Northern Italy to Sicily: Italy Tour for Second Timers

The small Italian Town of Umbria sitting on green rolling hills
A 14 day trip to Italy 
5 out of 5 stars
6 reviews

Open your eyes to the expansive plains of Umbria and vast olive groves of Puglia, the seaside ambiance of Calabria and the flavors of Emilia-Romagna during your personalized Italy tour that will immerse you in the marvels of discovery. Savor the authentic beauty of medieval towns and Baroque cities preserved in time and steeped in tradition. Greek theaters decorate the landscape of Sicily and caves pockmark the soft tufa limestone of Basilicata. Travel from the Adriatic’s turquoise waters to the Tyrrhenian’s azure hues and the Ionian’s sapphire glow uncovering whitewashed homes, pastel-colored cathedrals, and an endless inviting ambiance.

Customize This Trip For Me
Most tours are customized for private travel.

General Information

Day shot of the tropical Syracuse, Italy coastline
The Mausoleum of Theodoric in Ravenna, Italy
View from the ground of the Milan Cathedral in Italy
A walkway leading by a food market in Taormina, Italy
Basilica of San Francesco d'Assisi with statue of a horseback rider in the foreground
Woman holding a platter of prosciutto and cheese with a store stocked with meats and cheeses in the background
View of the Perugia, Italy skyline
Cluster of stone buildings and streets in Sassi di Matera, Italy
The Puglia coastline with the Trani Cathedral as the center of interest
Flower art on a stone street set up during the flower festival in Spello, Italy
Where the barren and lush landscapes meet of Etna National Park in Sicily, Italy
View of streets and buildings in the city of Ostuni, Italy
Detailed Itinerary

Places Visited 

Milan, Bologna, Perugia, Trani, Ostuni, Pizzo, Taormina, Acireale, Siracusa, Polignano a Mare, Alberobello, Spello, Assisi, Gubbio, Ravenna, Ferrara, Parma, Vieste, Lecce, Matera, Mount Etna

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Milan – Arrive in Marvelous Milan with an Introductory City Tour

The fast-paced city of Milan brims with creativity thanks to a dramatic history and inspiring artwork that has turned culture into a legacy and design into a treasure. Upon arrival, your private driver will greet you at Malpensa Airport before transferring into the heart of the city. The remainder of the day is yours to explore and experience the grandeur of Milan at your preferred pace. The Galleria Vittorio Emanuele II is a luxury arcade erected in the late-19th century. The soaring central dome floats above the mosaic floors at 157 feet. The classic industrial iron and glass construction highlights the eclectic beauty of the design while framing luxury stores like Prada.

The Galleria Vittorio Emanuele II hosts the first Prada shop ever opened, which dates back to 1913, while 2019 represents the 100th anniversary of the luxury brand acting as the official supplier of the Italian Royal Family. In a tradition dating back to 1919, Prada uses the royal rope from the prestigious coat of arms in their logo reflecting distinguished sophistication and recognized splendor fit for a king. The original store retains its sense of history blending in with the modern world with an elegant display on the original shelves handmade using mahogany and adorned with quality handbags, trunks, leather accessories, footwear, and clothes from the latest collection.

What’s Included: airport transfer, accommodation, tour

Day 2: Milan – Discover the Splendors of Milan History and Culture

In the morning, the fast-pace of the city begins with the local Milanese sipping espresso at a stylish neighborhood bar before starting work or riding the metro into the heart of the city. The sunlight washes over the flamboyant Gothic architecture adorning the Duomo in the city center with 135 spires. The filigree turns the religious structure erected between the 14th and 19th centuries into a fairytale castle shimmering with the largest stained-glass windows in the world. The combination of medieval and contemporary history merges at the Gothic brick architecture shaping the church of Santa Maria della Grazie.

Construction on the church began in the 15th century with an addition of a marvelous six-sided dome reflecting the aesthetic of the Early Renaissance. The interior nave contains the aroma of frankincense and myrrh as you make your way to the adjoining refectory. The small section in the church remained standing during World War II after a series of allied bombings of Milan resulted in much of the surrounding structure turning to rubble. The refectory contains the fascinating and world-famous work of Leonardo da Vinci’s The Last Supper, and the afternoon will be yours to wander through and enjoy the atmosphere around you.

