Seeking advice on Sept 2025 sail in Greece

[FlySailRepeat]

Hello! New here, and excited to learn from all of you!

My husband and I are fairly new to bareboating, although we both have had some limited sailing experience prior to getting our ASA courses. We have chartered in the BVI and the San Juan Islands (WA). We have another trip to the BVI booked for early 2025 and we are hoping to go to Greece later next year to celebrate our son's college graduation (and the release of said son from our family payroll haha!)

In an effort to avoid crowds, excessive heat, and higher airfare we usually like to travel in early to mid September. I'm seeing information about the Meltemi winds in Greece into August, but not a lot of info about the sailing conditions into September. Our plan is pretty loose right now in both timing and location. I initially was focused on the Ionian Islands, but really we are open to whatever.

We are an active family. We mountain bike, hike, backpack, sail, ski. My son is majoring in Recreation Management and he is working for a guiding company this summer, to give you a sense. My daughter will also be with us, she is 25 and also active. We are looking for warm waters, interesting places, historical and/or mythologically significant locations. We appreciate authentic food and experiences (and wine haha). We will likely spend a few days in Athens no matter where we end up sailing. We will be coming from a week in Switzerland (hiking and digging into WWII history)

Seeking your advice on best time to sail, if you have any not-to-miss locations, if the Ionian area is the best choice, etc. I'm researching like crazy, but always appreciate anecdotal information from real people