Day 1 – Arrival in Milan & Private Transfer to Florence

Upon arrival in Milan, you will travel by train through the Italian countryside to Florence. As landscapes shift from Lombardy plains to rolling Tuscan hills, you ease into the rhythm of the journey. Upon arrival, check into your centrally located 4-star hotel, just steps from Florence’s historic heart. The remainder of the day is free to relax after travel or enjoy a first gentle walk through nearby piazzas. Florence reveals itself slowly, through stone façades, soft evening light, and café-lined streets. Overnight in Florence.

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Day 2 – Florence: Private Walking Tour & Renaissance Icons

This morning begins with a private 2-hour guided walking tour led by a licensed English-speaking guide. You explore Florence’s historic center, uncovering stories behind its masterpieces, political intrigue, and artistic revolutions. From elegant squares to iconic landmarks, the city’s Renaissance soul comes alive. After the tour, the afternoon is yours to continue exploring independently, perhaps visiting artisan workshops or hidden churches. Florence invites curiosity at every turn. Overnight in Florence.

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Day 3 – Chianti Wine Region: Vineyards & Hilltop Villages

Today you venture into the Tuscan countryside with a full-day private transfer through the Chianti wine region. Scenic roads wind through vineyards, olive groves, and stone villages perched on gentle hills. You visit carefully selected wineries, where tastings reveal the character of local wines shaped by land and tradition. Between tastings, you explore charming villages that feel untouched by time. The day balances flavors, landscapes, and slow moments of discovery. Return to Florence in the late afternoon. Overnight in Florence.

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Day 4 – San Gimignano & Private Cooking Experience

A private driver escorts you into the heart of Tuscany for a day centered on tradition and taste. The morning begins at a countryside estate, where you take part in a private hands-on cooking class, learning to prepare classic Tuscan dishes. The experience concludes with a leisurely lunch featuring the dishes you’ve created. In the afternoon, you visit San Gimignano, famous for its medieval towers and timeless atmosphere. Strolling its stone streets feels like stepping into another century. Return to Florence in the evening. Overnight in Florence.

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Day 5 – Florence at Leisure

Today is dedicated entirely to Florence at your own pace. You may choose to visit world-class museums, enjoy shopping along historic streets, or simply sit in a piazza and observe daily life unfold. This free day allows you to deepen your connection with the city on your own terms. Florence rewards unstructured time with unexpected beauty. Overnight in Florence.

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Day 6 – Val d’Orcia: Pienza & Montepulciano

With your private driver, you journey south into the Val d’Orcia, a UNESCO-listed landscape of rolling hills, cypress-lined roads, and poetic villages. You visit Pienza, celebrated for its Renaissance harmony and breathtaking views over the countryside. Later, you explore Montepulciano, known for its elegant architecture and historic wine culture. The day is a visual and sensory immersion into Tuscany’s most iconic scenery. Return to Florence in the evening. Overnight in Florence.

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Day 7 – Cinque Terre Day Trip

Today brings a dramatic change of scenery as you travel by train from Florence to the Ligurian coast. With roundtrip train tickets and a Cinque Terre pass included, you explore two or more of the famed seaside villages, connected by rail and scenic paths. Colorful houses cling to cliffs above turquoise waters, creating one of Italy’s most iconic landscapes. Time is yours to walk, explore, and enjoy lunch overlooking the sea. In the late afternoon, return to Florence by train. Overnight in Florence.

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Day 8 – Florence to Venice & Private Gondola Ride

You depart Florence by high-speed train, traveling comfortably to Venice. Upon arrival, you check into your centrally located 4-star hotel. In the afternoon, you enjoy a private gondola ride, gliding through quiet canals and beneath historic bridges. Venice reveals itself from the water, intimate and timeless. The evening is free to wander the city as it softens under twilight. Overnight in Venice.

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Day 9 – Venice Highlights & Transfer to Milan

This morning is dedicated to Venice’s great symbols, with visits to St. Mark’s Basilica and the Doge’s Palace, uncovering the grandeur of the former Venetian Republic. After your visit, you travel onward to Milan later in the day. Upon arrival, check into your centrally located 4-star hotel. Milan’s atmosphere feels immediately different—elegant, modern, and dynamic. Overnight in Milan.

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Day 10 – Milan: Art, Architecture & Icons

Today you explore Milan’s cultural highlights, beginning with a visit to Leonardo da Vinci’s Last Supper, followed by the Duomo of Milan, including access to its panoramic terraces. From above, the city unfolds in a striking contrast of history and contemporary life. The afternoon is free to explore fashion districts or hidden courtyards. Milan offers sophistication without excess. Overnight in Milan.

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Day 11 – Lake Como Day Trip

A scenic train journey takes you from Milan to Lake Como. You explore the town of Como before ascending to Brunate, where panoramic views stretch across the lake and surrounding mountains. A 1-hour boat cruise allows you to admire elegant villas and peaceful shoreline villages from the water. In the late afternoon, return to Milan by train. Overnight in Milan.

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Day 12 – Departure from Milan

Your journey concludes with a private transfer to Milan Airport, ensuring a smooth and relaxed departure. You leave Italy with memories shaped by landscapes, flavors, and moments of quiet beauty.