21 Day Italy Grand Tour

Upon arrival at Milan Airport, you will be met by your private driver and transferred directly to your centrally located accommodation.

Milan Duomo & Rooftop Experience

Your guided tour begins at the magnificent Duomo di Milano, one of Europe’s largest and most impressive Gothic cathedrals.

Accompanied by your guide, step inside this extraordinary structure to discover centuries of history, craftsmanship, and religious significance. The experience continues above the city as you access the cathedral’s rooftop terraces, where intricate marble spires rise around you, and panoramic views stretch across Milan’s skyline.

Exploring the Brera District

Leaving the Duomo behind, continue into the charming Brera district, one of Milan’s most elegant neighborhoods.

Known for its galleries, artisan boutiques, and atmospheric streets, Brera offers a more intimate glimpse into local life. 

As you stroll through its historic lanes, your guide will introduce the area’s artistic heritage while highlighting the cafés, courtyards, and hidden corners that make it a favorite among Milanese residents.

The relaxed pace of the afternoon provides an ideal introduction to Italy before the journey continues in the days ahead.

Evening at Leisure

Following your guided experience, enjoy the remainder of the evening at your own pace.

Whether you choose to dine in one of Brera’s renowned restaurants, enjoy an aperitivo overlooking a lively piazza, or simply relax after your travels, Milan offers the perfect setting for your first night in Italy.

Today offers a deeper exploration of Milan’s cultural, historical, and artistic identity alongside your private guide.

While many visitors view Milan primarily as Italy’s fashion capital, the city possesses a rich history stretching back over two thousand years. Today’s experience uncovers the layers of history that have shaped the city while introducing the traditions and culture that continue to define modern Milan.

Through the Historic Center

Accompanied by your guide, explore the city’s historic core, where grand squares, elegant arcades, and historic landmarks reveal Milan’s evolution through the centuries.

As you move between important sites, your guide will connect the city’s Roman origins, medieval development, Renaissance achievements, and modern influence, creating a fuller understanding of Milan beyond its reputation for fashion and finance.

Along the way, discover hidden courtyards, local gathering places, and architectural details that are often overlooked by visitors.

Milan’s Artistic Heritage

Depending on your personal interests, the day can include additional time within one of Milan’s celebrated museums, galleries, or historic buildings.

Whether focused on fine art, design, architecture, or local history, these experiences provide further insight into the city’s important role within Italian culture.

Your guide will tailor the experience accordingly, ensuring the day reflects your own interests and preferred pace.

A Relaxed Evening in Milan

The remainder of the afternoon and evening are left free for independent exploration.

This is an excellent opportunity to revisit favorite areas, enjoy Milan’s celebrated culinary scene, or simply embrace the rhythm of daily life in one of Italy’s most sophisticated cities.

This morning, leave the city behind as you travel north into one of Italy’s most celebrated landscapes.

Your private driver will collect you from your accommodation and transfer you to Lake Como in a comfortable executive vehicle.

Arrival at Lake Como

As the lake comes into view, you’ll immediately understand why Lake Como has attracted aristocrats, artists, and travelers for centuries.

Surrounded by dramatic mountains and dotted with elegant villas, historic villages, and lakeside promenades, the setting feels worlds away from the city you left behind earlier in the morning.

Upon arrival, check into your accommodation and take time to settle into your new surroundings.

An Afternoon by the Lake

The remainder of the day is intentionally relaxed.

Perhaps enjoy a leisurely lakeside walk, discover the local village, or simply unwind while taking in the ever-changing views across the water.

Meet your private captain and board your vessel for a personalized cruise across the lake, discovering elegant villas, picturesque villages, and some of the region’s most celebrated scenery.

Cruising Lake Como

As you glide across the lake, your captain will share stories of the historic villas, famous residents, and local traditions that have shaped life along the shoreline for generations.

Passing grand estates surrounded by manicured gardens, you’ll gain a greater appreciation for the history and prestige that have made Lake Como one of Europe’s most desirable destinations.

Bellagio

Your first stop is Bellagio, often referred to as the “Pearl of Lake Como.”

Here, you’ll have time to wander through charming streets lined with boutiques, cafés, and colorful buildings while enjoying beautiful views across the lake’s intersecting branches.

The town’s elegant atmosphere and scenic waterfront make it one of the most photographed locations on the lake.

Varenna

The experience continues to Varenna, a quieter and more traditional lakeside village.

Its narrow alleyways, historic waterfront, and relaxed pace provide a striking contrast to Bellagio while offering an authentic glimpse into local life on the lake.

Following your time on the water, return to your accommodation and enjoy the evening at leisure.

Today offers a more relaxed pace, allowing you to further appreciate the beauty and elegance of Lake Como.

Historic Lake Villas

A visit to one of Lake Como’s celebrated villas provides fascinating insight into the region’s history and culture.

