The Best of the Cyclades, Part 2: Santorini and Milos

The village of Oia, Santorini, at sunset

In the first week of our 12-day Greek island tour, we were introduced to Mykonos, Paros, and Ios.  Over the remaining five days, we’d visit two more popular destinations in the Cyclades island chain, Santorini and Milos.

As we headed into June, we experienced slight trepidation at the thought that we may begin encountering the suffocating crowds that certain islands have a tendency to draw in the summer months (I’m looking at you, Santorini), but we forged on nonetheless, convinced that regardless of trivial things like traffic, restaurant waiting lists, and exorbitant amounts of selfie sticks, we’d have a great time.

I mean, it was still Greece, for crying out loud, and we weren’t about to forget how special it was for two first-timers to Europe to even be there in the first place.

SantoriniThe village of Oia, Santorini, at sunset

Santorini had always been one of the destinations my travel dreams were made of.  If you’ve seen my Instagram account, you probably know that I’m something of a sunset enthusiast, and if you’ve been living anywhere other than under a rock, you probably know that Santorini is known to deliver in this arena.

Not only that but as a result of the volcanic eruption the island experienced in the 16th century BC, the landscape is quite unique when compared to the rest of the islands.  The caldera (crater) consists of jagged cliffs in a half-moon shape that you just won’t see on any other Greek island.Caldera views in Santorini, Greece

We were based in the main city of Fira at a hotel called Sea of Aegeon which, despite being on the opposite side of the island from the caldera where watching sunsets wasn’t possible, we had a lovely view of the sea to the east and were no more than 10 minutes away from the main plaza by foot.Hotel Sea of Aegeon, Fira, SantoriniHotel Sea of Aegeon, Santorini, Greece

In order to make the most of our two short days on Santorini (which is not enough, for the record) we made sure to get ourselves a set of wheels to more easily cover ground on this rather large island.  We were surprised to learn that motorbike rentals are not possible without a proper motorcycle license (even to rent an automatic) but were happy enough to settle for another ATV rental–especially now that we knew how little gas we had to put in the tank to last us two days.  A word to the wise: Don’t listen to shop owners who tell you that you need 10€ worth of petrol in the tank for a day of sightseeing–it’s a bald-faced lie!Riding ATVs in Santorini, Greece

The majority of our sightseeing was done in a single day.  Santorini has a number of unique volcanic beaches, so we aimed to see a few of those, even if we knew we probably wouldn’t swim.  Our first stop was Red Beach on the southern tip of the island near a town called Akrotiri.  The beach was an interesting enough landscape but certainly not a place I would ever choose to sunbathe.  The sand wasn’t so much sand as it was piles of dusty, dried seaweed and there was no shade whatsoever.  A quick look to take a few photos was all we needed.Red Beach, Santorini, Greece Red Beach, Santorini, Greece

Next, we headed east in the direction of Perissa to find one of the island’s famed black sand beaches.  Perissa Beach is a much more suitable beach to spend a day on, in my opinion.  It’s 7km long and composed of fairly fine-grain sand, and lined with shops and restaurants that provide shaded areas as well as alternative activities to sunbathing (afternoon glass of rosé?  don’t mind if I do) if that’s just not your thing.  I don’t find much joy in baking my skin in the sun these days, so this won me over. We stumbled upon a pair of hammocks and decided without much hesitation that Perissa Beach would be a perfect place to spend the rest of our afternoon before making the trek that evening to the northern village of Oia, the home of the most iconic Santorini sunsets.Perissa Beach, Santorini, Greece Perissa Beach, Santorini, Greece Perissa Beach, Santorini, Greece Perissa Beach, Santorini, Greece

On our way back to Fira, we caught some incredible views of the caldera and couldn’t resist stopping to snap away furiously with our matching Canon SL1s (and a few with my GoPro Hero 3+ for good measure).Santorini, Greece Santorini, Greece Santorini, Greece

That evening, we hopped back on our trusty steed to head north in the direction of Oia to catch the final show of the day (the sunset, in case you haven’t been following along).The village of Oia, Santorini, at sunset The village of Oia, Santorini, at sunset

Until that point in the day, we’d dealt with crowds in the form of heavy traffic on the roads, but not much else.  After all, it was still technically shoulder season–high season on Santorini is typically late June to early September.  But when we arrived in Oia?  Damn, you could have fooled me.  The pedestrian streets were choked with tourists all scrambling to get a prime sunset watching spot, preferably atop the Castle of Saint Nikolas if they were lucky.

