An Assortment of Experiences in Santorini, Greece (May 2023)

After Naxos, Paros, Mykonos, and Milos, our next stop was Santorini. We had some relatively bad luck with the weather. The guides told us Santorini gets a handful of rainy days per year and we seemed to be there for all of them. Apparently mid April was beautiful - sunny, 70s - but early May decided to bring the clouds. Fortunately it didn't rain all day. Mostly at night at I recall. The last night in particular was a rainout. But we made the most of the hours when we could roam around the island.

Our base was Caldera Premium Villas in Oia. This was a nice spot in a good location offering pretty good value for Oia. Cliffside, rooms with views, the typical steps cascading down to your room. Which is nicer on the way down than the way up. 85 steps to the street. First time I forgot my phone in the room was the last time I forgot my phone in the room.

Room itself was solid and basic. I wasn't on my honeymoon. Didn't need a private infinity pool. Cave-style room with some nice views out the window.

And some nice views as you make your way up some of the stairs to breakfast and the pools.

We did a highlights tour around some of the villages, starting conveniently in Oia. As you expect, something picture-worthy every which way you turn.

I did give in to the urge to buy one of the Yellow Donkey beer shirts. Nice soft blue one in my closet right now.

Of course the pottery caught my eye. Attractive, but nothing I was going to carry around with me for the next week through Crete and Barcelona.

At first glance this might look like a picture of people enjoying a nice coffe with a view. But it's really about that dog lounging on top of the ledge oblivous to the view. What's his deal?

And while there were a fair amount of fellow tourists around, it wasn't bad. There are advantages to visiting in early May. Just might want to give yourself an extra night or two in to minimize the likelihood of rain spoiling too much of your time.

Our excursion also included some time walking through Pyrgos, which I enjoyed. If I were to go back to Santorini I'd look to spend a bit more time around Pyrgos and Megalochori. Just a free day walking / wandering / eating. Seemed pretty relaxed.

If you do pass through Pyrgos, stop by E-sterna Handmade Creations. Very nice little shop with a variety of things that looked / felt both unique and of higher quality than a lot of other shops I saw walking around the island. Pics below from its google maps listing, as I didn't take any.

The next day was spent visiting a range of hotel partners getting a sense of the locations, property characteristics, etc. Snapped a few shots of the views as we went around.

Also snagged a couple at Mythical Blue. Nice place for a shorter visit. Could work for longers stays as well if you're very specific about what room you get.

Across from Mythical Blue is Volkan on the Rocks, which is a great spot for a casual meal / drink with some views.

At this stage of our market tour my younger colleagues were still perplexed by my insistence to receive payment for using my likeness in their photos. This was a creative response posted to the group chat, indicating how a 'normal' person would have participated in the selfie.

Photo post (mostly) of a catamaran tour in Milos, Greece (April 2023)

Milos was an interesting island to visit. Definitely different than the others we had just passed through (Naxos, Paros, and Mykonos). The sense I came away with is that you need a few days to really do it well and comfortably. I personally would aim to stay near Pollonia, which struck me as having the best overall vibes. Definitely a vacation spot with beaches and small hotels and holiday apartments. But it also had a least a couple / few streets with some restaurants and coffee shops. I would also want to have a car rental to get around. Or, more precisely, probably a 4x4 rental to access some of the more remote parts of the island. We stayed in Adamantas, which was logistically convenient but a little less charming.

We were not in Milos very long, but had a full schedule to cover a lot of ground. Arrived by ferry at 8pm and went immediately to dinner at Mikros Apoplous. It's well-reviewed and I was happy with my meal, but I played it simple with salad and beer. My colleagues, however, were more adventurous with some kind of seafood dish which disappointed.

Packed it up right after dinner because we had an early bell to answer for a 6-7 hour catamaran ride around the island, with Milos Adventures.

As you can see in the stream of photos below, it was cloudy. Not too cool, as I recall. Maybe mid 60s. The scenery was in turns dramatic, serene, spectacular. Braver souls hopped off for some swimming and cave exploration. I kept my butt on the boat. Overall an experience I recommend. Just dress for the weather. Or visit Milos later in the season. Or both.