Ah Santorini & Mykonos Greece, where do I even start, you literally can’t put their beauty into words. It’s 100% true what others say about Greece’s most popular islands, you can’t describe them in words or pictures or videos, you just need to see them with your own eyes to truly appreciate their beauty. This was my first international trip across the pond.
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The thought of going to Greece came into perspective in late summer of 2017 and almost one year later, that idea became a reality. I remember it like it was yesterday. As I was sitting with my girlfriend Amanda on a perfect summer’s night on her porch, we were discussing our must-hit destinations to travel to. Greece was a top three choice for both of us, along with Thailand and Costa Rica.
After countless hours of researching and deciding on the specific areas of Greece to visit, we decided on Athens, Santorini and Mykonos. Santorini and Mykonos are a top choice for many travelers because of the famous Caldera in Santorini and the beaches (and party’s) in Mykonos. The islands have a lot more to offer than just those two examples and I’ll talk about them in more detail in the paragraphs to come.
Planning the pursuit of happiness…
I booked our first flight to make sure we were on our way to our destination months before our scheduled departure date. Usually you can find the best prices around 80 days out to a European destination from the US using sites such as SkyScanner. Our round-trip airfare ended up being about $715, which is not a bad price, but not budget friendly either. A price I was willing to pay this time to fly half way across the world.
Our flight path would be from Chicago (ORD) to Philadelphia (PHL) to Athens (ATH) on the way there. And Athens (ATH) to Madrid (MAD) to Chicago (ORD) on the way back. With only one-stop there and one stop back, we were sure there was little room for delay.
Next up, we had to book our connecting flights to the island of Santorini and a ferry boat to Mykonos. Then, another connecting flight from Mykonos to Athens. We chose to use Ryanair because of its cheap prices ($105 RT that included priority boarding, carry-on, checked bags) and short flight times. We could’ve booked a ferry from Athens to Santorini, but it would’ve taken around 8.5 hours, not the time we wanted to sacrifice.
We used ferryhopper.com to book the ferry from Santorini to Mykonos. The cost was $151.35 for two people and the cruise would take around 2hrs and 20minutes. After the main transportation was booked, we then looked into hotels, hostels, apartments and Airbnb’s. We ended up staying in a combination of almost all those options besides a hostel.
Traveling as a couple, a shared-room hostel just wasn’t going to be our thing this time around. There was a lot of research and time spent on finding the right hotels at the right locations wile keeping budget in mind. And as you know, location, location, location!
I use AirBnb to find many of my accommodations while traveling. Use the link below if you’re interested in saving $25 off your next stay on one of the most trusted travel sites.

The first place I ended up booking was an apartment near the Athens city center, about a half mile from the Acropolis. The Airbnb was called “Comfy Home in Vibrant Neighborhood”. Check out my YouTube room tour of this apartment and let me know what you think in the comments section of the video on YouTube.
Let’s start from the beginning of our trip, now that everything was booked, and we were ready for takeoff…
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