Day 1 – Welcome to Tuscany | Where Time Begins to Slow

Your Italian journey begins at Pisa Airport, where you’ll collect your rental car before leaving the city behind and heading into the gentle landscapes of the Florentine Hills.

As vineyards replace highways and cypress trees line the winding roads, Tuscany gradually reveals its true character. Soon you’ll arrive at your charming countryside agriturismo, a peaceful retreat surrounded by olive groves, rolling hills, and timeless rural scenery.

Spend the afternoon exactly as Tuscany invites you to: lounging by the pool, enjoying a glass of local wine, or simply listening to the silence of the countryside as your holiday gently begins.

Overnight in the Florentine Hills.

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Day 2 – Tuscany | Living Like a Local

Today, there is nowhere you need to be.

Wake slowly, enjoy breakfast overlooking the vineyards, spend the morning by the swimming pool, or set off to discover the hidden villages scattered across the Chianti countryside. Stop whenever a panoramic viewpoint catches your eye, browse a small artisan shop, or enjoy lunch at a family-run trattoria where recipes have been passed down for generations.

This is Tuscany at its finest—not rushed, not scheduled, simply experienced.

Overnight in the Florentine Hills.

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Day 3 – Florence | Walking Through the Renaissance

Today the countryside gives way to one of the world’s greatest artistic capitals.

Together with your private guide, wander through Florence’s elegant streets where every square, palace, and church tells the story of the Renaissance. Artists, merchants, and visionaries shaped this remarkable city, leaving behind masterpieces that continue to inspire centuries later.

During the afternoon, continue your discovery with access to Florence’s extraordinary cathedral complex. Climb to spectacular panoramic viewpoints, admire remarkable architectural achievements, and explore monuments that together represent one of the greatest accomplishments in European art and engineering.

As evening approaches, return to the peaceful Tuscan countryside—a perfect balance between vibrant city life and rural tranquility.

Overnight in the Florentine Hills.

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Day 4 – San Gimignano | A Taste of Tuscany

This morning, travel to the medieval hill town of San Gimignano, where ancient towers rise above vineyards and olive groves like a scene frozen in time.

Before exploring its cobbled streets, step inside a traditional Tuscan farmhouse for a private culinary experience. Guided by your own chef, prepare authentic regional dishes using seasonal local ingredients, learning the gestures and traditions that have defined Tuscan family cooking for generations.

When everything is ready, sit together for a leisurely lunch accompanied by estate-produced wines, fragrant extra virgin olive oils, and carefully selected balsamic vinegar.

The afternoon is yours to wander through San Gimignano’s picturesque streets, browse artisan boutiques, and enjoy breathtaking views across the Tuscan countryside.

Overnight in the Florentine Hills.

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Day 5 – Siena | The Soul of Medieval Tuscany

There are few places where history feels as alive as Siena.

Spend the day wandering through beautifully preserved medieval streets before entering the spectacular Cathedral Complex, a masterpiece where marble, light, sculpture, and centuries of devotion come together in extraordinary harmony.

Take time to linger in Piazza del Campo, enjoy an espresso in the sunshine, and simply absorb the elegant rhythm of one of Italy’s most captivating cities.

Overnight in the Florentine Hills.

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Day 6 – Chianti | Beyond the Usual Route

Many visitors discover Chianti from behind the wheel of a Vespa.

Today, you’ll experience it differently—and arguably in the most rewarding way.

Glide effortlessly through vineyards, forests, and quiet country roads on an e-bike, following panoramic routes that cars and scooters rarely reach. Without engine noise or traffic, you’ll experience Tuscany through its scents, sounds, and breathtaking landscapes, stopping whenever a view deserves another photograph.

It’s a slower, safer, and far more immersive way to connect with one of Italy’s most celebrated wine regions.

Overnight in the Florentine Hills.

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Day 7 – From Vineyards to the Sea

This morning, Tuscany slowly fades into your rear-view mirror as the road leads toward the sparkling Ligurian coastline.

Nestled among green hills just above Levanto, your charming countryside retreat offers the perfect gateway to the Cinque Terre while preserving the peaceful atmosphere of rural Italy.

Spend the afternoon unwinding by the pool or enjoying the fresh sea breeze before the coastal adventures that await.

Overnight near Levanto.

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Day 8 – Cinque Terre | Villages Between Sky and Sea

Today begins your exploration of one of Italy’s most iconic landscapes.

Using your included Cinque Terre Train Card, travel easily between the colorful villages of Monterosso and Vernazza. Wander narrow alleyways, admire tiny harbors filled with fishing boats, pause at panoramic terraces overlooking the Mediterranean, and discover why these villages have enchanted travelers for generations.

There is no rush here—only spectacular scenery around every corner.

Overnight near Levanto.

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Day 9 – Cinque Terre | The Remaining Jewels

Your journey continues through the remaining villages of this extraordinary coastline.

From the peaceful hilltop charm of Corniglia to the dramatic cliffs of Manarola and the colorful waterfront of Riomaggiore, each village reveals a different personality while sharing the same timeless relationship with the sea.

Take your time, stop often, and let the beauty of the Cinque Terre unfold naturally.

Overnight near Levanto.

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Day 10 – Gulf of Poets | Italy from the Water

Some coastlines are best admired from land.

This is not one of them.

Board your shared boat and cruise through the legendary Gulf of Poets, where secluded coves, colorful villages, dramatic cliffs, and crystal-clear waters reveal a side of Liguria that few visitors truly experience.

It is easy to understand why generations of writers, artists, and dreamers found endless inspiration here.

Overnight near Levanto.

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Day 11 – One Last Taste of Liguria

Your final full day is intentionally left open, allowing you to enjoy it exactly as you wish.

Perhaps visit elegant Portofino, with its glamorous harbor and pastel-colored houses, enjoy a leisurely seafood lunch overlooking the sea, or simply remain at your agriturismo, relaxing by the pool and savoring every last moment of the Italian dolce vita.

Sometimes the best memories are made when nothing is planned at all.

Overnight near Levanto.

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Day 12 – Arrivederci Italia

After breakfast, make your way back to Pisa Airport, return your rental car, and begin your journey home.

You leave Italy with much more than photographs: the flavors of Tuscany, the colors of the Cinque Terre, the silence of the vineyards, the sound of the sea, and memories of a journey experienced exactly as Italy is meant to be—slowly, authentically, and beautifully.