Amazing 14-Day Italy Itinerary with Capri

A 14 day trip to Italy 
4.75 out of 5 stars
16 reviews

Bask in the authentic charm and the simple wonder of Italy during your custom-tailored tour taking you from Rome to Capri, Lake Maggiore to Assisi. Travel across breathtaking horizons to uncover hidden sagas while gaining cultural insight into more than 3,000 years of history. Engage with the stories of the Medici family and witness the fruits of Michelangelo’s celebrated hands. Wander through lavish galleries showing the wealth of the former aristocracy and sample the treasured flavors of the remarkable wines. Engage with the extraordinary local specialties, travel the historical castles, and bask in the majestic landscapes discovered from the Amalfi Coast to Italian Alps. 

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

General Information

Detailed Itinerary

Places Visited 

Rome, Sorrento, Amalfi Coast, Vatican City, Capri, Assisi, Venice, Verona, Lake Maggiore, Lake Como, Florence, Pisa, Machiavelli Villa, Milan, Chianti, Montalcino, San Gimignano, Monte Cassino, Pompeii 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Rome – Arrive in Rome for a Fascinating Introductory Highlights Tour

The beauty of Rome derives from the combination of haunting ruins and inspiring artwork with vibrant life filling the piazzas with an indelible culture shaped over more than 2,500 years. Your flight will land at Fiumicino Airport, where your private transfer will greet you upon arrival in Rome. The historical legacies of the city form a remarkable skyline spreading from church spires to tiled rooftops, medieval bell towers to the ancient dome of the Pantheon. The aroma of traditional Roman cuisine emanates from trattorie filled with roast pig and freshly made pasta topped with black pepper and pecorino cheese. After settling into the comforts of your centrally located accommodation, your guide will meet you in the evening ready to lead you on an orientation of Rome through the piazzas and fountains for which the architecture is famous. 

Baroque palaces border the gorgeous cobblestone space of Piazza Navona alongside charming cafes and working street artists. The public square took shape in the 15th century atop the 1st-century BC Domiziano stadium. Gian Lorenzo Bernini created the stunning Fontana dei Quattro Fiumi in the 17th century as an ornate work depicting allegorical representations of the Nile, Ganges, Danube, and Rio de la Plata, the rivers on the world’s four known continents at the time. The soaring obelisk stands at the center of the four river gods representing the power of the Papal State surrounded by doves, the symbol of the Pamphili. The feature was initially brought to Rome in the 1st century AD during the reign of emperor Domitian. 

What’s Included: airport transfer, accommodation, tour 

Day 2: Rome – The Works of the Vatican and the Ancient History of Rome

In the morning, you will journey into the past with a visit to Vatican City. As one of the smallest independent states in the world, the Vatican boasts some of Western Civilization’s most prominent works of art filling both St. Peter’s Basilica and the Vatican Museum. The dome of St. Peter’s Basilica reaches 450 feet tall towering above the cobblestone square below. 

Michelangelo designed the architectural feature based on the breathtaking ancient enterprise of the Pantheon at the center of the historical city. The galleries inside the museum reveal the treasures of the Vatican collected through the centuries to span various Mediterranean civilizations from the Etruscans to Egyptians, Byzantines to celebrated Italian artists. The grandeur of the Vatican Museum welcomes you with lavish halls and towering ceilings. Walking through the gilded walls and ceilings of the Map Gallery glints with gilded edges in the natural light spilling through the windows. 

The walls contain the magnificent images of historic Italy as documented in the Middle Ages using the Apennines as a partition. You will reach the Sistine Chapel at the end of the tour. The famous rectangular hall was erected in the 15th century under the papacy of Sixtus IV. Michelangelo was one of the artists faced with decorating the chapel with frescoes amid the rise of Renaissance artistic tenets. The artist crafted one of the most celebrated collections of biblical scenes from the period along the ceiling embodied in the fascinating portrayal of Genesis beginning with the birth of Adam and Eve. 

