Italy’s Greatest Cities Tour with Sicily

A 11 day trip to Italy 
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Italy offers a dreamlike escape filled with magnificent architecture, ancient ruins, delicious food, breathtaking art, and embracing natural scenery. The opulent waters of the Mediterranean lap at sandy beaches. The power of the Colosseum emanates from the preserved stone walls. The charms of the fabled Romeo and Juliet radiate from a storied courtyard and emanate from hopeful lovers’ handwritten letters decorating the walls. From the Sistine Chapel to Michelangelo’s David, exuberant palaces to magnificent towers, your custom-tailored Italy tour with Sicily takes you to unforgettable cities, each brimming with historical delight and treasured enchantment.

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General Information

cathedral in a city at sunset with pink clouds
Detailed Itinerary

Places Visited 

Rome, Pisa, Florence, Verona, Venice, Ferrara, Rome, Taormina

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: The Greatness of Rome

Rome is Italy’s vibrant capital city, evoking a powerful ancient empire and a strong connection to legendary popes and artists. Cathedral domes add to the historic skyline. Narrow cobblestone lanes open up to hidden piazzas. The aroma of fresh pasta filters through a charming local restaurant specializing in family recipes passed down for generations. Ancient wonders lead to Baroque beauty. Your private transfer greets you at Leonardo da Vinci-Fiumicino Airport upon your arrival. Soon you find yourself in a luxurious hotel near the heart of the city.

The Arch of Constantine stands between the Colosseum and Palatine Hill. The 4th-century structure frames the Via Triumphalis; the pathway emperors took to enter the city after a military triumph. The arch stands more than 68 feet tall and 84 feet wide. It is the perfect image to welcome you to the city, flouting the grandeur of the ancient empire in the well-preserved friezes detailing the triumphs of the past. 

What’s Included: dinner, transfer, accommodation

Day 2: True Splendor of Rome

In the morning, the sunlight glints off of the marble staircase known as the Spanish Steps. The boat-shaped fountain at the bottom of the steps provides a soundtrack of trickling water, creating a romantic atmosphere in the glowing city. The Baroque architecture leads into Via Condotti, the fashionable district filled with opulent window displays. After breakfast, your guide meets you in the hotel lobby eager to show you the wonders of Rome. St. Peter’s Square is an iconic plaza known across the world. The 17th-century piazza has an elliptical shape encompassing 787 feet wide by 643 feet long.

Semi-circular colonnades border two sides of the piazza with Doric columns. At the heart of the square is an obelisk standing 135 feet tall that was originally located at Heliopolis in Egypt. St. Peter’s Basilica crowns the square to the west. Michelangelo designed the imposing dome, and Bernini created many of the fabulous monuments decorating the façade. The faint aroma of frankincense (herbal oil) drifts through the nave. Stunning brass air vents decorate the marble floors and lead into the catacombs networking around the foundation.

What’s Included: breakfast, tour, accommodation

Day 3: Continued Greatness of a Maritime Past

In the morning, the aroma of fresh espresso blends with the scent of brioche still crisp from the oven. The city comes to life with people venturing to work while others bask in the sunlight, sipping their espresso, and enjoying the morning. After breakfast, your private transfer meets you at the hotel and escorts you northbound to the acclaimed city of Pisa. Once a maritime power that rivaled the likes of Genoa and Venice, Pisa displays its stature with magnificent monuments and a dedication to education. The University of Pisa was erected in the 14th century and has maintained an elite status across Italy for centuries. Student life thrives in the city, bringing jovial life to sidewalk cafes and bohemian bars.

The Palazzo dei Cavalieri borders a grand piazza. The ornate façade boasts a lavish coat of arms and six busts representing six Medici Grand Dukes of Tuscany. You reach the Piazza dei Miracoli to find the tremendous style and architectural wonder of the Leaning Tower of Pisa. The marble structure contains undeniable elements of Pisan Gothic décor, from the thin columns encircling each tier, to the immaculate stone chosen to help erect the tower. The foundation was laid in the 12th century and today the tower leans nearly four degrees, creating a difference in alignment of over 12 feet.  

