They call them the Cyclades, a shimmering ring of islands scattered across the Aegean like jewels on a faded velvet cushion. Each promises sun-bleached villages, cerulean waters, and a quiet, ancient grace that whispers of a world older than time. Here is the story of three of those islands—my winding path through Serifos, Sifnos, and Milos.
Need a quick shortcut? Use these anchor links to jump directly to each island section in this article.
Planning Your Cycladic Adventure
You’ve long dreamed of wandering the Cyclades, and you’ve finally decided to make it happen. Sound familiar? If so, you’re in the right place. Here, I’ll share insights and lessons learned while charting my own island-hopping route—so your trip can be just as memorable.
Between Greece and Turkey—More Than Just Santorini
Nestled in the Aegean Sea, the Cyclades form a dazzling tapestry of cultures and landscapes. When people picture these islands, they often think of Santorini or Mykonos—and worry about overpriced meals, tourist traps, and overcrowded beaches. Those tales prompted me to seek out the lesser-known gems where travelers can still experience the authentic spirit of these heavenly isles.
1. Getting There: Athens, Santorini, or Crete?
The first big question: where to begin your island-hopping adventure? Flights into Santorini drop you in the heart of the Cyclades, but that can mean steep airfare and tourist hordes. Crete can be equally expensive. For my fall getaway, Athens was the perfect launchpad—reasonably priced flights, two days to explore iconic sights like the Acropolis, and more flexibility with ferry options.
2. Crafting the Ideal Route
In a sea of possibilities, focusing on islands close to each other helps keep ferry costs manageable. After skimming the map, I landed on three islands: Serifos, Sifnos, and Milos. Serifos with its mining history, Sifnos with its lower profile, and Milos with its postcard coves—geographically convenient and less plagued by peak-season chaos. Other islands like Naxos, Paros, or Folegandros could fit, too, but do check if ferries still run regularly in autumn.
3. Ferries and Timetables
Island connections are run by various ferry operators, and not all appear on every booking site. During summer, ferries link most Cycladic isles almost daily; in the off-season, services can be sparse. I found Let’s Ferry, Ferryhopper, and Greek Ferries especially useful for checking routes. If needed, you can also turn to Ferryscanner, though it tends to handle one route at a time rather than an entire multi-stop itinerary.
In the end, I settled on two nights in Athens, four in Serifos, three in Sifnos, and six in Milos—an itinerary that felt both practical and adventurous. To avoid cancellation fees, I booked my ferries just a few days in advance via Let’s Ferry—feasible in the quieter autumn months. Come high season, plan to reserve at least a few weeks ahead.
Whether you decide on a grand circuit or a shorter jaunt, keep an eye on timetables, distance-based fares, and the overall ease of local travel. Because sometimes, the simplest route can lead to the richest experiences—and the Cyclades are ready to show you their magic, one ferry crossing at a time.
Day 1 – Journey to Athens
We set off in the late afternoon, giving ourselves the entire day to pack. Two suitcases to fill, each stuffed to the seams with clothes, towels, and extra jackets tucked in any gap we can find. Rumor has it that security lines at the airport are impossibly long, so we arrive early, only to see there’s hardly any queue at all. A pleasant surprise, though the mood turns briefly sour when the self-check-in kiosks refuse to cooperate. We end up at the Lufthansa Business counter, where a rather self-important agent reminds us—pointedly—that it’s no longer meant for Economy passengers. My wife intervenes, words collide, but the moment passes soon enough. Before heading through security, we sneak up to the viewing terrace, watching planes lift into the overcast sky.
Last-Minute Delays
Contrary to the horror stories, security moves quickly, even if our backpacks get thorough searches. (“It’s like a hidden-object puzzle in here,” one agent jokes.) But at the gate, we see a worrying announcement: our flight is delayed by 15 minutes, then 30, then 45. That leaves only five minutes to make our connection in Munich—virtually impossible. My wife discovers that 30 other passengers share the same onward flight. Comforting, in a way; surely the airline won’t strand us all. By some luck, we keep our takeoff window and finally get airborne. The short hop to Munich is smooth enough, though we exit in a hurry, everyone anxious about connecting gates. In the scramble, I suspect I lose my cheap in-ear headphones, recently bought online for next to nothing.
Making the Connection
Stepping off the plane, a Lufthansa staffer beckons us toward the next flight. We even have to take a gate shuttle, but somehow we make it. The second aircraft is massive—over 50 rows—and halfway through the flight to Athens, my knees start to ache from the cramped seat. Once we land, tension spikes: Did our suitcases make it with us? Relief flows when both bags roll out onto the carousel, none the worse for wear.
Athens After Dark
Outside the airport, we find the buses lined up. I’m set on buying tickets; my wife and daughter would rather just climb aboard. I manage to grab passes at a kiosk for the “Airport Express,” and it’s lucky I do, because a conductor checks them right away. Then comes a long wait at a toll station, stuck in Athens traffic.
We opt to get off at the terminus and walk the rest of the way to our hotel—heavy suitcases in tow, weaving through the city’s nocturnal pulse. Bars overflow with music and chatter, and we’re an odd sight dragging luggage past revelers. Our hotel sits in a building that looks run-down from the outside, but inside, it’s newly renovated. I’m the only one who dares use the rickety elevator. Our daughter can barely keep her eyes open and collapses into immediate sleep. I glance out the window at a beautifully lit structure, thinking it’s the Acropolis; turns out it’s the Observatory. In a few minutes, I’m in bed too, letting the excitement settle into dreams of islands soon to come.
