Your tour begins at the magnificent D’Amboise Gate, the grand entrance to the medieval walled city of Rhodes. Cross the impressive moat and step back in time as you reach the 14th-century Palace of the Grand Masters, an architectural masterpiece that once served as the residence of the Knights of St. John. Take time for close-up photos of this imposing landmark and the surrounding historical monuments. Then, enjoy a leisurely stroll along the cobbled Street of the Knights, one of the best-preserved medieval avenues in Europe, before exiting the Old Town to continue your journey by vehicle.

Next, enjoy a scenic drive along the elegant esplanade of Mandraki, the main harbor of Rhodes. According to historians, this very site once hosted the legendary Colossus of Rhodes, erected in 292 B.C. — a monumental bronze statue dedicated to Helios, the Sun God, and celebrated as one of the Seven Wonders of the Ancient World. As you explore, you’ll notice a fascinating blend of architectural styles — a living legacy of the Italian era that shaped the island’s character in the early 20th century. Take in the view of the magnificent Church of San Giovanni (St. John) and the harbor’s most beloved symbols, the graceful Rhodian deer statues standing proudly at the port’s entrance, welcoming visitors to this timeless harbor.

Continue along the windward coast, where the turquoise and azure hues of the Aegean merge in a breathtaking display of color. Your journey then ascends to Monte Smith, the highest vantage point overlooking the city of Rhodes. From this panoramic viewpoint, enjoy sweeping views across the Aegean Sea, the coastline, and the ancient Acropolis of Rhodes — a place where history and natural beauty meet in perfect harmony.

The next landmark on your private tour is Ialysos, one of the island’s ancient cities dating back to the Minoan period. Ascend Mount Filerimos, where panoramic views of the Aegean Sea and the nearby islands unfold before you — a truly breathtaking sight . At the summit, explore the Church of Our Lady of Filerimos, built upon the remains of an ancient temple. Wander among the ruins , where centuries of history and faith intertwine. These sacred grounds offer a profound glimpse into the spiritual heritage of Rhodes and the civilizations that once flourished here.