The village of Imerovigli is often called the “balcony of the Aegean. My partner and I immediately felt this charm as we wandered its narrow whitewashed lanes, bougainvillea-draped terraces, and quiet church courtyards.
Here, away from the bustle of Fira and Oia, time slows to a dreamy pace. We spent our days exploring scenic walking trails that reveal breathtaking vistas at every turn, and our evenings lingering over sunset toasts on clifftop patios.
In this article, I invite you along on a guided tour through Imerovigli’s most enchanting walking trails and scenic spots, all tailored for couples seeking a blend of adventure and intimacy.
We’ll cover moderate-level hikes that reward you with panoramic caldera views and hidden romantic settings.
Along the way, you’ll discover historical chapels, sunset viewpoints, and cozy places to pause for a glass of wine or a candlelit dinner. Each trail description includes highlights, cultural landmarks, the best times to go, and nearby dining or lodging perfect for two.
So grab your partner’s hand, lace up your walking shoes, and let’s explore the magical trails of Imerovigli together.
Caldera Rim Trail from Fira to Oia
Trail Overview:
The Fira–Imerovigli–Oia Caldera Trail is Santorini’s most famous walk, and for good reason. This 10 km (6 mile) point-to-point hike connects Fira to Oia along the edge of the volcanic caldera.
It passes right through Imerovigli, the highest village on the route (at about 350 m elevation).
Couples will traverse a mix of smoothly paved village paths and rustic dirt trails, with constant Aegean panoramas unfolding beside them.
Highlights:
Beginning in Fira’s charming alleys, you’ll head north through Firostefani and then up into Imerovigli, all the while treated to postcard-worthy scenes – blue-domed churches perched on cliffs, white Cycladic houses spilling down the caldera, and the volcanic islets black against the vivid blue sea.
In Firostefani, don’t miss the short detour to the famous Three Bells of Thira viewpoint overlooking a blue dome and the caldera – a perfect spot for a couple’s photo.
Continuing uphill into Imerovigli, the views only get better; this village’s vantage point is the highest and often the most breathtaking. We took a moment to detour to the Anastasi (Resurrection) Church, one of Imerovigli’s beautifully situated blue-domed chapels, and were rewarded with spectacular views of the volcano framed by the brilliant dome.
Every few steps in Imerovigli reveal a new angle on the caldera – it truly feels like walking through a dreamscape.
Beyond Imerovigli, the trail becomes a dirt footpath winding along the rim. Here you’ll encounter the quaint Profitis Ilias chapel, sitting on one of the trail’s highest hills.
We arrived just as the late afternoon sun cast a golden glow on its white walls. From this lookout, you can gaze down the length of the island toward Oia in the distance. It’s an unforgettable panorama – a dramatic spot where many couples pause to share a quiet moment.
In fact, thanks to its elevation, Profitis Ilias offers stunning 360° views of the caldera and is especially magical at sunset. If you prefer a more private sunset away from Oia’s crowds, timing your hike to reach this chapel by dusk is a wonderfully romantic alternative.
The final leg of the hike leads you up and over a ridge and then descends into Oia. As you crest the last hill, the sight of Oia’s white buildings and iconic windmills comes into view.
We timed our walk to arrive in Oia at sunset, and it was pure magic – the sky turned tangerine and rose over the Aegean as we stood at Oia Castle ruins with countless others, awed by the legendary sunset.
Be aware Oia is very popular at sunset, so it won’t be as quiet or intimate as Imerovigli, but it’s a must-see spectacle at least once.
Trail Difficulty & Timing:
This hike is moderate in difficulty and typically takes about 3 to 5 hours one-way , depending on your pace and how often you stop to take photos (trust me, you will stop a lot!). There are plenty of uphill and downhill sections, but anyone in decent shape can handle it.
The most strenuous stretch is the short, steep climb between Fira and Imerovigli (if starting in Fira), whereas the long incline from Oia up to Imerovigli is more gradual if you do the reverse.
When to go: To avoid Santorini’s intense midday heat and to have a more intimate experience, start early in the morning or in late afternoon. In summer, we began at 7 AM from Imerovigli and enjoyed a lovely cool walk with very few people around, reaching Oia before noon.
Alternatively, a late-day start from Fira (around 3–4 PM) can get you to Oia right at sunset – just bring a flashlight for the last part or your return trip, as it will get dark.