Day 2 – Athens, The Acropolis
We sleep in, taking our time after yesterday’s journey. Once we venture out, we find ourselves at Psirri Square—a lively spot brimming with cafés and eateries. The moment we spy a towering stack of pancakes on someone’s table, the decision is made. Our daughter goes for pancakes, I opt for toast with fried eggs, and my wife chooses a savory chicken pie.
Up Toward the Acropolis
After breakfast, we cross Monastiraki Square, meander through a bustling market, and gradually climb through the Anafiotika quarter—a warren of narrow lanes scrawled with graffiti but offering marvelous glimpses of the city below. Our wanderings eventually lead us to the Acropolis entrance, where we present a student ID for free admission. Thanks to my press credentials, we’re also offered a special elevator, complete with an electric golf cart ride. Quite the show.
Once on top, we find the Acropolis itself less dramatic up close than in photos, but it does grant a majestic sweep of Athens spread out in every direction. Beneath the midday sun, we pause to catch our breath, the ancient stones radiating heat and the soft murmur of tourists echoing off marble columns.
Return to Psirri Square
Our walk back is far simpler—twenty minutes downhill sees us once more in Psirri, where Greek salad beckons my wife and daughter, while I wait (perhaps a bit impatiently) for a plate of sizzling souvlaki. Live music pulses across the square, mingling with lively chatter—plenty of locals among the visitors. We return to our room for a mid-afternoon siesta, lulled by the muted hum of the city.
Evening Excursion to Lykabettus Hill
Come nightfall, we hail a taxi to Lykabettus Hill, paying 15 euros to ride about halfway up. We catch only the last glimmers of the sunset—sadly, not the best view of the Acropolis, which appears only on our descent. Another taxi whisks us back for just 5 euros. Back in Psirri, we treat ourselves to a quick gyro pita before turning in early.
First Impressions of Athens
- A city wrapped in chaos, teeming with late-night energy
- Throngs of revelers converge in the neighborhoods around the Acropolis
- Streets alive with a loud, boisterous spirit that truly awakens after dark
- The crowd is roughly three-quarters Greek, with a mixture of other Europeans, Americans, and Japanese visitors
- Entire blocks appear rundown at first glance—what we call “artfully shabby”—while interiors often gleam with unexpected modernity
- Warmth, openness, and hospitality shine through in every encounter with the locals
Day 3 – Ferry to Serifos: Island-Hopping
We bid Athens farewell after a final round of pastries and pies at our trusty pancake haunt. The city’s Metro, adorned inside and out with riotous graffiti, clatters us to the port. Even as the train squeals through tunnels, it feels fitting—its rust and rattles a last echo of Athenian chaos.
Setting Sail on the Super Jet
At the harbor, we find our “gate” easily enough and spot the Super Jet—a sleek, towering ferry that looks more spacecraft than seafaring vessel. Inside, rows of airplane-style seats greet us, yet we soon discover we can slip out on deck to watch islands drift by. The cost of snacks is steep, but the view is worth every euro. A cluster of wind turbines appears off the port side, perched on a tiny isle as though forging a kingdom of their own.
First Glimpse of Serifos
Soon, Serifos itself emerges from the sea. At first sight, it seems harsh and windswept, a lone lighthouse carved into rugged cliffs. Then, after rounding a pair of rocky outcrops, the island softens—revealing a bright, welcoming cove lined with white houses on steep hillsides. Down on the ferry’s lower deck, among the din of sirens and exhaust, we watch the ramp drop—and there’s Serifos in all its understated grace.
Arrival at Livadi Beach
Waiting for us is Dimitri, the brother-in-law of our hosts. After the ferry pulls away and the harbor quiets, he bundles our suitcases upright into the back of a compact Nissan. During the short ride, we learn he spends winters in Athens and summers working nonstop on this secluded island.
A maze of narrow, winding roads brings us to Vassilia on the Beach. We’re greeted by Frieko, who jokes that his real Greek name is unpronounceable for our foreign tongues. He’s spirited and warm, upgrading us to a two-room suite before launching into tales of ancient myths rooted in these very hills.
The Afternoon Swim
Naturally, we head straight for the shore. Soft, cool waves roll in, and the sand leads gently into the Aegean. The beach chairs belong to the hotel, and a nearby bar sends out drinks on a tab—classic island hospitality. Salt and sunshine melt away any memory of city clamor.
Evening in a Serene Harbor
When I wander into town, I stock up on sandwich fixings, tomatoes, beer, and—of course—those irresistible oregano chips. A quick check at the local car-rental booth reveals tiny vehicles for 30 euros a day, a tempting option for exploring.
Later, twilight casts a gentle glow on Livadi Beach. Gnarled cedar trees, their trunks painted white, seem to sprawl across the sand—an oddly poetic sight. We dine next door at Aleksandro’s, learning only afterward about a family feud behind the scenes. The meal is passable: a robust tomato salad, decent moussaka, rather underwhelming calamari. We vow to try our hosts’ own taverna the following evening, if only to keep the peace.
