Phase One - The RS DIY car routes are usually fast-paced. They are often the same pace as the RS guided tour, where a veteran bus driver handles the road, and mostly gives you door-to-door service (hotels, sights, etc.). You will have to navigate the unfamiliar roads (possibly with limited signage in places) and find all the sights, hotels, and parking on your own. Nor will you have a guide to take you from place to place and usually skip the lines at sight entrances. You will want a day or two in Athens to get over jetlag before renting the car, and you'll want at least one night there before your flight home. If you are interested in archaeology, there's definitely enough for 3 full days in the city.
In October I spent a week on Crete and a second week split between Santorini (3N) and Naxos (4N). I was on Santorini right around mid-month and although it was end of season, there were 1 or 2 large cruise ships tendered off Santorini every day. I arrived by ferry from Crete and it was nearly an hour to get to my hotel in Firostefani (on the outskirts of Fira) by private car. The driver told me it was his last week of the year, there'd by no work after that. Still there were 1 or 2 large cruise ships in port every day I was there. I found a budget place to stay and chose Firostefani because it was walking distance to Fira but without the crowds. I thought both Fira and Oia were very touristy. The classic views in all the photos are from Oia. Instead of going early in the morning, before the cruisers, I ended up arriving around 10.30. While it wasn't overly crowded, there were lots of people and way too many tourist shops. So I was able to enjoy a bit of the "classic" views and a couple of okay sunsets in Firostefani - reputed to be just a tad less than those in Fira - and they were not nearly as wonderful as I'd expected. Santorini was the most expensive place for food and drinks by far - even more so than Athens. In all I came away thinking it was mostly hype. If you are willing to rent a vehicle and avoid these highly touristed areas, I think you can have a very enjoyable time for 3 nights. Because Santorini is so popular, both the ferries and the airport are often very crowded and disorganized. Allow enough time to arrive and leave.
On the other hand, Naxos was a great place to relax. I stayed in a small apartment on St. George beach. It's very shallow water so it attracts many families but not in October (or, presumably in April). It was walking distance to the center of town and to a couple of very good restaurants. I took a full day guided island tour that was interesting.
By far I enjoyed Crete the most. I spent 5N in Chania and 2N in Heraklion. Chania is charming, not too touristy, has interesting sights and some great places for late afternoon cocktails and great dinners. I stayed in Heraklion in order to visit the ancient site of Knossos and the archaeology museum. It is possible to do both in a single day, but I wanted a very slow pace for this trip. If you rent a car, you could easily spend 2 weeks just on Crete. There are direct flights between Chania and Athens. To get anywhere else, by plane or ferry, you need to go from Heraklion.