Best of Italy and Sicily Tour 2019

A 15 day trip to Italy 
4.75 out of 5 stars
4 reviews

Culture perpetually surrounds you, and the depths of history arise anew on your custom tailored Italy and Sicily 2019 tour. Gondolas float down the maze-like network of canals in Venice. The eclectic, historic cultures that once called Palermo home remain strong in the traditions of the marketplace. The summits of Mount Etna and Mount Vesuvius loom over cities both ancient and contemporary. Roman ruins and Doric temples, opulent beaches and Renaissance artwork combine for breathtaking vacation, showing you the unparalleled wonders of Italy expanding from north to south.   

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

General Information

Pearl of the Ionian Sea. Photo Credit: Sea Spirit Diving Resort
Diving with Sea Crabs. Photo Credit: Sea Spirit Diving Resort
Isola Bella. Photo Credit: Sea Spirit Diving Resort
Detailed Itinerary

Places Visited 

Rome, Pisa, Florence, Venice, Giudecca Island, Assisi, Pompeii, Naples, Palermo, Agrigento, Taormina, Valley of the Temples, Sorrento, Capri, Monte Cassino

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Introducing Rome

Rome is known as the Eternal City and has been able to reinvent itself over the millennia, from the capital city of a global empire to an encapsulation of antiquity and modernity. The wonders of the city shine in hidden piazzas brimming with fantastical fountains, Baroque palaces lining quiet streets, and the sensational aromas of fresh food emanating from celebrated local restaurants and open apartment windows. Cathedral domes and church spires dominate the skyline. You arrive at Leonardo da Vinci–Fiumicino Airport. Your transfer greets you at baggage claim and escorts you to your hotel located in the heart of the city. Small flower shops blossom on the street corners, providing a stunning floral aroma to the city. After you settle into your comfortable room, your guide meets you in the hotel lobby, eager to introduce you to the splendor of the Eternal City on an orientation tour. 

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

Day 2: Radiant Rome

In the morning, the sunlight washes over the Tiber River. The ancient waterway shimmers in the light. Houseboats moor on the riverbanks next to quiet cobblestone walkways. Locals traverse the riverside paths throughout the day, jogging in the morning and taking the time during lunch to lounge in the shade and listen to the river’s rippling. After breakfast, your guide meets you at the hotel. Today you are eager to venture out into the city for a deeper exploration of Rome’s powerful and influential history. You start at the Vatican Museum. Pope Julius II founded the museums in the 16th century.

There are approximately 54 galleries in the Vatican Museum containing priceless artwork demonstrated in paintings, sculptures, and even the architecture itself. You traverse the spiral staircase, circling deeper into the lavish depths of the museum. When strolling through the Gallery of Maps, you notice the graceful paintings decorating the walls. Gilded frescoes line the arched ceiling of the gallery, creating a glistening effect. The crown jewel of the museum is the final gallery, known to the world as the Sistine Chapel. The room contains a slight aroma of burning candles. The brightness radiates from the frescoes painted on the ceiling. The various panels contain scenes from the Bible. The moment you look up and find the original image of “The Birth of Man” is momentously breathtaking.

What’s Included: breakfast, guided tour, accommodation

Day 3: The Tower and More

In the morning, Piazza di Trevi is quiet, filled with the tranquil sound of the water from the Trevi Fountain bubbling into the large pool. After breakfast, your transfer meets you at the hotel, marking the end of your time in Rome. You venture northbound, waving goodbye to ancient circular walls of the Colosseum. The golden grass of the countryside outside of the capital of Italy shifts to the rolling green hills of Tuscany. Cypress trees line country lanes; vineyards climb the foothills, and in the city of Pisa, you enter the treasured grounds of the Square of Miracles. The 12th-century Tower of Pisa is known for its famous leaning of almost four degrees.

It was erected using white marble and contains approximately 295 steps. Behind the tower is the sensational edifice of the Pisa Duomo. The Cathedral was erected in the 11th century and accentuates the Pisan architectural style of thin structural columns. Magnificent bronze doors provide entrance to the nave. The interior has vaulted ceilings and an immaculate fresco decorating the central dome. Your eyes catch the unique lamp dangling from the nave’s ceiling. The scent of burning incense wafts from the light fixture. It was this particular lamp that inspired Galileo to formulate his theory of the universe. 

