Arrive in Florence where your Tuscan journey begins. You will be met by our representatives who will greet you and escort you to your motorcoach transportation. Depart for an approximate 90-minute drive through the enchanting landscapes of Tuscany on your way to Cortona. Rolling hills, vineyards, olive groves, and cypress-lined roads introduce the timeless beauty of the region. Your scenic transfer becomes the first chapter of an unforgettable story.

Perched gracefully atop a hill, Cortona appears like a Renaissance painting: stone walls glowing in warm hues, terracotta rooftops layered against the horizon, and sweeping views across the Val di Chiana. Upon arrival, you will check in to your hotel and have time to relax. The afternoon is free to do as you wish. Time is intentionally unhurried, an opportunity to settle into the rhythm of Tuscany and appreciate the tranquility that defines this refined destination.

As evening falls, your journey is officially inaugurated with a Welcome Dinner at a local restaurant.

Meals: Dinner
Overnight: Hotel San Luca, Cortona

After breakfast, depart for an immersive exploration of one of Tuscany’s most atmospheric hilltop towns, a place where art, devotion, and ancient civilization intertwine.

The journey unfolds through narrow medieval streets lined with stone facades and artisan workshops.

At the highest point of the hill stands the Sanctuary of Saint Margaret, spiritual heart of the city and a place of serene contemplation overlooking the sweeping Val di Chiana. From here, panoramic views stretch toward Lake Trasimeno, creating a moment of pure Tuscan poetry.

The exploration continues at the Cathedral of Cortona, custodian of important Renaissance artworks, before wandering along Via Jannelli, where medieval houses preserve the authentic character of the town. In Piazza della Repubblica, elegant palazzi frame the historic Town Hall, while nearby Piazza Signorelli evokes centuries of civic life and cultural refinement. A gentle walk leads to Piazza Garibaldi, offering one of the most enchanting viewpoints over the Umbrian-Tuscan landscape.

Lunch is included at a local restaurant.

In the afternoon, your experience deepens with a private journey into Cortona’s ancient origins. At the MAEC (Museum of the Etruscan Academy), extraordinary artifacts narrate the story of a sophisticated civilization that flourished here long before the Romans. Bronze masterpieces, funerary objects, and archaeological treasures reveal a culture of refinement and power. Your visit continues to the Archaeological Park and the monumental Melone II del Sodo, an impressive Etruscan burial mound set within the Tuscan countryside. Surrounded by olive trees and silence, history feels tangible, almost sacred.

Your evening and dinner are on your own.

Meals: Breakfast, Lunch
Overnight: Hotel San Luca, Cortona

Today unfolds as a tribute to Tuscany’s most celebrated landscapes, a harmonious blend of noble wines, Renaissance vision, and breathtaking panoramas. A private drive leads through the rolling hills of the Val d’Orcia, a UNESCO-protected landscape where vineyards, olive groves, and golden fields create a living painting.

Perched high above its surrounding vineyards, Montalcino exudes understated nobility. Explore its charming medieval streets and visit the imposing Fortezza di Montalcino, whose ancient ramparts offer sweeping views across the hills that produce the legendary Brunello wine. The highlight of the day is a private visit to a prestigious Brunello di Montalcino estate. Within historic cellars lined with oak barrels, expert vintners introduce guests to the philosophy, terroir, and craftsmanship behind one of Italy’s most revered wines. A curated tasting reveals the complexity, structure, and refined character that have made Brunello a global icon.

Your journey continues to Pienza, jewel of the Renaissance and visionary “Ideal City” conceived by Pope Pius II.

Lunch is served in the heart of the historic center of Pienza.

After lunch, your guide will lead you on a stroll through harmonious piazzas and elegant Renaissance palaces. The Duomo di Pienza stands as a symbol of humanistic vision, while panoramic terraces reveal one of Tuscany’s most iconic landscapes, gentle hills dissolving into soft horizons. Time seems to slow in Pienza, inviting quiet appreciation of beauty, balance, and proportion. Return to Cortona in the late afternoon.

Dinner is included this evening.

Meals: Breakfast, Lunch, Dinner
Overnight: Hotel San Luca, Cortona

This morning, a private scenic drive leads you through the gentle Tuscan countryside to Arezzo, an elegant town rich in artistic heritage and authentic charm.

