Perfect Two Weeks in Italy Tour 2020

The Roman Colosseum at midday surrounded by tourists | Italy
A 14 day trip to Italy & Vatican City 
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Classic beauty and indelible charm will radiate from ancient ruins, Renaissance artwork, and captivating coastlines during your custom-tailored Italy tour. The iconic wonder of Italy will seduce you with panoramas of the rugged Amalfi Coast and the glamour of St. Mark’s interior shimmering with gilded mosaics. The Colosseum reflects remarkable achievement of ancient engineering and the Uffizi Gallery displays the triumphs of spirited expression. Wander along the cherished shores of Lake Como and travel into the past while strolling down the streets of Pompeii. Embrace Italy as an embodiment of culture with classic style and timeless charisma. 

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Most tours are customized for private travel.

General Information

View of Florence, Italy with the Cathedral of Santa Maria del Fiore in the background
View of colorful buildings and boats on Murano Island in Venice, Italy
A canal with gondolas running underneath the Bridge of Sighs in Venice, Italy
Beautiful view of traditional gondolas on Canal Grande in Venice, Italy with a cathedral in the background
Lake Maggiore with European town and mountain range in the background
Inside view of glass dome in Galleria Vittorio Emanuele in Milan Italy
Coastal view of colorful buildings and boats in a Cinque Terre harbor in Liguria, Italy
The Leaning Tower of Pisa and Piazza Dei Miracoli standing side by side in Pisa, Italy
A courtyard view of the Cathedral Basilica of St. Francis of Assis in central Italy
Ceiling paintings in the dome of the Vatican Museum in Roma, Italy
A cloister of Chiostro di San Francesco in Sorrento, Italy
An inside courtyard view of the Basilica di Santa Maria at sunset in Roma, Italy
Detailed Itinerary

Places Visited 

Milan, Como, Venice, Florence, Pisa, Lucca, Rome, Vatican City, Sorrento, Pompeii, Bellagio, Verona, Murano, Monterosso al Mare, Vernazza, Manarola, Riomaggiore, Corniglia, Amalfi, Ravello, Positano, Vietri sul Mare, Minori, Assisi, Borromean Islands  

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Milan – Italy’s Economic and Fashionable Capital at your Leisure

The city of Milan embraces its elegance and sophistication that are displayed through the preserved architecture, ravishing artworks, and famous connections to the fashion industry. The fast pace of the city thrives on creativity that celebrates the modern metropolis and the cultural grandeur that dates back to the 5th century BC under Celtic settlers. Your flight will land at Malpensa Airport, where your private transfer greets you. Settle into the luxuries of your fantastic accommodations at the heart of the city with the remainder of the day at your leisure to discover the beauty of Milan. 

The Duomo sits at the center of the historical city embodying the elegance of the past with a flamboyant Gothic design begun in the 14th century and completed in the early 19th century after the occupation of Napoleon. The spires and pinnacles crowning the cathedral are decorated with approximately 2,245 statues glinting with marble. The interior boasts 52 marvelous pillars accentuated by the light drawn into the nave by the colorful stained-glass windows. The scent of frankincense and myrrh drifts through the gallery contrasting the aroma of espresso and pastries emanating from the cafes in the piazza.  

What’s Included: airport transfer, accommodation 

Day 2: Como – Lakeside Como to Visit the Surrounding Towns

After breakfast, you take the train northbound into the radiant slopes of the Italian Alps to reach the treasured shores of Lake Como. The eponymous town sits on the southern tip of the water with a marvelous historical ambiance captured in colorful buildings reflected off the water. Julius Caesar established the settlement in the 1st century BC memorialized in the preserved Porta Pretoria at the center of the town acting as the entrance gate leading into the winding cobblestone streets. 

Medieval lanes twist and turn inside the Romanesque fortifications leading to Piazza del Duomo and the imposing Tower Gate in Piazza Vittoria. The featured defensive stronghold was erected in the 12th century reaching 132 feet tall flanked by the antique fortification. The creamy façade of Villa Olmo looks out over the water with the extravagant design of an 18th-century mansion erected for an aristocratic family related to the pope. The interior contains lavish artwork personifying Italian art nouveau, which features the naturally curved lines of forms, structures, and plants. 

