Italy’s Gems: Verona, Bologna, Florence, Assisi & Pienza

From Verona’s romance and Bologna’s flavors to Florence’s art and Assisi’s serene landscapes, this journey captures the heart of Italy.

Duration

10 days

Group Type

Private

Season

Spring/Autumn

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Overview

Enjoy a seamless journey through Italy’s most enchanting regions, from the romance of Verona and the shimmering beauty of Lake Garda to the rich culinary heritage of Bologna and the Renaissance brilliance of Florence, and onward through the spiritual charm of Assisi, the architectural elegance of Pienza, and the world-class wines of the Val d’Orcia.

With private transfers, expert-guided tours, Brunello tastings, and scenic countryside drives, this itinerary blends culture, history, landscapes, and culinary excellence into one effortlessly memorable Italian experience.

Day to Day

	Days 1-2: Get introduced to northern Italy through Verona, blending Shakespearean charm, ancient Roman history, and the tranquil beauty of Lake Garda.
	Days 3-4: Experience a rich blend of medieval architecture, culinary heritage, and vibrant local tradition in Bologna, Italy’s gastronomic capital.
	Days 5-6: Wander through Renaissance masterpieces, architectural icons, and centuries of artistic genius in the heart of Tuscany.
	Days 7-8: Travel from Florence and discover Assisi’s medieval streets and the iconic Basilica of St. Francis.
	Day 9: Journey through Tuscany’s Val d’Orcia, exploring Pienza and tasting Brunello wines.
	Day 10: Enjoy a private transfer from Pienza to Siena Train Station for your onward journey.

Day to Day

	Days 1-2: Get introduced to northern Italy through Verona, blending Shakespearean charm, ancient Roman history, and the tranquil beauty of Lake Garda.
	Days 3-4: Experience a rich blend of medieval architecture, culinary heritage, and vibrant local tradition in Bologna, Italy’s gastronomic capital.
	Days 5-6: Wander through Renaissance masterpieces, architectural icons, and centuries of artistic genius in the heart of Tuscany.
	Days 7-8: Travel from Florence and discover Assisi’s medieval streets and the iconic Basilica of St. Francis.
	Day 9: Journey through Tuscany’s Val d’Orcia, exploring Pienza and tasting Brunello wines.
	Day 10: Enjoy a private transfer from Pienza to Siena Train Station for your onward journey.

This itinerary can be further customized according to your wishes & preferences

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Day to Day

DAYS 1-2 : VERONA

Your adventure begins in Verona, where a private walking tour takes you through its UNESCO-listed historic center. Stroll past elegant palaces and medieval streets, visit Juliet’s Balcony, and admire the impressive Arena di Verona, one of the best-preserved Roman amphitheaters. This tour offers a perfect mix of history, culture, and romance.

On Day 2, enjoy a full-day escape to Lake Garda, starting with a drive through the Valpolicella wine region. Visit the peaceful Punta San Vigilio, explore colorful Bardolino, and continue to Sirmione for a private boat ride showcasing lakeside villas and the Grotte di Catullo. Conclude with leisure time in the medieval town before returning to Verona.

DAYS 3-4 : BOLOGNA

Arrive in Bologna and discover its historic center on a private evening walking tour. Explore highlights such as Piazza Maggiore, the Neptune Fountain, the Two Towers, and the vast Basilica of San Petronio, home to the world’s largest sundial. Your evening ends with a delicious tasting of local specialties.

Day 4 offers an immersive culinary experience through Emilia-Romagna’s food excellences. Visit a Parmigiano Reggiano cheese factory, tour a traditional balsamic vinegar producer, and enjoy wine tastings at a family-run winery in the hills. This journey concludes with a typical regional lunch, showcasing the area’s authentic flavors.