Far from the well-trodden paths, Arezzo reveals a more intimate Tuscany, where history lingers in stone facades and quiet piazzas.

Explore the city’s most treasured landmarks. The majestic Cathedral of Saints Peter and Donato rise proudly above the town, its luminous stained-glass windows casting colored reflections across Gothic interiors. The journey continues to the Romanesque Pieve di Santa Maria, a masterpiece of medieval architecture distinguished by its harmonious facade and sculpted columns. In Piazza Grande, one of Italy’s most beautiful sloping squares, time seems suspended. Framed by elegant palaces and the Logge Vasari, this square evokes centuries of civic life and refined power.

A highlight of the visit is the Basilica of San Francesco, where Piero della Francesca’s extraordinary fresco cycle The Legend of the True Cross unfolds in breathtaking narrative beauty: a defining masterpiece of the Italian Renaissance. Continue past the Church of San Domenico, home to Cimabue’s celebrated crucifix, and along streets once walked by poets and humanists, including Petrarch.

Lunch is included today at a local restaurant.

After lunch you will have some free time to explore artisan boutiques, antique shops, or simply relax in a café overlooking a sunlit piazza before returning to Cortona.

Dinner is included this evening at a local restaurant.

Meals: Breakfast, Lunch, Dinner
Overnight: Hotel San Luca, Cortona

After breakfast and hotel check-out, depart for Florence with an exclusive stop in Siena, one of Tuscany’s most captivating medieval cities. You will begin your exploration through a labyrinth of narrow, atmospheric streets lined with noble palaces, artisan workshops, and centuries-old traditions. The soft hues of Siena’s warm terracotta facades create an unmistakable palette that has inspired artists for generations. The walk gradually opens onto the breathtaking Piazza del Campo, one of Europe’s most extraordinary medieval squares.

With its distinctive shell shape and harmonious proportions, the piazza unfolds like a natural amphitheater, framed by elegant Gothic buildings and crowned by the soaring Torre del Mangia. Twice a year, this iconic square becomes the stage for the historic Palio horse race, a centuries-old tradition that embodies the fierce pride and identity of Siena’s contrade (districts).

From here, your journey continues to the magnificent Duomo di Siena, a true jewel of Italian Gothic architecture. Its striking black-and-white marble facade rises in dramatic contrast against the Tuscan sky, adorned with intricate sculptures and delicate decorative details.

Lunch is included in Siena at a local restaurant.

After lunch, continue your journey toward Florence. Upon arrival in Florence, check-in at your hotel where the remainder of your afternoon is at leisure. Unwind and gently acquaint yourself with the surroundings of your hotel. Whether enjoying a quiet stroll through elegant streets, discovering

nearby artisan boutiques, or savoring a first espresso in a historic café, this relaxed introduction allows Florence to reveal itself at an unhurried pace.

This evening you will have a welcome dinner in Florence.

Meals: Breakfast, Lunch, Dinner
Overnight: Grand Hotel Baglioni, Florence

After breakfast, this morning is devoted to discovering Florence’s architectural grandeur and civic beauty. The highlight of the tour is the magnificent Duomo di Santa Maria del Fiore, an architectural icon that defines the Florentine skyline. Its elegant facade of white, green, and rose marble rises in harmonious grandeur, while inside, the vast and luminous interior inspires quiet awe. Beneath Brunelleschi’s revolutionary dome, a masterpiece of engineering and vision, you can admire the dramatic fresco of the Last Judgment, suspended high above in breathtaking scale.

Your guide will share the fascinating story of innovation and rivalry that led to the creation of this enduring symbol of Florence.

The experience continues in Piazza del Duomo, where Giotto’s Bell Tower and the Baptistery complete the spiritual heart of the city. A gentle stroll then leads toward Piazza della Signoria and the iconic Ponte Vecchio bridge, where historic goldsmith shops line the Arno River.

Lunch is included at a local restaurant.

In the afternoon you will enjoy a dedicated visit to the Accademia Gallery, home to Michelangelo’s iconic David. Standing before this masterpiece is a profoundly moving experience, an encounter with the very spirit of the Renaissance. Following the museum visit, the remainder of the afternoon is at leisure.