Depending on availability and your interests, explore either Villa Balbianello or Villa Carlotta, both renowned for their magnificent interiors, landscaped gardens, and spectacular lakeside settings.

As you wander through the grounds, you’ll discover how these historic estates played important roles in shaping the character of the lake while enjoying some of the finest views in the region.

The remainder of the day is yours to enjoy as you wish.

Today, travel from the Italian Lakes to one of the world’s most extraordinary cities.

Your private driver will transfer you to the railway station, where you’ll board a first-class high-speed train for the journey east towards Venice.

Private Water Taxi Arrival

Upon arrival in Venice, the experience becomes uniquely Venetian.

Instead of continuing by road, you’ll board a private water taxi and travel directly through the city’s canals to your accommodation.

Gliding past historic palaces, bridges, and waterfront buildings provides a memorable first introduction to Venice and offers an experience unlike anywhere else in Italy.

After checking into your hotel, enjoy your first evening in the city at leisure.

Today is dedicated to discovering the landmarks that shaped Venice into one of Europe’s great maritime powers.

Accompanied by your private guide, explore the heart of the Venetian Republic while gaining a deeper understanding of the city’s extraordinary history.

St. Mark’s Square

Your experience begins in St. Mark’s Square, often described as the drawing room of Europe.

Surrounded by magnificent architecture and centuries of history, the square provides the perfect setting for understanding Venice’s rise as a powerful trading republic.

Your guide will explain the significance of the surrounding buildings and the events that shaped the city’s development.

St. Mark’s Basilica

With skip-the-line access included, enter Venice’s most famous church and admire its extraordinary mosaics, architecture, and artistic treasures.

Your guide will reveal the influences that arrived in Venice through centuries of trade, helping explain why the basilica differs so dramatically from many other churches throughout Italy.

Doge’s Palace

The experience continues within the Doge’s Palace, once the political and administrative center of the Venetian Republic.

Exploring grand chambers, council rooms, and historic passageways, you’ll gain insight into how Venice governed a vast maritime empire while maintaining its independence for centuries.

Today takes you beyond the canals of Venice itself and into the wider Venetian Lagoon, where centuries-old traditions continue to thrive on a collection of islands scattered across the water.

Board your private boat and set off alongside your captain, enjoying a more flexible and comfortable way to explore the lagoon while discovering destinations inaccessible to most day visitors.

Murano & The Art of Glassmaking

Your first stop is Murano, an island synonymous with glassmaking for more than seven centuries.

Here, visit a traditional workshop where master craftsmen continue to practice techniques that have been passed down through generations. As you watch artisans transform molten glass into intricate works of art, you’ll gain a deeper appreciation for one of Venice’s most famous exports.

Burano’s Colorful Streets

Leaving Murano behind, continue across the lagoon to Burano, perhaps Venice’s most picturesque island.

Famous for its brightly painted houses and peaceful atmosphere, Burano provides a welcome contrast to the busier streets of Venice. 

Strolling through its colorful lanes, you’ll discover a traditional fishing community where daily life unfolds at a gentler pace.

The island is also known for its historic lace-making tradition, which has played an important role in local culture for centuries.

Following your time in the lagoon, cruise back towards Venice while enjoying views across the water and the city’s distinctive skyline.

This morning, bid farewell to Venice and continue south towards Florence, the birthplace of the Renaissance.

Your day begins with a private water taxi transfer through Venice’s canals, offering one final opportunity to experience the city from the water before arriving at the railway station.

Board your first-class high-speed train and relax as you travel through some of Italy’s most beautiful landscapes.

Upon arrival, your private driver will meet you and transfer you directly to your accommodation in Florence’s historic center.

The remainder of the day is free to settle into your new surroundings.

Perhaps enjoy an evening stroll through the historic center, cross the Ponte Vecchio, or simply relax in preparation for the days of exploration ahead.

Today offers an introduction to Florence, a city that shaped the course of European art, architecture, and intellectual thought.

Accompanied by your private guide, discover the landmarks and stories that transformed Florence into the center of the Renaissance while gaining a deeper understanding of the city’s remarkable influence.

Florence Cathedral

Your exploration begins at Florence Cathedral, one of Italy’s most celebrated architectural achievements.

Dominated by Brunelleschi’s revolutionary dome, the cathedral represents a turning point in Renaissance engineering and design. As your guide reveals the story behind its construction, you’ll gain insight into the ambition and innovation that defined Florence during its golden age.

Piazza della Signoria

Continue to Piazza della Signoria, the historic political heart of Florence.

Surrounded by elegant palaces and remarkable sculptures, the square has served as the backdrop for some of the city’s most significant events for centuries. Your guide will explain the power struggles, political intrigue, and influential families that shaped Florence’s history.

