Sailing, Santorini & Sunset Oia

Sailing, Santorini & Sunset Oia

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At 9AM the shuttle arrived, air-conditioner already blowing and full of passengers. A smiling driver opened the sliding door and nodded to the back row of the mini bus. Squishing to the window seat I watched the coastline slide in and out of view as we buzzed our way across the island en route to a small harbor below the famous village of Oia (“e-ya”). The sun beamed through the salty haze as we passed vineyards and hillside villages. 

Unloading from the van, I eagerly scampered towards the water’s edge. Below me the vibrant blue-green Mediterranean unveiled every detail of the sandy seafloor. Nearby fisherman tugged bits of seaweed from their nets, already having reached the end of their day. 

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As Sunset Oia‘s bright white catamaran slowly pulled into the harbor the other passengers and I grinned as we eyed the boat. On board we could hear the deckhands chatter while the captain cautiously maneuvered the yacht towards the concrete barrier. 

After being instructed to kick off our shoes, we each clamored aboard by way of a narrow wooden plank. Once on deck we were given a short welcome and safety briefing then each of us quickly settled into various spots around the boat. I nabbed a seat at the couch-like forward cockpit, just behind the trampoline. 

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As the tiny port slowly dissipated behind us, a chipper sailor solicited drink requests from the passengers. Naturally, I went with a glass of white wine. Our first stop was made at Santorini’s famous volcano heated hot springs and therapeutic mud bathes, available to those willing to swim to them.

I however channeled vacation-Margo and did absolutely nothing but soak up the sun and sip my wine. 

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Continuing on our journey, the cat (still under motor at this point) headed upwind towards Santorini’s famous Red Beach. The breeze picked up significantly as we exited the island’s moon-shaped bay. While the water grew choppy, the other passengers and I chattered about our travels and impressions of the island. For many of us, Santorini was more beautiful than expected. Then late April, the island was still in shoulder season and remarkably peaceful (though I’ve heard the exact opposite from summertime visitors).   

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With the occasional cold spray of the waves and relentless rock of the boat, the crew opted to retreat rather than charge forward to the Red Beach. The other passengers and I agreed that we weren’t disappointed, still appreciating the simple pleasure of being out on the water. 

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Turning back, the captain guided us to tiny port of Thirasia on an island just off Santorini. In unison, an anchor was dropped and more libations distributed. This time I opted for the local Hellas Pils (the wine was a bit bitter for my liking). At the stern of the boat a massive grill was erected and skewers of marinated chicken and pork began to sizzle while in the kitchen traditional Greek sides were prepared – stuffed grape leaves, eggplant salad, Greek salad (of course!) and pasta salad. 

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The rest of the passengers and I called out our skewer requests and filed into the cabin to collect our sides, cafeteria-style. Lunch was absolutely delicious and ended up being one of my favorites during my week in Greece. The tangy marinade and juicy chicken was nothing short of addictive.

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After a peaceful hour or so the anchor was raised and we slowly navigated back to Oia. All of us fat and happy from our lunch, I was delighted to see the main sail raised as we did a broad reach towards Oia’s harbor. 

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Back at the port, all of us were reluctant to exchange our seating on the boat for those in the shuttle. Bidding farewell to the crew, I couldn’t imagine a more peaceful way to spend a morning on the island. I would absolutely recommend a sail with Sunset Oia to anyone visiting. During my visit the sunset sail wasn’t yet available but can only imagine how beautiful it’d be to see the sun sink below the Med from the water. 

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This post is sponsored however all opinions are (of course!) my own. Furthermore, experiences that I would not recommend to my nearest and dearest are not shared on this space.
  • HandLuggageOnly

    I went sailing with these guys in Santorini – they’re really good! πŸ™‚

  • I’ve been lusting after Santorini for so long!

  • Feyi A
  • Oh my. I’m so impressed with your photography skills while afloat! I’ve always had a hard time taking good photos on a boat. You really captured this trip here! Love it!

  • These photos are wonderful! I especially like the pics of the sea. Will definitely have to visit Santorini one day.

  • GORGEOUS photos!

  • One word: Swoon!

  • Diana Maria

    These photos are amazing- Santorini looks stunning, it doesn’t even look real in some of these photos! I’ve always wanted to visit- hopefully one day I will!

    Diana xo | My Lovelier Days

  • Your storytelling girl, so good! Love those shorts!

  • Very timely post! I am looking into a cruise just like this one for next month, so it was good to read about your experiences to help the comparison shopping process along! I was surprised to see other passengers sunning in bikinis in April…. had no idea it was that warm there so early in the year. How cool! Of course we’ll be right in the heart of the tourist season, but eh…. being in Imerovigli will make it seem like no one is around (I hope!). Can’t waiiiiit :))

  • emilygrapes

    How do you FIND these great tours and excursions?!!? This looks absolutely fabulous! And also…never would my brain have thought to pronounce it e-ya..

  • I love your description of this trip!

  • This is great! Getting excited for our trip to Greece this summer… we’ll be on a 7 day sailing trip from Santorini to Mykonos. Looks amazing!

  • The slow pace

    Oh Margo, you’ve just given me the best idea! Our best friends are getting married in a couple of weeks and they will be honeymooning in Santorini! I’m going to book a sunset sail for them!!!
    Thank you!!!

  • Loved seeing the catamarans pull into Red Beach! They looked like they were a lot of fun! I have to say….we went to Santorini during August and I never really felt like it was too crowded! I guess maybe bc we had a four wheeler and went to the beach everyday? Anyway….its a wonderful place in all seasons!

  • Santorini is definitely on my list of places to visit before we leave Europe! This cruise looks amazing!

  • Beautiful! May I ask which filter/s you use on your photos? There’s this grayish effect. Thanks in advance!