What’s Included: accommodation, tour, breakfast

Day 3: Bologna – Enjoy the Flavors and Sites of Parma en route to Bologna

After breakfast, your private transfer will greet you in the hotel lobby to escort you south to the region of Emilia-Romagna and the city of Parma. Romans settled the colony along the main road leading into the mountains giving way to the powerful Farnese dukes and the French influence of Napoleon’s wife, Marie Louise. The historical center brims with beauty nearly absent of cars and filled cheese shops and delis among the colorful art-nouveau cafes. The neoclassical architecture of Teatro Regio was completed in 1829 as the private theater of the Ducal with singers and musicians performing in front of one of the toughest audiences in all of Italy. The connection with composer Giuseppe Verdi attracts opera lovers from around the world while also inspiring a certain heightened level of appreciation for music. Outside the city center, you will meet with a cheese producer crafting the delicious Protected Designation of Origin Parmigiano Reggiano.

The classic cheese is made with cow’s milk from the surrounding provinces of Parma, Reggio Emilia, Modena, and parts of Mantua or Bologna. Producers let milk gathered in the evening rest until morning in large vats allowing the natural fats to rise before mixing newly collected milk from the cows. After the process of elaboration, heating, and maturation, you enter the warehouse possessing blocks of cheeses nearly 84 pounds. Your guide taps a new wheel of cheese listening for air pockets. Finding none, he opens the cheese resulting in a puff of pungent, aged aromas filling the air.

Arriving in Bologna can give you direct access to the Giro d’Italia, considered the Tour de France of Italy. In 2019, the cycling race celebrates 110 years since its first competition stopping only during the First and Second World Wars. The route can take participants all over the Mediterranean with the 2019 tour traveling south from Bologna and looping around the nation before ending in Verona after a course of 2,220 miles over 21 stages. The medieval arcades adorning the historic city center create the majestic ambiance accompanied by the ever-present aromas of simmering ragù sauce embodying the decadent culinary mastery for which the city is known.

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

Day 4: Bologna – Explore Renaissance Ferrara and Byzantine Ravenna

The Renaissance cultural gem of Ferrara welcomes you in the morning with preserved medieval walls, and magnificent colossal palaces often overlooked for the fame of Venice. The streets are frozen in the past amid the tranquil ambiance crafted by the Este family in competition with Florence’s powerful Medici. An arcade hides a collection of shops with a café filling the square with the aroma of fresh espresso fading beneath the delicate scent of produce deriving from the morning market. The cathedral shines with a Romanesque lower section designed in the 12th century supporting the upper Gothic loggia constructed in the 16th century with pink and white marble.

Continue to the fascinating city of Ravenna, which retains a sense of distinct history unlike anywhere else in Italy deriving from its base for the Roman Adriatic Fleet and centuries acting as the capital of the Western Roman Empire. The artistic influence illuminating the antique churches and palaces reflect the treasured Byzantine mosaics, each crafted with exquisite detail. The golden age of the city deflected Barbarian invasion for centuries providing a fertile space for skilled craftspeople to explore the marvels of art covering terracotta brick religious structures with symbols of devotion.

What’s Included: accommodation, tour, breakfast

Day 5: Perugia – Travel to Perugia Stopping First in Gorgeous Gubbio

You will travel to Perugia after breakfast with your private transfer leaving behind the culinary brilliance of Emilia-Romagna for the overlooked scenic grandeur of Umbria, often overshadowed by neighboring Tuscany.  The town of Gubbio embodies the iconic image of medieval architecture winding up the hillside. The preserved streets narrow into hidden alleyways and steep staircases resembling the set of a film more than a settlement containing a semblance of contemporary life. Below the town stands the Roman Theater, which was erected during the 1st century AD. Locals continue to use the structure in the summer for open-air concerts with a backdrop of the hilltop town holding up to 6,000 spectators.