Nightfall on Serifos
Clouds swallow most of the stars, yet the island’s silence carries its own enchantment. Our bed is a bit short, and we’re crowded in, but I drift off all the same, lulled by the hush of gentle surf. Serifos—initially so forbidding—has revealed a softer face. The hush of the bay, the warmth of local families, and the simple pleasure of a salty swim promise days of unhurried delight to come.
Day 4 – Exploring Serifos
We start the day before dawn. Our daughter’s alarm rings, and she wants to swim at sunrise—how can I resist? The sky turns crimson above the rocky headland to our left, splashing the entire bay in a deep, fiery glow. It’s breathtaking to wade into the cool water just as the sun crests the cliff.
Morning by the Sea
We settle in for breakfast at Vassilia’s beachside bar, savoring mini-wraps, scrambled eggs, and cappuccinos as the sun climbs higher over the horizon. The Aegean sparkles, and we lounge on the sand for a while—until it’s time to pick up our rental car in Livadi.
Renting a Car, Meeting the Locals
At BlueBird Car Rental, we’re greeted by the owner’s daughter, who seems fascinated by my daughter’s anklet. Despite the language barrier, we manage to secure a little Nissan for 30 euros a day. No insurance details are forthcoming, but we decide to roll with it. The car is surprisingly spry on the island’s steep roads—a sturdy manual that handles every incline without complaint.
Up to the Chora
We pack a few supplies and drive to the Chora, that cluster of white-walled houses perched dramatically on the hillside, visible from the port below. Zigzag roads lead us higher and higher until we reach a spot near some old windmills. We park and climb on foot through winding alleys. The place feels almost deserted, save for a few ever-watchful cats slinking about. Halfway up, a tiny café is open, along with a small market. I grab a cold cola, only to lose sight of my family. We eventually reunite at the church crowning the village—a spectacular vantage point with sweeping views over the coastline. The midday sun gleams on these whitewashed walls, and a quiet hush pervades the narrow streets.
Crossing to Sikamia Beach
Back at the car, I launch the drone for a brief flight over the rooftops—plenty of distance, few passersby. Then we decide to continue across the island to Sikamia Beach, known for its solitude and a rumored taverna. The road is a challenge: deep potholes, narrow paths, and hairpin curves. At last, we arrive at a deserted-looking stretch of sand. The taverna’s chairs and tables are stacked inside, seemingly closed.
Yet we discover an old dog, Romeo, padding over to greet us. He’s large, friendly, and nearly blind. His owner soon appears, welcoming us with warm, if broken, English. Romeo, she explains, has spent his life here by the sea. He’s too old to roam far, but more than happy to receive our pats and ear scratches. The taverna, though quiet, is open enough to serve us Greek salad, moussaka, chickpeas, and fries—a hearty, delicious feast. We linger, enjoying the carefree hush of a nearly empty beach.
Farewell to Romeo
With a gentle wave goodbye, we leave Romeo gazing after us. On our drive back, we stop briefly at the parking area below the Chora, hoping to find the sunglasses I seem to have dropped earlier. No luck. As dusk approaches, we settle in at Vassilia’s bar for salad and spaghetti carbonara, watching the evening sky shift to soft blues and purples over the bay. The day ends in a mellow glow, the quiet rhythms of island life a welcome lullaby.
Day 5 – The Serifos Mining Camp at Megalo Livadi
The day begins, as ever, with a morning swim in the cool, calm sea and a leisurely coffee in a beach chair at Vassilia. Then, breakfast: pita, scrambled eggs, and toast at the bar. We pass a few serene hours on the sand—snorkeling, reading, letting the island’s gentle rhythms guide us.
Venturing West: A Wrong Turn to Megalo Livadi
Around midday, we set off to explore the island’s western reaches, hoping to find a hidden cove accessible by foot. But with no GPS signal, we miss our intended turn and end up in Megalo Livadi, once the bustling heart of Serifos’s mining industry. Along the winding roads, we pass tasteful holiday homes and modern bungalows, signs of local prosperity and Athenian visitors seeking idyllic retreats.
Soon we descend into the remnants of an old mining settlement, where rusted ore carts lie toppled and broken rails stretch across abandoned bridges—a timeworn backdrop that begs for drone photography. The hush of the place is profound, the echo of industry long since fallen silent.
Cooling Off at Vagia Beach
On our way back, we seek refuge from the heat at Vagia Beach. The water is clear, refreshing, though the stony seabed calls for careful footing. There’s a peaceful air here, far removed from the echoes of metal and smoke back in Megalo Livadi.
Evening under the Stars
As dusk settles, we retreat to our apartment for a simple meal of toast and fresh melon. Later that night, I step outside to photograph the stars, and the view takes my breath away: the Chora perched in soft light, the Milky Way stretching overhead, and the occasional meteor flickering across the sky.
The history of Megalo Livadi lingers in my mind—a stark reminder that beneath the island’s tranquil shores lies a story of toil, strife, and resolve. Established in 1861 for iron ore extraction, the mining operations drew ambitious entrepreneurs, culminating in a French-led venture under the direction of German mineralogist A. Grohmann. Tragically, poor working conditions sparked unionization, culminating in a violent strike in 1916 where miners and their families faced lethal force.
