With extra time before his summer job and a high-school graduation on the books, our youngest had long admired photos of the classic blue and white Greek architecture and dramatic Aegean scenery. My husband and I had backpacked Greece in our twenties and understood the appeal immediately, particularly Santorini. Researching which islands to hit, however, also uncovered Kalymnos: a world-class rock-climbing destination that we planned the trip around. While our son is not an expert climber, he enjoys the activity on trips, and it seemed like a great spot for me to also fulfil that Mamma Mia-like fantasy. We would also be having my husband's brother and two of his kids join us partway through.