My family and I have now been to Greece twice, both times on *A business in June. First time we stayed in Boutique hotels, second time, just this June we stayed at Hilton, Holiday Inn, and Sheraton.

First things first, find a way over the Atlantic. This is the worst part. First time we flew ORD - IAD (UA), IAD - VIE (AS), VIE - ATH (AS) stop over 3 days, ATH - HER (A3) destination 5 days, HER - ATH (A3), ATH - MUC (LH), MUC - ORD (LH)

This second time we flew ORD- YUL (UA), YUL - ZUR (LX), ZUR - ATH (LX) stopover 3 days, ATH - RHO (A3) destination 6 days, RHO - FRA (LH),
FRA - ORD (LH).

I found each of these routings myself using various search sites and fed them to UA segment by segment for ticketing.

We stayed with points at the Athens Hilton, highly recommended especially if you can get the Executive Lounge. The Sheraton on Rhodes was lovely with 3 pools and a private beach.

On Crete we stayed at the Nymphs (you need a car and not for the faint of heart driving up a literal goat path - but oh so worth it when you get there), we also stayed at the Knossos Beach, incredible to have large patio overlooking the water in the evening.

Each trip was booked ~280 days out.

Not sure what other info you want or need. Fire away.