Airline: Turkish Airlines to Athena (layover in Istanbul) (yes they call it Athena there not Athens)
We were picked up from the Athena airport in a really nice Mercedes cab which had wifi in it. It was 38 euros. If you want the exact driver we had who was wicked nice: Venediktos Kontzialis
First few nights we stayed here: Fenix Best Western Glyfada, if you don't want two twin beds put together get a premium room, breakfast was really good for free.
(Glyfada/Vouliagmeni is where Greek locals vacation.)
This hotel is located near vouliagmeni beach which is a very nice beach, there is a shack to get food there too, it costs 5 euros to get in per person
There is a hotel next to that that has water sports off the dock of a fish restaurant we ate at called BlueFish in Vouliagmeni.
This ice cream/dessert place is a must if you go to this area: Waffle House
We then went took an uber/taxi from the hotel in glyfada to the ferry stop in Piraeus (this is where most boats leave from) We bought our tickets to Poros from there.
Once in Poros, took a small little taxi boat across the water for 1 euro (2 min ride) Then took a taxi to our next stop which was the Drepani Waterski Resort.
From there we took the ferry back to Pireaus and then got on a ferry to Santorini/Thira. We took the overnight ferry and got a cabin. This should be done in advance. Cabins book up fast and the ferry is 9 hours long. In the cabin you have beds and a shower. Very basic but totally worth it so you are showered and ready to go once on the island. We had an airbnb on the caldera in Oia for the first night. The taxi from the port took us to a stop where a guy met us and carried our bags to our airbnb.
Oia Airbnb : This was the most amazing airbnb we stayed in. It was right in the middle of the two iconic blue churches and tourists don't come down to where you are so its pretty private. This one had three beds so it might be too big but the view was unlike any place I've stayed before.
Food in Santorini/Oia: We ate at the only breakfast place that was open one morning lol it was rediculous nobody was open yet. This place had incredible food and fresh squeezed juices including watermelon juice and is located in between the two blue churches on the top of the caldera. We did some shopping and also walked down to Ammoudi Bay for lunch. We ate at Dimitrius which is the famous place to eat: Dimitris Ammoudi Restaurant. After lunch we walked past the restaurant and followed a small path to a rocky beach where people were sunbathing and swimming from. This is where you can jump from the church cliff which is awesome too. The water is crystal clear. After that we went back up the steps of Ammoudi Bay by MULE!!! I believe it costs 5 euros per person. It was a memorable frightening experience yet memorable. You won't stop laughing the entire way.
We also booked a catamaran trip for one day (4 hours) where we drank and ate, swam in the hot springs, and swam at red and black beaches. (we stayed offshore of those beaches so we didn't go on the beach to see the colors. The food was decent for the amount of people and free bar. Couldn't find the exact company we did but here is one similar: Catamaran in Santorini
We then took a ferry from Santorini (just took a cab to the port) to Mykonos: This was about a 3 hour ferry (no AC on boat) so be prepared. They do have some food to buy. No wifi usually
Here is where we stayed in Mykonos: Airbnb mykonos
Some things to know about Mykonos: its freakin expensive, we didn't go where most go on the island which is Paradise Beach/Nammos beach area. We stayed in Kalo Livaldi which is more tame and we found a little area to swim in off the rocks which was awesome. That's my perspective. Very much the new Ibiza.
Here's a link to learn more about what to do there: Mykonos
After a day in Mykonos, we took the ferry back to Pireaus and taxi'd to our last airbnb of the trip: Airbnb Voula which wasn't close to much of anything. We wish we had just stayed at the Fenix again.
Overall the trip will be an amazing, memorable one if you go. We were there the beginning of August which was HOTTTTTT (80s-100s) and it's there peak season so very crowded. Locals said it starts to die down