Santorini is definitely the most well-known of the Greek islands. There’s a bunch of different areas to stay, and there’s plenty of articles outlining the vibe in each neighborhood. From what we read, the two main spots are Thera and Oia. Oia being the more romantic neighborhood, Thera being a bit bigger and more exciting. I think Thera also has the better sunsets because of the direction it’s facing.
Flights: Athens-Santorini (JTR) there on Olympic, return on Aegean
Olympic is a tiny airline, but I never felt unsafe. Their planes were in good shape and their staff is super nice. Like I mentioned in the blog about this overall trip, the weather on the islands is highly unpredictable. We had the first flight out and got delayed 3.5 hours because of the winds. I’d highly recommend leaving Santorini the night before an international flight. Don’t take the chance.
Hotel: El Greco Resort and Spa. We booked super last minute – meaning sometime that week, and this was the nicest hotel closest to town that wasn’t $500 a night. It had a bunch of pools, the rooms were cute, and the bathrooms were clean and big. It was within walking distance to Thera as well. Santorini hotels in general are known for their individual rooms built into the cliffs that are super romantic and essentially built for honeymooners. They’re stupid expensive, but probably worth it for a honeymoon setting. For a weekend with friends or kids, El Greco would suit your needs just fine.
For lunch we just stopped into a gyro place on the street. As usual, you really can’t go wrong.
For dinner, our hotel recommended a restaurant overlooking the water during sunset. I honestly can’t even remember the food or the name of the place, but the view was stunning. Just ask your hotel for a recommendation and to make you a reservation. Most of the restaurants on the cliffs in Thera have the view, so you’d have plenty of options.
What to do/see:
Wandering around Thera – there’s so much to see with the cute shops
The donkey ride down the mountain. This is kind of the cliché thing to do in Thera. You can just google search the donkeys – it’ll find them. Then there’s just a bunch of older guys with a whole line of donkeys and you pay them cash and they take you down. It’s almost so informal that you feel like they’re going to con you, but they’ve been doing it their whole lives. Same with the donkeys. If you don’t go on them, they literally just sit there doing nothing all day. Might as well go for it.
Once you’re at the bottom of the mountain, there’s another set of unique stores and streets to wind through before you hit the water.
We ended up taking the tram back up the mountain rather than the donkeys. I think it was just faster and cheaper.
Oia: You can take the bus or rent a 4-wheeler to get up to Oia, which is where you’ll find most of the classic blue roofs that will get you the cliché Santorini pictures. Same thing here as in Thera. Just wander through the streets. You can’t go wrong.
I’ve heard a lot of people that said they rented 4-wheelers. Wish we had done that, but we were only there a day and it wasn’t worth the time. The bus system was super useful – crowded and there was a line, but they came pretty consistently and I think they were only 2 EUR per person.
You can either take the ferry or a flight to Santorini. Just make sure you know exactly which stop to get off the ferry. Also we hear that upgrading to “first class” on the ferry is cheap and worth it.