And so the ruins of Megalo Livadi stand as a testament not only to natural beauty and unhurried island life, but to the human struggles that shaped Serifos and its people. Watching the stars wheel overhead, it is hard not to reflect on the laborers who once toiled here under a very different sky.
Day 6 – Lia Beach
Once again, the day begins in a wash of gentle sunshine over the Aegean. A small ridge of sand has formed overnight at the water’s edge—like a tiny dike—only to be swept away by the wake of a passing ferry. We indulge in toast and scrambled eggs at Vassilia’s bar, but our morning glow dims when my wife realizes she’s developed a urinary tract infection. A quick detour to the island’s Medical Center near the Chora follows. The young physician there is thorough and kind, scribbling a prescription on what looks like a mere slip of paper, but the local pharmacist accepts it without issue.
A Solo Adventure to Lia Beach
While my wife rests, I take the car and head out alone for Lia Beach on the island’s western side. The drive is part sand track, part narrow gravel—a challenge, but I manage to reach a small eco-hotel, where a short footpath winds among prickly shrubs to a crescent of sunlit sand. At first, only two Greek sunbathers occupy the cove, eyeing me warily. I keep my distance, eventually opting to join them in the spirit of a naturist beach—shedding my swim trunks for a refreshing snorkel. The water is crystalline, though fish are few. Over time, more visitors arrive, so I slip my bathing suit back on and politely ask if I can fly my drone overhead. They appreciate the courtesy.
Detour to Paralia Agios Sostis
Sated by sunshine and sea, I drive on to Paralia Agios Sostis, where a solitary chapel graces a secluded, untamed beach. The sight is near otherworldly: white walls and azure waters framed by rocky hills. Finally, on the return trip, I stop at a roadside overlook. There, someone has placed a single chair in a spot so perfect it feels almost like an art installation, with sweeping views of Serifos’s rugged coastline.
Evening and a Star-Lit Walk
Back at Vassilia, we wind down with a spirited card game of Phase 10 (I claim a triumphant victory!) and mouthwatering souvlaki. Later, the night sky draws me out once more—this time toward the nearby village. Under the brilliance of Orion and the Milky Way, I photograph the interplay of graffiti-strewn walls and dilapidated structures against the cosmic backdrop. Yet again, Serifos shows its ability to be both timeless and modern, its small island streets blending with the infinite sky above.
Day 7 – Serifos <> Sifnos Island-Hopping
A Serene Farewell to Serifos
Our final morning on Serifos dawns with the same tranquil beauty we’ve grown used to. My daughter slips into the sea at sunrise, while I linger onshore with Greek coffee and fresh orange juice in hand, scribbling notes into my journal. The water glistens, the cove remains as peaceful as ever. Over breakfast at Vassilia’s, we exchange heartfelt goodbyes with Frieko, Dimitri, and the chef—apparently they’ve decided our daughter must return someday to work on the island, if only she were old enough.
Luxurious Crossing to Sifnos
At noon, we set off for the harbor to drop off our trusty rental car. Without so much as a glance, the staff waves us on—here, trust prevails. I pick up snacks, a cheap new pair of sunglasses, and the obligatory fridge magnet, then watch the lively bustle on the pier. A tanker is being secured by an energetic Greek woman on a teetering scooter; no one bats an eye.
Our ferry arrives—a vessel far more opulent than expected. Wide escalators lead us above deck, past plush lounges reminiscent of a cruise ship. A quick search confirms it once sailed Nordic waters as a cruiser. Not long into the journey, Sifnos rises into view: steep cliffs tower on either side of a snug little port, white chapels capping the slopes like watchful beacons.
First Steps on a New Island
We roll our suitcases along the waterfront, which soon merges into the main street. Restaurants line the harbor, a sliver of beach on one side, ferry offices and cafés on the other. We sample spinach-and-feta pastries from a local bakery—delicious beyond words—and head to SunTrail, the rental agency we booked by phone. The place is immaculate, the staff thorough. With a large fold-out map, they circle key sights and beaches, including the cove we’ll be staying in—apparently the best on Sifnos.
A Drive through the Green Hills
Our small Fiat Panda is stuffed with upright luggage, a trick we’ve learned by now. Off we go, winding up roads flanked by lush olive groves—quite a contrast to Serifos’s barren hills. The single gas station is in Apollonia, the island’s main town, so we fill up just in case. Then the road tumbles downward, revealing glimpses of a tiny coastal village. After half an hour, we reach Vathi but discover cars aren’t allowed on the final stretch. We park and lug our bags along a narrow walkway to find a narrow shore dotted with tavernas, bars, and small beach homes.
Settling in at Studio Anna
Eventually, we locate Studio Anna. Though the language barrier poses a minor hiccup, we get our key. The room is compact, the amenities modest—my daughter is underwhelmed at first. Yet the balcony offers a clear view of the sea, and we’re staying in the midst of a welcoming Greek family. It’s all spotless and radiates genuine warmth.
Provisioning and an Octopus Surprise
While the girls take a late-afternoon swim, I venture out to gather essentials. A sandwich-maker awaits in the room (a ubiquitous Greek lodging staple), so toast, cheese slices, tomatoes, and olives should do. Alas, the tiny mini-market lacks fresh veggies, but at least I secure water, pasta, and coffee.
