Top Italy Trips & Tours in May 2026

Discover Italy’s highlights on this 10-day tour, from Lake Como and exploring Milan’s Gothic splendor to savoring limoncello in Amalfi. Visit Pompeii’s ancient ruins and unwind on the stunning Amalfi Coast.

Discover Italy’s top highlights on a family-friendly adventure through Venice, Florence, Tuscany, and Rome. Enjoy hands-on experiences like mask-making, cooking, and cycling, visit iconic sites such as the Colosseum and Ponte Vecchio, explore the Ferrari Museum, and experience Italy’s rich culture, history, and flavors together.

On a 10-day Italian tour, discover the historic city of Turin, home to some of the country's most important art and architecture. Explore the world-famous wineries of Langhe and taste some of the region's finest wines, including the famous Barolo. Take a train from Sestri Levante and visit the Cinque Terre, one of Italy's most picturesque landscapes and enchanting medieval villages clinging to the coast.

Experience the nature and culture of the Aeolian Archipelago on this 8-day tour. Visit Lipari, Vulcano, Panarea, Stromboli, Filicidu, and Salina, which form one of the most active geological structures in the Mediterranean. Explore these beautiful coastal towns, visiting incredible volcanic rock formations and seafront black sand beaches.

Sail from Venice to Rome on an 11-day cruise aboard the S.S. La Venezia. Experience early access to St. Mark’s Basilica, Vicenza’s Teatro Olimpico, Murano’s glassblowers, and Rome’s ancient wonders. Explore Chioggia, Burano, and Padua while enjoying unforgettable cultural, historical, and culinary moments.

Experience an 8-day roundtrip cruise from Venice aboard S.S. La Venezia. Discover the Doge’s Palace, Burano’s colorful houses, Chioggia’s markets, and the Po Delta’s tranquil waterways. Visit castles, art museums, artisan studios, and lively piazzas, while enjoying authentic cuisine and unforgettable views of the Venetian Lagoon.

During this 9-day cruise around Sicily aboard the new luxury expedition ship Le Bougainville, you'll be able to explore mythical places at the crossroads of Eastern and Western civilizations. Discover Sicily's most beautiful historic cities and ancient sites.

Sail on this 8-day Western Mediterranean cruise from Civitavecchia to Nice aboard Emerald Sakara. Explore Corsica’s Calvi, Tuscany’s Livorno and Marina di Carrara, the UNESCO-listed town of Porto Venere, the coastal gems of Santa Margherita Ligure and Portofino, and the glamorous cities of Monte Carlo and Nice.

Set sail on a 12-day cruise from Civitavecchia to Venice on the Star Clipper, exploring Italy and Croatia's hidden gems like Ponza and Otranto. Experience historic towns and local cuisine, and enjoy onboard relaxation and adventure across beautiful coastal seas.

Set sail for a 10-day Mediterranean cruise from Valletta, Malta, to Civitavecchia, Italy, on the Emerald Sakara. Visit Sicilian beaches, Amalfi's historic sites, and enjoy stunning views from Capri and Sorrento, balancing relaxation with exploration.

Discover Tuscany on this 8-day tour. Explore the Via Francigena, savor wine tastings, visit Siena and Florence, and enjoy scenic walks through Chianti vineyards and San Gimignano.

Discover Slovenia and Italy on a 14-day cruise from Ljubljana to Rome aboard S.S. La Venezia. Visit Lake Bled, Venice’s Doge’s Palace, Chioggia’s markets, and the ancient wonders of Rome. Savor regional wines, explore medieval towns, and enjoy private after-hours access to St. Mark’s Basilica.