Florence invites elegant exploration from haute boutiques and renowned Italian designers to traditional leather ateliers, goldsmith workshops, and artisanal perfumeries. Whether indulging in luxury shopping or simply enjoying the vibrant atmosphere of the city, the afternoon offers the perfect blend of culture and refinement.

Your evening and dinner are on your own.

Meals: Breakfast, Lunch
Overnight: Grand Hotel Baglioni, Florence

This morning, Florence gradually gives way to the rolling poetry of the Tuscan countryside. Cypress-lined roads, sun-drenched vineyards, and silver olive groves frame a scenic drive toward a charming panoramic estate nestled near San Gimignano.

Upon arrival, you are welcomed into an authentic working farm where tradition is not staged, it is lived. A guided visit introduces the estate’s wine cellar, olive groves, and the prized Chianina cattle, symbols of Tuscany’s agricultural excellence. The experience continues with a hands-on pasta cooking class led by a local chef.

Divided into two panoramic settings, a veranda overlooking vineyards and an elegant terrace embraced by nature, you will learn the art of handmade pasta: kneading the dough, rolling it by hand, and shaping it into traditional forms passed down through generations.

A Farm Lunch is included in this panoramic setting. The freshly prepared pasta becomes the centerpiece of a refined yet authentic meal, perfectly paired with estate-produced wines. Laughter, aromas, and the rhythm of the countryside create an atmosphere of effortless joy.

In the afternoon, the journey continues to nearby San Gimignano, the legendary “Manhattan of the Middle Ages.” With your guide, you will wander through its UNESCO-listed historic center, where soaring stone towers rise dramatically against the sky. Along Via San Giovanni and into the picturesque Piazza della Cisterna, medieval architecture blends with artisan boutiques and artisanal gelaterias. At Piazza del Duomo, the heart of the town, centuries of history converge in an atmosphere that feels suspended in time.

Afterwards, enjoy a bit of leisure time exploring at your own pace before returning to Florence.

Dinner is on your own this evening.

Meals: Breakfast, Lunch
Overnight: Grand Hotel Baglioni, Florence

Join an Optional Tour to Chianti (additional cost), or have a free day to explore Florence on your own. Visit a museum, relax in a coffee shop, or shop for treasures.

OPTIONAL CHIANTI TOUR | $250 per person
Instead of a free day, you can choose to join an optional tour to one of Italy’s most iconic landscapes: the Chianti region. Leaving Florence behind, the journey unfolds through a cinematic panorama of undulating hills, patchwork vineyards, ancient stone farmhouses, and cypress-lined avenues, the quintessential image of Tuscany.

A stop in Greve introduces you to the heart of the Chianti Classico territory. Its elegant triangular Piazza Matteotti, framed by arcaded galleries and historic wine shops, offers a charming interlude to browse artisanal products and regional delicacies. The highlight of the day is an exclusive visit to a prestigious castle wine estate. Behind ancient stone walls, centuries of winemaking tradition come to life. A guided tour of the historic cellars reveals oak barrels resting in cool vaulted chambers, where time patiently transforms grapes into celebrated vintages. Guests are then invited to a curated wine and olive oil tasting, discovering the complexity, structure, and elegance of Chianti’s noble wines, perfectly complemented by the estate’s extra-virgin olive oil.

Lunch is served within the estate’s refined setting, where a menu showcases seasonal Tuscan ingredients paired with locally produced wines. The experience blends rustic authenticity with understated elegance.

In the afternoon, return to Florence.

This evening, as the sun sets, a final celebration awaits. Transfer to a panoramic restaurant nestled in the hills of Florence just outside the city center. A historic, casual family-run restaurant set within a timeless hillside village will offer a captivating view over the Tuscan countryside. A serene and evocative backdrop for a refined farewell dinner paired with excellent regional wines.

Meals: Breakfast, Dinner
Overnight: Grand Hotel Baglioni, Florence

Arrivederci Toscana!

After breakfast, a private transfer escorts you to the Florence Airport for your return flight home. Memories of art, wine, landscapes, and authentic Italian elegance accompany the journey home.

Meals: Breakfast