Meanwhile, snorkeling proves unremarkable fish-wise—until I spot an octopus holed up inside a discarded plastic cup. An unexpected greeting from Sifnos indeed. With that, we settle in for the evening, already sensing the charms of this different—yet no less enchanting—island.
Day 8 – Sifnos Kastro
We couldn’t be more content here: lulled by the constant wash of waves through the night, awakened by the gentle clanging of goat bells in the distance. A cool breeze drifts through our window, and the air outside carries a heady mix of sea salt, warmth, and that quintessential Greek scent. I sit on our balcony, gazing at the blue expanse, penning these notes.
Morning Rituals and a Trip to Kastro
We fuel up on sandwiches courtesy of our trusty sandwich-maker—seemingly every Greek rental has one—and sip powdered cappuccino. Then we set off for Kastro, a half-hour’s drive away.
Kastro proves to be a picturesque village clinging to steep cliffs, its whitewashed lanes interrupted by bursts of vivid flowers and azure shutters. An ancient fortress once stood here, but only its foundations remain. Below, a tiny rocky outcrop cradles the Chapel of the Seven Martyrs, which I reach after descending countless steps. The scene is almost surreal—stone, sea, and a wild swirl of wind. Along the way, we pass a cliffside bar whose walls are plastered with graffiti, from the crude to the artistic. One imagines it thronging with summer crowds. Meanwhile, my daughter befriends a pack of cats, though she only has eyes for the smallest one.
Searching for Groceries and Pottery
On our way back, we stop at a few open supermarkets to stock up on noodles, water, and assorted snacks. Sifnos is famed for its pottery, so we scour three workshops for a new wine jug—without success, but we linger over the exquisite plates, vases, and hand-painted marvels.
An Afternoon at Vathi Beach
Once returned to Vathi Beach, we bask in the sunshine and snorkel through its elongated bay. Our old octopus friend is nowhere to be found, his plastic cup vacant on the seafloor.
Later, I hike a footpath to the right of the cove—a steep route barred by a rickety goat gate. Though it’s a rough climb over loose rock and prickly shrubs, the sweeping sea views are worth it. The sunset, however, is modest at best.
Dinner at Taverna Symposio
We settle down at Taverna Symposio, famous for its homegrown produce and a chef who brims with enthusiasm—when he isn’t cooking, he’s out fishing from the shore with a simple hand line. The dishes, while decent, don’t quite match his grand promises, but the experience is unforgettable. An eccentric host if ever there was one, embodying the laid-back pulse of island life in every gesture.
Day 9 – Roaming across Sifnos
Waves, crowing roosters, and the wild chirping of tiny birds usher in the morning light. Sometime after midnight, I half-woke to the jarring sound of a neighbor getting violently ill—a harsh reminder of close quarters in these snug island lodgings. Still, I slept well overall, and now brew myself a powdered cappuccino on the balcony while the family stirs. I prepare our dependable breakfast of toasted sandwiches, plus scrambled eggs with tomatoes.
Venturing South: Platis Gialos & Chrisopigi
Today, we set our sights on the island’s southern reaches, but they turn out somewhat underwhelming. Platis Gialos, a broad bay that likely buzzes in summer, stands almost deserted in late October. A lone ceramics shop is open, yet our elusive wine jug remains nowhere to be found—though we glimpse a perfect specimen in a locked, closed-up store, tantalizingly out of reach. We move on to Chrisopigi, a coastal church clinging to the rocky shore. The view is serene, though marred by the sad sight of a lifeless kitten by the path. A short stop by the sea, a bittersweet panorama, and then we continue on our way.
Strolling Apollonia’s Narrow Streets
Next, we explore the old quarter of Apollonia. The car stays outside the center, as these slender alleyways offer no real space for vehicles. We wander through a small shopping lane dotted with boutiques, snag some local honey and cookies at a gourmet shop, and discover the best supermarket on the island—a veritable treasure trove of fresh produce, meats, and regional specialties. Oddly enough, it’s missing from any map we’ve seen.
Sifnos: A Hiker’s Haven
Sifnos prides itself on its many hiking trails, well-marked and replete with signage identifying local flora. It’s a rarity in Greece to see such careful labeling. A bus stop placed strategically at the trailhead speaks to the island’s dedication to ramblers. We poke around for a bit, imagining longer forays into the hills if we had the time.
Back to Vathi, Then Off to Kastro
Returning to Vathi, we cool off in the bay. The choice of this quiet beachside lodging feels more inspired every day—no sign of our octopus friend, whose old plastic cup lies abandoned on the sandy bottom. In the late afternoon, I can’t resist a return to Kastro with my drone, capturing footage of the tiny church perched dramatically by the sea. The drive itself, filmed on a GoPro in 4K, promises cinematic memories.
Sunset Pasta on the Balcony
Sunset at Vathi is pure poetry, the sky flaring gold and crimson over calm waters. We whip up spaghetti with tomato sauce and crumbled feta, savoring the meal on our little balcony. It’s simple fare, but nothing tastes finer than dinner served with the hush of the evening tide and the warm glow of a Sifnos dusk.
Day 10 – Sifnos to Milos: Island-Hopping
Saying goodbye is part of traveling, and so we take our leave of Sifnos—and the tranquil cove of Vathi Beach—where we’ve whiled away glorious days. I sip my final balcony coffee, listening to waves crash ashore and roosters crow their morning salute. Small birds fill the distance with their high, excited chatter.
