Lost in the Blue: Greek Island Hopping

Milos

Moonscapes, jade coloured secret beaches reached only by rope ladder or boat, red cliffs warmed by the Grecian sun, tables of incredible island cooking that taste like someone’s yaya just made it for you. Milos sits in the western Cyclades and is ringed with more than 80 beaches thanks to its volcanic geology. 

Sarakiniko 

Sarakiniko is where Milos reveals her most otherworldly beauty. Vast chalk-white rock, sculpted smooth by wind and waves, stretch out like a lunar landscape, luminous beneath the sun and ethereal under sunset. Here, the sea moves in shades of turquoise and inky sapphire, a breathtaking contrast to the stark whiteness of the cliffs. Cliff jumping here is thrilling and easy because you can postion yourself as high or low to the water as you like!

At sunset, the rocks blush softly in gold, the only soundtrack is the hush of waves and the sigh of the breeze. Sarakiniko is not just a beach, it is a dreamscape. 

The most photographed location on Milos for good reason.

Kleftiko

Once a pirate hideout, Kleftiko is a cathedral of white rock arches, grottos and the bluest water on Milos. Only accessible by boat, a day spent sailing Kleftiko is not just an excursion, it’s an immersion into the raw romance and untamed spirit of Milos. This is absolutely a day not to be missed! 

The clarity of the water swimming and snorkelling here is unrivalled. We found some thermal springs on the edge of the beach and we also managed to land the drone into the water straight after this photo above. I think thats our third drone we've lost!

Tsigrado

Tsigrado Beach is one of Milos’ most adventurous treasures, and part of its allure lies in the way you reach it. Hidden between steep cliffs, the beach is accessible only by descending a narrow passage where ropes and wooden ladders guide you down to the sand. At first, you ease yourself through a small gap in the rock, gripping the rope to lower your steps carefully. Then, a series of ladders fixed to the cliff face leads you the rest of the way, until your feet touch the soft sand below. It feels a little scary, and that sense of adventure makes the arrival more rewarding. 

Fyriplaka 

Next door to Tsigrado, Fyriplaka is a sweep of soft orange sand with dramatic crimson and white cliffs. Good for a classic beach day with room to spread out. Food is available at this beach. There are little caves you can explore by swimming out to the rocks.

Firopotamos 

Arriving here, you’re immediately struck by the classic Greek imagery: the handful of “syrmata” (boat garages carved into the rock and painted in vivid hues), and small church perched on the cliff. Firopotamos is not a beach for loud music or crowds, it’s a place for slow swims, sun-warmed stone, and the sound of the sea echoing against the village walls.

Mandrakia

The heart of the village is its tiny natural harbor, a sheltered curve of turquoise water dotted with fishing boats and syrmata. A postcard-perfect scene that photographers and dreamers alike fall in love with. 

For many visitors, Mandrakia is the place to savour the flavours of Milos. The beloved taverna Medusa sits right on the waterfront, serving up fresh seafood and traditional island dishes against a backdrop of sweeping Aegean views. Grilled octopus, crisp white wine, the sea breeze on your skin…. we came at sunset and highly recommend.

Venetian Castle

The Venetian Castle of Milos crowns the village of Plaka, watching over the island since the 13th century. Climbing up through the narrow, whitewashed lanes, you eventually reach its stone ramparts, and the reward is one of the most breathtaking panoramas in the Cyclades. The Aegean stretches endlessly in every direction, villages fade into soft pastel light, and the wind carries that unmistakable island stillness.

As sunset approaches, the castle transforms... crowds begin to gather along the walls waiting to catch that perfect moment when the sky turns molten gold, everyone collectively breathing in the beauty as the sun slips below the horizon. A moment that feels timeless, like being suspended between sea and sky.

Klima

Klima is one of Milos’ most postcard-perfect treasures, a tiny, colorful fishing village where the sea laps right up to the doorsteps of traditional syrmata, the brightly painted boat houses carved into the rock. Each one glows in shades of blue, green, red, and yellow, creating a rainbow along the curve of the shoreline. The scene feels storybook: fishermen mending nets, cats stretching in the late-afternoon sun and gentle waves reflecting the colours of the homes. Charming and deeply authentic, it’s Milos at her most timeless.