Through the Historic Center

The experience continues through Florence’s atmospheric streets, where workshops, churches, palaces, and hidden courtyards reveal the city’s rich heritage.

Throughout the day, your guide will connect the landmarks, people, and events that transformed Florence into one of the most influential cities in Europe.

Following your guided exploration, enjoy the evening at leisure.

Accompanied by your private guide and benefiting from skip-the-line access throughout, you’ll explore some of the most important collections in Italy while gaining a deeper understanding of the artists who changed the course of Western art.

Uffizi Gallery Tour

Begin at the world-renowned Uffizi Gallery, home to one of the most significant collections of Renaissance art anywhere in the world.

As you move through its galleries, your guide will introduce works by Botticelli, Leonardo da Vinci, Raphael, and Michelangelo, explaining both their artistic innovations and their importance within the broader story of Florence.

Rather than simply viewing famous paintings, you’ll gain a greater appreciation for the cultural movement that transformed Europe.

Accademia Gallery

The experience continues at the Accademia Gallery, home to Michelangelo’s masterpiece, David.

Standing before the sculpture in person is one of Florence’s most memorable experiences. Your guide will explain the remarkable story behind its creation while highlighting the artistic techniques and symbolism that have made it one of the world’s most celebrated works of art.

Today marks a transition from Florence’s urban elegance to the slower pace of rural Tuscany.

Leaving the city behind with your private driver, travel through rolling hills, vineyards, olive groves, and historic villages as you make your way towards your countryside accommodation.

Boutique Winery Experience

A highlight of the day is a visit to a carefully selected boutique winery.

Explore the cellars alongside local experts while learning about the production methods, grape varieties, and traditions that define Tuscan winemaking. 

Guided tastings provide an introduction to the wines of the region while offering insight into the close relationship between landscape and agriculture.

Following your winery visit, continue to your accommodation and settle into your surroundings.

The remainder of the afternoon is left free, allowing time to relax and embrace the slower rhythm of life in rural Tuscany.

Today is devoted to two of Tuscany’s most celebrated medieval towns, each offering its own unique character and history.

Traveling with your private driver, journey through some of the region’s most beautiful countryside as you explore destinations that have retained their historic charm for centuries.

Discovering Siena

Upon arrival in Siena, meet your private guide and begin exploring one of Italy’s most fascinating historic cities.

Its narrow streets, distinctive neighborhoods, and remarkable architecture reveal a city whose identity remains deeply connected to its medieval past. 

As you walk through the historic center, your guide will explain the traditions, rivalries, and customs that continue to shape life in Siena today.

Piazza del Campo & Siena Cathedral

At the heart of the city lies Piazza del Campo, one of Europe’s most beautiful public squares and home to the famous Palio horse race.

Nearby, Siena Cathedral showcases extraordinary artistic and architectural achievements, with intricate marble work and remarkable interiors that rival many of Italy’s more famous churches.

San Gimignano

The afternoon takes you to San Gimignano, whose skyline of medieval towers has earned it the nickname “The Medieval Manhattan.”

With time to explore independently, wander through its historic streets, browse artisan shops, and enjoy spectacular views across the Tuscan countryside.

Your final day in Tuscany is intentionally unhurried, allowing time to fully appreciate the surroundings and enjoy the region at a slower pace.

Private Culinary Experience

For those wishing to deepen their connection to Tuscan culture, a private cooking experience offers the opportunity to learn traditional recipes and techniques alongside local hosts.

Using fresh regional ingredients, you’ll gain insight into the culinary traditions that have shaped Tuscan cuisine for generations while enjoying the results of your efforts in a relaxed countryside setting.

Alternative Wine Experience

Alternatively, choose to continue exploring Tuscany’s celebrated wine culture with an additional tasting experience at a carefully selected estate.

Meet local producers, learn about different production styles, and enjoy further opportunities to sample some of the region’s finest wines.

The remainder of the day is left free to enjoy as you wish.

Today, leave the rolling hills of Tuscany behind as you travel south to Rome, the Eternal City and one of the world’s most historically significant destinations.

Your private driver will collect you from your countryside accommodation and transfer you through the Tuscan landscape to Florence’s railway station. From here, board a first-class high-speed train and enjoy a comfortable journey towards Italy’s capital.

Arrival in the Eternal City

As you enter the city, Rome immediately reveals its unique character. Ancient monuments, Renaissance churches, elegant piazzas, and bustling streets coexist in a way found nowhere else in Italy.

Perhaps take a leisurely stroll through the surrounding neighborhoods, enjoy your first Roman dinner in a traditional trattoria, or simply relax and prepare for the days of exploration ahead.

While Rome’s history stretches back more than two thousand years, many of its most celebrated landmarks can be discovered on foot, allowing you to experience the atmosphere and rhythm of the city as you move between its famous squares, fountains, and monuments.