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

Day 4: Accessible Florence

Florence is a city glowing with medieval splendor and Renaissance charms. The historic city walls continue to guard around the fringes of the city center. The Arno River separates the heart of Florence, filled with palaces and museums, from artisan workshops. The old bridge, known as the Ponte Vecchio, was erected in the 14th century and helps connect the two sides of the river. Elegant jewelry shops line the bridge overlooking the water. A secret passage known as the Vasari Corridor is situated over the shops and has connected the Uffizi Gallery to the Pitti Palace since the 16th century.

You follow your guide through the city after breakfast, taking in the accessibility of the cobblestone streets and historic atmosphere. Red tiled roofs reflect the sunlight. The scent of fresh pastries drifts past the open boutique shops hiding near Piazza Santa Croce. The basilica towers over the square, adorned with neo-gothic façade. The Franciscan symbol embellishes the main entrance. Inside the cathedral, you find Michelangelo’s tomb ornamented with stunning statues lamenting the artist’s passing. Exquisite paintings capture the master artist’s style to make it look as though angels are pulling down blankets from heaven to cover the tomb.

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

Day 5: City on the Lagoon 

In the morning, boats glide along the canals, turning Venice into a labyrinth of waterways and walkways. Treasured masks decorate shop windows alongside traditional bakeries filling the air with indulgent aromas of fresh brioche. A row of moored gondolas gently floats on the water near a café, creating a picture-perfect moment of Venice. Your guide leads you onto a private launch, where you board your boat ready to take you to St. Mark’s Square. The cobalt water of the lagoon laps against the piazza. The brick façade of the Campanile rises to 323 feet tall, casting a shadow over the Venetian Gothic style of the Doge’s Palace. Crowning the square is the stunning Byzantine edifice of St. Mark’s Basilica, for which the square is named. The cathedral was consecrated in the 12th century. Gold mosaics shine in the sunlight decorating the upper sections of the multiple-arched façade. A golden Venetian winged lion adorns the top of the façade beneath a statue of St. Mark, symbolizing the connection of St. Mark to Venice.

What’s Included: breakfast, guided tour, accommodation

Day 6: Brilliant Basilica

Assisi has influenced religious expression and the artistic history of Europe, intertwining medieval aesthetics with the significant life of St. Francis di Assisi. After breakfast, you board a ferry to cross the Grand Canal and venture south, surpassing the rugged mountaintops and stunning cliffs of San Marino, and entering into the rolling golden plains and hill-topped villages of Umbria. Assisi climbs over the valley at an elevation of 1,300 feet, with a view of the once longtime enemy of the city, Perugia. Roman ruins speckle the landscape. Cobblestone streets wind along the upper reaches of the hilltop.

Quaint restaurants and olive oil shops fill the antique buildings. Inside the city gates overlooking the valley, is the 13th-century St. Francis Basilica. Verdant manicured grass leads to the soft-spoken white façade of the oldest Gothic church in Italy. A rose window provides space for natural light to filter into the nave. The four-bay nave is cross-vaulted and decorated with a fresco resembling the night sky. Famous artists, including Giotto, provided artwork to show their devotion to the legendary piety of St. Francis. A stairway connected to the nave of the lower basilica leads to the crypt where St. Francis is buried. Iron ties encircle the ancient burial site. 

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

Day 7: Historical Streets of Mythological Cities

Pompeii is a legendary city, spoken as though it was a myth written into the history books. After breakfast, your guide escorts you southbound to the ancient, preserved city to experience the splendor of the streets that have provided insight into the daily lives of ancient Roman citizens. Mount Vesuvius erupted in 79 AD and encased the city in nearly 20 feet of ash. The city walls encompassed almost two miles. Archeologists have uncovered approximately three-fifths of the covered city and have left many of the preserved artifacts in place to create an impression of ancient life, from homes to shops, and even the public squares.

The city maintains an earthen quality inside the walls but elements of greenery flourish in the piazza, where the Temple of Apollo once stood. Details of cobblestone streets remain. Your guide points out columns and pottery. You pass well-preserved homes. You reach Villa of the Mysteries, a mansion erected in the 2nd century BC. The eruption magnificently conserved the wall paintings, one of which stretches more than 55 feet long. The radiant colors and almost life-like characteristics of the work make for a unique and humbling experience. 

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

Day 8: Borders of Palermo

In the morning, your cruise ship arrives in the port of Palermo, the capital of Sicily. Palm trees wave in the sea breeze. The city has a golden hue glistening in the sunlight. The aroma of the ocean blends with the fresh citrus scent of oranges wafting through the city streets. Palermo embodies the rich history of the island, showcasing the variety of cultures that have traversed the landscape of Sicily throughout the millennia.

