Italian Vacation of a Lifetime 2016: Venice, Milan, Florence, Rome

A 12 day trip to Italy

Italy is for lovers and historians, foodies and hikers, art enthusiasts and fashionistas. In other words, Italy is for everyone. Especially designed for 2016, this Italian vacation of a lifetime will take you on 12-day journey through the most famous Italian cities as you will be wined and dined, and ultimately swept off your feet, immersing yourself in the wonders of Roman history and the romance of Venetian canals. Discover the iconic fashions of Milan and the graceful artistry of Florence. You set the pace and revel in the beauty of Italian splendor.

General Information

A golden moment in Florence that takes your breath away
Detailed Itinerary

Places Visited 

Venice, Milan, Florence, Rome

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: City on the Lagoon

Vaporettos ferry locals and visitors across the Grand Canal. Iconic gondolas glide across the water. The remarkable Byzantine domes of St. Mark's Cathedral towers over the waterline edging against the piazza. Charming cafes line the cobbled pathways where you can hear the water lapping against the nearby antique steps leading into the lagoon. Carnival masks decorate window displays. Murano glass reflects the sunlight and captures your eye with elegant colors and graceful shapes.

You have just arrived in Venice and already the city enchants you, filled with marbled piazzas and stunning palaces, remarkable history and elegant decor. One of our Italy travel companies will arrange for a private transfer from the airport to your hotel. Your accommodations are located in the heart of the City of Bridges, where the Rialto Bridge arches over the waterway, showcasing its elaborate 16th century construction alongside rows of exuberant boutiques.

What's Included: transfer, accommodation

Day 2: Luxuries of the Lagoon

In the morning, the golden weathervane atop the 323-foot tall St. Mark's Campanile glints in the rising light. The cobblestone streets of the city begin to fill with locals en route to work and visitors eager to explore the iconic city on the canal. The Grand Canal reflects on the architectural and historical glory of Venice, with its signature walkways leading to the jewels of Palazzo Ducal and the Basilica di San Marco.

After breakfast, the day is yours to revel in the famous city at your preferred pace, wandering the labyrinthine streets that range from wide avenues to narrow alleyways. When you reach St. Mark's Basilica, you find one of the most recognizable churches in the world, filled with 45,639 square feet of gold mosaics decorating the domes and the walls. The basilica was constructed between the 11th and 12th centuries with the tallest onion-shaped dome reaching a height of 141 feet. The gilded lining of the exterior arches adds an extra layer of exuberance to the edifice. A winged lion, the symbol of the city and of Venice's patron saint, adorns the gable with a background of stars twinkling beneath a statue of St. Mark. The elegance of the historic church illuminates the history of the city alongside the grace of the marbled Doge's Palace.

What's Included: breakfast, accommodation

Day 3: Finding Venice

Byzantine windows decorate antique Gothic palaces. Pocket-sized piazzas open up the close-knit buildings where kids kick soccer balls against the walls of medieval buildings. The aroma of espresso drifts out of every cafe in the city in the morning. The day is yours to enjoy what the Venetian's call 'Dolce far neinte,' or, 'the sweetness of doing nothing.'

For something uniquely Venetian, you can always step onto a relaxing gondola to explore the narrow canals of the cityscape. The boat is long, sleek, and black with your gondolier steering the boat from the back. The gondola was the primary source of transport around Venice. You pass underneath bridges made of stairs, where you have to duck beneath the archway. Canal-side cafes provide decadent aromas for your journey along the placid water. You can hear a violinist practicing from one of the open windows, creating the perfect ambiance along the historic waterways.

What's Included: breakfast, accommodation

Day 4: In Fashion

Wake up to another day along the canals, and the charm of yesterday's gondola ride lingers in your thoughts. The colors of Murano glass continue to light up the display windows around the city. After breakfast, your private transfer escorts you across the Grand Canal to the train station where you settle into the comforts of your first-class train car en route to the iconic fashion city of Milan. Michelangelo and da Vinci, along with the composer Verdi, and the designer Giorgio Armani, have called the city home.

Upon your arrival at the Milano Centrale Railway Station, your private transfer takes you to a remarkable hotel located near the center of the city. The cathedral stands in the heart of Piazza del Duomo, shimmering with flamboyant Gothic bravura. Construction on the cathedral began in the 14th century and lasted until the 19th century. More than 130 stone pinnacles create an undulating skyline topped with over 2,200 marble statues. The grandeur of the cathedral illuminates the atmosphere of the city, from its history to its sought-after aesthetic.