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

Day 4: Immersion into the Renaissance

In the morning, local Florentines set out onto the Arno River in rowboats provided by the Florence Rowing Club. The sunlight glistens on the water and highlights the controlled movement of the men and women propelling their boats up stream. The cobblestone streets of the city meander around the central cathedral known as the Duomo. Brunelleschi designed the magnificent brick dome, which remains the largest brick dome ever constructed. The cathedral reaches a height of 376 feet, shining with green, pink, and white stone. After breakfast, you are eager to meet with the guide to begin your exploration of the celebrated Renaissance city. You make your way to the doors of the Galleria dell’Accademia, home to the city’s school of fine arts and a scintillating museum.

The walls of the interior are completely whitewashed. In one gallery, historical instruments stand on elaborate pedestals, including a remarkable 17th-century viola created by the violin-making master Stradivari. Your guide leads you down a long hall, at the end of which stands the breathtaking figure of Michelangelo’s David. The statue stands 17 feet tall and represents the biblical figure holding his slingshot over his shoulder. The details of the statue are marvelous, taking in the intimate details of every muscle, and even the curly characteristic of David’s hair. His face is stern but stoic, with soft eyes casting his gaze into the distance.  

What’s Included: breakfast, tour, accommodation

Day 5: The Home of Star-Crossed Lovers

The scent of fresh brioche emanates from a collection of secret bakeries cast across the city. Each store specializes in different forms of pastries, hiding along the narrow lanes and secluded piazzas of the city center, encircled by the medieval walls that continue to outline Florence’s historical borders. After breakfast, you make your way northeast towards the celebrated city of Venice, stopping in the charming city of Verona along the way. Verona is best known internationally as the home of Shakespeare’s star-crossed lovers, Romeo and Juliet.

The Adige River rushes down from the Alps and gently coils around the cityscape. 10 bridges connect the city center to the neighborhoods situated on the left bank. The sights of the Roman occupation remain in the amphitheater located near the heart of Verona. The edifice was erected in the 3rd century AD and can still accommodate up to 22,000 spectators, many of whom come to enjoy the music in July and August at the Verona Opera Festival.

Your guide leads you along the main boulevard of the city, lined with chocolate shops and bakeries. You turn a corner off of Piazza delle Erbe to a quaint courtyard adorned with a balcony and a bronze statue of Juliet. People from around the world venture to the fabled home and leave love notes in the tunnel leading to the courtyard. A team of volunteers even answer the letters left by lovelorn visitors in search of the type of love Romeo and Juliet shared.

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

Day 6: Looking Around the Lagoon

The Venetian lagoon is world famous for its beauty. The city is considered one of the most romantic cities in the world. Gondolas glide down the stoic waterway underneath the venerable bridges for which the city has received its name the “City of Bridges.” Narrow passageways twist and turn into a stunning labyrinth lining palaces and passageways, crossing over canals and passing enchanting cafes overlooking the water. At breakfast, you step onto the dock of your hotel and enjoy a private boat ride along the Grand Canal to St. Mark’s Square where you meet your guide. The exquisite marble structure of the Palazzo Ducale matches the grandeur of the Byzantine style of St. Mark’s Cathedral.

The gothic palace acted as the seat of the Venetian Republic’s government beginning in the 9th century and remained there for the following seven centuries. The opulence of the structure is summed up in the 24-carat gilt stuccowork of the Golden Staircase, which connects to the second-floor rooms. The scent of rich stone emanates from the foundation. The exuberance of the décor is so vast you can practically catch the aroma of perfume lingering in the air in the Grand Council Hall where you find the Doge’s throne and a marvelous painting by Domenico, called Paradise.

What’s Included: breakfast, tour, accommodation

Day 7: Power of the Este

In the morning, the sunlight glances over the top of the Bridge of Sighs. The bridge connects the Doge’s Palace to the depths of the prison and was named by the Romantics in the 19th century, who told lavish tales of hearing prisoners sigh as they took a final glance at their beloved city of Venice. Similar feelings are invoked in you, as you depart the city after breakfast, watching the opulent marble facades overlooking the lagoon fade. You come to the fair city of Ferrara. Medieval walls remain intact, and the palaces look as though you have traveled back in time to their heyday. Verdant trees shade bike-friendly streets. The scent of chocolate lingers in the air.