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

Day 3: Como – Beauty around Lake Maggiore and Borromean Islands

In the morning, the sunlight washes over the serene waters and surrounding verdant peaks of Lake Como. After breakfast, you venture to the shores of the second-largest lake in northern Italy, Lake Maggiore, whose shoreline stretches for upwards of 40 miles. The air surrounding the waters retains the grandeur of the Belle Époque during which time travelers from around Europe grew enamored with the natural beauty sweeping across the water and into the sloping woodlands. Board a ferry in the charming town of Stresa bound for the extravagant Borromean Islands. As the boat glides across the stoic water, your view of the lakeside promenade features colorful facades glinting with elegant boutiques and chic restaurants. 

The crisp alpine aroma has hints of pine and fresh water before you reach the Isola Bella and the 17th-century villa of Count Vitaliano Borromeo. The elegant architecture stands atop six grottos made from artificial walls encrusted with shells, pink marble, and pebbles taken from the lake bed. The period furnishings accentuate the refined style of the aristocracy featured in the Flemish tapestries and Lombard paintings with many works crafted by masters like Titian, Van Dyck, and José Ribera. White peacocks parade through the gardens with feathers as pristine as a wedding train. The garden contains ten tiered terraces rising to 105 feet above the garden ground boasting rows of lemon and orange trees, magnolias, and blossoming camellias. 

What’s Included: accommodation, tour, breakfast

Day 4: Venice – Venice for an After-Hours St. Mark’s Basilica Tour

The scenic ride through the slopes of the Alps leads into the plains of Veneto and the waterways of Venice. Your private vaporetto will meet you at the train station and escort you across the water to reach the dock of your hotel. Venice is the image of audacity and refinement, and this is thanks to the collection of marble palaces that have been built on a lagoon over 118 small islands connected by hundreds of bridges. Your adventure through the classic Italian city begins when your guide greets you in the hotel lobby, and you can wind through the labyrinth of cobblestone streets weaving alongside the quiet canals for which the city is famous. 

Gondolas glide past with their gondoliers ducking beneath arching bridges, and nearby St. Marks’ Square symbolizes the luster of Venice crowned by the bulbous domes of the eponymous basilica, the soaring bell tower capped with a golden weathervane depicting Archangel Gabriel, and the Venetian Gothic façade of the Doge’s Palace. The foundations for the cathedral began in the 9th century after merchants fled Alexandria returning to Venice with saintly relics. The original structure burnt down resulting in a complete remodel of the basilica imagined, designed, and decorated with treasures brought from Syria, Egypt, and Palestine during the Crusades.

Marble, alabaster, and jasper adorned with precious gemstones create the sense of inspiring awe experienced with your first glance at the remarkable feat of design and engineering. Entering the grounds after hours brings a sense of privacy and intimacy with the Byzantine mosaics carpeting the lofted ceiling covering nearly 45,640 square feet with gilded biblical stories and ethereal figures. St. Mark remains the most notable depiction at the heart of the nave featured with a celestial light accentuated by gold leaf and colored glass pieces framed by the surrounding five domes, at the center of which Jesus stands amid flickering stars. 

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

Day 5: Venice – The Canals of Venice and the Island of Murano

The Jewish Ghetto of Venice is located in the contemporary neighborhood of Cannaregio. In the 16th century, the Venetian Republic first decreed that Jewish residents such as lenders, doctors, and merchants were allowed to commence their business in the city during the day, but must return to the confines of the ghetto by night. Two synagogues in the Campo di Ghetto Vecchio were erected for the Sephardic community and rebuilt in the 17th century with an intricate wooden pulpit and traditional Venetian architectural flair, such as geometric details and windows with high arches. It was not until the reunification of Italy in the 19th century that the Jewish community in Venice gained their emancipation from the Ghetto.

After exploring the unique histories of the neighborhoods around the city, you can board your boat bound for the island of Murano, settled with artisan glassblowers after the Doge removed them from the main city in the 13th century due to a fear of fires. Artisans continue their craft in the city shaping glass by hand, and you can meet an artist in their studio and experience the intense heat emanating from the kiln for yourself. The artist uses the heat to make the glass pliable as they shape, bend, and twist the glass into new distinct shapes. 

What’s Included: accommodation, tour, breakfast

Day 6: Vernazza – Famous Cinque Terre by way of Lovely Verona

After breakfast, you will travel west toward the coast of Liguria and the famous towns of Cinque Terre. Make your first stop in fair Verona, a city famous for its history and ambiance of romance as woven by Shakespeare in his play of star-crossed lovers Romeo and Juliet. The soaring figure of the Roman amphitheater captures your eye in Piazza Brà. The edifice was erected during the 3rd century AD nearly two centuries after the Romans settled the city on the banks of the Adige River. The theater contains 44 rows of seating and can still accommodate up to 22,000 people during the summer Verona Opera Festival. In 2019, the Verona Opera Festival celebrates the 95th anniversary of celebrated composer Giacomo Puccini with performances of La Traviata and Tosca highlighting the contribution of the music through the display of sophisticated composition intertwined with gripping storytelling. 

