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Whenever we spoke to someone about our trip to Santorini, they told us we had to do the sailing trip. Every blog I read mentioned it. Every person we met on the island raved about the sailing tour. Clearly, this was the must-do Santorini activity! And, let’s be honest, they didn’t have to exactly twist our arms. Booking a Santorini sailing tour with Sunset Oia was one of the easiest decisions we’ve made in a while.

Lounging in the sun all day with gorgeous island views, snorkeling in the cool Aegean Sea, unlimited refreshing white wine, and a lunch made with fresh local ingredients? Please take our money.

santorini sailing tour must-do santorini activity with sunset oia

Read other Santorini Adventures and tips for visiting Greece here.

Our Morning Cruise with Sunset Oia

After going back and forth for a whole day on whether we should take the day cruise or sunset cruise, we finally locked in our decision to go during the day on the 5-hour ‘Red Cruise.’ While a sunset cruise looked stunning, we knew it would be HOT during the day and spending those hottest hours on or in the water sounded divine.

Plus, it would save us a little bit of money that way as well. (The morning tour is €95, as opposed to €105 for the sunset option).

santorini sailing tour must-do santorini activity with sunset oia

The morning sailing tour turned out to be a fantastic decision! Not only was the weather perfect (albeit a tad windy on our return), we also happened to end up on a boat with some other awesome travelers that we became quick friends with.

I think everyone was in such a friendly mood because we felt like millionaires getting to sail around on a catamaran for half the day. And the way everyone was posing for photos showed it! Ha! I mean, it’s kind of hard not to indulge … so, of course, we snapped a few too.

santorini sailing tour must-do santorini activitiy
Who even AM I?!?! haha

I had a good laugh with two guys from New York when I told them they looked like they were in a music video, the way they were letting the wind blow their flowy shirts for photos! Apparently, that is exactly what they were going for. #DoItFortheGram

During the cruise, we loved getting to lounge on the deck while sipping wine and chatting with the other tourists. Yes, we made up about 98% of the boat, and it was a blast. This is definitely a touristy thing to do, but so what!?! Just embrace it and have a good time.

santorini sailing tour must-do santorini activity with sunset oia

Santorini Sailing Trip Itinerary

While this trip would have been totally worth it just to relax on the boat all day, we did make some stops to get a closer look at unique places on the island – as well as for chances to hop in the cool, salty water!

Departure from Picturesque Ammoudi Bay

After getting picked up near our hotel and driven to the port, we got to spend some time admiring this gorgeous, scenic location of Ammoudi Bay before boarding the catamaran. It was a striking and unique perspective of the iconic Greek town of Oia – perched above us on the cliff, with its stark white buildings contrasting the colorful shops and bright blue water below. Breathtaking!

santorini sailing tour must-do santorini activity

Upon arrival, they give you a colored sticker, then they call out that color when it is your turn to board. So, don’t wander too far! ๐Ÿ˜‰

santorini sailing tour must-do santorini activity with sunset oia

Volcanic Hot Springs

While not the typical hot spring pools you may be used to, this area is filled with mineral water from the volcano and is a unique place to take a dip.

santorini sailing tour must-do santorini activity with sunset oia

It is not hot by any means, but it is a bit warmer than the other water we swam in. And it has the added benefits of minerals. But, be warned – this area can dye your suit orange if it’s a light color!

santorini sailing tour must-do santorini activity

Red Beach for Swimming

This stop offered amazing views of the iconic Red Beach. We loved getting to enjoy the cool (and surprisingly very salty) water with our small group, as we admired the crowded beach from afar. If you are a good swimmer, you could swim over to lounge on the beach also, but why do that when you have a sailboat to lounge on?

santorini sailing tour must-do santorini activity with sunset oia red beach
santorini sailing tour must-do santorini activity with sunset oia

White Beach for Snorkeling & Lunch

As one of the members of the crew told me, they save the best stop for last. The water near the beautiful White Beach is extremely clear. Which is why this is where they break out the snorkeling equipment.

santorini sailing tour must-do santorini activity with sunset oia snorkeling

We loved getting to swim around in the cold water, looking for fish, and admire the Santirini views from that unique perspective. But, it was also very nice to warm up in the sun after (just remember to wear sunscreen!)

From what we were told, sharks are extremely unlikely and the water is usually pretty calm!

Barbecue Lunch by Sunset Oia

We also had a lunch break at the White Beach stop. At the onset of our journey, we were asked if we would like chicken, pork, or vegetables on the grill. And we were pleasantly surprised by the amount and quality of food.

We both got two skewers (chicken for Buddy and veggies for me), stuffed grape leaves, tzatziki with bread, and other delicious sides. Everyone was full and happy!

santorini sailing tour must-do santorini activity with sunset oia

Gorgeous Sights Along the Way

Of course, as we sailed along, we got to enjoy great views of the imposing cliffs. We saw the caldera, Akrotiri Lighthouse, Fira, Oia, and other small towns along the way – in addition to the beaches we stopped at.

Then when it was all over, we hopped back in the shuttle van to go back to our hotel. Such a great perk to not have to drive ourselves – especially with all that wine!

santorini sailing tour must-do santorini activity with sunset oia

After our cruise, we had plenty of time to take a quick nap, go to Oia by bus for the iconic sunset experience, and then meet our new-found friends out for drinks – a great couple from New York (who got engaged a few days later!) and two fun friends from Las Vegas.

So glad we opted for the morning option! That nap was key in allowing us to stay out until 3 a.m. partying with them! A perfect end to a perfect day in Santorini – truly one of our favorite days (and nights) from all our travels.

Special thanks to Sunset Oia for providing us with a discounted rate for their morning Red Cruise. As always, all opinions are our own.

Must-Do Santorini Sailing Trip: An Unforgettable Perspective of the Island