I'd love to get thoughts on how best to structure a 2.5 week trip (June 2022) with our 18-and-20-year-olds. My husband and I traveled in Naxos, Santorini and Crete for 4 months back in the 1990s, but that's the last time we've been to Greece!
So the questions: If we do 3 nights in Santorini, then 3-4 nights on a sailboat that starts and ends in Paros, we will have a week (plus/minus a day or so) to play with in the islands. Should we stay on Paros and explore Paros, Antiparos, and a day trip to Naxos? Go to Milos, which seems to have really cool stuff to see and funky beaches? Stay on Naxos, which has great hiking and of course great beaches, (but more typical wide sandy ones, and less unusual funky ones)? Split our time between two islands, or is that going to involve too much time in transit?
Some other info: we will be traveling approximately June 9-26; starting in Santorini because the grad really wants to see it ; We are likely going to book a 3-4 night private sailing charter that starts/ends in Paros and -- depending on weather/wind/etc -- could sail around and do day trips to Paros/Antiparos, Sifnos, Naxos, etc.; We are hikers and eaters and wanderers and laze-around-with-our-books-on-the patio-ers and beach-goers, especially interesting or funky beaches with rock formations or something else cool. (We live right near a lovely beach in Massachusetts so simply being on a beach isn't a novelty). The kids are old enough to hit discos and bars, and would like some nightlife with younger folks. We prefer low-key tourist options, which is to say having some good restaurants/shopping, local markets/sights but would skip the biggest/best/most popular in exchange for fewer crowds. We will likely rent a car whenever that makes sense, but also like the idea of being able to walk to some things (beaches and/or towns) since we will not want to all be joined at the hip the whole time. We tend to stay in rental houses or Airbnbs over hotels, just for cost reasons, since the siblings are not going to share a bed and may not want to share a room for 2+ weeks straight.
Many thanks for any and all thoughts -- I realize there are a lot of ways to do this right and no real way to do it "wrong" (except trying to cram in everything!) but grateful for any wisdom people want to share!