The surrounding city retains the grace of its past embodied in the central feature of Piazza delle Erbe. Cafes and restaurants border the public square erected atop the former Roman forum in the 16th century. A fountain trickles with a figure of the Madonna repurposed from an original marble feature of a Roman deity. One of the classic highlights of the city pertains to Juliet Capulet, the heroine of Shakespeare’s tragic play. The palazzo is located near Piazza della Erbe offering visitors access to the charming courtyard. The beautiful display of medieval architecture hosts a small archway as an entrance, and you will notice the letters clinging to the brick written by visitors from around the world hoping for guidance from their champion of romance. A bronze statue stands near a balcony added in the 1930s as the missing ingredient from which visitors can reenact scenes from the mythical love story in their heads.  

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

Day 7: Vernazza – Prominent Trail Connecting the Towns of Cinque Terre

In the morning, the aroma of basil and lemon groves drifts down from the terraced orchards along the mountainside blending with the sea breeze. The town of Vernazza wraps around the natural marina along the edge of the mountainous terrain. Bakers make delicious focaccia bread and restaurants specialize in crafted delectable pesto. The five towns of Cinque Terre were once alienated from greater Italy due to the rough terrain separating the towns from one another and the nearest cities until the arrival of the first train built in the 19th century. Vernazza was fortified in the 11th century by the Genoese to defend the people, shops, and goods from raiding Saracen pirates exemplified in the original watchtower standing on the promontory. 

The clear waters of the Ligurian Sea shine on the western side of town with the verdant mountain slopes glinting to the east. Cobblestone streets and stairways create deep ravines that carve between the colorful tower homes. The railway connects the five towns together, but a number of trails also highlight the original connection between towns when traveling by land instead of the sea. Travel along the Blue Path to Corniglia in the south leading you through lush forest between the elevated promontory and Cinque Terre’s smallest hamlet of San Bernardino. The length of the trail is approximately two miles with an elevation changing between 329 and 722 feet above sea level. Corniglia stands atop a 328-foot tall plateau surrounded by serene vineyards and a fabulous view of the water. Terraces create the perfect panorama from the only spot on the coastline where all five villages are visible at once. 

What’s Included: accommodation, tour, breakfast

Day 8: Florence – Remarkable Pisa and Lucca before Arriving in Florence

At breakfast, the aroma of espresso and sweet focaccia fills the dining room of your accommodation. After a leisurely start, you will depart Vernazza at the train station and continue to Lucca, a city famous for its preserved Renaissance walls and beautiful piazzas. The city quickly endears itself to you with cobbled lanes and quiet promenades. Walkways circle around the thick former defensive walls of the city restored by Maria Luigia of Bourbon in the 19th century by turning them into public parks. The featured walls stand nearly 40 feet tall and 100 feet thick defending the historic cafes, classic restaurants, and stunning climbing towers at the heart of the city. 

Torre Guinigi glows with red brick from the 14th century and stands 148 feet tall. The rooftop supports seven oak trees planted in a horseshoe-shape reachable by 230 steps. The tower is perceived as having helped to usher in a moment of prosperity for the town beginning in the 15th century. The façade of San Michele in Foro resembles a wedding cake deriving from the inlaid marble and decorative pillars intricately woven into the fabric of the 12th-century structure. While in Lucca, you can enjoy lunch at Giglio, a restaurant awarded a Michelin Star for 2019. The long-established restaurant brims with enthusiastic recipes from three young chefs working classic Tuscan dishes with a mosaic of complimentary international personalities. 

Continue to the famous city of Pisa, a powerhouse of maritime trade in the 11th century until defeat by the rival Genoese navy in the 13th century. The city has maintained a prevalent space in the history of Italy and Tuscany with popular university and gorgeous architecture influenced by the Medici family. The Leaning Tower remains the most iconic structure in the city with an incredible list of nearly four degrees creating a distance of 12 feet between the base and the top of the tower. Architects began building the structure with the charismatic thin columns of Pisan Gothic design in the 12th century.  