DAYS 5-6 : FLORENCE

Arrive in Florence and begin your private walking tour at Piazza della Signoria, an open-air gallery of statues and fountains. Cross the iconic Ponte Vecchio, stroll through historic streets once walked by Dante and Michelangelo, and admire the Duomo, Brunelleschi’s Dome, and the Gates of Paradise at the Baptistery.

Your tour ends with skip-the-line entry to the Galleria dell’Accademia, where Michelangelo’s David awaits, one of the most celebrated sculptures in the world.

DAYS 7-8 : ASSISI

Take a picturesque train ride from Florence to Assisi, passing rolling hills and green valleys. Upon arrival, a private driver greets you at the station, handles your luggage, and transfers you comfortably to your accommodation; the easiest and most relaxing way to start your stay in this spiritual town.

On day two, accompanied by a private guide, explore the highlights of Assisi, birthplace of St. Francis. Visit the magnificent Basilica of St. Francis, Piazza del Comune, the Temple of Minerva, Chiesa Nuova, and Basilica of Santa Chiara. Learn about the town’s Roman roots, medieval history, and spiritual heritage while enjoying personalized storytelling and insider insights.

DAY 9 : PIENZA & VAL D’ORCIA

Begin with a private transfer from Assisi to Pienza, taking in the scenic Umbrian and Tuscan countryside along the way. Arrive in Pienza, the “ideal Renaissance city,” and enjoy an hour of free time to stroll cobblestone streets, admire harmonious architecture, and soak in breathtaking countryside views.

Continue to Montalcino for a visit to a boutique winery, exploring the cellar and savoring Brunello wine paired with a light Tuscan lunch. This day is a seamless blend of culture, scenic landscapes, and culinary delights.

DAY 10 : DEPARTURE

After breakfast, your private driver will take you from Pienza to Siena Train Station, ensuring a comfortable and stress-free journey.

Relax and enjoy the rolling hills and charming villages one last time before continuing your Italian adventure.

Our preferred hotels

Brunelleschi Hotel

Discover the epitome of luxurious comfort and historical charm at Brunelleschi Hotel, where every moment becomes a timeless and unforgettable experience.

Gallery Hotel Art

Where Art and Luxury Converge: Discover the Splendor at Gallery Hotel Art

Glance Hotel

Elevate your stay in Florence to unparalleled heights at Glance Hotel, where captivating design, modern luxury, and a prime location converge for an unforgettable experience.

Hotel Calimala

Indulge in the essence of timeless elegance and exceptional hospitality at Hotel Calimala, where every moment is a refined blend of luxury and comfort, creating an enchanting stay in the heart of Florence.

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Hotel Cerretani Firenze - MGallery Collection

Indulge in the timeless charm of Florence while experiencing impeccable luxury at its finest by staying at Hotel Cerretani Firenze!

Hotel Continentale

Indulge in the timeless allure of Florence's rich history and captivating beauty at Hotel Continentale, where luxury and sophistication await to elevate your stay to unforgettable heights.

Hotel Lungarno

Elevate your Florence experience to new heights of elegance and sophistication by choosing to stay at Hotel Lungarno, where art, culture, and unparalleled views of the Arno River come together in perfect harmony.

Hotel Spadai

Indulge in the epitome of luxury and hospitality at Hotel Spadai, where every moment is a captivating blend of comfort and elegance.

Palazzo Castri 1874

Discover true luxury and timeless elegance at Palazzo Castri 1874 - an exquisite haven where every moment is a masterpiece.

San Firenze Suites & Spa

Experience the epitome of luxury and relaxation at San Firenze Suites & Spa for an unforgettable stay in the heart of Florence's historic charm.

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The Moon Boutique Hotel and Spa

Indulge in an unforgettable retreat of luxury and relaxation at The Moon Boutique Hotel and Spa, where every moment is a celestial escape waiting to be experienced.

These are our top accommodation options for this trip. We only feature particular hand-picked hotels, which our team has carefully inspected. These hotels have received great feedback from our previous guests.

Inclusions & Exclusions

Inclusions