The Pantheon

Your exploration begins at the Pantheon, one of the most remarkable buildings to survive from Ancient Rome.

Entering beneath its vast dome, your guide will explain the engineering achievements that continue to astonish architects today, while also revealing how the structure evolved from a pagan temple into one of Rome’s most important churches.

Piazza Navona

A short walk brings you to Piazza Navona, one of Rome’s most elegant public spaces.

Built upon the site of an ancient Roman stadium, the square is surrounded by baroque architecture and animated by cafés, artists, and street performers. Here, your guide will explain how the city’s layers of history continue to overlap in fascinating ways.

Trevi Fountain

Continue through Rome’s atmospheric streets to the Trevi Fountain, where centuries of art, mythology, and engineering combine to create one of Italy’s most iconic landmarks.

Your guide will share the stories behind the fountain’s design while revealing details often overlooked by visitors passing through the busy square.

Spanish Steps

The experience concludes at the Spanish Steps, where Romans and visitors alike gather to enjoy one of the city’s most vibrant meeting places.

From here, you’ll gain a deeper understanding of the layout and character of the historic center, making future exploration both easier and more rewarding.

Today is dedicated to Vatican City, home to some of the world’s most important artistic, religious, and cultural treasures.

Accompanied by your private Vatican guide, you’ll explore the collections and monuments that have made this tiny independent state one of the most visited destinations in Europe.

Vatican Museums

With skip-the-line access included, bypass the lengthy queues and enter the Vatican Museums through a carefully curated route designed to maximize your experience.

Rather than attempting to see everything, your guide will focus on the most significant galleries and masterpieces, helping bring centuries of artistic achievement into context.

Along the way, you’ll encounter works collected by popes over generations, reflecting the Vatican’s extraordinary role as a patron of the arts.

Sistine Chapel

Before entering the Sistine Chapel, your guide will prepare you with insight into Michelangelo’s vision, techniques, and the immense challenge of creating one of the most celebrated artistic achievements in history.

Once inside, you’ll have the opportunity to fully appreciate the famous ceiling and The Last Judgment with a deeper understanding of their symbolism and significance.

St Peter’s Basilica

Where access permits, continue directly into St Peter’s Basilica through a reserved internal passage, avoiding the main visitor queues.

Inside, discover one of Christianity’s most important churches, home to remarkable architecture, sculpture, and centuries of religious history.

Today takes you deep into the heart of Ancient Rome, exploring the monuments and ruins that once formed the center of one of history’s greatest empires.

The Colosseum

Your experience begins with skip-the-line access to the Colosseum, the world’s most famous amphitheater.

As you explore its immense structure, your guide will explain the engineering innovations that made its construction possible while sharing stories of gladiators, emperors, and the spectacles that once captivated tens of thousands of spectators.

Roman Forum

Leaving the Colosseum behind, continue into the Roman Forum, the political, religious, and commercial heart of Ancient Rome.

Among temples, government buildings, and public spaces, your guide will recreate the daily life of the city while explaining how decisions made here influenced much of the ancient world.

Palatine Hill

The experience concludes atop Palatine Hill, where Rome’s elite once built their grand residences overlooking the city.

In addition to spectacular views, the site offers important insight into the origins of Rome itself and the emperors who shaped its history.

Board a first-class high-speed train to Naples before continuing with your private driver towards one of Italy’s most scenic regions.

Upon arrival, settle into your accommodation and take time to appreciate your surroundings.

Colorful villages cling to steep cliffs above the sea while terraces of lemon groves and vineyards cascade down the hillsides.

Enjoy the remainder of the evening at leisure, perhaps with dinner overlooking the coastline as the sun sets across the Tyrrhenian Sea.

Today is dedicated to experiencing the Amalfi Coast and Capri from the water, providing a completely different perspective on one of Italy’s most beautiful regions.

Board your private boat and spend the day cruising alongside dramatic cliffs, hidden coves, and picturesque villages that line the coastline.

Cruising the Amalfi Coast

As your skipper navigates the coastline, you’ll enjoy uninterrupted views of colorful villages, rugged cliffs, and secluded beaches that are inaccessible by road.

The flexibility of a private boat allows the day to unfold at a relaxed pace tailored to your preferences.

Discovering Capri

Continuing across the water, arrive at the island of Capri, long favored by artists, writers, and travelers seeking beauty and tranquillity.

Cruise around the island to admire its dramatic rock formations, sea caves, and spectacular coastal scenery before choosing whether to spend time ashore.

Should you wish to disembark, there is time to discover Capri’s elegant town center, visit Anacapri, browse local boutiques, or simply enjoy a leisurely lunch overlooking the sea.

As the afternoon draws to a close, return to the mainland while enjoying one final opportunity to admire the coastline from the water.