What’s Included: accommodation, tour, breakfast

Day 3: Sorrento – The Monte Cassino Abbey and Magnificent Ruins of Pompeii 

In the morning, the natural sunlight pours through the oculus at the pinnacle of the Pantheon’s renowned dome providing enough light to fill the interior gallery. The splendid display of ancient Roman engineering continues to inspire architects and designers from around the world. After some time in the morning to take it in, your private transfer will greet you at your hotel after breakfast and escort you out of Rome and lead you down to the seaside city of Sorrento, located on the Bay of Naples. Before reaching the city, you can stop at Monte Cassino, an abbey perched atop a rocky outcropping at an altitude of 1,706 feet above sea level. 

The complex belonging to the Benedictine order was established in the 6th century and rebuilt in the 10th century. The monks became custodians of Italy’s history and treasures after the formation of the country in the 19th century before the Battle of Monte Cassino during World War II resulted in the Allies bombing the structure with the Germans attempting to stem the push of the Allied forces northward. Exploring the Abbey offers a sense of the ancient foundations supporting the contemporary walls reflecting the rich history and treasured artworks collected over time. 

During the Second World War, the complex houses up to 1,400 valuable works of art ranging from manuscripts to paintings that were moved to the Vatican at the beginning of the infamous battle. Not all of the 120 trucks loaded and bound for Rome made it to their final destination with a number of cases rerouted to the private collection of Hermann Göring. You will continue south to reach the captivating city of Pompeii, which was preserved in pumice and ash for nearly 2,000 years after the eruption of Mount Vesuvius in 79 AD. Nearly two-fifths of the vast design remains covered with many important discoveries made providing insight into the lives of Roman citizens in the former port city. 

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

Day 4: Sorrento – Capri’s Grandeur and Beauty with a Full Day Excursion

The mornings in Sorrento fill with the scent of freshly made espresso drifting through the dining room of your luxury accommodations. The view over the Bay of Naples brings an illustrious shine and the refreshing aroma of the sea breeze. You will catch the ferry bound for the captivating island of Capri. The seawall soars up to 200 feet above the water growing in magnitude as the boat reaches closer to the Marina Grande. The natural grandeur of the island has attracted Roman emperors and Hollywood stars alike eager to bask in the pleasures of the island away from the rush of mainland Europe amid dripping wisteria and tangled bougainvillea. 

A charming chairlift allows you to glide above the beautiful terraced gardens and hazy hillsides leading to the island’s highest mountain of Monte Solaro at 1,930 feet above sea level. The panorama along the summit spreads over the whitewashed homes of Anacapri town reaching across the Bay of Naples for a marvelous view of the Calabria mountains and cliff-side homes scattered across the Amalfi peninsula. The town of Anacapri remains a tranquil hideaway from the crowds of Capri Town. The piazzas in the historic center alight with blossoming geraniums and dangling bougainvillea leading to the Museum of Villa San Michele. The former home of a Swedish doctor, the museum now displays a timeline of the villa and the priceless artifacts amassed during the doctor’s life in his private collection.

What’s Included: accommodation, tour, breakfast 

Day 5: Assisi – Enjoy Mystical Ambiance in Historic Assisi and Mount Subasio

The scent of fresh pastries overtakes the dining room at breakfast accompanied by the familiar aroma of espresso. Your private transfer meets you in the hotel lobby after breakfast eager to lead you northbound into the often-overlooked region of Umbria and the fascinating city of Assisi. The walled city climbs the slopes of Mount Subasio situated beneath the summit reaching 4,232 feet above sea level crowned with the crenulated walls and dramatic towers of the picturesque Rocca Maggiore. The city hosts a marvelous portico belonging to the Temple of Minerva, which was erected in the 1st century BC but converted into a church in the 16th century. 

While the interior possesses a Baroque style, the face retains the original Roman flourishes such as the beams resting on the Corinthian capitals. Your guide leads you into the welcoming ambiance of the Basilica di San Francesco. The structure encompasses two separate but connected churches with the oldest foundations dating back to 1228 with Pope Gregory IX placing the first stone the day after Francis was canonized. The aromas of frankincense and myrrh sweep through the naves as your guide takes you into the lower church to view the magnificent frescoes depicting the life and times of St. Francis as painted by the celebrated artist if the 13th and 14th centuries, Giotto. 

