Santorini, Greece



With breathtaking sunsets and views that are out of this world, Santorini is truly a romantic haven and we totally understand why there are countless proposals, weddings, and honeymoons on this island we visited for 10 days. We chose to stay on the Caldera side of the island in the town of Fira at Sweet Pop, a small and newly renovated hotel close to the main square. It was clean, affordable, and our room had a great view of the eastern side of the island. It was also located directly across from a drop-off laundry service which was convenient (and expensive – 9 Euro for one load!). Although we would have much preferred to stay in one of the amazing hotels along the Caldera, it wasn’t quite in #OOWT budget but there will definitely be many more trips back for that! All in all our stay was very comfortable and we were happy to be so close to the action, however Fira was packed with tourists during peak hours so we will probably stay in neighboring Firastefani, Imerovigli, or Oia when we return.

The first couple days we got acquainted with Fira and took a few walks along the Caldera path which was at times relaxing, and others a bit of a calf burn dodging tourists taking countless pictures of the fantastic views. One morning we set out to make the five and a half mile trek from Fira to Oia not really realizing how far it was or how tough it would be. The first mile was familiar because of our previous walks, up and down steep steps but once Skaros Rock approached, we decided it was time for some climbing. At the time we had no idea what it was but wanted to join the people that we could see on top from afar. After about 200+ steps down, we ended at base of the rock and then hiked back up to the top which required legit rock climbing skills toward the end. It was a little scary since the one-way ascent was pretty narrow and there were people stopped along the way taking pictures and those who seemed to have changed their minds about climbing to the top. With dusty hands and knees (and a scraped shin for Jenn) we made made it, endorphins buzzing! The views of the Caldera and the Volcano were so awesome and the feeling of accomplishment got us ready to tackle the rest of the hike. We walked the many steps back up to the Caldera path and continued on not realizing how much further we had, or how challenging it would be especially in the blistering sun. Beyond the two mile mark the number of people dwindled and we found ourselves alone a lot which was pretty cool. We stopped for photo op’s and to chug water and declined an offer for a donkey ride up another long, steep mountain which we didn’t regret but understood the strategic placement of the donkey stand once we reached the top. The motto of the hike soon became “so close yet so far” as our eyes were on the Oia prize though we still weren’t there! Fast forward another hour or so of hiking and we finally reached Oia and were ready for lunch and a beer! After consulting TripAdvisor we decided on this great little Greek tapas spot called Melitini. The octopus was just as outstanding as the view from the rooftop terrace – so tender in a light and very tangy vinegar sauce. We also split a champagne-size bottle of Santorini Brewing Company’s Crazy Donkey IPA (its the only size available and really good) for a toast to reaching the finish line. After we finished up lunch we hopped on the next bus back to Fira. 🙂

(click on pictures to enlarge)

We used public transportation instead of renting an ATV or car which was convenient since the bus station was a ten minute walk from our hotel. We took the bus to Oia one day to visit Atlantis Books and take advantage of the free pool at Lioyerma Pool Bar. Atlantis Books was a recommendation from Jenn’s brother and sister-in-law and we loved it! The place had so much charm and we had a chance to meet one of the owners (an expat originally from the U.S.) and learned more about how the book shop started and where it is today. It also had a small rooftop terrace with a hammock and areas to sit and read and enjoy the views – such a special place. The pool at Lioyerma was pretty chill and had good music – we loved being able to relax on comfortable chairs to read with a view! Its located right at the tip of Oia so we were pumped for the sunset experience which was the best one yet – just ah-mazing.

