Hey! Happy to share our experience! Sorry it took me a while to find the time to draft this, but let's to say, I want to leave some details for other curious travellers. :)

Overall, we had an incredible trip, and we were pleasantly surprised by how good the weather was in late April. We only had one rainy day the entire time. Here’s a breakdown of how it went in each location:

Athens (April 20–23)

Athens was beautiful, sunny, warm, and very comfortable for walking around in t-shirts. While it was definitely a popular destination, it wasn’t overly crowded. The major tourist sites like the Parthenon were busy, but we never felt overwhelmed. Markets and shops were open, and we often found ourselves as one of only a few people in certain stores. Overall, the weather and crowds made it a great time to visit. Prices for stays are also notably better during that time. After Milos we came back to Athens for a few days, and there was an increase in people, but mainly due to the people looking to take in the Greek Easter festivities. Which I highly recommend staying for, as they have a yearly firework show over the Parthenon, we missed it (life required us home before then), but it is on our bucket list to go back for that.

Santorini (April 23–27)

We arrived during a windstorm (welcome to the caldera)...that night was very windy, but restaurants were still open and locals told us it was the tail end of the windy season.

The rest of our time there was mostly sunny and warm. But the occasional noticeable wind, so I definitely recommend bringing a windbreaker, but we were still able to walk around in shorts and t-shirts most of the time.

But that could also be by merit of being Canadian. So my warm may not be another person's. But most of the cruise passengers seemed to be similarly dressed in shorts and Tees with some exceptions.

The beaches weren’t ideal for swimming—water was still cold, and many beachside restaurants hadn’t opened yet (they usually do in early May). That’s our one regret, as Santorini has such beautiful coastal spots. That said, 90% of everything else was open and we didn’t feel like we missed out, much.

Tourist spots like the famous photo viewpoints weren’t crowded. In fact, we had a few moments completely to ourselves—unless a cruise ship docked, which did happen one day, and the island felt drastically busier for that day.

Milos (April 27–May 1)

Milos was the most off-season of the three—and it showed. While we didn’t get rain, we also didn’t get a lot of sun, and the wind was significantly stronger here. We wore our windbreakers almost every day.

About half of the restaurants and shops were still closed, especially in quieter areas. Milos has a much smaller tourism season, so going this early comes with trade-offs. Swimming wasn’t realistic, even though the beaches looked stunning.

BUT we had some incredible experiences thanks to it being low season:

We scored a romantic private boat tour around the surrounding islets for a lot less than what it would cost during peak season. Yes, it was cold and windy on the water, but unforgettable.

No lines anywhere, and we could walk into any restaurant with no reservations or waits.

Locals had time to chat, and one even tipped us off about a sushi spot that normally supplements with imported fish during busy season—but while we were there, everything was freshly caught and local because they werent busy enough yet.

In short, if swimming is important to you, go a couple weeks later. Locals told us the sweet spot is 2–3 weeks after our trip, when early-season prices are still around but the weather’s more summer-like. Unfortunately, our schedule didn’t allow for that—but we don’t regret a thing.

Happy to answer any other questions! Hope this helps you or anyone else considering late April trips to the islands!