New for 2026: Italy's Classic Cities, with Venice

Each of our five distinctive and delightful small group tours to Italy offers something different. For lovers of Mediterranean culture and cuisine, Sicily and Italy's southern regions beckon. History buffs and art lovers will be drawn to Rome and Florence, while those looking for stunning natural beauty and world-famous destinations like the Cinque Terre can look no further than northern Italy. To make your decision easier, we've created a comprehensive breakdown of each Italy tour here.

Our newest Italy tour is the sublime Italy's Classic Cities itinerary. Travelers begin their journey in cosmopolitan Milan before exploring a handful of the country's most beloved municipalities, including Verona (the "little Rome"), medieval Bologna, and Renaissance-tinged Florence. And new for 2026 departures, we've added a stop in timeless Venice, because nothing says magnifico more than two magical nights in the floating city.

Explore the new itinerary: Italy's Classic Cities for 2026

Kick back and cruise through Venice's legendary canals

With multiple nights in every city on this tour, plus an enhanced four-day, three-night extension in Rome, guests will enjoy an unparalleled opportunity to immerse themselves in these romantic destinations. Peruse the tour highlights and a selection of photography below, and head to the 2026 tour page to see full details, departure dates, and pricing; and to reserve your spot.

Tour Highlights (new offerings for 2026 noted in blue)

• Leisurely paced, unique itinerary through timeless Italian cities
• Visits to several outstanding art collections: Brera Gallery (Milan), Galleria dell’Accademia and Uffizi Gallery (Florence)
• Milan touring, including Duomo, La Scala opera house, and Galleria Vittorio Emanuele II
• Cruise on beautiful Lake Como
• Bergamo’s Città Alta (Upper Town)
• Verona, city of history, art, and culture
• Immersive wine experience at Gaetano Bertani family estate
• Two-night stay in timeless Venice, including a guided walking tour and ample time at leisure
• Modena, featuring Ferrari Museum tour and visit to traditional balsamic vinegar-making acetaia
• Bologna touring, including Piazza Maggiore landmarks and Quadrilatero Market
• Bologna cooking class and dinner
• Legendary Renaissance-influenced Florence
• Visit to esteemed Scuola del Cuoio leather school and foundation
• Optional four-day, three-night Rome extension with an ideally located hotel in the Trastevere neighborhood
• Pleasing mix of guided touring and free time to explore independently

After a tranquil cruise along Lake Como, we disembark for lunch and an exploration of the lake's namesake town

"In fair Verona, where we lay our scene..." We see Juliet's balcony in this Shakespeare-tinged city

A walking tour and ample free time introduces us to Bologna, before we sample the city's wares firsthand during a private, hands-on cooking class.

In Italy, ancient and modern collide at every turn

Ready to experience all that Italy's classic cities have in store? Reserve your spot today, and we'll see you on the road in 2026!