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

Day 6: Venice – The Charms of Verona before Reaching Elegant Venice

Fair Verona brims with history around every corner hidden behind the lavish preserved walls of the ancient Roman amphitheater decorating Piazza Brà. The remarkable feat of engineering during the 3rd century AD could hold up to 22,000 spectators and continues to support thousands of visitors each summer across the 44 rows of stadium seating during the celebrated Verona Opera Festival. Giusti Garden was designed during the Renaissance along the eastern edge of the historic city center. The stunning landscape contains shading trees and elaborate fountains, secret grottos and ancient inscriptions spanning several levels. A gargoyle was erected above a stalactite cave depicting tongues of fire emerging from its mouth. 

The upper terraces provide spectacular views of the city and look down onto the complex hedge maze considered one of the oldest in Europe. A person cannot visit Verona without meeting with the city’s patron of love, the renowned Juliet Capulet made famous for her part as the heroine of Shakespeare’s star-crossed love story Romeo and Juliet. The home of the Capulet family has a stone archway littered with letters of hope and praise from lovelorn fans eager for Juliet’s blessing in their lives. A bronze statue of the teenager stands near the balcony, the latter of which was erected in the 1930s to emphasize romance of the specific scene in the play, as well as form a deeper connection with the family villa. 

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

Day 7: Venice – Venice’s Secrets at St. Mark’s Square and the Doge’s Palace

The gondolas and barges of Venice return to the bustle of the Grand Canal in the morning, winding along the 2-mile waterway. The morning Rialto Market fills with vendors selling fresh seafood like bream, squid, and octopus while produce vendors growing crops on the farm island of San’Erasmo offer colorful displays of apples, eggplants, and artichokes. You wander alongside the canals and through the narrow network of labyrinthine lanes to reach fascinating St. Mark’s Square. The grand image of the basilica frames the public space adjacent to the Gothic Venetian façade of the Doge’s Palace. 

The structure was originally erected as the private chapel for the Doge and decorated with Byzantine artistry and aesthetic brought back from Constantinople. The five bulbous domes tower above the piazza at 141 feet tall. The interior shines with gilded beauty spanning the columns, walls, and ceiling encompassing more than 45,639 square feet. Later mosaics dating back to the Renaissance were contributed to artists like Tintoretto and Titian. The walls and columns shimmer apart from the gilded aplomb due to the addition of 2,000 precious stones and gems. 

Inside the Doge’s Palace, the dramatic aesthetic emboldens the ambiance of the former center of the Venetian Republic. A figure depicting Doge Francesco Foscari kneels before a Lion of St. Mark indicating how the power of the state takes precedence over the individual. Inside the halls of the lavish palace, your guide leads you into the secret chamber of the Sala del Consiglio dei Dieci, where the Council of Ten met. The council was considered the power behind the throne in charge of the republic’s secret police state. The elegant room contains wood paneling and gilded adornments, as well as a remarkable painting depicting Jupiter launching thunderbolts at the vices. 

What’s Included: accommodation, tour, breakfast

Day 8: Lake Maggiore – Milan’s Splendor and History en route to the Alps

The gorgeous gondolas of Venice spread out through the canals of the city in the morning with artisan crafters returning to their workshops shaping new iconic boats in the Squero di san Trovaso. Your water taxi will meet you at your hotel to ferry you over the water to reach your private transfer bound for Lake Maggiore. Before venturing into the Lake District in the Italian Alps, you spend time discovering the treasures of Milan. The capital of Italian commerce and fashion contains layers of ancient and contemporary history ranging from the baptism of St. Augustine to the crowning of Napoleon, as well as hosting the beginnings of Mussolini’s Fascist party. The main feature of the city stands at the heart of Piazza del Duomo in the form of the enchanting drama of the cathedral, also referred to as the Duomo. 

The interior can hold up to 40,000 people making it one of the largest cathedrals. Construction began in the 14th century but was not completed until the 19th century during the rule of Napoleon. 2,245 hand-carved marble statues decorate the rooftop capturing the iconic image of a Gothic structure while 52 large pillars support the interior with natural light pouring through in radiant colors from the stained-glass windows in the nave. The roof offers a terrace open to visitors interested in taking in the views leading across the rooftops to the snow-covered Alps and a stairwell near the central doorway allows visitors to descend beneath piazza into the Basilica di Santa Tecla, which was first erected in the 4th century. 