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

Day 9: Florence – Art and History in the Uffizi and Accademia Galleries

Florence is a majestic city revolving around the medieval walls and Renaissance art, grand palaces, and marvelous churches. The scent of espresso drifts through the bars opening in the morning with locals sipping their coffee before heading to work. The sunlight glints against the tip of Brunelleschi’s dome at 375 feet above the surrounding piazza adorning the lavish marble façade of the cathedral. After breakfast, your guide will greet you in the lobby of your luxurious accommodations in the heart of the city and escorts you to the Uffizi Gallery. 

The structure was erected in the 16th century under the patronage of Cosimo I de’ Medici as an office for the Florentine magistrate. The gallery displays works from masters of artistry in consecutive order allowing you to witness the variety of artistic aesthetics at work during the same period between the 14th and 18th centuries. The portraits of the Duke and Duchess of Urbino by Piero della Francesca were painted around 1465 and well known for their humanistic approach to their subjects with the artist including the wrinkles, thin lips, stocky build, and aquiline nose of the duke instead of trying to flatter his subject. 

The day of captivating art continues in the Galleria Accademia dell’Arte, which was erected in the 18th century. Magnificent sculptures grace the halls of the museum including the famous statue of David by Michelangelo. The figure of the biblical king stands 17 feet tall and looks stoic before his battle with the giant Goliath. While other artists depicted David as conqueror gloating in victory above the head of his conquest, Michelangelo gave the world the warrior from a different perspective. The amount of detail stands out in how the veins bulge from the arm and the curls in his hair. 

What’s Included: accommodation, tour, breakfast

Day 10: Rome – Beauty of Assisi before an Introductory Tour of Rome

For a magnificent view of Florence, you can wake up before dawn to visit Piazzale Michelangelo located across the Arno River on a plateau overlooking the city. The city glows a rosy pink as the sun spreads across the skyline to reveal the tiled rooftops and scattered bell towers framing the central dome of the Duomo. After breakfast, you can travel south to cross the border into Umbria to reach the celestial town of Assisi. The streets wind up the slopes of Mount Subasio with the foundations of the Basilica of San Francesco erected in the 13th century to commemorate venerated saint. 

The entire structure encompasses two churches, with the lower church boasting a Late Romanesque design featuring high vaulted ceilings against the upper church’s vertical Gothic lines. Fascinating frescoes by Giotto decorate the upper nave depicting the life and times of the saint. Outside the church the scent of olive oil and balsamic filter out of a quiet artisan shop. The cobbled lanes lead past the Temple of Minerva, a 1st-century BC edifice converted into a church in the 16th century and refurbished with Baroque designs in the 1600s. The Roman Corinthian columns remain providing an extravagant history and touch of lavish charm to the façade. 

You will then continue to Rome, the Eternal City, for an introduction into the ever-evolving streets encompassing 3,000 years of history. The scent of pasta mixed with cheese and black pepper becomes a staple aroma emanating from the restaurants around the city. The inspiring skyline sweeps from bell towers to the dome of St. Peter’s Basilica and the soaring walls of the Colosseum. Your guide’s eagerness is infectious as you step out into the enchanting streets to discover the historic sites of Rome ending at the famous Pantheon. The structure is nearly 2,000 years old after being rebuilt in the 2nd century AD. The porch contains 16 granite Corinthian capitals each with a width of 108 feet. The interior has an indelible sense of symmetry emanating from the harmonious design with the height of the dome reaching the same measurement as the diameter of the dome at 142 feet. You find the tomb of famous Renaissance artists Raphael, as well as the Vittorio Emanuele II, the first king of a united Italy. 

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

Day 11: Rome – Sensational Art and Unique History of Vatican City

Vatican City became the world’s smallest sovereign state in 1929 after the Pope made a deal with Mussolini touching the ancient, Renaissance, and Baroque with Italy’s contemporary history. The dome designed by Michelangelo tops the basilica of St. Peter and reaches 450 feet tall. After breakfast, you can meet your guide in the center of St. Peter’s Square in the shade of the ancient obelisk. The museum galleries of the Vatican host a spectacular array of antiquity ranging from Etruscan relics to Egyptian reliefs, Roman tombs to Byzantine mosaics. Inside the former apartments of the popes, your guide points to the artwork of Raphael whose distinct style followed the classical symmetry by which the characters maneuvered around a focal point in the fresco, School of Athens

The captivating artwork uses the Golden Age of Greece as an analogy for the enlightenment featured in his use contemporary masters as classical figures, such da Vinci as Plato and Michelangelo as Heraclitus. The marvels of the Raphael Rooms fade in comparison to the grandeur of the Sistine Chapel. The rectangular hall was decorated in the 15th century with biblical scenes from the Old and the New Testaments. The captivating depictions on the ceiling capture the mastery of Michelangelo’s artwork embodied in the central panel featuring the Birth of Adam. 