What's Included: breakfast, transfer, accommodation

Day 5: Magnificent Milan

In the morning, the fashionable city resembles a magazine cover, filled with elegant locals sitting in cafes and sipping their morning espresso. The Grand Galleria Vittoria Emanuelle II is a shopping gallery that resembles a palace. Natural light spills through the glass vaulted ceilings and dome standing 157 feet above the tiled floor.

The day is yours to explore Milan and its surrounding countryside any way you wish. Take a tour to experience the pristine beauty of Lake Como or meander through Castello Sforzesco, a stunning palace home to one of the wealthiest families in Milan for centuries. The unassuming Gothic brick church of Santa Maria della Gracia has a six-sided dome designed and constructed in the early Renaissance. The refectory overshadows the sophisticated architecture, as it houses the extraordinary Last Supper by Leonardo da Vinci. Da Vinci painted the piece on the wall in the 15th century. The size and bright colors enhance the story da Vinci wanted to tell. Inside the room, you find faint traces of myrrh.

What's Included: breakfast, accommodation

Day 6: Remarkable Renaissance

In the morning, your private transfer takes you to the central train station where you board your luxurious first-class compartment on your way to the famous city of Florence. You will arrive at Firenze Santa Maria Novella. Medieval walls continue to border the historic city center. Cobblestone paves the wide avenues lining buildings dating back to the Middle Ages, including stunning palazzos.

Your private transfer escorts you to your centrally located hotel where you can see the tremendous Renaissance era dome of the Florence Cathedral. The dome was designed by Brunelleschi in the 15th century and remains the largest unreinforced brick dome in the world. The marble cathedral's exterior shines under the afternoon light, bursting with green trim. The cathedral is emblematic of the entire city, encompassing history and showcasing the beauty of its heritage, all while existing in the modern world.

What's Included: breakfast, transfer, accommodation

Day 7: Segway into the City

In the morning, the shops along Via de'Tornabuoni open their doors. The doors resemble something from a medieval castle. The scent of foamy cappuccino lingers in the air blending with freshly baked brioches from the local bakery. You meet your guide for the day and begin your exploration of Florence's encompassing history, traveling through the streets on a Segway. Your guide points out the marble signs hidden on the buildings, each noting the moment in Dante's Divine Comedy when the street, building, or person who once lived in that area of town, was mentioned.

The stalls in San Lorenzo overflow with pashminas, scarfs, hats, and famous Florentine leather goods, from coats to purses. The aroma of the leather drifts from the shops. Your guide points out the Basilica of San Lorenzo, one of the largest churches in the city, and the burial site of the principal members of the Medici family. Ornate, polished tile fills the interior, lined by a colonnade leading to the high altar. Michelangelo began the new Sacristy in the 16th century composed of three registers and topped by a pendentive dome.'?

What's Included: breakfast, tour, accommodation

Day 8: Marvels of Tuscany

Under the Tuscan morning sunlight, the hillsides glow with greenery. Italian cypress trees run alongside succulent vineyards. After breakfast, your private guide meets you at your hotel and escorts you into the famous countryside, taking you through the emerald grasses leading to medieval towns across the region.

The charming town of San Gimignano dates back to the Middle Ages, when pilgrims traveling to Rome would stop en route. The town originally had 70 towers creating an immense stone skyline, of which today only 13 remain. The tallest tower is Torre Grossa, constructed in the 14th century and standing 177 feet tall. The historic center bustles with activity at all times of year winding along narrow cobblestone alleyways leading to the triangular main square of Piazza della Cisterna. The towers and fortified homes became a status symbol for the families who constructed them, and a cluster of the towers encircle the central piazza. The scent of fresh gelato entices passersby.

On the northern edge of town is an unassuming Gothic style church constructed in the late 13th century. The interior contains an elaborate cycle of 15th century frescoes decorating the choir and painted by Benozzo Gozzoli, depicting the life of St. Augustine.'?

