Where to Visit in Italy Based on Places You Already Love

Tuscany’s allure is undeniable. It’s a sun-drenched dream of Renaissance grandeur, rolling cypress-clad hills, and world-class vineyards. But if you have already basked in its golden light and traced its artistic lineage, a new discovery awaits in its more introspective and spiritual sibling, Umbria.

Known as the “Green Heart of Italy,” Umbria offers the same soul-stirring landscapes and passion for rustic, farm-to-table cuisine, yet it exudes a quieter, more mystical charm. This is a land of saints and pilgrims, where medieval hilltop towns like Assisi and Orvieto feel suspended in time. It's a region where the pursuit of beauty feels less like a grand tour and more like a personal meditation, trading the crowds of Tuscany for a sense of peace and authenticity.

What to Expect in Umbria

Prepare to discover a region of serene beauty, deep spirituality, and understated luxury.

• Enjoy a Private Tour of Assisi: Explore the magnificent Basilica of Saint Francis with an art historian, who can reveal the revolutionary genius of Giotto’s frescoes in a contemplative, unhurried atmosphere.
• Taste Umbria’s Powerful Wines: Visit a top-tier estate in the Montefalco region for an exclusive tasting of the bold and complex Sagrantino, a rare local grape prized by collectors.
• Indulge in an Artisanal Workshop: Discover the region's celebrated crafts with a private tour of a family-run ceramics studio in Deruta or a behind-the-scenes look at the production of luxurious cashmere in Perugia.
• Stay in a Restored Castle or Monastery: Experience the region's history by staying in a beautifully appointed luxury hotel that was once a medieval fortress or a tranquil monastery.
• Partake in a Black Truffle Culinary Experience: Join a private truffle hunt in the Umbrian woods, followed by a hands-on cooking class dedicated to preparing the region’s famed black truffles and cured wild boar.

On Zicasso’s Soulful Italy: Umbria, The Marches, and Abruzzo Tour, we will guide you into the “Green Heart of Italy,” a land of serene landscapes and profound soulfulness.

To love Rome is to be captivated by its epic scale. It’s an eternal city where the sheer weight of history lives and breathes alongside vibrant modern life. After exploring the heart of the Roman Empire, the next logical step for the history aficionado is not another city, but an entire world: Sicily.

Sicily is a cultural crucible where the legacies of the Greeks, Romans, Arabs, Normans, and Spanish collide and fuse into something utterly unique. The island is wilder, more elemental, and its history even more complex and layered than that of Rome. Here, the grandeur of the capital’s ruins is met by the breathtaking Greek temples of Agrigento and the cuisine is woven from the volcanic soil of Mount Etna, the bounty of the sea, and centuries of multicultural influence.

What to Expect in Sicily

Embrace an island of epic history, dramatic landscapes, and vibrant, multi-layered culture.

• Witness the Valley of the Temples at Sunset: Take a private, after-hours tour of the magnificent Greek temples at Agrigento as an archaeologist brings their history to life against the backdrop of a fiery Sicilian sunset.
• Soar Over an Active Volcano: Experience a breathtaking private helicopter tour over the smoking craters of Mount Etna, followed by an exclusive wine tasting at a celebrated vineyard on its fertile volcanic slopes.
• Explore Palermo’s Markets with a Chef: Dive into the vibrant, chaotic energy of Palermo’s historic street markets on a private tour with a local chef, culminating in a cooking class in a private palazzo.
• Discover the Baroque Jewels of the Val di Noto: With an architectural historian as your guide, explore the stunning UNESCO-listed towns of Noto, Ragusa, and Modica, celebrated for their exuberant Sicilian Baroque style.
• Charter a Yacht to the Aeolian Islands: Spend a day cruising the crystalline waters of the volcanic Aeolian archipelago, dropping anchor at the chic island of Panarea for lunch and swimming in secluded bays.

Allow us to craft your grand tour of Sicily, an epic journey through a land of myths, titans, and timeless beauty. Take a look at our Sicily tours and vacation packages for more inspiration.

The Amalfi Coast is a world-renowned icon of vertical glamour, a breathtaking drama of pastel villages clinging to vertiginous cliffs above a sapphire sea. Having experienced its undeniable allure, you might seek a coastal paradise that is just as beautiful, but with a more relaxed and authentic soul.

Welcome to Salento, the sun-bleached stiletto heel of Italy’s boot. Part of the Puglia region, this peninsula offers a different kind of coastal chic. It’s less about vertical drama and more about a rugged, pristine shoreline lapped by the crystalline waters of the Adriatic and Ionian seas. It’s a land of ancient olive groves, whitewashed fortified towns, and stunning sea caves, where luxury is found in beautifully restored farmhouses known as masserie.

What to Expect in Salento

Discover Italy’s chic, sun-drenched southern peninsula, where understated luxury meets raw coastal beauty.

