Athens' Monastiraki, Plaka, and Koukaki districts put you within walking distance of the Acropolis. Boutique hotels in Plaka's neoclassical buildings have great character. The trendy Psiri neighborhood suits younger travelers.
Santorini's cave hotels in Oia and Fira cling to the caldera cliff and offer iconic views at premium prices — book 6+ months ahead for peak season. Mykonos Town's maze of white alleys is perfect for nightlife lovers. For quieter escapes, consider Naxos, Paros, or Milos.