Our friends Hayley and Jeff who had just visited Santorini recommended a wine tour through Santorini Wine Trails, so we decided to go on an afternoon Wine Lovers Tour which ended up being private since we were the only ones who booked that day/time! Our guide, Iliana was so sweet and knowledgeable and took very good care of us during our three stops along the tour. She picked us up at our hotel and gave us a brief history of wine making in Santorini which was really interesting since it’s completely different from most areas of the world that produce wine. There are some vines that have roots that are centuries old and still producing (very limited) grapes every season! We stopped in one of the vineyards to see the vines that grow in a basket shape low to the ground (versus vertically) to protect the grapes from the harsh wind and sun on the island. We also learned that the vines don’t need to be watered to survive and on an island where there’s very little rain, they’ve learned to adapt over the thousands of years that wine has been produced on Santorini. The sea mist and porous pumice rocks, which hold moisture and are strewn across the vineyards, provide the little water needed. Pretty interesting. After our lesson we headed into Estate Argyros Winery, the first of three wineries we would visit during the tour. The wine tasting included four whites, a rose, a red and 2 Vin Santo vintages accompanied by a piece of decadent chocolate you can only get there. It was fun to get to know our upbeat and delightful wine hostess and tell her about our journey. All the wines were wonderful and we left with our favorite, an oaky barrel-aged white. Next, we headed down to the beach (literally the winery is directly on the beach) and had a small table waiting for us that looked directly out on the water at GAIA Winery. Along with our wine we had some sustenance to keep us going – fabulous cheeses and a delectably sweet tomato paste spread amongst some adorable kittens! Last was Venetsanos Winery which had more great wine and an equally wonderful view of the Caldera where we enjoyed another Santorini sunset before Iliana dropped us off. It was a really nice afternoon and definitely worth the cost, especially since we had Iliana all to ourselves!

Eating out on a budget isn’t hard when you’re in Greece mainly because of four things – greek salad, souvlaki, tzatziki, and gyros, which we had our fair share of in Santorini where eating out can cost an arm and a leg. We found our souvlaki spot early and stayed with it after trying one other place which wasn’t nearly as good and fresh. We went to Yogi’s Gyro’s nearly every day for lunch and a few times for dinner. It was delicious – especially the grilled-to-order marinated chicken breast skewers which we happily dipped in their awesome tzatziki with greek salad and one pork souvlaki gyro (for Jesse) – all for around ten euro. Nearly every morning we would grab a strong coffee from Svoronos, a 24-hour bakery just down the street or from Mickey D’s right next door (thankfully it tastes the same as home). We also enjoyed some really great dinners out, the first at Nikolas Taverna which we read was one of Santorini Dave’s top places for authentic Greek food on the island. The TripAdvisor link says it’s closed but it was open when we walked by and it was great and really affordable. The Moussaka wasn’t as good as what we had in Paros but it was close and the lemon chicken was tangy, tender and oh so tasty. Another authentic Greek dinner we had was at Theoni’s Kitchen where we enjoyed an awesome eggplant salad and excellent chicken souvlaki at really affordable prices. We planned to go back to try their Moussaka (it looked so good and a lot of people were ordering it!) but didn’t end up making it. Iliana had recommended some restaurants during our wine tour so we took her advice one afternoon and had a fantastic late lunch at Vanilia in Firastefani after a long walk. The tomato balls and the lamb meatballs were a home run – so, so delicious! On our last night we had a post-sunset dinner at Argo and enjoyed a great meal with the standout being the grilled octopus in tomato sauce over fava puree, a Santorini staple and it was heavenly. One other place went to watch the Caldera sunset was PK Cocktail Bar, which served a great Aperol spritz along with many other good but overpriced drinks. There was a big group from the UK sitting in front of us taking up several tables and after two drinks and the epic sunset countdown, we witnessed one of the gentleman take his girlfriend by the hand and propose (she said yes) – such a perfect setting!





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  1. Jack Jones
    September 29, 2016 at 11:23 am — Reply

    Very jealous! Glad you guys are having so much fun.

    • Jenn
      September 30, 2016 at 11:38 am — Reply

      Thanks Jack! It’s been so amazing – hope all is well!

  2. Elana
    September 29, 2016 at 12:48 pm — Reply

    Got the test post! Have a great day! Love Elana

    • Jenn
      September 30, 2016 at 11:38 am — Reply

      Thanks Elana – hope all is well with you! Hi to Tyler!

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