For a first trip, it is tempting to put Santorini and Mykonos at the center of the plan. Both can be exceptional, particularly for couples who enjoy polished hotels, restaurants, and an energetic scene. But Greece’s most memorable romantic escapes are often found in islands with a more distinct sense of place – where dinner follows a swim, ferries set the day’s pace, and the evening belongs to a small harbor or a hilltop village. Travel timing matters as much as destination. May, June, September, and early October usually offer the strongest balance of warm water, manageable crowds, and better...