Every so often we diverged from the main paths to find side streets with breathing room and some lesser-photographed (if only slightly) viewpoints.The village of Oia, Santorini, at sunset

When we finally decided to search for our own sunset watching vantage point, there weren’t many great options left to be had.  Seeing as we hadn’t yet eaten dinner, we decided instead to just grab a table at a restaurant called Sunset Cafe and let the others fight it out.  In fact, we probably had more fun just watching the spectacle that was the sunset-hungry mob of people pushing and shoving each other for a chance to get their selfie sticks higher than the next guy than we did watching the sunset.  As a side note, I believe selfie sticks have their place, but this instance was not one of them.  Talk about inconsiderate!The village of Oia, Santorini, at sunset

Several hours later after a fabulous meal, plenty of wine, and some on-the-house strawberry ouzo from our gracious waiter, we decided to call it a night.  We stopped a few times on the way back to our possibly-illegally-parked vehicle to admire the caldera and the cliffside villages all lit up at night, I had my hand at long-exposure photography (spoiler alert: I failed) and promised to return to Santorini sooner than later to discover the rest this gorgeous island has to offer.The village of Oia, Santorini, at sunset

People can hate on Santorini all they want for being an overcrowded tourist trap; for me, it lived up to all the hype and then some.  I WILL be back.

MilosAdamas, Milos, Greece

If you’re like me, Milos isn’t an island that immediately springs to mind when you think of Greece.  Despite being one of the principal islands (and biggest) of the Cyclades, Milos doesn’t get nearly as much recognition as it deserves.

I was pretty pleased to find that it was far less crowded than Santorini, but something tells me this might change in the next few years.  For adventure lovers especially Milos has plenty to offer, and if I dare say, its sunsets are just as good if not better than those you can see on Santorini.

The main port city of Adamas turned out to be a perfect home base for exploring the island.  Ippocampos Studios are located just a few minutes’ drive from the center and offer fantastic views of the bay.  The staff were beyond lovely and the breakfast they delivered each morning was full on–I’m talking bread, cakes, fruit, yogurt, coffee, tea, cheeses, and probably a few other things I’m forgetting.  I’m a morning person and bona fide breakfast lover, so I thought this was a delightful touch.Ippocampos Studios, Adamas, Milos, Greece Ippocampos Studios, Adamas, Milos, Greece  This time around, a car rental helped us get from one place to the next, although ATVs and motorbikes are readily available for renting as well.  Our first day was mostly spent catching up on work and enjoying the little oasis of Ippocampos.  Well, I suppose enjoying is a bit inaccurate–I spent a lot of that first afternoon sick in bed as a result of, uhh, who knows?  But at least I had a nice place to sleep it off so I could recover in time for the next day’s activities.

Our first outing on Milos would be a half-day sea kayaking adventure with Alternative Milos on the southern coast of the island.  We’d be exploring volcanic rock formations (some more intimately than others, as it would turn out) as we paddled and swam our way from Agia Kyriaki Beach to Palaioxori Beach where we’d enjoy a local lunch at Sirocco, a restaurant touting “volcanic food,” meaning it is cooked underground by the heat of volcanic emissions.Sea Kayaking with Alternative MilosSea Kayaking with Alternative Milos

We set off with a group of five including our guide and a couple from France.  The sun was shining fiercely, but a breeze helped take the edge off.  En route to our lunch destination, we stopped to have a swim in the chilly waters and pass through an underwater cave.  Unfortunately for my travel companion, this innocuous-seeming activity wouldn’t end well; as it turns out, volcanic rock formations can be rather jagged, and he learned the hard way.

“I need to go to the hospital” isn’t something any tour guide likes to hear.

My friend had swum a little too close to the rock and in one swift kick had sliced his foot open deep enough to require several stitches.  We quickly paddled to the beach where we’d eat lunch and sent him off to the local hospital in a taxi (I stayed behind to return the kayak and retrieve the rental car).  The silver lining in all of this was that all of his hospital visits, treatments and follow-ups were completely free of charge thanks to Greece’s national health insurance scheme.  He had to purchase extra bandages and an antibacterial spray for maintenance, but nothing beyond that.  All in all, it could have been worse.Sea Kayaking with Alternative Milos

It did mean we would have to pass on a full-day sailing tour we’d had planned for the following day (which would have involved nothing but swimming and sandy beaches, two things that were entirely out of the question for the wounded one), but we made the most of that time by visiting the moon-like landscape of Sarakiniko Beach and wandering the streets of Plaka, the best village for catching Milos’s spectacular sunsets.Sarakiniko Beach, Milos, Greece The village of Plaka, Milos, Greece The village of Plaka, Milos, Greece

And I can’t forget to mention the heavenly food we ate on Milos.  The first night we dined by the harbor at the seaside restaurant Mikros Apoplous where, naturally, freshly caught seafood is the specialty.  Barriello in the village of Trypiti served us incredible local dishes, including a mouth-watering moussaka as well as a few quirky items like a “cheesecake” that looked like the dessert but was actually created with savory ingredients like Milos cheese.  In Adamas, we enjoyed a delicious dinner at O! Hamos!, another restaurant offering the typical Greek dishes with an emphasis on fresh ingredients from Milos.The village of Plaka, Milos, Greece

As our 12-day trip through the best of the Cyclades island chain came to an end, exhausted though I was, I couldn’t help but grin thinking back on all the adventures we’d had in such a short space of time.  The Greek islands are so diverse, I could easily spend months exploring and still not see all there is to see.  I can tell you with absolute certainty that this trip was far from my last.  I look forward to revisiting these islands and discovering new ones on subsequent trips to Greece.  The only question is…who’s comin’ with me?