A Farewell to Vathi
I use up the last of our groceries to make sandwiches—my daughter insists they taste best when I do the assembling. We pack with calm efficiency, though paying for our stay is less straightforward. The family’s elderly matriarch struggles with the card reader, eventually calling her daughter to confirm we can pay by card. After several false starts, a young woman helps run the machine—she has slicked-back hair and a nose of heroic proportions, giving her face a certain gravitas. Payment goes through, and we’re free to depart.
Before we go, I send my drone skyward for a final glimpse of Vathi Beach, though the battery soon gives out. With the tide noticeably higher than usual, we trudge our luggage along the sand on a well-worn wheelbarrow, feet getting soaked by the waves surging up the shore. My daughter lingers to say goodbye to the local cats, then begrudgingly hauls the wheelbarrow back to the house. Such are the trials of teenage travel.
En Route to the Ferry
From Apollonia, we follow the coastal road to Kamares Harbor, noticing how thick morning clouds drape the sea in a soft, luminous veil. We consider stopping at the monastery on a hill above the harbor but are discouraged by the lack of parking (and enthusiasm). I do wander up a short pass road for a sweeping view and cross yet another of the many well-marked trails crisscrossing Sifnos.
At the harbor, returning the rental car is a breeze—no inspection necessary. We spot a pretty, affordable wine jug at a nearby shop (finally!), then retreat to a café for a second breakfast overlooking the fishing boats and small, sandy beach in Kamares. My daughter orders a lavish waffle crowned with chocolate ice cream, while we watch the tide gently bob little rowboats in the bay.
Crossing to Milos
Waiting on the pier, we chat with a friendly Australian couple heading from Milos to Nafplion, a place we fondly remember. Before long, our now-familiar ferry arrives with its grand escalators and spacious lounges—a relic once used in Norway, outliving multiple retirements. Sailing toward Milos, we pass a mysterious outlier island swathed in haze, reminiscent of some lost Jurassic outpost. Soon, we glimpse the pastel fishing huts of Klima beneath Plaka, the island’s historic heart.
Arrival on Milos
Milos feels distinctly livelier than the islands we’ve left behind. We stroll through a bustling harbor, picking up another rental car—digital paperwork that never arrives, but all seems fine. The drive to our suite reveals an island softer in contour, with rolling hills, more trees, and fewer of the sharp hairpin turns we’d grown accustomed to on Sifnos.
Kapetan Tasos Suite greets us with dazzling white walls, a luxurious interior, and a balcony gazing out on the glittering sea. Our hostess, Stella, welcomes us warmly. But the day’s excitement fades when our daughter complains of ear pain—a nasty rash with some discharge, likely from cheap in-ear headphones we regret having purchased. We rush to Milos’s Medical Center, where the staff treats her swiftly and kindly. No insurance forms, no fuss: once again, Greek healthcare opens its arms with quiet grace. Antibiotics and ointment, and a ban on snorkeling for several days—leading to a few tears.
Evening in Adamas
Afterward, we wander the port town of Adamas, grabbing pita and souvlaki from a local grill specializing in Greek fast food—likely a place we’ll return to often. Later, we wind down with a quiet evening at our suite, sipping cold beer from a nearby market (overpriced and none too friendly, alas). But no matter; the gentle night breeze on our pristine balcony is enough to carry us into tomorrow’s promise.
Day 11 – Milos
I spent a restless night, my mind adrift until nearly dawn. Yet as the first streaks of pale light touch the sky, I’m already out on the balcony, enthralled by a sunrise perfectly framed—save for one overhead cable, because in Greece there’s always a wire cutting across your view. My wife joins me early; we treat ourselves to breakfast delivered to the suite: fresh tomatoes, olives, honey, yogurt, and little feta-filled pastries, all enjoyed on our sunlit balcony.
Seeking a Seafaring Adventure
Stella, our host, warns of rising winds over the next few days. If we want to rent a boat for Kleftiko, she says, best do it now. We drive some 30 minutes to Agios Kiriaki, where Google Maps shows several boat rental spots. Everything’s shut—off-season woes. Eventually, I call a number for “Crystal Rent,” and a woman arrives from Adamas. She reeks of garlic, quotes a steep price: 150 euros for two hours plus 60 euros for fuel. She’s willing to go as low as 110 euros plus gas, but something about the rushed contract, the heavy penalties, and her off-putting demeanor sets my nerves on edge. At the last second, pen in hand, I back out. My daughter is disappointed but understands.
The Hidden Gem of Agios Kiriaki
Instead, we savor the deserted beach and its crystal-clear shallows—an expanse of turquoise hugging the coast. A feast for the eyes. Then we swing by some “colorful cliffs” nearby, next to the aptly named Deep Blue beach bar—a party hub in high season, judging by the faded signs and sprawling parking lot.
On the drive back, we pass a vast mining operation, an otherworldly industrial scar carved into the hills. Hard to look at, but presumably the source of prosperity on this island.
Quiet Afternoon and Sunset at Poseidon Rock
We pass the midday hours in our suite, then decide on a short outing to Poseidon Rock for sunset. It’s a calm, unassuming spot, though the sun slips behind a cliff faster than we’d like.
Dinner finds us at Rifaki by the harbor—everything fresh and flavorful, served by a gracious waiter.
