Top Mediterranean Trips & Tours in May 2026

Embark on an unforgettable 9-day Greece island-hopping adventure, exploring the stunning islands of Athens, Paros, and Santorini. This journey will take you through a perfect blend of ancient history and breathtaking landscapes. Be ready for a trip filled with azure waters, sun-drenched beaches, delicious cuisine, and picturesque villages.

Embark on an 8-day cruise through the stunning Cyclades on the Gemaya, exploring charming islands like Milos, Sifnos, and Delos, rich in culture and natural beauty. Experience pristine beaches, delightful hiking, and vibrant local cuisine before concluding your adventure in Lavrion.

This 7-day tour of classical Greece will explore Athens and its rich cultural heritage. Visit the charming town of Nafplion and its beautiful architecture. Learn about Greek mythology and history at the Temple of Apollo and the Delphi Archaeological Museum. Finally, see the stunning rock formations of Meteora and the monasteries perched atop them.

Embark on a cultural journey through Athens with the 4-day Athens City Explorer. Experience the unique and captivating journey through the ancient and modern wonders that describe Athens. Discover its rich history, vibrant culture, and stunning beauty as Greece's capital city.

Embark on a 12-day cruise aboard the Emerald Kaia, exploring the Adriatic, Ionian, and Aegean seas from Dubrovnik to Athens. Discover scenic landscapes, historic sites, and charming ports, including Kotor, Corfu, and Lefkada along the way.

Embark on an 11-day cruise from Athens to Dubrovnik aboard the Emerald Kaia, exploring the Ionian and Adriatic Seas. Visit historic sites, enjoy local culture, and relax in stunning coastal towns before concluding your journey in Dubrovnik.

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.

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.

Set sail for an 8-day cruise on the Royal Clipper, visiting Monaco, Portofino, Corsica, Sardinia, and St. Tropez. Experience stunning landscapes, rich culture, and gourmet dining before returning to Nice with lasting memories.

Embark on an 8-day cruise from Dubrovnik to Split aboard M/S Ambassador, exploring Croatia’s stunning islands, historic cities, and vibrant culture. Enjoy medieval towns, crystal-clear waters, and timeless traditions.

Discover the beauty of unspoiled beaches, historical architecture, blue caves, cobbled streets, national parks, and much more on this 8-day voyage aboard M/S Ambassador from Split to Dubrovnik.

Experience an 8-day Mediterranean sailing adventure from Civitavecchia, exploring Sicily, the Amalfi Coast, and the Aeolian and Pontine Islands aboard Star Clipper. Sail past Stromboli’s active volcano, wander historic Messina, and admire the coastal beauty of Amalfi and Sorrento. Explore Ponza’s unspoiled charm before returning to Rome’s port.