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

Day 9: Lake Maggiore – The Picturesque Waters and Towns of Lake Como

The elegant blue of Lake Maggiore resembles a painting with the water lapping against the distant shores decorated with snowcapped mountain peaks with sporadic medieval towns sprouting up between craggy slopes. Many of the colorful buildings lining the cobblestone streets and piazzas retain an ambiance of the Belle Époque, when the region became a major tourist destination due to the opening of the Simplon Pass between Switzerland and Italy. You can see the gorgeous palace rising above the water an Isla Bella where small shell-shaped grottos and sophisticated statues adorn grandiose garden terraces. You will venture to the popular shores of Lake Como to wander along the towns at the edge of the cobalt blue water reflecting the breathtaking alpine scenery. 

The town of Como boasts a medieval ambiance at its historical center emanating from the 14th-century Gothic façade of the cathedral. Statues crafted from stone and marble features surround the bright rose window. The narrow lake resembles a fjord reaching 31 miles long. The town of Bellagio is known as the region’s prettiest town settled on the banks where the three arms of Lake Como meet. The grandeur and charm of the town rises from the narrow, cobbled lanes and well-maintained buildings filling the town with a mixture of vibrant aromas like chocolate, coffee, marzipan, and pine. Villa Serbelloni was erected in the 16th century and designed with a combination of coffered and vaulted ceilings. The grounds enclose a wooded hill on a promontory dominating the Bellagio skyline. 

What’s Included: accommodation, tour, breakfast

Day 10: Florence – To Pisa for Remarkable Architecture and Dine at a Villa  

From your luxury accommodations, you can watch the boats passing over the Lake Maggiore as the morning ferries crisscrossing between towns and fishers setting out on the water for the day’s catch. After breakfast, your private transfer whisks you down the slopes of the Alps bound for the Renaissance city of Florence. Before reaching the captivating architecture and renowned artwork brimming in the capital of Tuscany, you make a stop at Pisa to uncover the famous and lesser-known wonders of the former maritime powerhouse. 

The majesty of Pisa surrounds the Campo dei Miracoli, the public space possessing the infamous Leaning Tower. The remarkable structure remains a marvel of engineering wit maintained since the 12th century when the first stone of laid. The foundation began to sink before the third story was erected with engineers counterbalancing the structure over time. The tower holds 294 steps to the top floor retaining a nearly four-degree list causing a more than 12-foot distance between the base and tip. 

When visiting the Campo Santo, you find one of the unique and often-overlooked structures in Italy. The grounds were built knights returned from the Fourth Crusade with dirt taken from Golgotha in the 13th century. During the Allied bombing in the Second World War, the tin roof melted badly damaging the frescoes inside. However, the loss of color and paint revealed the original sinópie, the sketches made in red pigment on the wall crafted by the original artist instead of students or apprentices. 

In the evening, you can make your way to Villa Machiavelli for a traditional Tuscan meal set inside the mansion where the famous philosopher spent his exile from Florence. The 14th-century structure is tucked away in the majestic countryside and acts as a boutique hotel spanning 600 acres of lush vineyards, olive groves, and cypress trees. The aroma of freshly made picio fills the dining room accompanied by the scent of a decadent ragù. The kitchen takes its time preparing the famous T-bone beefsteak known as Bistecca Fiorentina. 

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

Day 11: Florence – The Captivating Art and Architecture of the Renaissance

The morning sunlight washes over Florence to reveal the remarkable skyline that is decorated with church towers, tile-rooftops, and crowned with the impressive dome of the cathedral. The city acted as the “Cradle of the Renaissance,” inspiring artists like Michelangelo, Botticelli, Donatello, and Leonardo da Vinci, as well as the famous epic poet Dante Alighieri.  The iconic structure of the Duomo took almost 150 years to complete and contains 44 stained-glass windows filling the long nave with fantastic colorful light. 

The neo-Gothic façade shines with layered green, white, and pink marble harmonizing with neighboring Giotto’s tower. The interior is nearly barren of ostentation leaving the soaring Gothic arches and stone pillars to strike awe in the hearts of visitors drawing your eye to the floating transept. A stunning portrait on the north aisle depicts Dante standing beside Florence with the mountain of Purgatory leading to Paradise. Standing beneath the reveals the enormity of the largest unreinforced brick-dome in the world. The striking images of Giorgio Vasari’s Last Judgement circles the feature encompassing 43,055 square feet with 24 old men of the Apocalypse at the center of the dome looking outward. 