What’s Included: accommodation, tour, breakfast

Day 12: Sorrento – Vast Ancient Pompeii en route to Sorrento

The market in Campo de’ Fiori fills with locals and visitors alike in the morning. The scent of fresh produce drifts through the aisles passing bundles of fresh flowers. After a short wander, you will depart and travel by fast train through the countryside south of Rome to reach Naples and the famous ancient city of Pompeii. The fascinating urban expanse covers 170 acres and was once a large port city connected with the Roman empire covered in pumice and ash after the eruption of Mount Vesuvius in 79 AD. 

The legendary eruption looms large over the grounds with the peak of the active volcano visible from the streets of Pompeii. Much of harsh conditions and captivating legend of the eruption derives from the accounts of Pliny the Younger, who witnessed the dark clouds and combustible stones spread across the sky. Mount Vesuvius remains the only active volcano on the European mainland, which last erupted in 1944. The 75th anniversary of Mount Vesuvius’s most recent volcanic eruption takes place in 2019. 

While exploring the captivating streets of Pompeii, your guide leads you beyond the Antiquarium filled with artifacts too fragile to move--such as preserved furnishings or clay pots carrying oil—to pass a fast food restaurant called a thermopolia along a former busy road. The stoves held fresh food cooking throughout the day where Pompeiians could buy a quick, hot meal with wine. Archeologists discovered a cloth bag in one of the many thermopolia in Pompeii possessing nearly 1,000 coins representing the popularity of fast food in the city. The House of Menander embodies the prestige of the merchant class in the city with lovely flourishes like the Corinthian capitals and a wooded atrium preserving a small temple. An opening allowed water to collect and drain while the interior hosts a beautiful collection of scenes from Homer’s Iliad

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

Day 13: Sorrento – The Natural Splendor of the Amalfi Coast

The charming coastal town of Sorrento embraces the refreshing aromas of citrus and the sea breeze in the morning. The craggy cliffs forming the Bay of Naples border the city and reach 180 feet above sea level. Your private driver will meet you at your hotel after breakfast eager to introduce you to the legendary beauty of the Amalfi Coast. A 25-mile long road connects Positano in the west to Vietri sul Mare in the east with intermittent towns clinging to the promontories and coves overlooking the shimmering waters of the Tyrrhenian Sea. 

The town of Minori was once prosperous due to its history of shipbuilding and maintained a sense of its lavish past with a contemporary charm. Locals lounge under umbrellas on the small pebbled beach listening to the sea lap against the shoreline. Visitors from around Italy stay in Minori to sample the gourmet dishes for which the town is known sampling delicious pizzas or fantastic seafood cuisine. The preserved Roman villa has conserved elegant mosaics and frescoes dating back to the 1st century AD. Continuing to the eponymous town of Amalfi brings the past to life through the historic architecture lining the narrow streets. 

The former maritime powerhouse grew in importance from a combination of shipbuilding and trade with far-off cities like Constantinople until the 14th century. The influence of the Byzantine Empire is most notable in the architectural design of cathedral, which was erected between the 9th and 10th centuries with refurbishments adding Arab-Norman, Gothic, Renaissance, and Baroque elements to the style. The imposing stairway contains over 60 steps leading to the dramatic porch decorated with striped marble and stoned. The bronze doors were cast in the 11th century in Constantinople during the height of trade between the two cities. 

What’s Included: accommodation, tour, breakfast

Day 14: Sorrento – Depart for Home

The morning light washes over the blue of the water returning the vibrant colors to the small fishing vessels moored in Marina Grande. The cafes open along the boardwalk placing tables on terraces and the street for impressive views over the Bay of Naples. A small fishing village bustles in the early hours of the day with fishers returning to shores with fresh seafood bound for the restaurants. The city walls were originally built by the Greeks nearly 3,000 years ago and remain standing along the edges of Sorrento reflecting the fortifications strengthened by Romans and the settlement during the Middle Ages before attacks by the Turks in the 16th century. After breakfast, your private transfer greets you in the hotel lobby and escorts you around the Bay of Naples to reach Naples International Airport where you board your flight home. 

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.