14 Days in Italy Tour

Your Italian journey begins beyond the crowds, exploring a side of Rome that many visitors never experience.

With your private guide, travel along the ancient Appian Way, once one of the most important roads in the Roman Empire. As you walk sections of this remarkably preserved route, your guide will explain how goods, armies, and travelers moved across the empire from this very road.

Continue beneath the city into the Catacombs, where early Christian communities created vast underground burial chambers. As you explore these atmospheric tunnels, you’ll gain insight into the religious and social history of Ancient Rome far from the grandeur of its imperial monuments.

The day concludes at Aqueduct Park, where towering Roman aqueducts still cross the countryside. Here, your guide will explain the engineering achievements that supplied water to one of the greatest cities in history while you enjoy one of Rome’s most scenic and lesser-known landscapes.

This experience offers a fascinating introduction to Rome before exploring its more famous landmarks later in the itinerary.

Today is dedicated to Vatican City, which you will explore with your own private guide.

With skip-the-line access, follow a curated route through the Vatican Museums, focusing on key galleries and masterpieces. After preparing you in advance, your guide will lead you into the Sistine Chapel for a deeper appreciation of Michelangelo’s work.

Next, head directly into St. Peter’s Basilica, where your guide will highlight its most important features.

Explore Ancient Rome with your private guide, beginning with the Colosseum and continuing through the Roman Forum and Palatine Hill.

Through expert interpretation, your guide will explain how these spaces functioned at the height of the Roman Empire, transforming the ruins into a clear and engaging narrative.

Following your arrival in Florence after the one and a half hour high speed train journey, meet your private guide for an introduction to the city that goes beyond its famous monuments and museums.

Begin in the Oltrarno district, long regarded as Florence’s artisan quarter. Here, narrow streets and historic workshops preserve centuries-old crafts that continue to shape the city’s identity today.

Visit a traditional leather workshop to learn about one of Florence’s most famous industries before continuing to a goldsmith’s studio, where skilled artisans continue techniques passed down through generations. 

Along the way, your guide will lead you through elegant squares, hidden courtyards, and scenic viewpoints that reveal Florence from a local perspective while introducing the stories that transformed this small Tuscan city into the birthplace of the Renaissance.

Today is dedicated to Florence’s artistic heritage, explored in depth with your private guide.

Begin with skip-the-line access to the Uffizi Gallery, where your guide will lead you through a carefully curated selection of works rather than attempting to cover the entire collection. Through clear explanation and storytelling, you’ll gain an understanding of key masterpieces by Botticelli, Leonardo da Vinci, and Michelangelo, as well as the development of Renaissance art.

Continue to the Accademia Gallery for a focused visit centered around Michelangelo’s David. Your guide will explain the story behind its creation, the techniques involved, and its importance within both Florence and the wider art world.

Throughout the day, your guide ensures a structured and engaging experience, allowing you to fully appreciate the art without feeling overwhelmed.

Today, leave Florence behind as your private driver escorts you into the rolling hills of Tuscany.

After settling into your countryside accommodation, enjoy a private winery experience where you’ll learn about local wine production and sample regional varieties while overlooking vineyards and olive groves that stretch across the landscape.

Later, take part in a private farmhouse cooking lesson hosted by local experts. Using fresh seasonal ingredients and traditional techniques, you’ll learn how classic Tuscan dishes are prepared before sitting down to enjoy the meal you’ve helped create.

This hands-on experience provides a deeper connection to Tuscan culture and offers an authentic glimpse into the region’s culinary traditions.

The evening is spent surrounded by vineyards, cypress trees, and the peaceful rhythm of rural Tuscany.

Today is dedicated to the landscapes that have made Tuscany famous worldwide.

With your private driver-guide, travel through the UNESCO-listed Val d’Orcia, a region of rolling hills, cypress-lined roads, vineyards, and hilltop villages synonymous with the Tuscan countryside.

Your first stop is Pienza, a beautifully preserved hilltop town conceived by Pope Pius II during the Renaissance. Stroll through its elegant streets with your guide, discovering panoramic viewpoints overlooking the Val d’Orcia and learning how this small town became one of Italy’s earliest examples of urban planning.