An Encounter with Kapetan Tasos
Walking to Rifaki, an elderly Greek man hails me from his tiny front garden, struggling to knock a ripe pomegranate off a high branch with his walking stick. He speaks in rapid Greek, I can only guess at his meaning. I say, “Germania” for myself, and “Kapetan Tasos” for where we’re lodging. The mention of Kapetan Tasos brightens his face—he taps his chest and repeats the name. It dawns on me I’m standing before the very man the hotel is named for.
Taking his stick, I manage to snag the fruit from its branch and hand it over. He passes it right back to me—a gift from the captain, as if to say welcome, and thank you, all in a single gesture. A moment of unspoken warmth that sums up the island’s spirit better than any words.
Day 12 – Klima
Another spectacular sunrise unfolds beyond our balcony, accompanied by my morning coffee. Today, our daughter takes charge of breakfast, faithfully deploying the apartment’s ubiquitous sandwich press—no Greek rental seems complete without one.
Coastal Explorations in the Morning
We begin our day at Paralia Papafragkas, just along the coast. Here, the shoreline is carved by narrow gorges and jagged inlets, forming a surreal lunar landscape of cliffs and craters. While we wander, I send up the drone for a bird’s-eye view.
Next, we stop at Alogomandra Beach—also known as Hockey Beach—where we discover shimmering turquoise waters. We swim out to a sea cave, then snorkel back through a slender gap in the rock. Something large darts away in the depths, but we can’t identify it. The beach is deserted, and after our swim, we warm ourselves in the sun’s gentle heat. Afternoon siesta calls us back to our suite, an oasis of calm we find increasingly hard to leave.
A Visit to the Iconic Fishing Village of Klima
Later, we head to Klima, one of the island’s showstoppers. A row of brightly painted fishermen’s houses sits at the water’s edge, once serving as both shelter and boathouse for the island’s seafaring folk. It’s a scene that feels almost too picturesque for reality. Unfortunately, this evening brings no vivid sunset to gild it all.
On our way back, we pause in Adamas for a hearty meal of gyros and souvlaki at Yankos—the island’s best fast-food joint, in our view—rounding out the day with simple yet irresistible Greek fare.
Day 13 – The Venus of Milos
Clouds roll in today for the first time on our trip. Over our usual sandwiches, we decide to visit the discovery site of the Venus de Milo, perched above the fishing village of Klima. On the way, we meander through narrow alleys and watch workmen repaint road markings on a small town square.
Searching for the Venus
The site lies near an ancient theater with a sweeping view of the sea. A simple, elegant replica of the Venus now stands where, legend says, she was once unearthed in a small cave or rocky niche. We roam the theater—apparently still in use for summer concerts. Our daughter offers us a mock performance from the stage, and we sit in the stands, smiling at the blend of antiquity and playful spontaneity.
Firopotamos and an Afternoon in Adamas
From there, we venture along steep lanes to Firopotamos, a tiny fishing hamlet tucked among craggy outcroppings. An old church nestles between the rocks, gazing out over the turquoise water. Later, in Adamas, we wander the shops in search of new earphones for our daughter. The first store reeks of cigarette smoke, so we head next door and find a more pleasant option. We also stop by the pharmacy to pick up fresh antibiotics—her ear infection has improved but still needs careful tending. A scoop of ice cream with a harbor view completes our stroll.
A Feast at O! Hamos!
At midday, we dine at O! Hamos!, a tavern recommended by friends. It turns out to be the culinary highlight of our journey: crisp-fried eggplant, a rich cheese casserole, succulent roast pork, fries, bread, salad, and couscous—every bite a triumph.
By afternoon, we retreat for a short rest. The evening sky remains veiled by clouds, so no dramatic sunset to admire. We end the day with a few rounds of Phase 10—a card game where I’m soundly beaten, but the loss is softened by the gentle lull of the island’s rhythms.
Day 14 – Sarakiniko
Sunrise returns in a blaze of color, and I watch it unfold from our balcony with immense gratitude – whilst writing this travel log. We fix toast with a simple melting cheese for breakfast—since the small, overpriced, and notoriously unfriendly market around the corner offered little else. Somehow, the scenic view makes even basic fare taste divine.
A Morning at Sarakiniko Beach
Sarakiniko greets us like a dreamscape: dazzling white chalk cliffs shaped into natural sculptures and gorges, with a narrow beach cut deep into the landscape. The water near shore is cloudy with sediment, but a short distance out, it becomes crystal-clear. I snorkel along the drop-off, spotting schools of bream and bass—and even a moray eel slithering across the rocky bottom some 30 feet below. Given the generally overfished Greek waters, this vibrant sight is especially thrilling.
Around the bend, a smooth chalk path leads to a favorite spot for cliff-jumping into a turquoise cove. We watch from a safe distance as someone attempts a backflip from the highest ledge—impressive indeed. Meanwhile, a pair of cats prowls about as if they’re the guardians of this surreal playground.
A Quick Stop in Mandrakia
Later, we drive to Mandrakia, a tiny fishing village with brightly colored steps descending to bobbing boats. Calm waves lap at the hulls, and the quiet hum of midday dozing settles over the scene.
