Sure, I can practice yoga at home. But a retreat in Santorini with The Travel Yogi? That’s on a whole different level. While they may be a bit more expensive than some group travel companies, they don’t skimp on anything. The lodging, the stay, the yoga instruction—it’s all top notch. And they pick some of the most stunning places in the world to practice, unwind, and explore.
Santorini is probably on a lot of people’s wish lists—and for good reason. It’s breathtaking. Part of the Cyclades, a group of islands in the Aegean Sea southeast of mainland Greece, it’s known for its dramatic cliffs, whitewashed buildings with blue domes, and incredible views. A massive volcanic eruption around 1600 BCE shaped the caldera, now filled with deep blue water. Villages like Fira and Oia sit along the rim, with narrow alleys, great food, and some of the most beautiful sunsets you’ll find anywhere.
Honestly, the itinerary sounded amazing, and I’d always wanted to go to Greece—this felt like the perfect opportunity.
I went in May, which turned out to be ideal. It was quiet—just ahead of the big crowds and cruise ships. We mostly had the island to ourselves, sharing trails and restaurants with locals instead of packed tour groups. It was rare to pass anyone else on the trail.
I flew into Athens and spent a few days exploring before heading back to the airport to meet my daughter, Connor, who was flying in to join me. From there, we caught a short flight to Santorini. Once we landed, we grabbed a cab and headed to our hotel—located in Imerovigli, a quiet village between Fira and Oia. It was the perfect spot, with wide-open views of the caldera and the Aegean Sea.
Just below the hotel runs the Fira to Oia trail, also known as the Caldera Trail—a scenic cliffside path that hugs the edge of the island. Facing the sea, turning right would take you toward Oia; left led through Imerovigli and Firostefani and eventually into Fira.
The trail actually stretches beyond Fira, continuing south toward Pyrgos and beyond, but the most popular section is the part between Fira and Oia. From Rocabella, we could hop on the path anytime for a quiet morning walk or a longer hike into town.
When we arrived, we checked in and made our way to the room—though honestly, it was hard not to get distracted by the views on the way. The caldera stretched out in every direction, and it was one of those moments where you just stop and stare.
The room itself was fantastic. Everything was white—clean lines, minimal furniture—and then there was the ceiling: a soft blue with tiny recessed lights that looked like stars scattered across a painted sky. A wooden ladder led up to a loft, where Connor slept, while I took the main bed below. There was a mix of modern and rustic touches: a glass-topped table set on what looked like a tree trunk, and a small archway leading to the bathroom.
And get this—we had our own private patio with two padded lounge chairs and a hot tub. The view stretched on forever. We hadn’t even unpacked yet, and I was already thinking about how I didn’t want to leave.
The whole place was gorgeous. The main pool was lined with cushioned lounge chairs and had a bar just steps away. That clean, white-on-white Cycladic style was everywhere, accented with wood and stone. Some rooms even had private plunge pools right outside their doors.
Connor and I toasted the week ahead with a glass of wine, swam a little, lounged by the pool, and then set off on the Caldera Trail, located just below the hotel. We followed it along the cliffside for about half an hour until we reached Skaros Rock—a chunk of volcanic cliff that juts out into the sea near Imerovigli. We climbed the stone steps and followed the narrow path around its base. Just wow.
After walking back, we cleaned up and joined our small group for dinner on the hotel patio. The breeze was warm, the food was great, and the light over the caldera was ridiculous—just insanely beautiful.
At sunset, the place turned even more magical. The sky lit up in soft pinks and purples, and the white buildings seemed to almost glow. It was clear from the start this was going to be an incredible week.
The next morning, Connor and I headed back out on the trail—this time walking to Oia, roughly a three-mile hike each way. The path had great views the whole way (yes, I sound like a broken record about the views—but really, they were stunning). We stopped now and then to take pictures—sometimes of the scenery, sometimes of each other—and had some of the best conversations along the way.
Off in the distance, we could see the whitewashed buildings of Oia stretching toward the tip of the island. In some spots, the trail was lined with cactus growing out of the rocky hillside. At one point, we passed a small roadside shrine built into the rock–quiet and peaceful.
Eventually, we made it into Oia—and wow, the town is just as beautiful as every photo you’ve ever seen. We wandered through narrow alleys that twisted between whitewashed buildings and churches with vivid blue accents—including a couple with those classic blue domes. One of the first things we noticed was a bell tower perfectly framed against the sea.
