Best of Rome, Florence, and Venice Vacation 2020

Skyline of St. Peter's Basilica at night reflecting off of the Tiber River
A 10 day trip to Italy & Vatican City 
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Authenticity and luxury will evoke the beauty of Rome, Florence, and Venice during your custom-tailored Italy tour. The charms of Italy will be found as you visit these three cities that have inspired epic poems, lavish songs, and enchanting stories. From the myth of Romulus and Remus to the legend of Murano glass, the glories of the Tuscan countryside to the historic streets of Rome, the picturesque piazzas of Florence, and the opulent canals of Venice, you will enjoy a collection of highlights that you will savor.  

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Most tours are customized for private travel.

General Information

Roman Colosseum at dusk
Outside Italian restaurant tables set up in alleyway
Fontana Di Trevi Ina, or the Trevi Fountain in Rome, Italy
View of Florence during sunset
Big pots of Italian ribollita soup
Church in Montepulciano, Italy on a foggy day
Masked and costumed couple in Venice during Carnevale
Gondolier navigating his gondola through a Venice canal
Boats on a canal on Murano Island in Venice, Italy
Canal in Padua, Italy
Basilica Papale di Santa Maria Maggiore in Rome, Italy
Fountain of Neptune in Florence, Italy
Detailed Itinerary

Places Visited 

Rome, Florence, Venice, Tivoli, Vatican City, Cortona, Arezzo, Montepulciano, Padua, Murano, Burano, Torcello 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Rome – Arrive in Rome with a Half-Day Fascinating Introductory Tour

Your flight arrives at Rome Fiumicino Airport, where your private transfer will greet you and take you into the city.  You will soon see that Rome is the result of a collection of wonders dating back nearly 3,000 years. Elegant bridges with statues designed by Gian Lorenzo Bernini span the banks of the Tiber River while medieval architecture lines the narrow cobbled lanes overflowing with artisan leather shops, modern furniture boutiques, and charming cafes. Rome is steeped in inspiring architecture and captivating artistry with famous designers taking motivation from ancient methods used in making the Pantheon’s magnificent dome. 

After taking time to settle into the comforts of your luxurious accommodations in the heart of the historical city center, your guide will greet you in the lobby to lead you through the splendor of the Eternal City. Your half-day walking tour will end at the preserved ancient spectacle of the Pantheon, which has stood in Rome for nearly 2,000 years. The structure was originally built in 27 BC over the site from which Romulus ascended into the heavens, and the current edifice was erected in 80 AD after a fire destroyed much of the original building. 

Much of the grandeur of the antique architecture and the feats of Roman engineering prevail in the 16 incredible granite columns on the porch topped with Corinthian flare and the massive cupola crowning the entire former temple. The marble floors provide a touch of prestige amid the harmonious ambiance that comes from the immaculate symmetry of the structural design with the height of the gallery reaching the same measurements as the diameter of the dome at 142 feet. 

What’s Included: airport transfer, accommodation, tour 

Day 2: Rome – The Grandeur of the Vatican and Frescoes of Villa Farnesina

Vatican City sits across the water from Rome’s historic city center with the dome of St. Peter’s Basilica looming over the long, regal boulevard of Via della Conciliazione that reaches into the heart of piazza. The world’s smallest sovereign state contains some of the most revered artworks in Italy and the whole of Western Civilization. Bernini designed the colonnade in the 17th century radiating from the wings of St. Peter’s Basilica to both frame the piazza and act as arms welcoming pilgrims into the heart of Christendom. Visitors from around the world linger in the square, wandering beneath the colonnade, and standing in the shade of the towering 82-foot tall obelisk at the center of the square secretly hoping for a view of the Pope from the balcony. 

During your visit to the Vatican, you will begin inside St. Peter’s Basilica. The scent of frankincense lingers in the great nave, which can hold up 60,000 observers at once. The grand structure was erected in the 17th century over the 4th-century foundations of the previous church. Your guide can point out Bernini’s remarkable canopy standing nearly 94 feet tall that was erected to mark the tomb of the saint. Michelangelo’s hauntingly stunning Pietàis also on display in the basilica, featuring a young Mary holding Jesus after the crucifixion. The 16th-century masterpiece was carved from a single piece of marble when the artist was only 24 years old, crafting the remarkable features with vulnerable humanity found in each intimate detail. 

