I don't like either one!
First of all August is a terrible time for group OR individual travel. In August the whole of Northern Europe jumps into Jumbo Jets and invades the greek isles AND any beachy portions of the mainland. The temps can get up to 100° + in the middle of the day, so one must go hide until the sun lowers. Next, if it's your ONLY trip to greece, spending 2-3 days going to Meteora isn't the best priority -- these are monasteries on top of high pillars in the mountains, and it's amazing that they were able to build them by hauling bricks up in baskets for decades ... but is this really what Greece is about??? The Greece that people remember involves sun and sea, and ruins and villages, and wonderful fresh fruits & veggies and sunsets and flowers, stuff like that. When you say "Crete" without saying anyting about what that means, it's very hard to say what's involved. I DO know that Santorini in August (and many other times) can be a crowd-scene nightmare. Because of the crunch & the degrading of island resources due to massive crowds, island authorities recently have set a daily limit of 8,000 cruise passengers allowed. 8,000. whew.
September is a better time but again -- so hard to understand what would be involved -- I cannot understand how GRoup B can take 13 days because it looks lilke a "canned" fast-forward. I don't trust it, and I know Crete.
May or June are even better choices, from standpoints of best weather, lack of crowds, and better hotel prices. Possible??
FOrtunately, you're looking at 2019, I'm guessing, so you don't have to choose yet. We could help more if you'd share more about yourselves -- are you a couple, how many are you, age range, interests? Are you still in workforce or are you retired and can be more flexible about when to travel? Is 2 weeks your desired time-frame for the trip (not counting arrival day or departure day) ? What's your budget range per person, not counting airfare to/from US? Are you somewhat into Classical Greece (ruins? Temples? Museums?) or into Byzantine? Medieval, Church stuff? or only mainly into dramatic landscapes, foodie experiences, upscale hotels? If you'd just share a few of these things, I know responders will come up with better choices than you've found so far ... so Please, tell us more!