Thanks for the replies! I'll try to cover most of the questions in this single response.

@Mwenenzi
What research have you done yourself on airline ffp's that could get the trip you want?
I read doctorofcredit, flyertalk, and thepointsguy. But it's all a bit overwhelming.

What research have you done yourself on airlines & routes?
There seem to be many ways to get to Athens. It sounds like Athens will likely be our way in and out. But choosing which route and points programs points to use is where I'm overwhlemed. Not sure how to best decide.

What ffp's are you a member of now? How many ff miles/points? Only UA?
I listed where most of my points are, but over the years I've joined other programs like Southwest, American Airlines, Delta, JetBlue. But I really don't fly often and have not accumulated points worth much value in these other programs.

What airlines are transfer partners of your credit card? (It does vary by the country of credit card issue)
I really don't know exactly. From what I've read, I have a good amount of options. It's almost as if having a lot of options is causing me to get overwhelmed.

You seem to be a frequent spender and not a frequent flyer
Correct. I haven't traveled much in recent years. The majority of the points I've accumulated have been from hitting sign up bonus's and normal spend. I accumulated most of the SPG points in particular years ago when I traveled for work a bit more.


@Romelle
Have you been to Greece before? Or other European cities?
Nope.

You need some sort of general traveling plan. How do you plan to move about? Public bus/train? Metro? Rent a car? Uber? Taxis? Guided tours about the country? Local guides for specific spots?
Based on the research I've done so far, I'm thinking something like this from a high level. But I'm really not tied to this... just a starting point.
-2 nights in Athens (arrival airport)
-3 nights in Santorini (via ferry or plane)
-3 nights in another island (via ferry) like Mykonos, Naxos, or Icaria.
-2 nights in Athens (via ferry or plane from previous location) (departure airport)


@Oxymore
Are you flexible within the month of September? It's a great time to visit Greece (nice and warm, but not the terrible heat you may endure in late July or August, and less tourists).
Yes, we're flexible within the month of September.

How do you plan to get around? I hate to say it as I do encourage the use of public transportation, but to be comfortable, I would encourage you to rent a car, especially if you want to tour the Peloponnese. KTEL buses do exist, and are cheap, but may not necessarily make for a cozy ride. Of course, while you stay in Athens or Thessaloniki, a car would be more a problem than a solution.
I'm not opposed to getting a car if that's what's suggested the best way to travel in the areas we visit...

When you say flying First isn't important, do you mean premium cabin isn't important or specifically First (as opposed to Business)?
I mean that I'm not quite a flying snob, and prefer to use points for as much as our trip as possible. If using points to sit First Class (or a more premium cabin) meant that I'd have to pay for all of our hotels with cash, then I'd rather sit in a less premium cabin and be able to use some of the points for hotels as well. Economy is fine with us and I'm glad to see you recommend it.

Since you have the Sapphire reserve, keep an eye out for sales to Europe: they happen pretty frequently these days - but it's maybe a bit early for September. You could end up spending a lot less booking directly with Chase UR travel if the ticket cost is around $500 - (you'd only need to spend 34,000 UR points per ticket). Again, just a suggestion!
This is exactly the type of thing that I want to learn about. That sounds like a great value and I wouldn't want to screw up booking a different way that sucks up all my points. What's the best way to find these? When you say they happen frequently, does that mean they come and go within like 48 hours or longer than that? 34,000 UR points per ticket sounds awesome!


Thanks again all.