Continue your exploration of Rome’s artistic contributions to the greater world at Villa Farnesina. The 16th century palace contains a mesmerizing collection of works painted by Raphael that decorate the ground floor and first-floor salon. The Loggia of Cupid and Psyche bring to light the love story of the Roman gods inside the veranda used for staging theatrical performances and celebrations. Raphael transformed the vault into a pergola utilizing his talent to craft hanging festoons and greenery as if a garden sprouted from the trestles. 

What’s Included: accommodation, tour, breakfast

Day 3: Rome – Charming Villas in Tivoli and Rome’s Capitoline Museums  

Follow in the footsteps of ancient Romans in the morning as you venture outside of the city to the summer retreat hilltop town of Tivoli. Situated along the Sabine Hills, Tivoli climbs along the limestone ridge above the winding waters of the River Aniene, which continues to carve the ravine deeper each year. Begin your exploration of the town at one of the two UNESCO World Heritage sites, Hadrian’s Villa. The magnificent complex encompasses more than 296 acres with a mixture of buildings and gardens erected in the 2nd century AD. 

Emperor Hadrian took inspiration from his travels across the Roman Empire, mainly from visiting the classic sites of Greece and Egypt. Long after the original statues and architectural gems of the classical world have faded, the Roman replicas crafted at the behest of Emperor Hadrian live on in the heritage of his “ideal city” built in Tivoli. The most photogenic spot in the villa leads you to the Maritime Theater, an island at the center of a large pool where Hadrian would retreat to escape the pressure of the government. The framing colonnade reflects in the tranquil water encircling the island. 

On returning to Rome, you can climb the steps that lead to the top of Rome’s smallest of the seven famous hills, Capitoline Hill. The piazza and surrounding museums date back to the 15th century to amass a mixture of classical and Renaissance design with one of the most highly-regarded collections of classical statuary. Your guide will take you to view the Lupa Capitolina, an image you have most likely seen around Rome as a symbol of the powerful city based on the myth of Romulus and Remus. The statue depicts the twins suckling from under a wolf. 

What’s Included: accommodation, tour, breakfast

Day 4: Florence – Florence’s Captivating Streets and View Artisan Shops

Florence has been celebrated as one of the world’s most beautiful cities thanks to its captivating skyline of church spires, bell towers, and the breathtaking brick dome of Brunelleschi’s design accentuated by the surrounding charm of the quintessential rolling hills of Tuscany. Upon arriving in the city from Rome, you will soon get acquainted with “Cradle of the Renaissance” with a half-day walking tour. The aroma of fresh espresso drifts out of the bars and cafes that are tucked along the narrow labyrinth of streets that lead to the central cathedral and its impressive dome that stretches south toward the banks of the Arno River. 

During your walking tour, your guide will introduce you to the Medici tombs in San Lorenzo. Vendors offering scarves and great deals on leather goods give the medieval lanes the ambiance of a bazaar. The Medici commissioned the church of San Lorenzo as a private family chapel and master artists of the day, such as Brunelleschi, Donatello, and Michelangelo helped design and decorate the church with additions made by Verrocchio and Lippi. The coffered ceiling and harmonious style allows plenty of natural light and reveal the ideals of the Renaissance emphasized by glinting marble pavement and rows of Corinthian columns. 

In the evening, you will continue to Oltrarno, the neighborhood on the opposite banks of the Arno River with narrow alleyways that host artisans that have remained in the traditions of their historical trades. Studios and workshops reveal boutiques in which jewelers craft elaborate silver earrings and book-smiths securing leather-bound volumes. 

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

Day 5: Florence – The Famous Duomo, the Accademia, and Palazzo Vecchio

Florence nearly overflows with art and artistry at every turn. While walking around the warren of medieval streets, the dome of the Duomo is nearly always visible above the tower homes. In the morning, you might notice the sweet scent of pastries drifting through the air from the collection of tiny bakeries working through the night to provide fresh confections for bars and cafes across the city. Your guide will eagerly whisk you into the heart of Florence for a better view of the Cathedral of Santa Maria del Fiore, referred lovingly and more memorably as the Duomo. The dome remains the largest unreinforced brick dome ever constructed reaching a height of 375 feet tall. 