We also found splitting the hike into two days worked well (staying overnight in Imerovigli in between) , which is a great option for couples who want to take their time and savor each segment.
Romantic Stops & Amenities:
Part of what makes this trek special are the little stops along the way. In Firostefani, consider a breakfast or coffee at a cafe with a caldera view (the village name means “Crown of Fira,” and it indeed offers crown jewel views).
By the time you ascend to Imerovigli, it might be perfect timing for lunch. We stopped at Avocado Restaurant in Imerovigli – a casual, friendly spot known as the best midpoint stop on the trail.
Sitting on their terrace, we cooled off with local white wine and amazing Santorinian salad while gazing at the caldera – a delightful midday date. If you’re doing the hike in the morning, Avocado opens for lunch, and no reservation is needed for a quick bite.
For those who end their day in Imerovigli instead of pushing on to Oia, an even more romantic idea is to pause the hike and dine in Imerovigli at sunset. In fact, many couples choose Imerovigli’s sunset over Oia’s – it’s just as spectacular and far less crowded.
You could enjoy a sunset dinner at The Athenian House, an elegant open-air restaurant with panoramic views of the sun melting into the sea. (It’s popular, so reserve ahead.)
As the sky turns pink, you’ll be toasting each other in a quiet atmosphere while Oia’s throngs fight for space – a blissful trade-off. Finally, if you do end the hike in Oia, you have the option to celebrate with a seaside dinner down in Ammoudi Bay (reached by steps or a short taxi) where tavernas serve fresh catch of the day by the water – a lovely reward after the long walk. Just note that after sunset, buses from Oia back to Fira/Imerovigli fill up fast , so consider a private transfer or taxi if you’re tired.
Skaros Rock
One of Imerovigli’s signature landmarks is the towering Skaros Rock, the remains of a medieval fortress protruding into the sea below the village. Hiking out to Skaros is a must-do couple’s activity in Imerovigli – it’s short and moderately challenging, yet delivers thrill and awe in equal measure.
Trail Overview:
From the heart of Imerovigli, a narrow path and a steep staircase lead down the cliff toward Skaros Rock. In about a 10-minute descent from the village (near Agios Georgios Church), you’ll reach the official trail that continues toward the rock.
The hike is roughly 650 meters one-way (0.4 miles), but involves many stone steps and uneven rocky paths, so plan for about 45 minutes to 1 hour round-trip including time to explore.
We’d rate it easy to moderate – the distance is short, but a few sections are steep or near drop-offs, requiring good footing and a bit of stamina on the way back up. Sturdy shoes are important (flip-flops not advised, though plenty of visitors have tried!).
History & Highlights:
As you make the descent, it’s humbling to imagine that Skaros was once the fortified capital of Santorini. Established in the 13th century by Venetian rulers, Skaros Rock held a thriving castle town on its summit called Castle Skaros (Epano Kastro).
In fact, this very stone trail was traversed by inhabitants centuries ago. Earthquakes eventually shattered the fortress (major quakes in 1650 and 18th century sent much of it tumbling into the sea) , and by the 1800s it was largely abandoned to the elements.
Today, only ruins of the castle remain, but exploring them hand-in-hand is a memorable experience for history-loving couples. We scrambled around old foundation stones, imagining the medieval villagers who once watched the sunset from this very precipice.
The scenery is simply breathtaking. Once you descend the main steps, the path hugs a narrow saddle of land connecting to the rock. There are no railings beyond this point, just you and the caldera’s vast expanse.
To one side, the white sugar-cube houses of Imerovigli crown the cliffs above, to the other side is open blue sea. We found ourselves stopping frequently just to absorb the 360° views – looking back at all of Santorini curving behind us, and forward to the endless horizon ahead.
On the far side of Skaros, tucked into the cliffs, you’ll come upon the chapel of Panagia Theoskepasti – a tiny white church with a blue dome, seemingly clinging to rock’s edge. This chapel (whose name means “hidden by God” in Greek) survived the earthquakes and is open to visitors during the day.
When we arrived, there was no one else around; we sat on the bench there, cooled by sea breezes, and rang the little bell together for good luck. It’s an incredibly romantic spot to share – just you two, the chapel, and the boundless sea.