The jovial calls of vendors reach a climax in the Ballarò market near the Church of San Nicolò. The market stalls radiate freshness, from the color of the produce to the sizzling sound of freshly made chickpea fritters. Your guide leads you through the city on a tour of the island’s history, beginning with the 9th-century Norman Palace. Consider learning more about your Sicily tour companies who carefully craft your itinerary so that it pertains to your particular interests and desires. The exterior blends medieval architecture and Baroque sensibilities, but the complex was erected on ancient foundations. The base of the palace stands on Phoenician walls erected around 700 BC.

The palace acted as the seat of the Kings of Sicily during Norman occupation and continued as the seat of power. Today it is home to the regional assembly. The palace’s Arab architectural elements date back to the 9th century. The lavish interior of the chapel has hints of incense and shimmers in the mixture of lighting, from open windows to light fixtures.  Saints and angels decorate the walls and archways. You continue to stroll along the meandering streets of the city, taking in the array of cultures that have created a distinctive island lifestyle. 

What’s Included: breakfast, guided tour, accommodation

Day 9: What the Greeks Left Behind

The splendor of antiquity rises out of the Valley of the Temples, situated near the modern city of Agrigento. The ancient city of Agrigento was once the fourth largest city in the known world. When you come across the valley, you can take in the sensational panorama of the mesmeric ruins, filled with Doric temples rising against the rugged rolling hillside. Settlers from Gela and Rhodes founded the ancient city in the 6th century BC. Columns continue to stand tall in defiance of the elements, commemorating the work of master architects.

The Temple of Juno Lacinia stands above the eastern row of temples, with columns positioned around a circular hall. There are 25 of the original columns that remain upright. A sacrificial altar was placed in front of the ramp leading up the eastern entrance. The largest temple in the valley was the Temple of the Olympian Zeus. Although the structure collapsed during an earthquake centuries ago, the remains of a single atlas have been compiled to showcase the enormity of the temple that was once capable of holding such a gigantic figure.

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

Day 10: Eclectic Sicily

The ancient grandeur of the island is unparalleled. The beauty of the landscape is alluring. Today your guide meets you at the hotel after breakfast and leads you through the inland of the island en route to Taormina. The hills begin to roll with greenery and lush vineyards draping across the hills. On the foothills of Mount Etna, you find charming vineyards decorating the fertile grounds of the volcanic soil. The peak of the volcano ascends to 10,991 feet above sea level. The countryside around the foothills is filled with stonewall terraces, the pleasant aroma of citrus trees, and sporadic prickly pear cacti.

The town of Motta Camastra is quiet and straddles undulating cliffs. The subtle differences in temperature and the configuration of the soil shapes the flavors of the produce grown in the foothills of Mount Etna and across Sicily. You can stop at a vineyard near Motta Camastra and sample the distinct wines that have grown on a family-owned property since the 19th century. The white grapes have a natural citrus aroma. The red grapes have a ruby coloration and a cherry scent. When you sip the Etna Red, the texture is smooth with a balanced fruity taste. You arrive in the luxurious seaside town of Taormina located on the shores of the Ionian Sea.

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

Day 11: Seaside at Leisure

The majesty of Taormina comes from the opulent view of the city perched on the hill and overlooking the indigo waters of the Ionian Sea. You can see into the crystal clear sea from the vista, as the water laps at the immaculate shores. Medieval churches rise out of town. Designer shops stand next to quiet local bakeries. Mount Etna rises in the distance behind the quiet glow of the Gulf of Naxos. The day is yours to indulge in the wonders Taormina offers at your preferred pace, allowing you to take in the ancient Greek theater or explore the Ionian Sea with a diving expedition within the wonderful Isola Bella Marine Park.

The street of Via Circonvallazione runs parallel to the pedestrian walkway of Corso Umberto. Steps pave the road and lead to Madonna della Rocca, the chapel carved into the rough rock of the cliff. You can follow the walkway upwards to Castello di Taormina, which overlooks the water at 1,276 feet above sea level. The castle stands on the ancient Acropolis and offers a stunning panorama of the water below. The breeze brings the subtle aroma of the sea upwards from the shore. The tranquil space on the hilltop lets you bask in the beauty of the land and sea.