The powerful Este family once thrived in Ferrara, and their presence lingers in the architecture and design of the city. The brick fortress known as Este Castle was erected in the 14th century to provide protection for the family from the citizens of the city. Their moat was once an extra line of defense against invaders but now acts adds charm to the imposing structure, serving more like a fountain than an obstacle. The scent of citrus rises from the orange garden. In the gallery room, you find remnants of original frescos encompassing aerial views of the city. The largest panel is a map of Ferrara during the Napoleonic era.

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

Day 8: Onward to the Riviera

The morning washes over the cobblestone steps outside of the Pantheon. The preserved monument has remained intact for over two millennia, having transitioned from a Roman temple to a Catholic church. Natural light pours in through the nearly 30-foot opening in the dome. The proportions of the structure add to its magnificence, having an equal height and diameter. You take some time to bask in the morning, enjoying the vibrant atmosphere of Rome. Your private transfer meets you at the hotel and escorts you to the airport with plenty of time to make your flight to Catania, Sicily.

When your flight lands at Catania-Fontanarossa Airport, your transfer quickly greets you and whisks you away to the seaside town of Taormina. Consider learning more about your Sicily travel agents who strive to ensure the finest Sicilian experience you could imagine. The setting is extraordinary, set atop a cliff with a panorama overlooking the Bay of Naxos and stretching to the peak of Mount Etna. Boutique shops line the cobblestone lanes. Gardens provide refreshing shade from the Mediterranean sun. A castle sits atop the summit of the hillside at the heights point of the town. You easily settle into the splendor of Taormina and relax in the laidback atmosphere.

What’s Included: breakfast, transfer, accommodation

Day 9: Remarkable Riviera

The crystal clear azure water laps at the shores of the Bay of Naxos. White puffs of smoke rise out of the active craters of Mount Etna in the distance. After breakfast, your guide meets you at the hotel. The city is filled with natural splendor and ancient charms. Locals stroll along the café-clad Via Pirandello as it coils up the mountainside. You make your way to the Greco-Roman Amphitheater, which was erected in the 3rd century BC.

The architects used the slope of the hillside to carve the perfect semicircular theater. The upper diameter of the structure stretches 357 feet. When standing in the top tiers of the theater, you can see the shimmering water of the bay and the looming peak of the volcano. The cliffs settle into pristine sandy beaches. You could sit on the antiquated stone seats and enjoy the view for the rest of the day.

What’s Included: breakfast, tour, accommodation

Day 10: Endless Sensations of Sicily

Locals and visitors alike enjoy the soft sandy beaches around Isola Bella. The nature preserve has a narrow path connecting the rocky-bound island to the mainland. Walkways encircle the landscape nestled between the sprouting Mediterranean trees and the large boulders rising from the water. After breakfast, the day is yours to bask in the beauty of Taormina and its surrounding wonders. Luxuriate on the beachside and take a dip into the temperate waters or traverse the cobblestone streets of Via Circonvallazione to stroll around the ruins of the castle at 1,305 feet above sea level. Outside of Taormina is the Alcantara Gorge.

The rushing river has carved smooth shapes into the rocks, separating the two sides of the canyon by only 16 feet. The gorge is 160 feet at its deepest point. The Alcantara River coils and maneuvers down the north side of Mount Etna. An ancient eruption blended with the water, which caused the lava to cool much faster than normal, turning the magma into rock columns and dramatic earthen shapes. You can hear the water thundering against the edges of the rock wall. The verdant trees and brushes at the top of the gorge lead to the botanical and geological park, providing access to the river level. You can dip your fingers into the river and feel the cold water careen past.

What’s Included: breakfast, accommodation

Day 11: Fond Farewell to the Taormina

The old district of Taormina begins in Piazza IX Aprile, framed by Baroque façade of San Giuseppe. The sunlight washes over the pink façade of the church. The interior contains pristine white Rococo stuccowork. Swirls decorate the nave walls. The 12th-century clock tower has ancient foundations. The beauty of the city is endlessly alluring. At breakfast, you take your time sipping a freshly brewed espresso, enjoying the morning like a local. After your meal, your private transfer meets you in the lobby. You make the short drive to Catania and board your flight home at the Catania-Fontanarossa Airport.

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.