Top Italy Trips & Tours in September 2025

Experience Tuscany's best on this 8-day tour. Begin at the family-run Hotel Le Renaie, then explore the Via Francigena from Gambassi Terme to San Gimignano, followed by a sensory wine tasting at a Certaldo estate. Discover the Chianti region's vineyards with a scenic walk and optional …

Discover the heart of Italy and immerse yourself in the enchanting city of Rome during this 4-day tour. Experience the city's most iconic landmarks and UNESCO World Heritage sites. Witness the grandeur of ancient Rome and explore famous ruins like the Colosseum, Roman Forum, Foro di Cesare, and …

Set sail on an 8-day Adriatic cruise aboard M/Y Callisto that begins in the city of Venice and winds its way through the coastal towns of Slovenia and Croatia before culminating in the historic city of Ravenna. This eight-day cruise offers a blend of guided tours and free time, allowing you to …

Step aboard Star Flyer and discover a new age of sail, where the traditions of the past merge with the amenitiies of the present day. Experience friendly and gracious service and a delightful menu of international foods from the far corners of the earth. Fall asleep to the gentle rhythms of the …

Explore the magical and historical heritage that Italy posses by boarding to La Bella Vita for this 7-day cruise. Travel by Venice's famous monuments and visit the Naval Museum that houses important vessels such as ceremonial barges and warships. Visit Chioggia and enjoy touring the colorful …

Embark on an 11-day Adriatic adventure aboard World Navigator, exploring the cultural and culinary delights of Italy, Croatia, and Montenegro. Venice captivates with its romantic canals and historic architecture. In Croatia, discover the ancient city of Zadar, the historical treasures of Split, and …

Embark on an 8-day cruise aboard the L'Austral, exploring the cultural and artistic treasures of the Ionian and Adriatic Seas. Visit Malta, Montenegro, Croatia, and Italy for its 4th Opera Festival at Sea, featuring Artistic Director Alain Duault and renowned musicians. This cruise includes …

Embark on an 8-day Adriatic cruise, starting in Venice and concluding in Dubrovnik, aboard M/Y Callisto. From the moment of embarkation in Venice, you'll be treated to exceptional service and unique experiences. Explore Rovinj’s charming old town, join a truffle hunt in Istria, and …

Begin your 8-day cruise of discovery in Venice, the gateway to Croatia. Cruise aboard the Emerald Azzurra and explore some of the Adriatic's most iconic destinations, including Rovinj, Zadar, Sibenik, Hvar, Split, Korcula, and Dubrovnik. Take a tour of Rovinj and visit the hilltop church of St. …

Discover a truly magical cruise aboard La Bella Vita on Italy's Venetian Lagoon, River Po, and Canal Bianco between Venice and the lakeside Renaissance city of Mantua. Visit the Naval Museum, which houses notable vessels like ceremonial barges and warships, as you travel with a guided tour of …