Venture over to your dive boat where you will begin your journey into the “Pearl of the Ionian Sea.” Friendly dive masters from Sea Spirit Diving Resort will accompany you to two regional diving locations. During your excursion you will discover several different species of marine life nestled in blue-toned caves. While you are lounging between dives, your dive-master tells you the ancient tales of the dive location you just emerged from. For lunch the crew will dock the boat and escort you a locally acclaimed Sicilian restaurant, where you will relish in the rich tastes of fresh on-site seafood. After a long day of diving the depths of the Sicilian coastline, sit back and admire the sparkling sea.

What’s Included: breakfast, dinner, accommodation, Dive Tour with Sea Spirit Diving Resort

Day 12: Splendor of Sorrento

In the morning, the Ionian Sea shines brighter with the sunlight casting a sapphire glow against the golden beaches. The Greek Theater is etched into the hillside, utilizing the natural slope of the landscape to provide a descending view to the stage. The simple pleasures of Taormina combine to form a captivating picture of the natural and historic beauty in and around town. After breakfast, you begin your ventures north, traveling across the Strait of Messina by ferry. The shores of Sicily are quiet. The Calabrian countryside on mainland Italy is rustic. Mountains rise and fill along the shore. Locals ride vespas through the city streets.

The culture of Italy is untamed and unchanged in the region located at the toe of Italy’s boot-shaped topography. You reach the town of Sorrento, located at the edge of the Bay of Naples. Craggy cliffs surround the city and climb more than 180 feet above sea level. The relaxed atmosphere of the city sweeps past elegant houses influenced by numerous cultures that have traversed the area throughout time. Charming fishing boats wade in the calm waters of Marina Grande and Marina Piccola, waiting to be taken out in the morning. The outline of Mount Vesuvius lingers in the distance across the bay. 

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

Day 13: Endless Island Grandeur

The magnificence of Capri is legendary, praised by classy Hollywood stars and Roman emperors alike. After breakfast, you venture to the marina and board a ferry to the island. The water in the Bay of Naples spritzes up alongside the boat. The sea breeze turns to calm winds with the movement of the ferry. You reach the Marina Grande and find a charming town nestled between the turquoise water and the towering rugged cliffs of the island. The buildings are painted bright colors historically to help call fishermen home from the water. Roman Emperors Augustus and Tiberius claimed the island as their home. You can visit remnants of their villas while exploring the island. Trendy cafes fill with visitors sipping espresso and enjoying the sunlight. Villas sparkle an opulent white, set against the shimmering sea.

Bougainvilleas add to the radiant colors of the island, sweeping over classic windswept mansions. On the secluded northeast area of the island, you find the villa of Tiberius, also known as Villa Jovis. The ruins encompass the undulating landscape, which provides an outline of the original size of the grounds. A former emperor resided in the villa until his death in 37 AD. The grounds are divided into separate parts to accommodate for the steep terrain. The gardens overlook the Salto di Tiberio, a cliff standing 898 feet above sea level looking down into the pristine water.

What’s Included: breakfast, guided tour, accommodation

Day 14: Territorial Abbey of Monte Cassino 

The water from the Bay of Naples quietly laps at the shores of the marina in Sorrento. Fishing boats depart from the Marina Piccola early in the morning, setting out to sea to find the perfect daily catch. The scent of freshly brewed espresso accompanies warm brioche at breakfast. After your meal, you leave the seaside behind, making your way northbound to the small town of Monte Cassino en route to Rome. The town is home to the monastery of St. Benedict, the founder of western monasticism. The grounds were consecrated in the 6th century AD and have seen pillages, natural disasters, and most recently, a large-scale battle during World War II. The large edifice overlooks the meandering valley.

You can see the Polish cemetery from the plateau. The monastery resembles a palace sprouting from the cypress trees crowning the mountaintop 1,706 feet above sea level. The library has a tremendous collection of manuscripts and books inside the refurbished stone structure. You stroll through the courtyard in the path of former monks who yearned for seclusion and a verdant plant life in the borders of a garden. The museum showcases the history of the monastery and the Vatican with lions etched out of marble and vibrant pottery of ancient societies. 

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

Day 15: Having Experienced Wonder

In the morning, the splendor of Rome returns. Artists set out their easels in Piazza Navona, attempting to capture the movement of water streaming from the fountains. Luxurious historic palaces border the cobblestone square. An Egyptian obelisk rises out of the center of the Fountain of the Four Rivers. The ancient statue of Pasquino decorates the southern edge of the square. Today it is known as the “Talking Statue,” because locals banner satirical poems and political movements across the base of the statue. After breakfast, your private transfer meets you at the hotel and escorts you to Leonardo da Vinci–Fiumicino Airport, where you board your flight home.

What’s Included: breakfast, transfer


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.