For adventurous couples, it is possible to carefully climb up to the very summit of Skaros Rock, though it’s not an official part of the trail. Be warned: it involves a bit of a scramble on a faint path and some mild rock climbing. Many people skip the summit due to the exposure and crumbling rocks.
We decided to attempt it – and while it was exhilarating to stand atop with the wind whipping around us, it definitely got our hearts racing! Only do this if you’re both sure-footed and okay with heights; otherwise, the loop trail around the base of Skaros provides equally fantastic views without the risk.
Best Time to Visit:
The Skaros Rock hike is accessible anytime from sunrise to sunset (it’s not gated). If you crave solitude and cooler weather, go in the early morning – you might have the entire site to yourselves as the rising sun bathes Imerovigli in soft light behind you.
We chose a late afternoon excursion, timing it so we’d be out on Skaros at golden hour. Watching the sun sink low over the water from this vantage was unforgettable. The rocky cliffs glow red, and the village starts to light up on the caldera rim – truly a photographer’s dream.
Many couples also go for sunset, which can be incredible from here. Just note that you’ll need to hike back up in twilight (bring a phone flashlight), and the path can be tricky in the dark.
Also, sunset attracts more people (Skaros is a well-known spot), so arrive a bit early to stake out a peaceful perch. Avoid midday in high summer, as the route offers little shade and the heat reflecting off the rocks can be intense. Whenever you go, carry water; even though it’s short, you’ll work up a thirst on the return ascent.
Consider packing a light picnic to enjoy out at Skaros. We saw a duo uncork a bottle of local Assyrtiko wine and toast their engagement as the sun went down – not a bad idea at all!
There are a few flat rocks near Theoskepasti chapel that make a lovely picnic seat with a view. Just be sure to pack out all your trash and be mindful of the wind (hold onto that napkin!).
For us, simply sharing a quiet moment at the edge of the world was the highlight – a memory we’ll treasure forever.
Nearby Dining: After the climb back up to Imerovigli, reward yourselves. You’ll find a handful of excellent restaurants in the village just steps from the trail’s end. One favorite is the aforementioned Athenian House, perfect if you timed the hike to finish at dinnertime.
Another is the casual Avocado, if you prefer something low-key for sunset cocktails and meze on their terrace. Even a simple café can feel luxurious after that workout – we grabbed gelato from a tiny shop and sat on a wall overlooking Skaros, watching the sky fade from orange to starry indigo.
For a truly private treat, many hotels in Imerovigli offer private dining on your terrace – which leads to our next topic!
Imerovigli Village
Not every memorable walk has to be a strenuous hike. Some of our most romantic moments were spent simply wandering the labyrinthine pathways of Imerovigli itself.
This tranquil village invites exploration and discovery at a leisurely pace, making it ideal for couples who want scenic views without breaking a sweat.
You can create your own self-guided walking tour through Imerovigli’s hidden gems – from its famous blue-domed churches to its panoramic little squares – all within 1 to 2 kilometers.
What to Explore: Start from Imerovigli’s central square and meander along the cliffside pedestrian paths that weave between hotels and homes. Every turn reveals a new vista or charming scene.
We found ourselves happily lost among whitewashed walls, climbing short staircases up and down the terraced village. One moment you’re passing a set of bright blue church domes (there are several in Imerovigli – each seemingly bluer and more photogenic than the last), and the next you’re peeking into a courtyard draped in pink bougainvillea where a local cat naps in the sun.
Two especially picturesque churches to seek out are the Church of the Resurrection (Anastasi) – the quintessential blue dome that often appears in Santorini postcards – and Panagia Malteza, which has an interesting backstory (local legend says a sea captain brought an icon of the Virgin Mary from Malta in the 19th century and built this church to house it).
Both churches perch near the cliff edge, offering perfect spots to take in the view and perhaps snap a keepsake photo of you two with the caldera behind.
As you wander north toward the edge of the village, you’ll come across the Agios Nikolaos Monastery (also called Saint Nicholas nunnery) nestled between Imerovigli and Firostefani. Founded in 1651, this little convent exudes peace.
If open, step inside the courtyard – you might be greeted by the scent of incense and the sight of golden icons crafted centuries ago. We happened upon it during the late afternoon and were enchanted by the silence and the history contained in its thick walls.