The interior of the cathedral remains a treasure of religious design reaching nearly 500 feet long and 295 feet wide. Natural light pours through the 44 stained-glass windows designed by Lorenzo Ghiberti while the spiced aromas of frankincense and myrrh bring to light the cathedral’s function as a working house of worship.  The walls are decorated with inspiring works of art, including the enormity of the dome’s interior, which contains the 16th-century work of the Last Judgement as begun by Vasari and completed by Zuccari. 

From there, you will continue to the Accademia, where Michelangelo’s famous sculpture of David is displayed. The hall leading down to the statue feels more like a palace than a museum as unfinished sculptures crafted by Michelangelo line the wall depicting slaves emerging from the rock as if stuck in perpetual birth. The impressive figure of David stands 17 feet tall with intricate details bringing the figure leaps and bounds above the replicas that decorate the piazzas of Florence. You will notice the veins on the arms bulging and humanistic expression of stoic worry in the warrior’s eye denoting the first time an artist in that period depicted David before the battle as opposed to in victorious reverie with Goliath’s head as a prize. In the evening, you can enter into the remarkable galleries of Palazzo Vecchio for an after-hours tour away from the bustling crowds inside the rooms and secret passageways once utilized by the Medici. 

What’s Included: accommodation, tour, breakfast

Day 6: Florence – Fascinating Arezzo, Cortona, and Montepulciano

Outside the city of Florence, the beauty of Tuscany rises from the emblematic verdant hills covered with cypress trees, olive groves, and vineyards. Your private car will take you through the country lanes in view of the charming, pristine medieval towns that have been untouched by time before arriving at Arezzo. The settlement was built as an Etruscan trading post and then as a Roman military outpost, but flourished as a center of art and literature during the Renaissance. 

Piazza Grande has a noticeable slope and is bordered by sophisticated palaces and an elegant colonnade. The 16th-century bell tower is one of the country’s oldest working clocks, and the cathedral boasts a marvelous stained-glass window designed by French artist Guillaume de Marcillat in the early 20th century. The combination of historical and contemporary artistry brings the cathedral out of its 13th-century foundations that continued along its timeline of renovations in the 14th, 16th, 19th, and 20th centuries. 

The town of Cortona will steal your heart with the spectacular vistas overlooking the magnificent Tuscan scenery. The scent of freshly made pici pasta emanates from the quiet traditional restaurants, and the Romanesque features of the town’s original cathedral add an extra layer of history to the Museo Diocesano. The museum displays marvelous works by local artists including Lorenzetti, Fra’ Angelico, and Signorelli. The first room holds a remarkably preserved Roman sarcophagus adorned with friezes where the Amazons and Dionysus engage in an epic battle. Standing on the walls of Fortezza del Girifalco provides a marvelous panorama sweeping across the Val di Chiana all the way to Lago Trasimeno over 12 miles to the south. 

By the time you arrive in Montepulciano, you will be ready to savor the fantastic complexities of the wines produced in the Val d’Orcia region of Tuscany. The medieval and Renaissance hill town rests on a rocky outcropping 1,985 feet above sea level and boasts one of the celebrated Vino Nobile of Italy.  Using mostly Sangiovese grapes grown around the medieval walls, antique cathedrals, and chalky hills of the surrounding vale, your tasting of the wine offers subtle aromas of spices and tobacco with a full flavor and smooth texture. 

What’s Included: accommodation, tour, breakfast

Day 7: Venice – Padua en route to Venice and Enjoy a St. Mark’s Night Tour

The narrow streets of Padua meander through the old center and lead to fascinating grand piazzas set beneath the marvelous Byzantine domes of St. Anthony Basilica. The city began as a Roman settlement and grew to become one of Italy’s wealthiest cities by the 14th century drawing artists like Donatello and Giotto. The rosy façade of Capella degli Scrovegni contains one of the most fascinating works of art maintained in Italy crafted by Giotto between 1303 and 1305 to decorate the Scrovegni family’s private chapel. 

