.

What s Included: breakfast, dinner, tour, accommodation

Day 4 Gray Stone and Greenery

This morning you will find yourself traveling through Valnerina. The countryside is blanketed with serene landscapes, and features the tallest waterfall in Italy, Marmore Falls. The lush hillsides bring you to the brink of a different world, one that you wouldn t expect of Italy, filled with blossoming colors in season, but always filled with the sounds and beauty of rushing water. Soon you will come to Spoleto, a fabulous medieval town known for a majestic cathedral located at the end of a narrow and long staircase.

The Romanesque facade is adorned with a fresco from the 13th century. The interior is pristine with lofted arched ceilings that guide you to the altar. The church is brimming with remarkable frescoes illuminating biblical scenes in fantastic artistry, including a cycle created by Fra Filippo Lippi in the 15th century. The town is filled with charisma, quiet along the hillside where you can see the wondrous arched bridge climbing over the valley below. After a lunch filled with the decadent flavors of black truffles and norcinerie, regional ham and sausages, you will marvel at castles and abbeys before arriving in Ascoli for the night.

What s Included: breakfast, lunch, tour, accommodation

Day 5 White Cliffs

Throughout the countryside are medieval towns that have persevered through troubled times and warring principalities. Some, however, have maintained their luster over the landscape, such as Castel Trosino. The village clings to white travertine cliffs. You can see the pearl colored buildings standing above the trees, shining within the clash of color and overlooking the remarkable canopy below. A stroll through the village brings you to the bell tower, the highest point of the city, where the view outward to the mountains is nothing less than magnificent. For lunch you can relax in a traditional restaurant where the luscious scents of garlic fill the open space. Try the local olive all'ascolana, fried green olives stuffed with meat, giving a delicious crunch to each savory bite.

What s Included: breakfast, lunch, tour, accommodation

Day 6 Puzzling Castles

You will find Castel del Monte standing alone along a hilltop overlooking the canopy below. The forceful octagonal shape is as remarkable in its construction as it is in its imagery. Dating back to the 13th century, the architecture is mesmerizing with 16 halls throughout the complex, eight halls on each floor. French windows open on the first floor where elements made for a wooden gallery can be seen. The stone is cool to the touch and present in every direction as you meander through the encircling hallways that feel more like disparate buildings merged together than a single design.

In the afternoon you will come to the coastal town of Trani, known for its cathedral which is caught halfway between the sky and the sea. The city itself is a historic fishing port; however, the Cathedral of San Nicola Pellegrino is a picture-perfect image of Apulian Romanesque architecture dating back to the 12th century. The calcareous color comes from the local mountains making the textured facade stand out against the sea. The gentle wake blends into the quiet city where you can see the high pointed archway creating a passage beneath the bell tower and leading to the water.

What s Included: breakfast, lunch, tour, accommodation

Day 7 Shapely Homes

The rolling hillside of the Puglia region is scented with earthen olive groves and vineyards. You can see the mixture of grass and trees give way to summerset landscape on your way to Locorotondo in Itria Valley. You can see the wooded slopes interrupted by trulli, the unique cylindrical homes that are popular in the valley. The area is more of a vale than a valley, filled with caves and trees, along with the delicate aroma of creamy pressed olive oil and cheese. The peculiar homes have been around since at least the 16th century, made of dry-stone allowing inhabitants to move them around when necessary. The bright white color helped keep the homes cool in summer and warm in the winter, while the painted roofs warded off the evil eye.

In the afternoon you will come to the whitewashed city of Ostuni, as it graces the hilly summit with marbled homes and a rocky cathedral. Known as the White City, Otsuni is truly hypnotic whether from a distance or within its calm streets, a version of Mediterranean architecture. Stroll through the narrow staircases and alleyways that give life to the cityscape, creating a maze-like construct but adding quintessence to more than just the buildings. The bright reflection off of the walls gives light to even the darkest niches during the day. The cathedral was built in the 15th century with Gothic characteristics, including a tripartite facade. The rose window is carved into 24 finely detailed ribs. No one would blame you if you just sat in the square with a strawberry gelato and enjoyed the view for a while as the olive orchards sway in the breeze below.

What s Included: breakfast, lunch, tour, accommodation

Day 8 A Southern Florence

Lecce is situated within the region of Apulia, located on the heel of Italy and is said to have been founded by Cretans, the inhabitants of the island of Crete. The Baroque architecture throughout the city brought about its nick-name, The Florence of the South. Walking through the streets you can feel the pulsing history, from a Grecian beginning to Roman handlings, all the way to modern times. You can find the Roman Amphitheatre near Sant Oronzo Square, half buried by other monuments throughout the centuries. The church of Santa Croce is a collection of imaginative images, from sheep to cherubs, decorating the magnificent facade while the interior boasts a Renaissance atmosphere of textured pillars, arches filled with light, and a lofted ceiling with a fresco at its center. In the evening you will find the calm streets coming to quiet life while you dine on a typical Southern Italian menu.

What s Included: breakfast, dinner, tour, accommodation

Day 9 Kissed by Sun and Sea

Along the stretch of ancient water that continues to glisten with a remarkable azure you will come to the narrow streets of Otranto. It looks as though you have fallen into the quintessential landscape of North Africa, with stone buildings drifting along the vibrantly multi-colored sea. The town dates back thousands of years to a Greek origin sitting towards the tip of Italy s heel. In places the walkway seems to only climb beside, and sometimes over, the water, until bringing you into the warmhearted city to see the Castle Aragonese. The castle was rebuilt in the 15th century with five sides and continuous moat. For a wonderful view of the landscape and the unparalleled waters you can climb one of the castle ramparts, with the thick stone beneath your feet, and lookout; on a clear day you might be able to see a distant island.