Continue to Montepulciano, one of Tuscany’s most celebrated wine towns. Surrounded by vineyards and medieval walls, the town combines stunning architecture with a long winemaking tradition.

Explore its historic center before visiting a local wine estate where you’ll enjoy a tasting of Vino Nobile di Montepulciano alongside regional specialties.

Throughout the day, your guide will include scenic stops at some of Tuscany’s most photographed viewpoints. Rolling vineyards, isolated farmhouses, cypress-lined roads, and golden hills provide endless opportunities for photographs and quiet moments to simply enjoy the scenery.

Travel north to Venice via the 2-hour high-speed train before transferring by private water taxi through the city’s canals to your accommodation.

Rather than focusing immediately on the major landmarks, your first experience of Venice takes place after many day visitors have departed and the city begins to reveal its quieter character.

Meet your private guide for an atmospheric evening walk through Cannaregio, one of Venice’s most authentic neighborhoods. Explore the historic Jewish Ghetto, discover hidden canals and lesser-known squares, and learn how Venetians have lived and worked within the city for centuries.

Along the way, stop at traditional bacari, wine bars where locals gather for a glass of wine and small cicchetti. Your guide will introduce you to Venice’s food and wine traditions while sharing stories that bring the city to life beyond its postcard views.

Experiencing Venice after dark offers a completely different perspective and is often one of the highlights of a stay in the city.

Today is dedicated to understanding Venice at the height of its power.

With your private guide, explore St. Mark’s Basilica, where glittering mosaics and centuries of history reveal the city’s connections across the Mediterranean world.

Continue into the Doge’s Palace, once the political heart of the Venetian Republic. As you move through grand council chambers, private apartments, and historic corridors, your guide will explain how Venice governed one of the world’s most influential maritime empires.

Cross the famous Bridge of Sighs and learn about the justice system that operated within the republic before continuing through lesser-known streets and hidden corners that reveal the city’s unique character beyond St. Mark’s Square.

Today is a dedicated travel day, carefully structured to ensure comfort and efficiency as you move from northern to southern Italy.

Your private transfer will take you to Venice station, where you’ll board a first-class high-speed train to Naples. On arrival, your private driver will meet you and continue the journey along the coastline toward your Amalfi Coast accommodation.

As you approach the coast, the landscape shifts dramatically, with cliffside roads, sea views, and coastal towns marking your arrival into one of Italy’s most scenic regions.

Today, explore the Amalfi Coast with your private driver, allowing you to experience the region at a relaxed pace without the stress of navigating its winding roads.

Begin in Positano, where you’ll have time to walk through its steep streets, browse local shops, and take in views across the coastline. Continue along the coastal road to Amalfi, where you can visit the Cathedral and explore the town’s historic center.

In the afternoon, travel to Ravello, set high above the coastline. Here, you’ll visit its villas and gardens, known for their panoramic views, which offer a quieter, more elevated perspective of the region.

Throughout the day, your driver will manage timing and routing, allowing you to enjoy each stop without feeling rushed.

Today, travel inland with your private driver to visit Pompeii, one of the most important archaeological sites in the world.

On arrival, meet your private archaeologist guide for an in-depth exploration of the site. With skip-the-line access, you’ll enter directly and follow a structured route through the ancient city, including the Forum, residential areas, bathhouses, and streets.

Rather than simply viewing ruins, your guide will reconstruct daily life in Pompeii before the eruption, explaining how the city functioned and how the eruption unfolded. This level of expert interpretation transforms the experience into a clear and engaging narrative.

Return to the Amalfi Coast in the afternoon.

Today offers a more relaxed and scenic experience with a private boat excursion to Capri.

Depart from the Amalfi Coast and cross the water, approaching Capri from the sea for a unique perspective on its cliffs and coastline. Your private skipper will take you along the island’s shoreline, passing grottos, rock formations, and hidden coves.

You’ll have the option to stop for swimming (season permitting) and to disembark on Capri to explore the island itself. Your time on land can be tailored to your interests, whether that’s visiting Anacapri, exploring the town center, or enjoying a leisurely lunch.

This day is designed to balance structure with flexibility, offering a more relaxed contrast to the previous guided experiences.