Nearby, a small sign pointed us toward a lookout platform, from which we gained a unique perspective of Skaros Rock from above. It’s these unplanned discoveries that make Imerovigli so special.
One highly recommended route is to follow the path towards Skaros, not to hike it again, but just enough to reach a panoramic terrace partway down (near the Agios Georgios chapel).
From there, you can see all of Imerovigli cascading down the cliff, with Skaros Rock and the Aegean in the background – a stunning composition. Many couples take wedding or engagement photos here for good reason. We simply took a seat and soaked it in, feeling on top of the world.
Sunset Stroll: If you haven’t had your fill of sunsets (is that even possible in Santorini?), Imerovigli is an amazing place to wander at dusk. In contrast to Oia, where crowds jostle for a glimpse, in Imerovigli you can often find a quiet perch to call your own.
We recommend walking toward the little promontory at the far end of the village (past Grace Hotel and other cliffside suites). Here you might find a secluded bench or just a low wall to sit on.
As the sun begins its slow descent, the white buildings around you glow honey-gold, and the caldera fills with evening shadows. We shared a bottle of local wine on a secluded overlook, and as cheesy as it sounds, it felt like the moment was ours alone. The reddish colors of sunset reflect on Imerovigli’s houses, amplifying the romance in the air.
If you prefer a venue for sunset, there are a few stylish lounge bars and restaurants with terraces – arriving on foot early can sometimes snag you a front-row view without a reservation. Or for the ultimate private moment, enjoy sunset from your hotel balcony (more on those amazing hotels in a moment).
Difficulty & Duration: Wandering around the village is easy on the legs, though note that Imerovigli is built on a slope – you will encounter lots of stairs and some steep lanes.
Wear comfy sandals or shoes. In an hour you can cover most nooks and crannies, but we often turned it into an entire lazy afternoon of exploring, shopping for local crafts, and stopping for gelato.
Unlike the defined trails, this is more of a choose-your-own-adventure, and you can’t really get lost for long. If you head downhill, you’ll eventually hit the main road; uphill leads back to the caldera path.
Local Dining & Hidden Cafés: During your village stroll, you’ll stumble upon several inviting spots to eat or drink. For a casual bite, we loved Mezzo, a little taverna with a rooftop terrace – perfect for a simple lunch of tzatziki and grilled octopus with caldera views.
If you have a sweet tooth, look for the bakery selling baklava and frozen Greek yogurt drizzled with Santorini honey (we followed our noses to find it!).
There are also tiny cafes where you can grab a freddo cappuccino (iced coffee) and watch daily life go by in the village square. One evening, we treated ourselves to a dessert at Five Senses Restaurant, known for its creative dishes and prime sunset vantage.
We arrived just for dessert and drinks – a great tip if you can’t get a dinner reservation – and savored a chocolate mousse as twilight fell. Whether you opt for a family-run taverna or a high-end restaurant, many Imerovigli eateries feature intimate patios and Caldera vistas perfect for couples.
Finally, don’t hesitate to chat with locals or the staff at your hotel for their favorite hidden spots.
That’s how we discovered a tiny church tucked at the village’s highest point (Prophet Elias, which we mentioned before along the trail) and a quiet rooftop that was open for visitors near the monastery.
The joy of Imerovigli is in these small moments of discovery – no rush, no crowds, just you two and the island’s timeless beauty.
Cozy Taverns and Cliffside Suites
No couple’s travel article would be complete without suggestions on where to wine, dine, and unwind after those scenic walks. Luckily, Imerovigli caters to romance at every turn, from its cozy cliffside tavernas to its boutique cave hotels with private plunge pools.
Here are some top picks and tips to make your evenings as special as your daytime adventures:
Romantic Dining with a View:
Imerovigli boasts several restaurants ideal for a romantic dinner, many literally hanging over the caldera. We’ve mentioned The Athenian House (fine dining meets sunset views – a top choice for anniversaries or any special night) and Avocado Restaurant (lively Greek/Mediterranean fare, great for lunch or a laid-back dinner).
Another excellent option is Five Senses, which offers modern Greek cuisine on an open terrace – the name says it all, as it’s a feast for the senses with each dish complemented by panoramic scenery.