What s Included: breakfast, lunch, tour, accommodation

Day 10 Ancient Stones Conferred

Today you will come to the countryside of Murgia, known for its rocky and mountainous conditions. However, within those conditions there have been cities that thrived, including Sassi di Matera, which means the Stones of Matera. The ancient cave dwellings date back to prehistoric settlements, believed to be the first in settlements in Italy, sculpted into the ravine. The medieval town now sits over the ancient homes on top of the cliff, while Sassi di Matera continues to inhabit the stone precipice. Whether from above or below you can wander though the labyrinthine alleyways and streets listening to echoes and seeing the interesting tunnels that lead down into the dwellings below. Sasso Caveoso and Sasso Barisano are the districts of the caves, where the stone keeps the abodes cool, and rocky churches continue to attract dedicated patrons.

What s Included: breakfast, lunch, tour, accommodation

Day 11 Remaining Greeks

Once you come to the ancient remains of Paestum you will see the rising Doric Greek temples standing above the open plain. The ancient city was colonized by the Greeks in the 6th century BC, and later by the Romans as well. The splendor of the area comes not only from the well-preserved ruins but from the quaint atmosphere filled out by the lush landscape that surrounds it. The remaining temples were dedicated to Hera and Poseidon, and as you stand at the portico there is overwhelming feeling in the magnitude of the temples remains. Within the museum you can find the Tomb of the Diver. Uncovered by an Italian archeologist in 1968, the tomb is made of five local limestone slabs; their painted interior creates a scene of the tomb s namesake: a man diving into waving water. The unique history of the image and the area creates a dramatic pearl within the already jeweled southern region. In the afternoon you will taste the sensational regional dish of fresh mozzarella di bufala, before arriving in Ravello, the entryway to the Amalfi Coast, where you can look out over the magnificent cliffs known as the Infinity Terrace.

What s Included: breakfast, lunch, tour, accommodation

Day 12 Treasured Coast

One of the most coveted coastlines in the world stretches along the Italian shore, known as the Amalfi Coast. Today you will venture along the legendary road that hugs the cliff, where you have the expansive view of the iconic sapphire sea on one side and the rising craggy cliff on the other. The journey itself is exhilarating and once you come to the captivating city of Amalfi you can relax along the delightful streets. The buildings line the cliff side standing out only by their colorful paint while the roads twist and wind and the mountains continue to rise. The origins of the city date back to the 6th century and it eventually became a maritime stronghold. The Cathedral of Saint Andrea is a splendid presentation of architectural design, rising above the open square with geometric shapes, from the arched windows to the icons hovering above the pediment. A wide berth of stairs leads you to the tripartite arches of the entrance. The large bronze doors were the first of their kind in Italy, giving a stronger presence to the already prominent basilica. There is endless sensation along the coast, from elegant architecture to marvelous vistas that will never be forgotten.

What s Included: breakfast, tour, accommodation

Day 13 Within Steps of the Volcano

Leaving behind the marvelous Amalfi Coast will take you along the imposing peak of Mount Vesuvius and onward to Pompeii. The city was covered in ash and has been preserved for almost two millennia, dating back to 79 AD. The only thing more impressive than the preservation of the ruins is the city s expanse, opening up with a view of the volcano piercing the sky, and stretching back into an unforeseeable distance. The scent of earth is still strong along the streets, where you pass by homes and earthenware, in some cases even citizens preserved in ash. Some of the most stunning remains are the intact mosaics that have helped illuminate more of the city s and Rome s past, such as the mosaic depicting Alexander the Great in battle at Issus. The colorful details of his armor and fearless eyes while leading the charge are examples of how he was revered. In the evening you will return the beauty of the Amalfi Coast to settle into the night.

What s Included: breakfast, lunch, tour, accommodation

Day 14 A Treasure Palace

All roads lead to Rome; however, today you will find that the road often stops at Caserta. The Royal Palace of Caserta is the Italian Versailles, constructed in the 18th century for Bourbon Kings and claiming the record of the largest royal residence in the world by volume. You can easily be captivated by the lavish nature of the palace s every inch, inside and outside, galleries to gardens. Making your way to the main facade is a journey itself, reaching a wide, long path where the expansive palace glistens pink as it comes ever closer. The throne room is a long open space with a lengthy, bright mural fashioning the ceiling. However, much like Versailles, as grandiose as the interior may be, the gardens are never less than breathtaking. The expansive greenery is lined through the center with ponds, each adorned by sculptures, leading away from the palace. In the afternoon you will find yourself back in Rome, traversing the antique streets and relaxing along the marvelous ruins.

What s Included: breakfast, dinner, tour, accommodation

Day 15 Unearthed Treasures of the South

Today you will have a private transfer to the airport leaving behind the magnificent gems of Italy but with a mind racing with rich memories. You have seen medieval towns straddling cliffs and stunning palaces that filled the lavish surroundings. From Greek ruins to cave dwellers and the hidden beauty of southern coastal towns, you have made your way through the fabulous wonders of the southern countryside, unearthing quality gems along the way. As your flight begins to lead you back home, you know that there will always be another time to return to the treasures of Italy.

What s Included: breakfast, transfer

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orient recommends the following guidelines for customized Italy tour packages, 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.