Top Italy Trips & Tours in October 2025

Join this 8-day Classic Dolomites Premium Adventure Group Tour in Italy for an exceptional small group tour experience that takes you through the breathtaking landscapes of the Italian Dolomites, a UNESCO World Heritage Site. It's a special blend of adventure, culture, and relaxation, allowing …

Explore the Treasures of Sicily on this 9-day small group tour from Viagrande to Taormina, a collection of extraordinary wonders found on the beautiful Italian island of Sicily. Sicily is home to well-preserved Greek temples showcasing the island's ancient past. The Valley of the Temples in …

On this 8-day small group tour, explore the breathtakingly beautiful region of Italy, the Amalfi Coast, located along the southern coast of the Sorrentine Peninsula. See the dramatic cliffs, picturesque villages, and crystal-clear waters. Visit the charming town of Positano, known for its colorful …

Embark on this premium small-group adventure through the heart of Italy and explore the timeless beauty of Rome, Assisi, and Umbria. This 8-day tour will take you through some of Italy's most beautiful and historic regions, where you'll experience unforgettable moments and create lasting …

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 …

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 …

Set sail on an unforgettable 8-day Mediterranean journey aboard L'Austral. Begin your cruise in Valletta, a UNESCO World Heritage site known for its majestic streets and historic landmarks. From the Grandmaster's palace to Saint John’s cathedral, immerse yourself in the rich history …

On this 9-day Sicily & Greece cruise from Piraeus to Valletta aboard the Star Clipper, embark on an adventure through ancient and historic destinations, starting in Athens, the birthplace of democracy. Visit Nafplio, a charming seaport town in Greece, followed by the fortified Byzantine city of …

Embark on a 14-day cruise aboard the Royal Clipper, discovering the Mediterranean, starting in Civitavecchia, and exploring Rome's iconic landmarks. Visit picturesque Bonifacio in Corsica, elegant Mahon in Menorca, and historic Palma de Mallorca. Sail to vibrant Ibiza, discover Cartagena's …

Join this 11-day Malta, Balearic, and Spain cruise aboard Star Clipper. Enjoy the easy-going informality aboard your tall ship, finding that there are no rigid schedules and you are free to do as you wish with your days and evenings. Start at the charming port of Valletta, Malta, featuring an …

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 …

Embark on an enchanting 8-day Ancient Jewels of the Mediterranean cruise aboard Le Bougainville. Starting in Valetta, indulge in included excursions at each port. Meet a famed puppeteer in Syracuse, explore quaint villages in Paros, and visit the historic Rodolico shipyard. Discover the ancient …