Anchors Aweight! Exploring Santorini by Sea with Sunset Oia Sailing Cruises

I’ve never been a good swimmer. Ok, that was a lie – I straight up don’t know how to swim. If you’d throw me into a pool (which you wouldn’t if you didn’t want me to potentially die), I’d likely just sink like a rock with a big piece of hair algae attached to it. Needless to say, I get a bit anxious boarding boats during any of my travels. That was until I was warmly welcomed by Sunset Sailing Oia on their five-hour premium semi-private catamaran cruise around the crescent-shaped island of Santorini. The entire cruise was an unforgettable experience which might have forever converted me to a water-loving sailboat addict.

The Itinerary

The adventure began with a pickup by the company’s driver at 9:30 from our hotel.

We boarded the boat at around 10:00 am and were on open waters shortly after.

Open waters have always had a great chance to be featured in my nightmares but on this beautiful and luxurious cruise felt like gliding over a dense blue cluster of clouds. We reached our first stop, the hot springs of Santorini’s active but sleeping volcano at around 10:30. This was a great opportunity to enjoy the warm ocean water.

The cruise continued after 30 minutes along the shore of the formerly round island, which was reshaped to form a crescent in the second millennium BCE after a massive volcanic eruption. I could only be grateful for this unsolicited topographical re-design as it is the reason Santorini can boast with the unique caldera it has today.

On our cruise we reached the white beach after some time, you know what they say, time flies when you are having fun? Well, I must have been having the time of my life as we already reached halftime of our trip after what felt like a blink of an eye. At this stop guests where given the opportunity to snorkel and enjoy the sun.

We continued our tour after 60 minutes for a final 30 minute stop at the famous red beach.

We returned to the port of Vlychada at around 2:30 pm from where we were taken back to our hotels to digest the bbq and what was likely the highlight of our stay in Santorini.


At 12:00m, the crew prepared a greek-styled bbq. Coming from Australia where I’ve enjoyed many amazing outdoor BBQs (it basically qualifies as our national dish), I have to say I’ve never quite experienced anything as memorable the one with Sunset Sailing Oia. Eating greek food on a catamaran with a view of Santorini’s white beach definitely tops the list.The BBQ included a large variety of local dishes including fish, meat and vegetarian options.

A welcome addition to keep up a jolly mood of all guests is the open bar which includes wine, beer, water and various soft drinks and juices and is available throughout the entire cruise.

The Boat

We opted for Sunset Oia’s Catamaran premium semi-private cruise which uses a 45’ catamaran the Lagoon 450. The yacht was very new and in extremely good condition. So much so, that I was super surprised by how clean my feet were when leaving the boat!

The Crew

From my past experiences holiday activities such sightseeing tours, the team of travel professionals are the make or break. We couldn’t have been luckier to be hosted by an incredibly friendly and welcoming team at Sunset Oia cruise. They left nothing untried and made sure every guest was having a fantastic time.

Our guide, Poppi, showed us her favourite spots around the island and was always available to share her knowledge about the history of Santorini. We felt like being on a trip with old friends. We felt so fortunate to be welcomed as guests to their adopted home.

Final Thoughts

No matter if you feel like quenching your thirst for marine adventures or would simply like to experience a kind of “sightseeing”, this day trip is for you. I’m not sure if its the Greek hospitality, the comfortable and luxurious yacht, the great food or the incredible views that impressed me the most, but I’m certain that if you want to make sure that your trip to Santorini stays memorable, then this trip is a must on your itinerary.

This post was made in collaboration with Sunset Sailing Oia. As always, thoughts are my own 💙


  1. My husband and I are booking this for our Santorini trip this June! Thanks a ton for sharing!
    Keep up the great work!

    Hugs from Canada 🙂

  2. Your pictures are amazing! I’ve never seen anyone share such an artistic take on travel blogging. Keep the amazing work coming! I’m a follower now!

    All the best from Canada!

  3. It looks amazing! I really want to Santorini in about two years after we sort out the wedding! Thanks for sharing.

  4. Hey Sarah! I have been following your Santorini story. We will be going in Spring, I will be sure to follow your tips here. xo.

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