A little farther on, we passed the famous windmill, now surrounded by restaurants and patios with front-row views of the caldera. Every turn offered a new postcard moment—blue domes, pastel buildings, and endless shades of Aegean blue stretching out below. It was almost hard to know where to look.
At one point, we spotted a small group of mules and/or donkeys—maybe six or seven—just starting their descent down a steep stone path, likely heading toward Ammoudi Bay. One man riding atop one of the donkeys managed the group as they made their way downhill.
I’m not totally sure, but I think they use both mules and donkeys here—mostly to carry goods and sometimes people up and down the long sets of stairs. I’ve read there’s been a lot of controversy around tourists riding them, so I’m not sure if that’s still common. Either way, watching them slowly step down that steep path was one of those scenes that looked exactly like in the movies.
We stopped for lunch at a little restaurant called Lotza. We both went with a Greek salad—kind of predictable, sure, but when in Greece, right? And honestly, it ended up being one of the best I’ve ever had. The feta was creamy, not overly salty or tangy like it sometimes is at home, and everything tasted fresh. We grabbed a table out on the balcony because, come on—when you’re in Santorini, you’ve got to soak up the view every chance you get.
After lunch, we wandered through a few little shops—ceramics, handmade jewelry, olive wood, soaps, that kind of thing. One had some beautiful scarves with scenes of Santorini—white churches, blue domes, all of it. I didn’t need one, but I really wanted one.
Eventually, we made our way back, just in time for an early evening yoga session. It was the perfect way to stretch out after all that walking. Then it was dinner—and honestly, by that point, we were more than ready to eat again.
Today we saw Santorini from a different vantage point—the water. We boarded our own private catamaran for an afternoon sail around the island. It was part snorkeling trip, part cruise, and all about relaxing. We stretched out on the deck or lounged in the netting, soaking up the sun and watching the cliffs drift by.
At one point, the captain dropped anchor at a quiet spot where we went snorkeling—or just floated around on noodles. While we enjoyed the water, the boat’s chef started preparing lunch: a small Greek-style BBQ set up right on the back deck. He grilled meat for the others and a plate of seasoned vegetables just for me. There were olives, tzatziki, stuffed grape leaves, tomato and feta salad, and baskets of warm bread. Simple and so good—one of those meals that somehow tastes even better out at sea.
As we sailed along, the captain pointed out Red Beach, with its rusty cliffs, and White Beach—tucked between pale rock formations. From the boat, you really got a completely different perspective: layers of volcanic rock, white buildings stacked high above, and the deep blue caldera stretching out in every direction.
It was a perfect day—and honestly, a catamaran trip like this is something I’d absolutely recommend if you’re visiting Santorini.
When we got back, we grabbed a cocktail and relaxed by the pool before heading out for dinner. We ended up walking to a little place called Avocado Restaurant. I’ll admit, I mostly chose it for the name—how could I not? But in the end, I didn’t even order anything with avocado. I went with the Greek salad instead, and it was perfect. Light and fresh after a full day on the water.
This was the kind of day that makes you think, yeah—I could really get used to this.
The next day, after yoga and breakfast, we headed out on the trail again.
This time we walked in the opposite direction—toward Fira (Thira). The path hugs the caldera, and even though we’d walked part of it before, going the other way gave us a whole new perspective.
At one point, Connor climbed up onto the ledge lining the trail and struck a yoga pose—balanced above the Aegean, with nothing but focus, wind, and open sky.
We passed more classic whitewashed buildings, a few tiny churches, and those same jaw-dropping views that somehow never get old. As we got closer to Fira (also known as Thira), the path stayed quiet. It was an easy, unhurried walk.
We eventually made it into town and stopped for lunch at Kapari Wine Restaurant—another Greek salad, of course. This time we added stuffed grape leaves and tzatziki. Connor and I were still pinching ourselves about Santorini—it was just so much more than we’d even dreamed. Even just sitting outside on the terrace, enjoying a salad, felt unreal.
After lunch, we made our way back to the hotel, where we had massages booked—could the day get any better?
And then, somehow, we made it to the evening yoga class and graced the group with our presence. We’d been having such a great time doing our own thing, we hadn’t always made it—but it felt good to be there. The session turned out to be really great—so grounding. Travel Yogi always seems to find the most amazing teachers.
On one of our last days in Santorini, we booked a full-day tour with Santorini Sea Kayak called “Round the Lighthouse.” It was a moderate to difficult paddle—about 8 nautical miles—and we used tandem kayaks, which made things a bit easier and more fun. It was just Connor and me, a couple from California, and our guide, Adonis, who was fantastic.
