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This post covers our 3-night trip to Oia, Santorini.

Lodging: 8.5/10

We found a great boutique hotel which can be located at Cavehouse VII did not disappoint as we learned to appreciate its privacy and close proximity to the action down in Oia. The staff was insanely helpful and friendly; willing to help us gain access to nice restaurants, assistance with rental car bookings and advising on top destinations and activities around the island. The private pool with its own grotto was delightful and it didn’t hurt that the walk into town is only about 15 minutes. While the hotels in town are nice, there is a definite fishbowl effect which intrudes on one’s privacy -so unless you’re into voyeurism, I would recommend staying away from booking a spot where everyone has eyes upon you!

Kara Shurmantine and Doug Parizeau joined us for this trip—it wouldn’t have been the same without them. We all went to Middlebury College together and barely knew each other. The evolution of the friendship over the past few years will always hold a special place in our hearts. We’re sad to see them leave the UK but excited to watch how their lives unfold as they begin business school at Tuck later this year.

The first night we arrived, we headed down to Finakis, which is directly across the street from the hotel. It was recommended that I try the anglerfish, so obviously I went hammer time on what I later learned was this:

A few bottles of wine and Greek salads to share made this a great way to kick off our vacation in style.

The next morning, we ponied up for a 7-mile hike from Fira to our hotel which provided Instagrammable caldera views. The natural scenery wasn’t quite as breath-taking as our hike in Amalfi (Path of the Gods) but I’m certainly not complaining as it wasn’t too far off. There were a couple portions of the hike where we had to “pound the pavement” so that obviously detracted from the natural feel.

After showering up, we frolicked to Feredini in the heart of Oia. Spoiled again by iconic views, we hit up some more Greek salads, eggplant with ground beef, Octopus, Fava beans and Asparagus with chicken. The service was a bit slow but when you’re in Greece, who really cares?

Perhaps the best scenery we had while dining took place at Ammoudi Fish Tavern. It was insane to see the amount of boats jockeying for position to capture the perfect shot of the Oia sunset. World renowned for its beauty, the Oia sunset is tricky to see from this beautiful location but you’re literally on the water so again, it’s tough to complain. Maggie and Kara picked out their own grouper and red snapper for the squad. Tomato fritters are a classic dish in Santorini so we couldn’t wait to dig in. Again, Greek salads galore; I’ll stop referencing these as they accompanied every lunch and dinner. We were later surprised with a cheeky gift: a house donut desert to share with ice cream. This made our evening!

The next morning, we hopped in the rental and headed south to explore Wet Stories beach club at Perivolos beach. The volcanic black sand was a first for me! We enlisted the help of the sun to aid our recovery from the previous evening’s late night dance party. The food at Wet Stories was delicious but the service was the slowest we encountered. We were there in off-season so I’m not too sure how much this differs as things begin to heat up during June, July and August. Octopus and Sea bass were fan favourites from our table and the group collectively agreed upon Wet Stories having a 7/10 rating (service weighs it down).

Argo. Oh Argo! We travelled to Fira for this restaurant which was recommended to us by the hotel staff. It deservedly boasts a certificate of excellence on Trip Advisor. The views are enchanting and the staff is lovely. For the first time in my life I refused a bottle of wine. We shared a bottle of local Santorini white wine with our meal and after that was polished off we asked for another of the same. The rest of the crew ordered coffees, I did not. The server uncorked the bottle and served a dash in my glass. I smelled the wine and instantly turned my nose up! Not believing what I had smelled, I tasted the wine and immediately proclaimed “no good!” Kara, Maggie and Doug all gazed at me as if I had ripped a loud fart. Maggie said, “really?”

Really! After everyone else tried a sip, they agreed it was bad. The manager came out and stated it was because we were drinking coffee even though I had not ordered one. Eventually, after we danced back and forth, they brought another bottle which tasted exactly like the first one. I felt like a total snob and didn’t like causing a scene but there was NO way this wine was okay. It smelled and tasted like doodoo.

Greece was magical and I can’t wait to go back and explore less active islands. We’re very privileged to have been able to witness the magic of Santorini—I’ll always remember the colour of the water, the blue domed churches and white concrete domiciles carved into the cliffs as well as the fresh and wonderful food.

Stay positive and stay blessed!

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