The priceless treasure has been praised by famous Italians like Dante and Leonardo da Vinci, who felt the work of Giotto helped bring artists out of the tunneled aesthetic of the times for a rebirth of expression. You will step into the sealed environment that protects the frescoes for a view of a life cycle of Jesus painted beneath a ceiling covered with a night sky glistening with stars. Giotto gave divine and biblical figures human characteristics allowing onlookers to better identify with the characters they would come to know as people instead of solely as holy beings through depictions of vulnerability, sorrow, pain, and joy.

After taking it all in, you will soon arrive in Venice and take a private water taxi across the Grand Canal to reach your gorgeous accommodations with a window overlooking serene lapping water against the marble exterior of the structure. You can venture out into the city for an after-hours exploration of the city’s most famous church, St. Mark’s Basilica, situated as the crowning structure of the eponymous square. Five Byzantine domes top gigantic pillars, with each supportive column reaching more than 42 feet in diameter. Mosaics adorned with gold-leaf embellishments envelop the interior accentuated by sporadic precious stones scattered among the structure spanning nearly 45,640 square feet. 

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

Day 8: Venice – The Highlights of Venice including a Gondola Ride

Your highlights tour of Venice will bring you back to Piazza San Marco, this time with your eyes set on the gorgeous Venetian Gothic façade of the Doge’s Palace. The secret tour of the remarkable structure will lead you along the foundations first placed in the late 6th century and rebuilt in the 15th century. Rich details decorate the Foscari Arch with elements of Renaissance influence along the turrets and niches while statues of Adam and Eve provides intricate décor with a touch of biblical connections. 

Stepping inside the Sala delle Quattro Porte will bring a view of the former secret society that once ruled the city behind the scenes. The Council of Ten oversaw the secret police who once controlled both private and public life on the streets of the city. The peculiar, and grand, room holds spectacular paintings that are accentuated with wood panels and flickering gilded adornments that allow the images of Juno presenting the Ducal crown to Venice to burst from the portraiture. 

The highlights of Venice also include the cuisine known as cicchetti, considered as the Venetian version of tapas. The small plates include traditional dishes like fried squid, salumi, and baccala—salted cod. Sample your way through the best bacari in the city, the small bars offering the small plates with glasses of wine or touches of grappa. After enjoying the small customary cuisine of Venice, you can step onto the iconic boat of Venice to enjoy a relaxing gondola ride around the narrow waterways acting as arms moving away from the wide banks of the Grand Canal. 

What’s Included: accommodation, tour, breakfast

Day 9: Venice – The Marvels of Murano, Burano, and Torcello Islands

After breakfast, step onto your boat bound for three fascinating islands on the Venetian Lagoon. The scent of the saltwater carries in the morning breeze as you arrive to Murano, an island famous for hosting the glassblowers of the Venetian Republic since the 13th century. The Doge relegated all glassblowers out of Venice due to a fear of fires but wanted to keep the illustrious and secret recipe for producing glass in the hands of the Republic. Small canals divide the island making it resemble a smaller version of grander Venice while workshops and studios fill with heat emanating from the furnaces artisans use to make the glass pliable. 

The Museo del Vetro provides unique insight into the history of glassblowing in Italy tracing the dynamic art back to the Romans with many later glassblowers learning the skills from the Byzantine Empire around the 8th century. Displays of fascinating glass pieces spa eight rooms with some artifacts dating back to the 5th century BC. The Grand Salon possesses a remarkable collection of three chandeliers floating beneath a ceiling decorated with an elaborate fresco. The chandeliers offer insight in the prestige of glassmaking between the 14th to 17th centuries as you step into a studio where the artisan will welcome you with a demonstration on the intricate techniques needed to shape the molten glass into proper casts. 

What’s Included: accommodation, tour, breakfast

Day 10: Venice – Depart for Home

Barges return to the loading dock at Piazza Rialto before dawn bringing to market fresh vegetables, fruits and delicious seafood caught around the lagoon and the Adriatic Sea. A marble decree posted on a building lists the market rules on the legal size of fish from the lagoon originally placed in the 16th century. After breakfast and one last wander of the city, your private transfer will escort you across the water to a waiting car ready to take you to Venice’s Marco Polo Airport for 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.