Perugia is the capital of Umbria and radiates regional history above the valley plaid with fields. Cobbled lanes nestle between towering buildings leading to arched stairways and wide public piazzas. The sophisticated past leans into modernity with a historical university opened in 1308 bringing in youthful students from around the world. Much of the vibrant life in Perugia settles in Piazza IV Novembre, where Roman and Etruscan civilizations meet reinforced by medieval structures and the contemporary political center. Budding opera singers raise their voices around the arcades, and the sweet scent of cones drifts out of the gelateria.  Alongside your guide, you can determine how you would like to spend your day in this very charming city.

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

Day 6: Perugia – Visit Alluring Assisi and Sensational Spello at your Leisure

The charming town of Assisi stands on the hillside across the plains from Perugia. The former rival to the capital of Umbria remains a gorgeous display of medieval architecture with a sense of devotion to its native son, St. Francis. The wide cobbled lanes lead to the summit capped with the dramatic walls and towers of Rocca Maggiore castle. The Basilica of St. Francis stands at the bottom of the hill on a small promontory. The two tiers of the religious structure highlight the different stages of the construction process with the lower, original tier consecrated in 1228. The Romanesque vaulting soars above the series of 28 frescoes depicting scenes from the life of the saint. The vivacious colors and humanistic characterizations in the artwork are attributed to Giotto.

Upon arriving in the town of Spello, the elegant honey-colored homes pouring over the hillside captivates you with the stout Roman gates connecting towers resembling storybook structures. In summer, the aroma of blossomed flowers gives the streets an elegant perfume emanating from the facades of homes on which locals dangle flowerpots combining the sweet aroma with a riot of enchanting hues.  With another relaxing day on your hands, settle into the pace of the Italians as you take it all in.

What’s Included: accommodation, tour, breakfast

Day 7: Trani – Relish a Scenic Coastal Drive to Vieste before Reaching Trani

You will depart Perugia early heading south to the enchanting pace and pleasures of Trani on the Adriatic coast of Puglia. Stop to visit the charming town of Vasto on the southern coast of Abruzzo as the medieval quarter seeps out into the sea with views of the calm turquoise water in the distance lapping against the pebbled sands. Much of the architecture dates back to the 1400s as the city grew in prominence through the support of poetry, art, and philosophy.

Continue south after a casual stroll along the historical streets and lunch at a seaside restaurant serving the famous brodetto alla vastese, a hot dish brimming with seafood cooked with tomato, garlic, peppers, parsley, basil, oil, and salt. Upon arriving in Trani, the sea breeze and wading boats in the small marina enchant you. Boutique shops line the narrow alleyways, and restaurants overlook the quiet esplanade. The limestone streets glint with a natural gloss and Jewish history dates back hundreds of years to the 12th century.

The medieval Scolanova Synagogue was erected in the 13th century before it was converted a church in 1380. In 2006, the structure was deconsecrated as a church and returned to its former design as a place of Jewish worship amid the Gothic architecture with 36-foot tall vaulted ceilings.  Explore the heritage of the area alongside your guide, and enjoy another quiet Italian evening.

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

Day 8: Ostuni - Traverse the Splendors of Polignano a Mare and Alberobello

The morning light washes over the layered colors of the Adriatic returning the turquoise, azure, and cobalt hues to the water. The town of Polignano a Mare glows with whitewashed walls along the cliffs above the eastern seaboard reaching an elevation up to 79 feet. Often referred to as the “Pearl of the Adriatic,” Polignano a Mare sings with the echoes of its favorite son, Domenico Modugno, writer and performer of the famous Italian classic “Nel Blu Dipinto di Blu,” or more commonly known as “Volare.” Teenagers and children leap off the limestone cliffs into the waiting water, and the coves lead to idyllic beaches covered in tiny pebbles.

