We are heading to Greece with our 18 and 20-year-old kids (their first time, our first in 30+ years!), in celebration of the younger one's high school graduation. After much discussion and research, we've landed on this as an itinerary, but there are a few elements we're debating tweaking.
June 9-12 (3 nights) Santorini - staying in Firostephani (fly there directly after landing in Athens)
June 12 - ferry to Paros to meet captain of charter sailboat
June 12-16 (4 nights) sailing, finish in Milos. Depending on wind/weather, will visit Paros, Sifnos, small Cyclades, etc.
June 16-22 (6 nights) Milos - staying in Pollonia w rental car
June 22-Fly to Athens, rent car and drive to Delphi (around 2.5 hours drive)
June 22-23 (1 night) Delphi
June 23 Drive back to Athens (return car)
June 23-25 Athens (2 nights)
June 25 Fly home.
The potential tweaks:
1) Is 6 days too long on Milos, or to put it differently, should we spend a few nights on a different island instead to see more/do more? We are travelers who like a mix of activities and chill time...we will hike, swim, snorkel, wander through towns, take photographs, eat good food, but also sit with a book in the shade or nap on a beach. Too much moving around tends to create cranky dynamics, but at the same time, we want to see a good range.
2) Is Pollonia too quiet for the young adults, who may want to head out in the evenings? This isn't a major party trip, but it would be fun for them to grab a drink and meet other younger travelers passing through...not sure if there's any of that in Pollonia. Seeking a compromise, since the real adults (who are paying) also don't want to sleep next to a disco!
3) On any of these locations, are there any "totally worth the money" excursions or private tours or activities that you recommend? We will definitely be sailing around Milos, and I think will also take a sail in Santorini. But beyond that, curious what folks - especially those who traveled with older kids - considered the top highlights worth splurging on!