Which of the Cyclades would you most like to visit?  If you’ve already been, which was your favorite?


I visited the stunning island of Milos as a guest of the municipality.  All opinions and sunset obsessions are entirely my own. 

12 comments

  • Camille

    It’s all so beautiful, I’m coming with you! Can I?! More seriously though, if you go back to Santorini I strongly recommend doing it in October/early November. It’s still really warm, much cheaper, and surprisingly quiet. The prices go down so much off-season that I even stayed in a cliffside cave in Oia, and we had our own private terrace and the hotel’s infinity pool facing the caldera to ourselves… 🙂 (Oh god, I’ve just made myself jealous of my own past self!)
    Camille recently posted…Tasting the Good Life in Parnu, the Summer Capital of EstoniaMy Profile

    • Leah Davis (author)

      Haha of course you can! I like the idea of going later in the year after the crowds have dissipated a bit. Plus, I was pretty bummed we couldn’t do much swimming this time around. Really wanted to be cliffside in one of those villages (I’m also jealous of past you), but I guess that’ll be for next time!
      Leah Davis recently posted…Month in Review: July 2015My Profile

  • Rachel

    All of this looks amazing! I’m with you on the baking in the sun – while I don’t hate it by any means, a few days of idly lying around on the beach is usually enough… I prefer snacks and wine BY the sea. And I can’t get over that moonscape of a beach in Milos! Sad you guys couldn’t go swimming and sailing, but free healthcare is always a plus!
    Rachel recently posted…As of Late: Things I’m Loving (and a Giveaway!)My Profile

    • Leah Davis (author)

      Haha YES to snacks and wine. I don’t like to be idle either…I’d much prefer to at least toss a frisbee around or something! The water was pretty chilly so I’m not terribly disappointed by missing the sailing trip, but next time I go to Greece I want to go later in the summer so I’ll actually WANT to get in the water!
      Leah Davis recently posted…Month in Review: July 2015My Profile

  • Lance Setzer

    Hi Leah (what an awesome name – same as my youngest daughter! 🙂
    I came upon your site while googling info on Greece.
    Thank you, your review is really great, and well written.
    My wife Cherie and I are spending 10 days in Greece later this month and your advice and insight has been priceless, thank you!
    We are really looking forward to spending time on the Mainland and the Islands.
    We are spending a few days on the mainland to visit my eldest Daughter who is currently modeling in Greece, and I have booked a 3 nights on Santorini.
    I do have an extra 2 days / 3 nights and am considering booking this time to spend on Mykonos.
    Do you agree that this is a good move, or would you rather recommend one of the other Islands instead?
    Thanks again for your wonderful insight!

    Cheers
    Lance
    Cape Town, South Africa

    • Leah Davis (author)

      Hey Lance! I think Mykonos would be a good choice! There are certainly other islands that are even closer, so if you want a shorter ferry journey to your next destination, you might consider Ios, which was actually one of my favorites and it’s very close to Santorini! Whatever you end up choosing will be great I’m sure, every island has something unique to offer but still with that Greek island charm! Enjoy your trip!

  • Kelsey Whitehill

    Leah! Loved reading about your adventures in Greece! I am Greek and we are FINALLY planning a trip for next summer. Did you plan out everything yourselves or go through an agency? Since it is our first time to Greece (and only my husbands second time out of the country) I am trying to figure out if using a travel agent would be helpful!

    • Leah Davis (author)

      Hey Kelsey! I went to the islands as part of a press collaboration, so a lot of the details were sorted out for us, like hotels and transport on the islands. We booked all of the ferries ourselves, and we probably would have done it all independently if it hadn’t already been arranged (but we are avid travelers so I understand that for some, using a travel agent is heaps more convenient). I say go with whatever you’re more comfortable with! If you decide to book independently, there are tons of agencies on the islands that can hep you book tours and whatnot (same in the cities on the mainland). I hope you enjoy your trip! Best of luck!

    • Leah Davis (author)

      I couldn’t get enough of Santorini! I see myself going back to that island a few more times for sure!

  • Jo noble

    How did you get from santorini to Milos how lon

    • Leah Davis (author)

      Hello Jo! We took ferries between all the islands. In most cases, it’s the only way to get from one to the next.

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