The storybook ambiance of Alberobello derives from the unique homes known as trulli. Cobblestone streets line the hilly landscape past approximately 1,000 whitewashed walls erected with limestone in circular shape and topped with a thatched conical roof. The beehive-style architecture has a practical purpose by keeping the interior cool in the summer and warm in the winter. Shops, restaurants, hotels, and homes line the Rione Monti district with picturesque bleached walls contrasting the greenery of sporadic palm trees leading to a panoramic terrace and the 20th-century trullo-style church of Chiesa di Sant’Antonio.  

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

Day 9: Ostuni – The Distinct Streets of Lecce and Enjoy an Olive Oil Tasting

Lecce mesmerizes visitors with an ornate charisma from the Baroque architecture built during the 17th century. The harmonious ambiance gave rise to the term barocco leccese, referring to the specific style of Baroque architecture in the city. Piazza Sant’Oronzo stands at the heart of the city and once marked an end to Via Appia, the ancient Roman road connected to the capital of the empire. The Roman Amphitheater is also located in the piazza, which was erected during the 2nd century AD and could hold up to 25,000 spectators for a single event.  

You can stay in Lecce and indulge in the inspiring flavors of Bros’, a restaurant awarded a new Michelin Star for 2019. Contrasting the Baroque, the chefs of Bros’ take notice of their surroundings while moving the classic flavors into modern aesthetics for innovative combinations paying homage to tradition but unrestricted by custom. The kitchen creates flawless dishes captured with deceptive complexity such as bread accompanied with oil, pork fat, and fruit berry juice or crab meat seasoned with chives, sweet Senise pepper, and white pepper.

Outside of Lecce, you can stop at a family-run olive grove to learn more about the differences in olives and olive oils. Puglia accounts for approximately 40 percent of the entire production of olive oil for all of Italy with product certified as Protected Designation of Origin to safeguard the integrity of the flavor and quality of the creation both for the producer and the consumer. Wander through the olive grove with your guide enjoying the herbaceous aroma emanating from the trees. You will find antique equipment used in the old days of production by stacking weighted stones atop the olives and collection the oil as it seeped out from the sides. In the tasting room, you will sample the purity of Extra Virgin Olive Oil finding a smooth texture and nutty flavor with a bit of spice lingering in your mouth.

What’s Included: accommodation, tour, breakfast

Day 10: Pizzo – Navigate the Caves of Matera and Relax in Coastal Pizzo

In the morning, you will wave goodbye to the sunrise and the turquoise waters of the Adriatic Sea heading inland to the fascinating city of Matera. The medieval streets and architecture climb the hills and plateau of the Gravina Gorge with natural caves cut into the porous tufa limestone. The grottoes of Matera have gained a new sense of importance in the city once considered the embodiment of poverty in Italy up until the 1960s with locals using the ancient caves as homes.

The white and golden architecture of the medieval city glints above the rushing waters of the Gravina River carving the walls of the gorge deeper. In 2019, Matera hosts the European Capital of Culture emerging from its reputation of scarcity with a focus on transformation turning the region into places of wonder and luxury with hotels, restaurants, or museum galleries. History lives in and around the city dating back to the Paleolithic era reflecting the timelessness of the architecture, caves, and cuisine. Walking through the ancient village situated inside the calcareous rock leads to a settlement blending into its natural environment.

The sassi now act as a newly developed district in which boutique shops and restaurants fill the caves with vivacious life. The scent of simmering meat and tomatoes drifts along the narrow walkways. In the Casa Noha, a former noble family home, a film retelling the long history of Matera projects onto the walls of the stone house. Entering a typical peasant home in Vico Solitario shows the distinct life of the past in a recreation of common residence with a bed, table, and dresser housing an entire family, often including a donkey, chickens, and pigs.

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

Day 11: Taormina – Ancient History in Reggio Calabria en route to Sicily

The bewitching town of Pizzo overlooks the pebbled sands of the Tyrrhenian Sea on the coast of Italy’s most southern region along the mainland peninsula, Calabria. The historical heart of the town lingers above the water with colorful homes painted with pastels winding around narrow lanes and a series of steep stairways built into the hillside. The city was founded in the 1300s by Basilian monks over the remains of the former Greek foundations that followed the story of the great King Odysseus who sailed along the shores of the fishing bay in The Odyssey.