After traversing the streets of the city and visiting the lavish churches decorated with works from venerated master artists, you enter the Accademia for a meeting with Michelangelo’s famous sculpture, the David. Walking down the long, bright marble hallway takes you past the artist’s unfinished slaves who are eternally emerging from the stone as if being birthed. The magnificent image of David stands on a pedestal reaching over 17 feet tall. The intricate detail of the figure’s bulging muscles and pulsing veins add to the lifelike quality of the figure celebrated both for his humanistic features but also the contemplative, fearful expression occurring before his battle with Goliath. 

What’s Included: accommodation, tour, breakfast

Day 12: Florence – A Sensational Tuscan Wine Tour and Accademia Visit

In the morning, the Tuscan countryside glows with an emerald hue from the famous rolling hills, rows of cypress trees, and vineyards growing along the undulating slopes. You venture outside of Florence for a day visiting the charm and beauty of Val d’Orcia where the picturesque landscape spreads from chalk plains to conical hills supporting medieval settlements and magnificent abbeys positioned along points of the famous Via Francigena, the road once leading between France and the Vatican. The narrow cobblestone streets of Montalcino weave around the numerous wine shops known as enoteche opening to panoramas of sweeping vineyards. 

Historically, Montalcino attempted to stem the tide of powerful Tuscan city-states like Florence and Siena before falling to the latter, sustaining the medieval presence in the historic city walls and colorful buildings. The 14th-century fortress crowning the town acts as a symbol of the history and the strength of the smaller settlement that stood in defiance of the Florentine Republic in the 16th century as well as carrying an important cultural component of the Val d’Orcia in showcasing local wines. You enter the tasting room in the wine shop surrounded by the remarkable ambiance of the dramatic fortress. Your guide pours a sample of Brunello di Montalcino, and the wine is made with 100 percent Sangiovese grapes. You will find aromas of leather, hazelnut, and anise emanating from the glass resulting in a chocolatey note coating your palate. 

What’s Included: accommodation, tour, breakfast

Day 13: Rome – The Tuscan Scenery at San Gimignano en route to Rome

The doors to the lesser-known Museo dell’Opera del Duomo open in the morning offering visitors glimpses of Ghiberti’s original 15th-century gilded masterpiece, The Gates of Paradise. The golden bronze doors adorned the Baptistry stand over 52 feet tall with panels depicting biblical stories. After breakfast, your private transfer will meet you at your hotel ready to take you back to Rome stopping in the fairytale ambiance of San Gimignano’s preserved medieval structures along the way. The pristine appearance captures 13 of the original 70 towers that created the city’s distinctive skyline representing the wealth of particular noble families. 

Walking through the preserved gates takes you back in time along lanes connecting to the Romanesque church of Santa Maria Assunta. The structure was originally constructed in the 12th century but enlarged in 1457 with an additional transept and side chapels. Fresco cycles attributed to 15th-century artist Benozzo Gozzoli. A fresco depicting Adam and Eve’s expulsion from Eden lines the top row of the wall along the series of biblical narratives decorating the main nave. The Torre Grossa is the tallest tower in the city reaching 177 feet above the surrounding streets. After its construction the civic council decreed another tower could be erected higher, thus affording Torre Grossa the best views of the surrounding countryside leading northward to the Apuan mountains over 120 miles away. 

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

Day 14: Rome – Depart for Home

The scent of roasted coffee beans filters out of Antico Caffé Greco, the oldest café in Rome, which first opened in 1760, second only to Venice’s Caffé Florian. The remarkable colors of fresh produce and the sweet scent of delicious homemade honey lingers along the aisles of morning market in Campo de’ Fiori. An early crowd of tourists often visit the rushing waters of the Trevi Fountain, one of the most iconic images of Rome. After breakfast and one last chance to take it all in, your private transfer will greet you at the hotel and escort you out of Rome with plenty of time to make your flight at Fiumicino Airport. 

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.