I’ll admit, I was a little nervous going into it. I really wanted to do it—but I’ve mostly kayaked on lakes, and this was the ocean. Not open ocean exactly, but still—different. The Aegean has more movement than a lake. The water has a rhythm to it—gentle swells and small waves that can catch you off guard at first. Adonis told me it might feel a little choppy at the beginning, especially near the cliffs, but that it would smooth out once we got going—and he was right. After the first stretch, it settled into a steady, manageable flow that actually felt great.
The route took us past some of Santorini’s most iconic coastal spots—Red Beach, Kambia, White Beach, Indian Beach, Mesa Pigadia, and the Akrotiri Lighthouse. At one point, we pulled into a quiet, rocky cove for lunch.
I still can’t believe the spread Adonis pulled out of his dry bag. He laid out a full picnic right there on a blanket—carrot sticks, cucumber slices, cherry tomatoes with feta on skewers, grilled veggies, caper spread, fresh bread, olives, cookies, fruit, and these amazing stuffed figs that were sweet, nutty, and so good I had to stop myself from finishing the whole container. Everything was homemade, colorful, and ridiculously good.
After lunch, we followed a rocky path up the hillside to visit Agios Nikolaos, a small church above the beach. It was simple inside—whitewashed walls, a few candle stands, and rows of icons. There were some fresh flowers tucked in the corners and that faint, familiar scent of wax.
After climbing back down the path from the church to the beach, we hung out for a while—snorkeled a bit, walked the shore, and just relaxed. The water felt amazing. Then we got back in our kayaks and continued along the coast, still surprised by how different the island looks from the water.
We paddled back to our take-out point and then headed to Asterias, a nearby seafood restaurant Adonis recommended.
By the time we sat down to dinner, I felt like a bit of a broken record—because somehow, it had been yet another great day.
Being our last full day on the island, Connor and I didn’t want to pack in too much. The only thing we had planned was a wine tasting at one of the nearby wineries. We took a cab to Hatzidakis Winery—Santorini is known for its volcanic soil, and the wines here are supposed to be especially good because of it, so we figured we had to see for ourselves. We’d made a reservation ahead of time, which I’d recommend—spots can fill up quickly.
We took a short tour and learned a bit about the winemaking process, then sat down to sample a few varieties. What really stood out was how the vines are grown—not climbing up on trellises like I’m used to seeing, but coiled into low, circular baskets right on the ground. It’s a traditional method that protects the grapes from the island’s strong winds and intense sun—and honestly, it looked like nothing I’d seen before. That was part of why I’d wanted to visit in the first place.
After the tasting, we got dropped back at our hotel, then hit the trail again and walked into Oia for one last wander. I don’t think it’s possible to get tired of those streets, the little shops, or those caldera views.
We stopped for a late lunch at Kastro Oia Restaurant, which has one of the best views in town. Don’t even guess what I ordered—you already know. (Yes, the Greek salad.)
Later that afternoon, we joined our final yoga class, then relaxed with cocktails by the pool. That evening was our farewell dinner with the group—our last meal together before heading off in different directions. One last cocktail, one more caldera view—it was the perfect wrap-up.
On our last morning, we wandered through Imerovigli, stopping at churches and snapping a few yoga poses along the way (some more graceful than others). Then it was time to say goodbye and head back to Athens for one final night before the journey home.
This week was more than I had hoped for—to have that kind of time with my daughter, just the two of us. Teenagers can be tricky, and back home things aren’t always easy. But here, we had space. Not just space around us, but space between us—to reconnect without all the usual distractions. We spent our days walking, snorkeling, watching sunsets, and yes—eating a lot of Greek salads. The catamaran and kayaking trips were definite highlights, especially because we got to share them.
Santorini had everything I needed—hiking, swimming, kayaking, great food, incredible views, and a reason to slow down—well, slow down for me. Yoga was there when it felt right, and we skipped it when it didn’t. That worked just fine for us. And a massage here and there didn’t hurt either.
I’m someone who usually tries to see as much as I can when I travel—but there’s something unexpected that happens when you slow down. Trips can be different, and this was exactly the kind of trip my heart and soul needed. Honestly, we both did.
I couldn’t have asked for a better place to unwind. Sure, I could’ve island-hopped—but the truth is, staying put for a full week in Santorini was exactly what I needed. I went as part of a yoga retreat with The Travel Yogi, and while I probably could have planned something similar on my own for less, that’s part of the learning. That said, if you’re looking for the ease of a well-organized group trip, The Travel Yogi really does it right. I’ve done two other retreats with them and hope to go again
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