• Retreat to a Luxurious Restored Masseria: Stay in an exclusive, five-star fortified farmhouse, complete with ancient olive groves, a stunning swimming pool, a world-class spa, and farm-to-table dining.
• Explore Sea Caves by Private Boat: Charter a private boat for the day to discover the dramatic sea caves and hidden beaches along the Adriatic coast, stopping for a swim in the turquoise waters.
• Dine in the Whitewashed Port of Gallipoli: Enjoy an exquisite, fresh-from-the-sea dinner at a renowned restaurant in the charming Old Town of Gallipoli as you watch the fishing boats bob in the harbor.
• Discover the "Maldives of Salento": Spend a day relaxing on the pristine white-sand beaches and in the shallow, turquoise waters of Pescoluse, a stretch of coastline that rivals the Caribbean for beauty.
• Taste the Rich Wines of the South: Indulge in a private tasting of the region’s powerful and complex wines, such as Primitivo and Negroamaro, at a historic, family-run winery.

Let us introduce you to Italy's best-kept coastal secret, a land of rustic elegance and sun-drenched soul. Find out more with our Southern Italy vacations and tours.

The Italian Riviera is the epitome of classic, old-world seaside elegance, a perfectly manicured string of pearls like Portofino and the Cinque Terre. For those who loved its charm, but now crave a landscape that is wilder, more ancient, and fiercely unique, the island of Sardinia is the ultimate destination.

This is not merely an extension of the mainland; it is a world unto itself, with its own language, distinct culture, and history that predates Rome by millennia. Its untamed interior is home to thousands of mysterious prehistoric stone dwellings known as nuraghi, while its legendary coastline ranges from the dazzling glamour of the Costa Smeralda to secluded, rugged coves of breathtaking natural beauty. Sardinia is perfect if you are part adventurer, part connoisseur.

What to Expect in Sardinia

Experience a mythic island of wild landscapes, ancient mysteries, and dazzlingly beautiful shores.

• Sail the Glamorous Costa Smeralda: Charter a private sailing yacht for the day to explore the emerald waters, granite rock formations, and stunning beaches of the world-famous Costa Smeralda, docking in the chic port of Porto Cervo.
• Explore Prehistoric Mysteries with an Archaeologist: Gain insight into Sardinia’s unique ancient past with a private tour of a major Nuragic complex, such as Su Nuraxi di Barumini, a UNESCO World Heritage Site.
• Venture into the Untamed Interior: Take a private 4x4 excursion into the rugged Supramonte mountains with a local guide to witness dramatic canyons, discover hidden caves, and enjoy a traditional shepherd’s lunch.
• Dive in a Protected Marine Paradise: Explore the vibrant underwater world of the La Maddalena Archipelago National Park on a private diving or snorkeling trip, discovering a dazzling array of sea life.
• Indulge in Sardinia’s Unique Cuisine: Experience a traditional spit-roasted piglet feast, sample the island’s renowned pecorino cheeses, and taste its powerful Cannonau red wines at a top agriturismo.

Embark on our One-Week Sardinia and Corsica Island Tour to uncover the wild heart and glamorous shores of the region.

Venice is an incomparable dream, a floating masterpiece whose romantic grandeur and unique liquid landscape rightfully capture the world’s imagination. If you were mesmerized by the art, architecture, and sheer audacity of Venice, then Ravenna offers a different, yet equally astonishing, artistic pilgrimage.

While it lacks the canals, Ravenna was once the capital of the Western Roman Empire and is the undisputed guardian of the world’s most breathtaking collection of glittering Byzantine mosaics. Stepping inside its UNESCO-listed basilicas and mausoleums will transport you into an otherworldly realm of shimmering gold, deep blue, and emerald green. Ravenna offers a more serene, compact, and scholarly experience, allowing for unhurried, crowd-free contemplation of masterpieces that rival any in Italy for their jaw-dropping beauty.

What to Expect in Ravenna

Step into a world of shimmering gold and imperial history in this serene artistic haven.

• Enjoy a Private Viewing of the Mosaics: Arrange for an after-hours tour of the Basilica di San Vitale or the Mausoleum of Galla Placidia, where a guide can illuminate these glittering masterpieces just for you.
• Create Your Own Masterpiece: On an 8-Day Cultural Journey of Emilia-Romagna, participate in a hands-on mosaic-making workshop in the studio of a local artisan. Learn ancient techniques and create your own unique souvenir to take home.
• Follow in the Footsteps of Dante: Take a privately guided tour focused on Dante Alighieri, the father of the Italian language, who spent his final years and is buried in Ravenna.
• Savor the Flavors of Emilia-Romagna: Indulge in a culinary tour or cooking class focused on the celebrated cuisine of the surrounding region, known for its fresh pasta, cured meats, and rich cheeses.
• Enjoy a Leisurely Cycle Through a City of Art: Explore Ravenna’s tranquil, pedestrian-friendly historic center on a guided bicycle tour, effortlessly gliding between its eight UNESCO World Heritage sites.

