Top Italy Trips & Tours in May 2026

Explore the heart of the Mediterranean on this 8-day Mediterranean Island Cruise with Smithsonian Journeys from Valletta to Nice aboard Le Bougainville. Discover Sicily, Sardinia, Corsica, and Elba's historical civilizations that left mark on these islands' language, cuisine, art, and architecture.

8-day cruise along the Adriatic aboard Emerald Kaia. Explore the coastlines and islands of Greece, Turkey, Croatia, Italy, France and Spain. Discover rich history, charming streets, and breathtaking landscapes on your unique cruise

Spend your week on an 8-day Classic Dolomites Premium Adventure hiking tour with the help of expert guides from Exodus Travels. Discover some of Italy's most breathtaking scenery while hiking safely and at a pace appropriate for your experience level.

Spend 9 days on this small group journey through the highlights of Sicily to step into a world where ancient ruins stand alongside vibrant cities and picturesque landscapes. Discover ancient ruins, bask in the island's natural beauty, and indulge in Sicily's culinary delights.

Discover one of the most fascinating and romantic destinations in the world, the Amalfi Coast. On this small 8-day group adventure, visit both Herculaneum and Pompeii, see the romantic coastal towns of Amalfi, Positano, and Ravello, and explore the island of Capri on this best-selling tour.

Experience a 7-day cruise on La Bella Vita, exploring northern Italy from Venice to Mantua, with guided tours of historic sites and art museums. Indulge in local cuisine, wine tastings, and stunning views of the Venetian Lagoon and Po River Valley.

Join this 8-day premium group adventure and discover Rome, Assisi, and the magical Umbria Region in Italy with an expert guide. Experience the best of Italy's history, culture, and cuisine in a luxurious and personalized way. Discover the beauty and magic of Italy's cultural and historical treasures on this unforgettable journey.

Embark on a 7-day cruise aboard the Star Clipper, starting from Civitavecchia and visiting Italy's beautiful coastal spots like the Aeolian Islands and Amalfi. Conclude your journey with easy access to explore Rome.

Experience a 7-day private cruise on La Bella Vita, exploring northern Italy from Venice to Mantua, with guided tours of historic sites and art museums. Indulge in local cuisine, wine tastings, and stunning views of the Venetian Lagoon and Po River Valley.

Discover Italy’s wild side on a 12-day Nature and Wildlife Tour through Tuscany, Rome, and Sorrento. Hike the Val d’Elsa, taste wines at sustainable vineyards, ride through Maremma Park, and spot dolphins in the Pelagos Sanctuary. Explore Rome’s Appian Way and end in Sorrento with a lemon cooking class and coastal trek.

On this 10-day tour, hike through the stunning Dolomites mountain range in Italy to see the panoramic vistas, beautiful mountain huts, and serene lakes and pass through enchanting mountain villages.

Explore Italy's rich culture, history, UNESCO World Heritage sites, and gourmet countryside on this 10-day classic Italian vacation. From Venice to Rome, tour the countryside and world-class sites in Florence, Siena, Colle di Val d'Elsa, and Rome.