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I went sailing in Santorini! Sunset Oia boat cruise: Greek islands tour, beaches, Ia architecture.

rupaul big blow out hairstyle

Hello from one of the world’s most fabulous beach destinations: Santorini, Greece! The Mediterranean breeze made me look like RuPaul for a moment…

(I’m dressed in this exact Iron Fist skeleton bones jacket. More items from this fun Gothic brand below).

oia santorini blue roof churches

In my first post from Santorini, I took you inside my luxurious villa overlooking the Mediterranean.

In addition to securing us the perfect stay, Blue Villas Collection helped us arrange activities on the island (they have a concierge service for all their guests).

oia windmill, ia houses

Before and during the trip, our Blue Villas concierge gave us personalized advice to make the most of our Santorini sojourn.

Thanks to her tips, we went to postcard-perfect Oia (Ia) during the best time of day, and relaxed on all the major beaches on the island. (All photos by Joey Wong)

irregular choice clothing, fashion

I told our concierge that I wanted to do a sunset sailing trip (when in Greece, one must spend time on the water!). She immediately recommended a half-day cruise with Sunset Oia, the leading company for yacht excursions in Santorini.

♡ Outfit Details ♡ I’m wearing cat-eye sunglasses by Moat House, and a unicorn fringe top by Irregular Choice (it is from the wardrobe of my friend Rose). While my shirt is no longer found online, it’s similar to this Carmen pom pom top and off-shoulder white dress with rainbow pom-poms.

traditional greek fishing boats

Sunset Oia has a handy shuttle service included in tour packages, which makes it easy to get to the starting point. A driver picked us up right outside our private villa, and took us to Vlychada port. Quite a few colorful, traditional Greek boats were tethered to the pier.

sunset oia sailing dinner cruise

Ahoy, mateys — here comes our Sunset Oia catamaran!

Sunset Oia is a local organizer of luxurious sailing tours, ranging from small group day-trips to romantic private cruises. Their fleet of modern, luxurious yachts brings guests to beautiful spots all around Santorini, including the beaches and therapeutic hot springs.

oia harbor dock greece

Joey and I had signed up for a 5-hour water excursion, which departs in the afternoon and stops in multiple locations. We got to dine on fresh Greek food on-board, then watch the sun set while drifting on the Aegean.

boat cruise santorini greek islands

Sunset Oia’s friendly and professional crew welcomed us on board, and walked us through safety instructions. We had to remove our shoes and put them in a basket for the duration of the journey — hence the barefoot photos!

For those of you who worry about sea sickness: fear not. We had a smooth ride throughout, with no choppiness. (However, the crew has ginger chews available in case you feel nauseous).

santorini sailing, luxury yacht boat

Our Sunset Oia trip stopped in several locations, starting with Akrotiri or Red Beach, famous for its rust-colored cliffs. We weren’t able to get off the boat, but guests had the opportunity to jump overboard and swim or snorkel for about 15-20 minutes. 

(As you might expect, I didn’t go into the water — but used this opportunity to sit in the corner seat and take photos!)

akrotiri red beach santorini

On a different day, I took the bus to Red Beach and took these snaps. (Give yourself at least 15 minutes to walk from the bus stop to the beach, and even longer if you go up the hill and down to the larger stretch of sand).

The peculiar rocks originate from volcanic lava, hence the reddish-brown hue.

santorini red beach church

Akrotiri is also an important archaeological site; starting in the late 19th century, excavators discovered the remains of a Minoan Bronze Age settlement. Above is a curving white church that currently sits near the beach.

sailing yacht fashion, greece

I’m a pirate at heart, and love the feeling of sailing o’er the seas. But leave your tricorn hat at home, as it would blow off from the wind. Instead, I wore layers (as it can get chilly), sunglasses, and lots of sunscreen.

– My unicorns top is by Irregular Choice, who are best known for their wildly original shoes. They have heels that look like Cinderella, Snow White and Star Wars Darth Vader for example! Scroll more mind-blowing designs:

boat tours day trips oia

Sunset Oia took us to intriguing spots on Santorini that are only accessible by boat. One of my favorites was this little hideaway, which is inhabited by one hermit. Doesn’t this look like a scene from an alien movie?

greek boating sailing trip

The white church and yellow boats stand out starkly against the dark cliffs. It must feel like being on another planet, living here…

sunset oia review, boats

Sunset Oia pipes music out onto the deck, and makes drinks available at all times. This is my happy place: sitting on the tarp, sipping ouzo, watching the horizon…

best santorini sailing tours cruises

High up above, we spotted the ancient lighthouse. A day cruise is well worth it, if you’re in Santorini — you can only see views like this here.

oia sunset view dinner

Yarr for pom-pom fashion. More designs from Irregular Choice here and below:

drinking party cruise greece

The ship’s crew prepared a spread of Greek food for us, including fresh BBQ. I filled my plate with dolmades, tzaziki, Greek salad, Mediterranean pasta… and washed it down with plenty of anise-flavored ouzo, the Greek aperatif that is similar to absinthe. Dessert was slices of green apples, drizzled in Greek honey and cinnamon — so good!

santorini catamaran sunset cruise

Santorini’s sunsets are infamous for their beauty. I can’t begin to describe the joy of watching the sky change color, from the vantage point of the sea…

As the light faded to black, the catamaran pulled up to the historic port of Ammoudi in the village of Oia. Time to disembark, and board the shuttle to return to our villa.

