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axariotisxy

Active member
I found this video of a sunset cruise in Oia on Santorini and I am intrigued! I'll share the video, and I am curious if any of you have tried this. I had a terrible experience fighting for a standing spot last time I was in Oia.

 
We did the sunset cruise with Sailing Santorini - it was excellent! Not pricey and lots of good food and fun. They have several types of cruises to choose from... depending if you are looking for a relaxed cruise or party. The Red Catamaran is the party boat - we did the Platinum and it was perfect. Everyone was nice and it was low key relaxed fun. Highly recommend!
 
We did the sunset cruise with Sailing Santorini - it was excellent! Not pricey and lots of good food and fun. They have several types of cruises to choose from... depending if you are looking for a relaxed cruise or party. The Red Catamaran is the party boat - we did the Platinum and it was perfect. Everyone was nice and it was low key relaxed fun. Highly recommend!
I am going to have to remember this for the next time I am in Santorini. I hadn't planned out where to watch sunset when I was there and it was a bit frustrating, wandering around, trying to find a spot.
 

Great Walking Paths on Santorini?

I’ve been thinking about Santorini specifically as a place for walking, and I realized it’s something I don’t hear Greeks talk about as much as food, wine, or sunsets. I’m curious how people who know the island well think about walking it, not just as visitors passing through but as a lived landscape.

So I wanted to ask: what are some great walking paths on Santorini? Beyond Fira–Oia, are there routes you’d actually recommend for the views, the quiet, or the feeling of the island itself? I’m especially interested in paths through villages, near vineyards, or stretches that feel more local and less performative. Are there walks that feel better early in the morning, in the wind, or outside peak season?

I’d love to hear which paths you return to or remember most, and what made them stand out for you.

Avoiding Santorini Crowds?

I’m starting to think about a trip to Santorini this year. It’s been a while since I’ve been, and I’d really like to go back, but I keep hearing how crowded it’s gotten.

I’m not expecting it to be empty or anything, but I’d love to time it so I can still enjoy the views, walk around without feeling packed in, and actually get into restaurants without a huge wait.

For those of you who have been recently, when do you think is the best time to go? I’m trying to balance decent weather (warm enough for walking, maybe even the beach) with fewer crowds. Is late spring a good window? Or is early fall better?

Santorini for an Anniversary Trip

A friend of mine is thinking about going to Santorini for an anniversary trip, and she asked me for suggestions. I’ve been to Santorini quite a few times over the years, but almost always as part of family trips, so my experiences there have been a little different from what she’s looking for.

She’s only been to the island once before and really loved it, so she wants to go back and make it a special anniversary trip with her husband. The problem is that I’m realizing most of my recommendations are things families tend to do, and I’m not as sure what the best ideas would be for a more romantic visit.

For those of you who have gone to Santorini as a couple, what did you enjoy most? Are there particular villages, hotels, restaurants, or experiences that felt especially romantic? I’d love to pass along some good ideas to her.

Considering Pyrgos in Santorini to Stay?

I’m considering spending some time in Pyrgos during my next trip to Santorini, and I’d love to hear from people who have visited. I’ve been looking for places that feel a little different from the busier parts of the island, and Pyrgos looks like it could be a great place to explore for a few hours.

For those who have been, what did you enjoy most about Pyrgos? Are there particular streets, churches, viewpoints, shops, or places to eat that you would recommend? I’m especially interested in wandering around, taking photos, enjoying the views, and getting a feel for the village rather than rushing through a list of attractions.

How much time would you suggest spending there? Is half a day enough, or would you stay longer? I’d also love to know whether you think Pyrgos is best visited during the day or closer to sunset.

Is May a Good Month for Santorini?

I’m considering a trip to Santorini and would love some firsthand insight on visiting in May.

I’m hoping for a balance between pleasant weather, fewer crowds, and a more authentic feel of the island before peak summer tourism takes over. I’ve read that May can be warm but not too hot, with flowers still in bloom and restaurants starting to fully open for the season, but I’m curious how this plays out in reality. Does the island still feel calm, or is it already busy with cruise traffic? That's my main concern.

If you’ve visited Santorini in May, I’d love to hear what stood out, both the pros and any drawbacks you noticed.
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