Lunch at Our Usual Haunt
On our way back, we pop into our beloved gyro spot in Adamas. A different server is on duty, and she stubbornly packs all orders to go, even if you plan to eat in. The overflowing trash cans attest to the waste. One disgruntled Greek patron flings his half-eaten souvlaki at the doorway in protest before storming off. We shrug at the drama and tuck into our pitas anyway, then cross the street to the best bakery in town for fresh pastries and bread.
Sunset at Plaka
After a restful afternoon at our suite (where Stella keeps the lobby stocked with donuts, coffee, and croissants—how could life be better?), we decide to chase the sunset from Plaka’s Kastro. The drive is slow, stuck behind a lumbering truck, and Plaka itself is a maze of narrow lanes, not all of them well-kept.
But the sunset is worth it: the island stretches out on one side, with smaller islets rising through the mist, while rugged cliffs on the other flank swirl in the shifting clouds. Vivid colors fill the sky, and I manage nearly a thousand photos in the golden light.
Back at our suite, we celebrate with a cool glass of wine, a simple dish of spaghetti, and another round of Phase 10—this time, I come out on top.
Day 15 – The South of Milos and Tsigrado Beach
The final full day on Milos dawns under a vibrant sun, and I sit with my coffee on the balcony, relishing the sweeping view. We indulge in the hotel breakfast this morning—fresh-pressed juice, iced cappuccino, olives, ripe tomatoes, thick Greek yogurt—the full measure of flavors and sunlight.
We aim for the island’s southern stretches, which we’ve yet to explore. The route takes us through the mining zone, where excavators carve scarlet wounds into the hills, terraces and dusty tracks forming a landscape of industry. The Greeks seem to be chipping away at their own island, its slopes partially dismantled in the pursuit of minerals.
Eventually, green valleys lead us to a surprisingly well-paved road and a parking lot complete with a bus stop. We could drive farther down, but the track looks too sandy—we want no part in a rescue mission. Instead, we follow signs toward Fyriplaka Beach, wading through mild surf and squeezing past a low wall that belongs to a misplaced house. Before us opens a narrow stretch of sand hugging a towering cliff, its rocky face crumbling in places. Out at sea, a lone boulder looms, dividing the beach in two.
Stirring waves crash ashore. Splashes of color hint at the painted cliffs beyond. Then a somber sight: a huge sea turtle, stranded on its back in the sand. No obvious wounds, but it has likely been here a while. Even in death, the turtle holds a kind of majesty. It’s a sobering reminder of the near-empty waters and plastic debris we’ve encountered. I silently vow to do something for marine conservation once I’m home.
We take a cooling dip in the pounding surf. The sun feels fierce on this beach with no shade, so after a time, we retreat. Feeling adventurous, we hike to Tsigrado, where a rope and ladder descend through a narrow crevice to a turquoise cove. The water below sparkles around a slim, stony shoreline—an astonishing vantage point.
Back in Adamas, we enjoy a farewell pita. The town is teeming with people today, celebrating Ochi Day. Stella mentioned that schoolchildren lead most of the official rites, with her own grandchildren partaking in ceremonies at a local monument.
A final midday break in our suite, and then one last swim in the Aegean just outside our door, the water as inviting as ever.
In the evening, we venture again to the Kastro. I drop the family off, then navigate a hair-raisingly steep road to a hidden parking area. One particularly sharp bend demands I reverse for a running start—an impressive grade for our little rental. Once at the top, we witness a radiant sunset from the highest point of the village. Opposite, a perfect full moon climbs the sky. Two young men launch a mid-sized drone (perhaps an Air 2?), attracting curious onlookers.
Afterward, we pick up simple fare—bread from our favorite bakery—and savor it on our balcony. The moon slips into a partial eclipse around half past nine, and I catch a brilliant meteor streaking over Kimolos, a final blaze of wonder for this island night.
Day 16 – Back to Athens: Island Hopping
Morning arrives with the clocks turned back, offering a glorious extra hour of sunlit stillness. Outside, the sky erupts in a sunrise so brilliant it seems to set the entire horizon ablaze. I sip coffee on the balcony one last time, lingering over the sweep of bay and shoreline I’ve grown to cherish. Stella surprises us with warm croissants and spinach pies, alongside our usual stash of sandwiches, feta, and tomatoes.
Eventually, I tear myself away from the suite’s balcony and we load up the car—a reliable little Opel Corsa that’s ferried us around Milos for just ten euros a day. Dropping it off is quick and painless. In the port of Adamas, we kill time at a waterside café, watching the bustle as people gather for the ferry. Our Zante Ferry arrives about fifteen minutes late. We initially settle on the rear deck, but the fumes of cheap fuel and the chain-smoking neighbor chase us forward, where at least the breeze is fresh and the view of open water is uninterrupted.
The crossing takes seven hours. Every island stop—Sifnos first, then Serifos—offers a fleeting chance to say goodbye to landscapes that have become oddly familiar. We chat briefly with a Canadian couple who escape harsh winters at home by migrating to Greece each year, their summer business in Canada paying for their off-season adventures. It’s a reminder of how these islands draw wanderers from every corner of the globe.
At last, the lights of Attica and Athens shimmer on the horizon. Our island-hopping odyssey closes here, under the hazy glow of the mainland. One last glimpse of the Cyclades recedes behind us, and with it, the gentle hum of distant waves—a memory now, to carry home.