Thank you Sunset Oia: your sailing experience was 5-stars from start to finish.

oia santorini windmill location

On another day, we traveled by bus to Oia / Ia (pronounced “Eee-yah”), the picturesque village at the top of the island. I suggest coming in the afternoon and making the most of golden hour, before enjoying the sunset.

oia ia blue church

We came right before the start of the spring tourist season, and turned out to be the right decision. The off-season meant we had the streets mainly to ourselves, and didn’t have to jostle with tour buses and tourists. At the same time, the sun was shining on the blue church domes (cupolas).

santorini greek orthodox church

Oia’s pastel and white colored homes are layered onto the high cliffs, and connected by snaking stairs. It’s like gazing upon an MC Escher drawing that meets the laws of nature.

I’m sure you have seen photos of this village before, with classic blue and white Greek Orthodox churches, and an old Aegean sea windmill. 

travel blogger instagram santorini

It’s a delight to explore Oia by foot — walking up and down the cobblestone steps, browsing Greek art stores, finding scenic points tucked around corners. Instead of following a map, simply wander and enjoy.

famous santorini windmill view

The cozy cave homes look out over the Aegean sea (Blue Villas has vacation rentals here as well). The Cycladic architecture is perfectly suited to its environment, and has lasted throughout the centuries.

cute sheepdog santorini cafe

I stopped by a cafe to eat a Greek salad, and watch the clouds pass over the caldera (volcanic crater sunk into the sea). The resident foofy sheepdog stole my heart!

oia ia architecture, stairs

Can you imagine living here, and having these views of the caldera and clear waters year-round?

santorini oia cliffs

Santorini’s other major village, Fira (Thira), has equally magnificent viewpoints. I shared photos and took you inside my accommodations, in Part 1 of Santorini.

santorini church bells, greek flag

Magic hour begins, as the sun begins to sink. (Photos by Joey Wong.)

female travel fashion blogger oia

The skies transform into pink, matching my hair.

pia watch sunset

Not bad, right?

oia sunset viewpoint

Santorini layers archtecture, cliffs and waters great

greek church sunset ia

No filter needed: the skies naturally turn into these rich, warm hues of pink. However, I suggest that you check the specific sunset time in advance, to avoid rushing and missing out.

oia santorini tourism tourists

Millennial pink and rose gold fans would feel right at home in Oia / Ia.

best sunset view in santorini

The best sunset viewing locations can get very crowded, especially during the high season. Try to avoid the pack of tour groups, which head to the same spot across from the windmill.

Joey and I found a side street that provided just as magnificent a view. There were only a handful of people next to us — hooray for unobstructed views and no chatterboxes to ruin the moment.

world's best sunset oia santorini

No wonder a Santorini sunset is on the bucket list of many a traveler. The light is radiant and dramatic, and one couldn’t have designed a better natural setting.

kamari beach santorini

One final must-visit spot: Kamari beach, located 10km southeast of Fira and easily reachable by bus. Kamari is known for its black pebbled beach — how Gothic!

greek bookstore cat atlantis books

Kamari is next to a little village that is worth a stroll. I said hi to this cat outside Atlantis Books, and stocked up on tins of sardines at the neighborhood grocer.

black sand beach santorini greece

Kamari has a long, black stretch of beach beneath the gloomy mountain of Mesa Vouno. The water is deep and blue, which gives the shore an unusual contrast.

prehistoric black egg rock

In 2002, locals discovered an archaic sanctuary dedicated to Achilles. Kamari’s dark volcanic rocks, which range in size from minuscule to massive, are even older.

black pebbles beaches greece

Doesn’t this look like a prehistoric dinosaur egg? The black rocks are polished by the waves into smooth circles and ovals.

skeleton bones jacket coat

A Goth beach requires a Goth outfit, don’t you agree? I’m wearing this exact Iron Fist jacket; find more styles below…

santorini beach ocean waves

There’s something about being by the ocean that thoroughly rejuvenates me. Do you feel this way too?

kamari beach big rocks

And that’s all she wrote about Santorini. If you’re interested in visiting any Greek island or mainland destinations, check out Discover Greece for lots of tips.

blue villas collection greece designer villa

Very grateful to Blue Villas Collection for hosting us in this futuristic-classic cave, and for the seamless daily arrangements. (Take a tour inside this villa in Part 1.)

sun setting oia santorini

The sun sets on Santorini — but there’s still one more post to come, from Greece.

I’ve saved the Acropolis for last... check back soon for photos from the ancient Athenian temple. And you can see previews of my Austin, Texas trip right now on Instagram @lacarmina.

SHARE & COMMENT

  • Jessie

    love your hair color.

  • Sassygirl

    Amazing, sassy girl

  • Darak

    It was awesome seeing these photos.

  • Sahunian

    Those sunnies look super cute on you, great choice!

  • Melisandra

    Loves it lady!

  • Nene

    I love the pics!!

  • yukiro

    Greek aperatif— Need this in my livelihood

    • I love ouzo and tsipouros.. anise-flavored, similar to absinthe!

  • Teddy

    a lil jealous. Wander lustin

  • Wendy

    Love that unicorn dress.

  • Thanks to Rose !

  • Iran

    Greece ❤️❤️

  • Mm

    Cute. m