You will then continue southwest to Reggio Calabria, the capital of the region often passed-over for more famous cities and towns across Italy. The charming seaside streets culminate at the lungomare, a coastal promenade providing captivating views over the Strait of Messina to the peak of Mount Etna approximately 75 miles away. Inside the Archeological Museum, the treasures of Calabria’s history emerge with one of the best assortments of artifacts pertaining to Magna Grecia in the world.   You will enjoy the leisurely pace with time to take it in before settling in for the evening.

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

Day 12: Taormina – The Summit of Mount Etna on a Full Day Excursion

The beauty of Taormina radiates from the sea lapping against the beaches nearly 670 feet below coastal cliffs. The prestige of the architecture glints in the sunlight with pastel hues as the neighborhood pasticceria open their doors in the morning. The summit of Mount Etna rises in the distance visible from Greek Theater first erected in the 3rd century BC during the reign of Hiero II of Syracuse and restructured during Roman rule in the 2nd century BC. After breakfast, your guide will lead you to the base of the volcanic slopes for an excursion around the famous mountain standing 10,990 feet above sea level.

As the tallest volcano in Europe, Etna graces the skyline of the northeastern end of Sicily producing an incandescent glow of red flowing lava only during eruptions. The cableway takes you up to approximately 9,500 feet crossing over the landscape as it turns from Mediterranean to lunar. Your guide leads you over the extinct craters with pocket of steam rising from the black, gray, and barren soil. Due to the altitude, snow often falls atop the crater even in the summer.

The wind carries the scent of sulfur through the air as fumaroles steam in pockets across the active craters. Once you descend the mountain, you stop at a local vineyard utilizing the rich nutrients in the volcanic soil to fortify the flavor of their wines. The vines line the lowers slopes away from the volcanic peak with many sections dedicated to growing Nero d’Avola grapes. You will enjoy your tasting outside with a view to the fascinating peak of the mountain and enjoy a glass of wine filled with a deep ruby color. The scent of smoke and fruits hints at wild spices. In the evening, you can enjoy a fabulous meal at Lido di Spisone, which was awarded a Michelin Star for 2019 thanks to excellence in service, ambiance, and cuisine.

What’s Included: accommodation, tour, breakfast

Day 13: Taormina – Indulge in Tranquil Acireale and Sensational Siracusa 

The Sicilian Riviera emerges from the Mediterranean light in the morning at Acireale. The lava terraces plunge into the turquoise sea beyond the imposing baroque city center and the neighboring fishing village of Santa Maria la Scala. Thermal baths attract Sicilians from across the island eager to bask in the compilation of natural temperatures combined with rich nutrients from the volcanic waters. If visiting in February, Acireale has taken on new life with a spectacular Carnevale festival with roots grounded in the splendor of the Renaissance and accentuated in the grandeur of the finely-crafted Baroque featuring folk poets, citrus fruits, and elaborate parades with outrageous floats.

The city of Siracusa, or Syracuse, is the oldest, largest, and best-preserved of any settlement of the Greek world with catacombs exceeding the vastness of those in Rome and the largest Roman amphitheater in existence. History remains a strong part of the local character regarding both ancient life, medieval and baroque expansion, and contemporary activity. The Greek Theater was originally constructed in the 5th century BC using the natural gradient of the hillside to support the stadium seating. The structure could hold up to 15,000 spectators and premiered two of Aeschylus’s tragedies, as well as works by Sophocles and Euripides. Alongside your guide, you can explore based on your interests, and enjoy spending some free time to wander.

What’s Included: accommodation, tour, breakfast

Day 14: Taormina – Transfer to Catania for your Flight Home

After breakfast, you can stroll the delightful pedestrian-friendly avenue of Corso Umberto I enjoying the ambiance shaped by the boutique shops and elaborate window displays as welcoming bakeries lead to the panoramic views from Piazza IX Aprile. When you are ready, your private transfer will greet you in your hotel lobby and escort you to Catania, Sicily’s second-largest city. You will continue to Catania’s international airport when ready with plenty of time to check in to your flight.

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.