Allow us to unlock the doors to Ravenna, a city where art history shimmers with an otherworldly light.

Visiting Florence puts you at the epicenter of the Renaissance. It’s a city of breathtaking and orderly genius, defined by the masterpieces of Michelangelo and Brunelleschi. If you have absorbed its intellectual beauty, a trip to Lecce, the undisputed “Florence of the South,” offers a thrillingly different artistic experience.

While Florence speaks in the restrained, perfect proportions of the High Renaissance, Lecce sings with the exuberant, theatrical, and joyful passion of High Baroque. The city’s unique, honey-hued sandstone was so soft and malleable that it allowed 17th-century architects to festoon every church and palazzo with an explosion of intricate, decorative details. The entire city is a flamboyant open-air museum, where daily life plays out against a backdrop of architectural fantasy.

What to Expect in Lecce

Immerse yourself in the joyful, exuberant, and sun-drenched "Florence of the South."

• Take a Private Tour of Leccese Baroque: Join an architectural historian for a guided walk to appreciate the stunning details of the city’s unique architectural style, from the Basilica di Santa Croce to the Piazza del Duomo.
• Discover the Art of Papier-Mâché: Visit the private workshop of a master artisan to see how the city’s famous and intricate papier-mâché sculptures are created, a craft passed down through generations.
• Indulge in the Cuisine of Italy’s “Heel”: Enjoy a private cooking class focused on the rustic, vegetable-forward cuisine of Puglia, known as cucina povera, followed by a tasting of local wines.
• Enjoy a Day Trip to a Stunning Seaside Town: Take a short, chauffeured drive to the beautiful Adriatic town of Otranto, with its massive medieval castle and stunning cathedral floor mosaic depicting the Tree of Life.
• Experience a Performance at the Roman Amphitheater: In the summer months, enjoy an open-air concert or theatrical performance in evocative ruins of the city’s 2nd-century Roman amphitheater.

Let our Luxuries of Puglia to Amalfi Coast Tour introduce you to the architectural fantasy and joyful spirit of Lecce, a true Baroque jewel.

The five villages of the Cinque Terre offer one of Italy’s most iconic images: a cascade of colorful tower homes clinging to cliffs above the Ligurian Sea. It’s a landscape of immense charm and beauty. If you have hiked its scenic trails and now seek a landscape that is even more ancient, unique, and profoundly moving, the UNESCO World Heritage city of Matera is an astonishing discovery.

Tucked away in the southern region of Basilicata, Matera is one of the oldest continuously inhabited settlements on Earth. Instead of colorful homes, its historic center is a labyrinthine complex of sassi, cave dwellings carved directly out of the limestone ravine. Wandering its streets will have you stepping back millennia, into a surreal, biblical landscape that feels completely detached from the modern world.

What to Expect in Matera

Prepare to inhabit history itself in one of the most ancient and surreal cityscapes on Earth.

• Stay in a Luxurious Cave Hotel: Experience the ultimate blend of ancient and modern by staying in a five-star hotel where luxurious suites have been masterfully built within the ancient Sassi caves.
• Take a Private Tour of the Sassi Districts: Join an expert local guide to navigate the maze-like alleys of the Sassi di Matera, discovering hidden courtyards and stunning rock-hewn churches adorned with ancient frescoes.
• Explore the Wilderness of Murgia National Park: Hike or take a guided 4x4 tour across the ravine into the Parco della Murgia Materana to explore more ancient cave churches and get the most breathtaking panoramic view of the city.
• Enjoy an Aperitivo with a Timeless View: Sip on local wines and enjoy regional delicacies from a panoramic terrace as you watch the sunset and the lights of the Sassi begin to twinkle, creating an unforgettable, magical scene.
• Learn the Art of Matera’s Famed Bread: Participate in a private bread-making class to learn the secrets behind Pane di Matera, a traditional, wood-fired bread that has been a staple of life here for centuries.

Zicasso’s Hidden Jewels of Italy’s Southern Route Tour, will put you in the timeless, soul-stirring landscape of Matera, a place you will truly never forget.

The true beauty of Italy lies in its infinite capacity to surprise and enchant. Moving beyond the iconic does not mean dismissing the famous. It’s about enriching your understanding and deepening your connection to the country’s soul. The journey from a place you love to a new, unexpected discovery is the ultimate luxury, an experience that trades crowds for authenticity and sightseeing for genuine immersion.

Discover how we can craft your second, third, or fourth bespoke journey through Italy with comprehensive Italy travel guide or our Italy tours and trip packages. Then, connect with our destination specialists to help you customize your trip.