For a more traditional vibe, Anogi (located just behind the cliff edge) serves authentic local dishes in a warm atmosphere; it doesn’t have a caldera view but makes up for it with flavor and hospitality. Many visitors also praise La Maison for its creative menu and romantic ambiance.
If you’re celebrating something truly special (or just feel like indulging), consider booking a private terrace dinner. Some hotels in Imerovigli arrange private chef dinners on your balcony.
There’s also a well-known experience in Oia at the Panorama Balcony (a single-table private dinner), but Imerovigli now has a few hotels offering similar one-table setups.
Imagine having an entire terrace to yourselves, candlelit, with the caldera and stars as your backdrop – we did this on our final night and it was absolutely unforgettable.
Sunset Drinks:
For pre- or post-dinner drinks, Imerovigli has a handful of chic bars. We enjoyed Astra Suites’ terrace bar (open to outside guests for cocktails) – sipping Santorini wine in an infinity pool lounge as the horizon glowed was heavenly. Some other hotels also have rooftop bars worth checking out.
And of course, you can always grab a bottle of local wine (the Assyrtiko white or Vinsanto dessert wine are renowned) from a shop and find your own quiet spot.
One evening, we joined a couple of new friends at the Aghios Nikolaos monastery square where a guitarist happened to be strumming – impromptu moments like these, with plastic cups of wine and music under the open sky, often become core memories.
Waking Up to the Caldera:
Imerovigli’s accommodations are famously romantic. Picture luxurious suites and villas built into the cliffside, complete with private terraces and plunge pools overlooking the volcano.
Many couples choose to stay here for the serenity and the unparalleled view (it’s less frenetic than Oia or Fira). Whether you’re honeymooning or on a weekend escape, you’ll find options from ultra-luxe to budget-friendly boutique.
For a splurge, Grace Hotel is iconic – known for its infinity pool and minimalist chic suites (and that jaw-dropping view you may have seen on Instagram). Astra Suites, another top-rated hotel, offers verandas perfect for sunset-watching; their pool area is gorgeous for daytime relaxation.
We stayed at Honeymoon Petra Villas, which truly lived up to its name – our cave suite had a hot tub on the balcony, and every morning we had breakfast delivered so we could dine while overlooking the caldera in our robes. Talk about bliss!
Other notable mentions include Kapari Natural Resort (boutique elegance), Santorini Princess Spa Hotel (a bit further along the trail toward Oia, offering more privacy), and Remezzo Villas (charming service and decor).
Even mid-range studios in Imerovigli often come with small terraces; you don’t need to break the bank for a romantic stay.
What’s consistent is the quality of the view – almost every place in Imerovigli faces west toward the volcano and sunset. And because the village is quieter at night, you can often enjoy a peaceful evening on your balcony with just the sound of the wind and distant bells from churches.
It’s worth noting that many of these hotels have lots of steps (no elevators on a caldera cliff!), so pack light and let the porters help with luggage if offered. Also, book early if traveling in high season, as couples’ accommodations fill up fast.
After days filled with hiking and exploring, having a comfortable and romantic base in Imerovigli elevated our trip to the next level. We’d hike in the mornings, lunch on the trail, spend afternoons by the pool, then get ready for a wonderful dinner each evening.
It created a perfect rhythm of adventure and relaxation. In Santorini, the days may be hot and active, but the nights are meant for romance – and Imerovigli provides the ideal stage. Whether it’s a simple picnic on Skaros, a sunset cocktail at a stylish bar, or a private dinner at your cave suite, this village knows how to cater to lovebirds.
Before we wrap up, here’s a handy summary of the top trails around Imerovigli, with key details at a glance for your planning:
Final Thoughts
Imerovigli proved to be everything we hoped for in a couples’ getaway: adventurous days of hiking to awe-inspiring vistas, and quiet evenings full of romance.
The moderate trails here strike a perfect balance, enough activity to feel the thrill of discovery, but not so strenuous as to leave you exhausted (after all, you need energy to clink glasses at sunset!).
Santorini will always be known for its iconic views, but experiencing them through these walks, away from the busiest spots, gave us a deeper appreciation of its magic. Imerovigli invites you to slow down and savor these moments.
If you and your loved one find yourselves in Santorini, take the time to wander these trails and scenic spots.
You’ll create your own story to tell, one of breathtaking views and intimate moments, set atop the caldera cliffs of Imerovigli.
