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Sometimes traveling long-term can make you a bit jaded. You find yourself halfheartedly remarking what a nice mountain that is while your thoughts wonder to what you are having for lunch or sighing, yeah, that beach isn’t bad while you fiddle with your phone. You become spoiled.

Oia

And then you go to a place that stops you in your tracks and makes you wonder how you got so lucky just to be there.

Santorini Cruise Ship Tender

As our ship entered the foggy caldera and I caught my first glimpses of Santorini, I knew it would be one of those places.  Santorini is a geographic anomaly, the remnants of a massive volcanic explosion that destroyed the island’s original civilizations and transformed it from one land mass into several. What remains is Thera (the main island that people are referring to when they say Santorini), Therasia (a much smaller and sparsely inhabited island), and Nea Kameni (the volcano in the middle). The water between the outer ringing island and the central volcano is the caldera.

Fira, SantoriniCan you see the zig-zag path the donkeys (and people!) use to walk to the top?

We had to take a small tender boat to reach the port, which was connected to the main town of Fira via a sheer cliff. There are three ways of reaching the top: by foot, by donkey, or by funicular. I was dying to go the traditional way and ride a donkey but after reading too many conflicting reports about the wellbeing of the animals I just couldn’t do it in good conscience. So flying up the funicular we went.

Santorini Funicular

Santorini Funicularour ship is playing peek-a-boo behind me

With our limited time in Santorini we chose to bypass the port town of Fira and instead head to the more beautiful Oia. We rented a car for the short drive because we were worried about the buses being overcrowded and slow with the taxi strike still in effect. It ended up being a bit of a splurge, but sometimes that’s what a holiday is all about. Plus we got to stop for as many photo ops as we wanted, something I don’t think a bus driver would have been so keen for, no matter how nicely I asked.

Santorini Rental Car

While the west coast of Santorini is sheer cliffs, the east coast rolls slowly out to the sea.

Santorini East Coast

Soon we had reached lovely Oia and parked to explore on foot. It was love at first sight.

Oia, Santorini

Everything in Oia seems perfectly in place. There are no jarring advertising banners, no unsightly internet cafes, no skies full of ugly power lines, no piles of garbage to pull you out of the fantasy.

Oia, Santorini

Instead there are amazing mosaics of colored roofs, an endless labyrinth of curving streets, and the most dramatic vistas across the caldera. My travel writing teacher once gave us a list of forbidden adjectives and topping the list was “charming.” I’m sorry, Mr. Farley, but there just isn’t a better word in the English language. This place was oozing with it.

Oia, Santorini

Oia, Santorini

Oia, Santorini

Having decided within moments that this was a place we were going to return to, we checked out a few hotels that caught our eye from above for future visits (the ones we could find in the maze of white at least!). That aside, we mostly just wandered around saying “wow” and repeating to each other how amazing it all was. Bystanders were surely impressed by our conversational skills.

Oia, Santorini

When our tummies started rumbling we were spoiled for choice of tavernas with million dollar views. While I’d never been a fan of Greek food before this trip, I thoroughly enjoyed nearly every meal I had. This lunch specifically featured the best bolognaise sauce I’ve ever tried. I later learned it was due to the tomatoes, which thrive on neighbor Therasia’s volcanic soil.

Oia restaurant

After lunch we sadly conceded it was time to head back to Fira for our evening adventure. As we began walking in the direction of our car we were met by a herd of donkeys, perhaps on their way home from work!

Santorini Donkeys

Santorini Donkeys

I loved Oia and anyone heading through the Greek isles would be mad not to stop in this special place. And I was comforted to see a hostel on the outskirts of town, so I know that when I return on my own steam I’ll be able to afford a place to lay my head.

Oia
The journey wasn’t over yet as we took a different route on the way back into Santorini (another benefit of renting a car!) and passed my first black sand beach (pretty big deal for a beach lover like myself) and through a beautiful farming community.

Black sand beach, Santorini

Santorini

After getting lost on the streets of Fira and having to be rescued by a kind stranger who spoke no English only to realize we were one block from our car rental destination, we were back down the funicular and onto Part II of our Santorini adventure…

Santorini Funicular

Santorini Donkey Rides

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32 Comments...
  • Kathryn
    September 21 2011

    Well if you can come up with a great headline like, “I left my heart in Santorini” when you are writing at “stupid o’clock” that’s a pretty good sign that you are a writer’s writer.

    These amazing posts make me feel like I’m back in Greece all over again – minus getting lost one block from my destination…and dying from the heat.
    Great job!

    • Bob Porter
      January 23 2012

      Hi Guys… Bob and Chris calling from AUSTRALIA… Just visiting your site and looked at the Santorini photos. Loved them and can’t wait to go there on our upcoming Med cruise in June this year.. Keep up the good work. Photos were really fantastic. Oia looks amazing..Can’t sleep thinking about being there, lol.

      Thankyou Bob & Christine.

      • Alex
        January 24 2012

        Hi Bob and Christine! So glad you enjoyed the photos! I’m jealous of your upcoming cruise, I wish I could go back and relive it every year! All the best, Alex

  • Absolutely gorgeous! What a special place to experience with your mom.
    Andi of My Beautiful Adventures recently posted..My Wedding & Honeymoon: Day 6-10 (Part 6)

  • Gram
    September 21 2011

    this was my favorite post of all. I remember the beautiful blue and white. I did do the donkey ride, which was memorable, but you saw and did much more while there. GREAT !

