DAY 1 | BOLOGNA Arrive in Bologna, affectionately called “La Dotta, La Grassa, La Rossa” — “the Learned, the Fat, the Red.” Known for its historic university, rich gastronomy, and terracotta rooftops, Bologna is the beating heart of Italy’s Food Valley. DAY 2 | BOLOGNA | RAVENNA | BOLOGNA Enjoy a full-day private tour of Ravenna, a city world-renowned for its dazzling Byzantine mosaics and architecture. Visit UNESCO treasures such as the Basilica of Sant’Apollinare Nuovo, the Basilica of San Vitale, and the Mausoleum of Galla Placidia. Wander through the “Zone of Silence” to see Dante Alighieri’s Tomb, the Franciscan Cloisters, and the Quadrarco of Braccioforte. Explore the Battistero Neoniano, the Archiepiscopal Museum, and the Chapel of St. Andrew while your guide brings Ravenna’s fascinating history to life. (B) DAY 3 | BOLOGNA | SAN MARINO | BOLOGNA Venture into the world’s fifth-smallest country, the ancient Republic of San Marino, a mountaintop enclave perched high in the Apennines. With your private guide, wander the cobbled streets of the medieval old town, where centuries of independence echo through stone walls and sunlit piazzas. Admire the neoclassical Basilica of St. Marino and pause in Piazza della Libertà, the heart of civic life, framed by the elegant Palazzo Pubblico. Continue your journey upward to the rocktop First Tower, one of San Marino’s legendary fortresses, and take in sweeping vistas that stretch from the Apennine peaks to the glittering Adriatic Sea — a view that captures both the beauty and the enduring spirit of this proud republic. (B) DAY 4 | BOLOGNA | URBINO | BOLOGNA Discover Urbino, a Renaissance jewel and UNESCO World Heritage Site, where art, architecture, and history intertwine in every stone-paved street. With your private guide, step into the birthplace of Raphael, one of the great masters of the Renaissance, and feel the creative spirit that still lingers in his childhood home. Admire the splendid Cattedrale di Santa Maria Assunta, whose soaring interiors reflect the grandeur of Urbino’s past, and continue to the magnificent Palazzo Ducale — a true masterpiece of Renaissance architecture. Once the seat of Duke Federico da Montefeltro, this palace became a cultural beacon of 15th-century Europe, housing one of the era’s most celebrated courts. As you walk through its grand halls and marvel at its harmonious courtyards, you’ll gain insight into Urbino’s extraordinary artistic and cultural legacy, a legacy that continues to inspire centuries later. (B)
DAY 5 | BOLOGNA | FERRARA | PASSIANO DI PORDENONE Travel from Bologna to Pordenone with a stop in Ferrara, a Renaissance treasure and UNESCO World Heritage Site. Once the proud seat of the Este dynasty, Ferrara flourished as a center of art and culture, leaving behind a cityscape of medieval lanes, elegant palaces, and grand boulevards. On your walking tour, admire the moated Castello Estense, the stately Palazzo dei Diamanti, and the Cathedral of San Giorgio, each reflecting the city’s golden age. With its harmonious blend of medieval charm and Renaissance brilliance, Ferrara offers a captivating glimpse into Italy’s past. (B) DAY 6 | PASSIANO DI PORDENONE | TRIESTE | PASSIANO DI PORDENONE Uncover the cosmopolitan charm of Trieste, the enchanting port once known as the “Little Vienna on the Sea.” Nestled between the mountains and the Adriatic, Trieste is a city where Mediterranean vibrancy meets Habsburg elegance. Stroll across the magnificent Piazza Unità d’Italia, one of Europe’s largest seafront squares, framed by elegant palaces that open onto the glittering gulf. Explore Roman ruins and medieval churches, then wander the Grand Canal lined with graceful bridges and historic cafés that once inspired literary greats like James Joyce and Italo Svevo. As your guide reveals Trieste’s unique blend of Italian, Austrian, and Slovenian influences, you’ll feel the city’s role as a true crossroads of cultures come vividly to life. (B) DAY 7 | PASSIANO DI PORDENONE | PROSECCO HILLS | PASSIANO DI PORDENONE Spend an unforgettable day in the UNESCO-listed Prosecco Hills, a landscape of sun-drenched slopes draped in endless rows of glera vines. Here, tradition and passion come together to create Italy’s most beloved sparkling wine. As you journey through these rolling hills, your guide will reveal the secrets of Prosecco production — a delicate process perfected over centuries to preserve its signature freshness and lively sparkle. Visit two renowned wineries, where vintners share their craft and invite you to savor guided tastings of their finest vintages, each sip paired with local delicacies that bring out the wine’s unique character. Surrounded by breathtaking views, you’ll experience the charm, flavor, and spirit that make the Prosecco Hills a true gem of Italian wine country. (B) DAY 8 | PASSIANO DI PORDENONE I VENICE TO USA (OR EXTEND YOUR STAY) Say “arrivederci” to Italy or extend your stay. (B)
(B) Breakfast - (L) Lunch - (D) Dinner
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