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3 Favorite Travel Destinations in Santorini, Greece

August 09, 2022 5 min read 1 Comment

3 Favorite Travel Destinations in Santorini, Greece

As promised, we’re not finished exploring Greece. I’ll share some of my favorite hidden treasures in Santorini, from great food to breathtaking hikes.

People often ask when is the best time to travel abroad. I am a believer that shoulder seasons are always the best. Lowered hotel rates are a bonus but not the impetus. For me, “off season” is when the world gets quiet with fewer humans. I have spent time in Greece during April, June and in late October. April is good, October best.

Solo travel in Greece is filled with delightful moments and explorations; choosing your own path (or going off the path) is a luxury. And, travel in Santorini is truly magical. While I have found Greek men can be more forward than perhaps the Brits or Germans, they generally disappear when ignored or politely asked to leave you alone. When traveling alone, or with friends, use the same common sense you would use anywhere else in the world. (And as I have said before — a good, cross-body bag is always a smart choice.)


You have likely seen the beautiful white buildings and blue domes of Oia on the island of Santorini. Many of you are familiar with the jet-setting nightlife of Mykonos. While these places deserve to be seen, they do not speak into my introvert’s soul when I am on holiday sharing them with thousands of my fellow humans.

My trip in May and June of 2022 gifted me with visits to Santorini three times in a four-week period. I was determined to try to get off the beaten path and find some way to breathe in this beautiful location and be away from the hordes of tourists.

It turns out the path I found in Santorini was not one less traveled, but definitely one that should not be missed.


A side note about the old port and its appearance of being one big “tourist trap.” There are great, locally-owned restaurants to be discovered, especially if someone gives you a recommendation.

Greece is a perfect destination for foodies. What stands out the most are the smell and visuals of the food. It is the only place I’ve ever been where I could smell the tomatoes and feta in a salad from across the table. I wanted to cry with happiness. My friends told me I was insane so I said I would “consult the oracles” (which is what I call Google). I suspected the volcanic soil made for fantastic veggies of all kinds. Here is what I found:

“One of the most intense and flavorful tomatoes on earth grows out of the Volcanic soil on Santorini Island.” Ha – vindicated.

I am not certain why Dimi’s Café has no google reviews. I ate there several years ago when it may have been under a different name and have been there four times over the past five years and have loved it every time. The cafe is just down the stairs to the old port of Fira (also known as Thira). The décor is the charming blue and white of Greece and the food is simple, fresh, and delicious.

Because it is located in the old port and right on the water, it offers a breathtaking view of the volcano. Almost completely in the shade, this sweet spot is ideal for taking a break after the effort of the descent from Fira or a quick meal before returning to your ship. They always have either freshly grilled sardines or anchovies and fantastic Greek salads, but the menu is much more extensive. I am a creature of habit and always thrilled to find myself back at Dimi’s.

Dimi's Cafe


A few years ago, my friend Sean Herron, a restauranteur and chef from Portland, and I visited some of the best open-air markets in the Mediterranean and Adriatic. Markets are always a wonderful glimpse into the true cuisine and soul of a culture. From Montenegro to Sicily and Spain to Greece - we visited and tasted delectable local treats at every market we could find. I wanted this tour of Greece to be about consuming the islands with my eyes along with ingesting that incredible Mediterranean cuisine.

It was the perfect time for this trip as I have been full-on Keto dieting for several months taking off more pounds than I care to admit. The food of these islands was the reward for my hard work and it was easy to maintain a healthy diet with so much delicious and fresh food from which to choose.


I highly recommend hiking from Santorini to Oia. In my opinion, exploration on foot is the best way to see many places. Santorini is no exception. Take the cable car, in the old port, up to the town of Fira if you are arriving by ship. Enjoy lunch or wander the shops before setting out on a glorious hike.

I read somewhere that Greece is 80% mountainous terrain. Be advised that it is not an easy place for people with mobility issues.

It is important to know the trail is not marked. You can hire a guide if you are not accustomed to venturing out on your own. That said, I promise this is an easy trail to navigate as it follows the sea, offering 10km/6mi of majestic views while meandering through the towns of Firostefani, Imerovigli, and Oia. You simply follow the path/road closest to the Caldera.

Greece may have more churches per capita than anywhere on earth, and I collect iconic Orthodox art, so the churches along this hike were an extra bonus.

Orthodox art



After hiking this route twice on my recent trip, I would suggest an early morning trek as there is not a lick of shade anywhere and the afternoon sun on the second trip almost did me in.



Always carry water when you hike. Even if you think it will be a "short" hike, water is essential.



Sturdy shoes are a must. While the terrain is mostly flat and downhill from Fira to Oia, there is much uneven ground and it requires being sure-footed.


My first hike took 5 hours as I stopped along the way every few moments. The second trip took 3 hours but be prepared to stop a lot and allow yourself extra time. The views are worth it.

The reward for this hike is arriving in Oia at the brilliant site of the iconic white buildings with blue domes.


My favorite breakfast/brunch spot in Oia is called Mes Ami. The entrance is off the main path and requires a bit of looking. Mes Ami offers amazing breakfasts but the added bonus is a truly magnificent view of the Caldera and great iced coffee. Iced coffee is not easy to find in Greece. They generally offer to pour hot coffee over ice and we all know how unsatisfying that can be.

So, there you have it. Some of my favorite memories and moments from Santorini. May you have delightful adventures if you find yourself in the sunny Greek Isles.

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    1 Response

    Elaine N Hagley
    Elaine N Hagley

    August 23, 2022

    Thanks for the wonderful tour from your hike The exquisite picture of the icons was spectacular!

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