    • Alex
      September 22 2011

      Well one of the reasons we chose the smaller cruiseline that we did was so that we could take advantage of the longer port times. And we enjoyed every minute!

  • Steve McKee
    September 21 2011

    GREAT headline!

  • Kris Koeller
    September 22 2011

    What a great trip. Looks amazing. The weather appears to be spot-on, but I would imagine its like all the time…
    Kris Koeller recently posted..A New York City Chinatown Food Tour

    • Alex
      September 22 2011

      We did not have one iota of bad weather in all of Greece! I guess what you pay for in crowds for peak season you make up for in perfect weather.

  • Cat
    September 22 2011

    Santorini looks like what I imagine when I think of Greece. Beautiful! And charming lol!

    I’m loving hearing about your cruise. It really looks like you figured out the best way to cruise on the first try by generally avoiding ship sponsored tours and DYI! Cruise lines do a great job of scaring people into going with them but I think my best excursion experiences have come from outside the ship not to mention the cost savings.

    Hope you had a successful visa run even after WordPress decided to nom your post!
    Cat recently posted..Florida & Natural Phenomena

    • Alex
      September 22 2011

      We did end up doing two ship tours (which you’ll read about soon!) in order to use up our credit and they just weren’t as fun as doing it on our own. Have you heard of cruise critic? I swear the whole site is set up to terrify you against going out on your own. I posted a question about it once and everyone was like “I WOULD NEVER GET BACK TO THE SHIP WITH LESS THAN TWO HOURS. BETTER SAFE THAN SORRY.” I guess we just live on the wild side! Ha.

  • Audrey
    September 23 2011

    Ahh! It seems like every turn is a picture perfect moment. Oia looks stunning!
    Audrey recently posted..A City Girl in Prince Edward Island

  • Christine
    December 9 2011

    I definitely felt the same way about Santorini when I studied abroad in Greece a few summers ago…so I went back three times! It’s such a magical place. Next time, make sure you stay a few days because there’s so much to see and do, and the island has great nightlife!

    • Alex
      December 9 2011

      While we were there my mom and I were already checking out hotels and planning our return!

  • Sara
    February 1 2012

    Hi, just ran across your blog for Santorini. Beautiful pictures. Where did you rent a car, and may I ask how much you paid for it for a day? Did you have a map to know how to get to Oia?

    • Alex
      February 1 2012

      Hi Sara! Thanks for the compliment! We just walked off the ship and spontaneously decided to rent a car, so I don’t remember the name of the agency. I think we paid 40 euros? I’m not exactly sure. And the rental agency gave us a map and pointed us to Oia. Sorry I’m not more help!

  • Kat
    June 29 2012

    I am slowly working my way through the entirety of your archives whilst bored at work! (Shh, don’t tell my boss…)

    Just a heads up for your return, the youth hostel in Oia is absolutely lovely. I was island hopping with a friend in 2008 and we stayed there for 3 nights; the owner is an absolute sweetheart and drove us out to some of the less accessible beaches after we befriended his daughter. He also makes amazing alcoholic milkshakes at the hostel bar.

    • Alex
      June 30 2012

      Glad to have you reading, Kat! Thanks for the heads up, as when I return to Santorini it definitely won’t be with the same budget I had traveling with my mom 🙂

  • Margarida Almeida
    October 6 2013

    Oia is beautiful but Pyrgos… Pyrgos is magical, believe me 🙂
    Margarida Almeida recently posted..Greenfest ’13

    • Alex
      October 6 2013

      I hope I get back to Greece soon so I can check that out! Thanks for the tip Margarida!

  • Maddy
    June 10 2014

    OMG OMG OMG Greece is my #1 travel goal. Ever. Ever ever. This post makes me so happy.
    Maddy recently posted..Wearables | Acting Shift-y

    • Alex
      June 10 2014

      Well surprise… I’m going back this summer! 🙂 More posts to look forward to. This reminds me I need to do an announcement post about my upcoming plans!

  • Sonia
    June 29 2014

    The donkeys are so typical of Fira….they looked so cute!

    Sonia recently posted..Santorini: Romance is everywhere!

    • Alex
      June 29 2014

      They are adorable, but that donkey picture was actually taken in Oia 🙂 Both beautiful!

  • Juli
    July 31 2015

    Hello, I really love your blog, especially this post about Santorini since it is my lifelong dream 🙂 I wanna go to Santorini for my next destination and this post give me heartwarming feeling to be even more closer! 🙂

    • Alex
      July 31 2015

      Santorini is magical! Well worth a spot on your lifetime bucket list 🙂 Enjoy, Juli!

  • Leelaboti
    October 4 2015

    OMG! Looks like heaven!

    • Alex
      October 6 2015

      This is definitely my idea of it, anyway!

  • Liam
    January 20 2016

    You’re not the only one who left their heart in Santorini. I think that island is filled with hearts that people have left behind! 😉 Good to see you got out and explored a lot. Looks like you had a great trip.

    • Alex
      January 21 2016

      I think you’re right, Liam. I’ve been back twice since and I still am itching for a third <3

  • Andrew Darwitan
    July 31 2016

    This place is too beautiful for words! Both Fira and Oia are gorgeous, but also the beautiful villages in between, such as Imerovigli and Firostefani.

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