Santorini, Greece – The Perfect Itinerary for First-timers


If you’re looking for fantastic food, amazing views, and friendly inhabitants, Greece is about as good as it gets!

After 12 hours of travel, our driver picked us up and zipped us around the Santorini cliff side. Everywhere I looked was a picture perfect moment.


First on our itinerary was the Santorini wine tour. The wine in Greece may not compare to those of France and Italy, but the tour was fun and took us to lots of interesting spots around the island. The island is known for their dessert wine, Vinsanto. It’s sweet and strong. Try it and bring home a bottle for someone you love. The mid-day sun burns hot on this island, so head down to the cellar and cool off.

wineryjmAnd when you’re good and tipsy, they will drop you off so you can get on with your day to enjoy the vibrant bougainvillea,


the beautiful vistas, and…

sunsetall the pretty blue domed churches your heart could desire!

When you get tired of all of the prettiness, and all you want is some adventure. You can find someone strong to carry you down the cliff side… This guy will do!

donkey2All joking aside, we walked down the path to Armenaki bay instead of taking a donkey as the working conditions for these animals seemed too cruel.


And just when the crowds become too unbearable…


You’ll get to the bottom and see the pirate ship you’re about to board!

We went on the Thalassa sunset cruise (a wooden ship). It left around 3pm from the old port in Fira.

boatYou’ll sail around the Aegean Sea, drink wine, dance, sing, and shout OPA! Jump in and swim to a hot springs that will add 10 years to your life. And finally, when you’re  fully waterlogged and just a little seasick, set foot on land to hike a volcano.

And when you make it to the top, you can celebrate with the most breathtaking sunset.


Santorini is truly one of a kind and a must see island if you are touring the Greek Isles! Put it on your bucket list.

*Wine tour –

You can find ideas on what to pack here and here. And travel tips for Mykonos and Athens here.

Happy travels!


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  1. 2.24.16
    Nicole said:

    Hi Jenny! I’m planning a trip and wanted to know where y’all stayed and how you were able to set up a driver? Thanks!

  2. 7.10.16
    Tina said:

    Hey! My boyfriend and I are planning to tour a few of the Greek Islands between our trips to Rome and Athens this fall. I was curious: how long were you in Santorini/how long would it take to do all of these things? Could you fit it into one day? Thanks!

    • 8.7.16
      Angie said:

      Oh Tina, you will want to stay more than a day! We stayed three nights, but the first doesn’t count since we arrived at midnight! We rented a car (with AC!!!) at the airport (there was 4 of us) and found it difficult to find our Airbnb as there are virtually no street signs (not that we could read them) and directions were in km-after a full day and then some of travel, these Americans were zombies! We loved having the car. We were able to drive up to the Monastery for some killer views of the entire island and beyond. We opted for the Fira to Oia hike (a somewhat strenuous, 10K, hot hike even in the morning) A MUST for breathtaking views and postcard perfect pics! We drove up to Oia on our last night and went down to Amoudi Bay for some seafood and sunset. It’s a relatively small island so with the car we were able to see a lot. If you had a third day you could visit the different beaches-black sand, red sand, white sand. Like I said, you will be sad to leave! We spent a total of 8 days in Greece on our 22 day vacation. Santorini, Athens, Olympia, Zakynthos, and Kefalonia. Not enough! Then we flew to Rome. Happy travels!

  3. 9.5.16
    Robin said:

    We are just starting to plan our trip. Is it better to fly from Athens to Santorini or go by boat? You recommend at least 3 full days in Santorini? Thanks!

    • 9.5.16

      Hi Robin, How fun! You will love Greece! We flew into Athens and then took a small plane to Santorini. On our return we took a boat from Mykonos to Athens. I found both flying to the islands and going by boat very easy, so perhaps see what is the least expensive? I would say have at least 2 days in Santorini, but you will definitely not be bored with 3 full days – it’s an incredible island!

  4. 9.7.16
    Kim said:

    Hi , I’m going to spain in 2 weeks and want to run over to santorini before the weather changes. What would you say is the best way to get there? I am a student and looking for cheap travels. Also any suggestions as to where I should visit and stay while there?

  5. 2.28.17
    Katherine said:

    Hello! We’re seriously considering island hopping in Greece for our honeymoon in July (Mykonos, Santorini, 3rd option still pending). I may just have to copy your itinerary since it sounds amazing. Do you have any recommendations on where to stay on Santorini?


  6. 12.7.17
    Christos Georgantzos said:

    hi your readers will find useful this weather guide of santorini if they plan to travel there. All year included.

  7. 7.10.18
    Vickie davis said:

    We are going in the middle of October are shorts going to be ok

  8. 12.14.18
    Jessica Hinson said:

    where do I go to see these amazing views?!?!