What's Included: breakfast, tour, accommodation

Day 9: Closing in on the Colosseum

The day brightens with the familiar aroma of a frothy cappuccino emanating from Caffe Scudieri. The bronze pigment of Neptune's Statue next to the Palazzo Vecchio glistens in the light. Your private transfer leads you to the train station where you once again board your first-class Orient-Travel compartment venturing southbound the remarkable city of Rome.

Arrive at Roma Termini and be whisked away to your sensational hotel located near the center of the Eternal City. Rome has maintained its classical appeal for millennia, with its iconic Roman ruins, medieval churches, and modern storefronts combining to make something tangibly special. Water spritzes from the Baroque statues at Piazza Navona. Elegant palazzos encircle the open square. Artists and architecture students settle in the plaza and recreate the buildings, attempting to capture the movement of the statues, especially Fontana dei Quattro Fiumi. The Fountain of the Four Rivers represents the four major rivers across four continents, with Roman Gods personifying the Nile, Ganges, Danube, and Rio de la Plata, each filtering into the single large basin. Plants and animals of their respective regions are etched into the marble near the personified rivers. A slender obelisk stands at the center of the fountain adorned with the dove and dating back to AD 81.

What's Included: breakfast, transfer, accommodation

Day 10: Eternal Images

The palm trees lining the Tiber River sway in the morning breeze. The sunlight captures the prestige of the white marble monument commemorating Vittorio Emanuele II, the king who unified Italy. The day is yours to explore the wonders of Rome, taking in the majesty of the Eternal City. Whether you choose to stroll around the Spanish Steps or tour the Colisseum, there is an endless amount of heritage and history to experience.

For a look into Roman prominence, journey to the Capitoline Museums on Via di Monte Tarpeo. The museum displays ancient sculptures and archeological discoveries from around Rome, including a relics dating back to the 1st century BC. The Palazzo dei Consevatori and Palazzo Nuovo house the collected museums dating back to the 15th century under the patronage of Pope Sixtus IV. The opulent interior stems as much from the polished tile floors and high ceilings, as from the art itself. An impressive statue of Marcus Aurelius riding his steed stands in the museum more than 13 feet tall. The emperor holds his hand out with an image of a conqueror, yet also casting an image of peace.

What's Included: breakfast, dinner, accommodation

Day 11: Roman Relaxation

The radiant colors of the Sistine Chapel brighten the interior. The unique story told in Rafael's School of Athens provides insight into the connection between the classics and Renaissance masters. Rome embraces you with a blanket of splendor, emanating from the meandering pathways that lead to iconic images of the city, such as the Trevi Fountain, and exquisite museums like the Vatican Museum. The remainder of the day is yours to see Rome in any and every way you wish to enjoy the city. You could even venture south to Naples for the day and visit the preserved Roman city of Pompeii.

The Pantheon stops you in your tracks when the cobblestone street opens up to Rome's best-preserved ancient monument. The 2,000-year-old temple has stood since AD 125. Gigantic bronze doors grace the entryway. When you walk in, you can't help but notice the unreinforced concrete dome, the largest of its kind ever built. The temple was originally dedicated to the classical gods but became consecrated as a Christian church in the 7th century AD. Sixteen Corinthian columns sustain the pediment. Marble paves the floor. The height from ground to ceiling is a staggering 142 feet tall. The structure and the fact that it still stands tall and strong, takes your breath away.

What's Included: breakfast, accommodation

Day 12: Tiber in the Distance

In the morning, the aroma of orange zest blends into the scent of freshly baked brioche. Cafes set their tables out along the streets and the flower stalls fill all over Rome with a blossoming fragrance. The Colosseum continues to stand as a symbol of the city and its impressive history, and overlooks the ruins of the Roman Forum.

Soon your private transfer will meet you at your hotel and escort you to the airport for your flight home. There is always so much more of Italy to see, you just need to take the time so see it.

What's Included: breakfast, transfer



Orient-Travelrecommends the following guidelines for customized Italy tour packages, excluding international flights:

  • 5-star: USD $450 - $1,000+ per person per day
  • 4-star: Minimum USD $350 per person per day
  • 3-star: Minimum USD $300 per person per day

The customized package will include hotels, airport transfers and other transportation within Italy, guided tours or activities, unique experiences, trip planning, and 24X7 support during your trip.

Please inquire for a custom quote. The price is customized based on final hotel choices, travel dates, and other custom preferences.