Where to eat: Beachy Treats & Cliffside Eats

Barriello 

Modern-creative Greek in a 150-year-old building above the sea, seasonal produce, local cheeses and a thoughtful wine list. Book for sunset; it’s one of the most coveted dinner tables on the island. During our dinner a large tractor squeezed past in the tiny stone street. Only in Greece! 

Medusa Milos

Medusa in Milos is the kind of taverna that steals your heart the moment you arrive, a little waterfront gem in Mandrakia where waves gently curl against the rocks and fishing boats sway in the tiny harbor. Tables spill out beside the water, the scent of grilled octopus drifting through the salty breeze, and everything feels wonderfully, effortlessly Greek. Come for dinner to watch the sunset, stay for the wine and soak up the kind of atmosphere you’ll wish you could bottle and take home.

Hanabi Seaside Sushi

Perched right by the water’s edge, this sleek, modern spot offers sushi and sashimi while waves gently lap against the shore. The atmosphere is effortlessly romantic and the cocktails are divine! 

Mikros Apoplous 

Mikros Apoplous in Adamas is a beloved seaside taverna that blends the charm of traditional Greek hospitality with a touch of elegance. Set right by the harbour the menu celebrates the island’s bounty of fresh seafood. We went across the road to their kitchen and chose a freshly caught Scorpion fish that was prepared tableside and was the best fish I’ve ever tried!

Perfect pairings: beach → lunch/dinner

• Sarakiniko → Medusa (Mandrakia)

  A 10-minute hop between the island’s most photogenic swim and its most photogenic taverna. 

• Kleftiko boat day → Barriello (Tripiti)

  After a long swim and cruise, clean up and toast the sunset over creative Greek plates.  

• Tsigrado/Fyriplaka → Sirocco (Paliochori)

  Keep the south-coast run going and eat “volcanic” at the beach you’re already on. 

• Pollonia → Hanabi

  Easy, breezy sushi and cocktails with your toes practically in the harbor. 

TWB Tips

• Getting around: Many beaches are on dirt roads; rent a small SUV/quad, or rely on boat tours to reach the west and south coasts easily (Kleftiko/Sykia are boat-only). 

• Safety: At Tsigrado you’ll descend by rope/ladder; at Papafragas the path is steep. 

• When to go: Late May to September offer the best warm weather and seas. July–August can get very busy!

Santorini

A caldera carved by fire, whitewashed villages spilling down cliffs, domes the colour of the Aegean, and sunsets that turn the whole island to molten gold… Santorini is Greece at its most dramatic. It’s a place where every moment feels suspended: slow mornings on terraces hanging above the sea, long lunches by the water, afternoons that stretch lazily into wine and starlight.

Oia

Oia is Santorini’s crown jewel, a cliffside maze of narrow lanes, sugar-cube houses, blue domes, and bougainvillea cascading in every shade of pink. At dawn, the village is soft and quiet, painted in pale lilac and peach; by sunset, it glows in hues so warm and radiant they feel almost surreal. Wandering Oia is an experience in itself, every turn reveals another postcard view: bell towers silhouetted against the sky, terraces spilling out over the caldera, and the wide, endless blue of the Aegean.

My tip is to splurge and stay in Oia. The crowds in the streets are overwhelming and there’s nothing like having your own secret spot in this sought-after location.

Armeni Village Rooms & Suites

Armeni Village cascades down Oia’s cliffs, offering suites with terraces that are high above the caldera. Waking up here feels like floating. Early light reflecting off white walls, the Aegean stretching endlessly beyond your window. Plunge pools, crisp white linens and that serene Oia quiet make every morning soft and slow.

It’s intimate, romantic and perfectly positioned for sunsets you’ll talk about forever. We loved our stay here.

Ammoudi Bay

Tucked just below Oia lies Ammoudi Bay, a tiny harbour where red cliffs rise dramatically above a curve of sparkling water, fishing boats bob in the shallows, and tavernas sit right at the edge of the sea, their tables almost touching the waves. The air smells of salt and grilled fish, and everything feels warm, lively, beautifully Greek.

Ammoudi Fish Tavern

Lunch at Ammoudi Fish Tavern is an island ritual. Tables spill across the water’s edge, and the kitchen serves some of the freshest fish on Santorini. Octopus dries on lines outside, seafood arrives straight from the boats and the atmosphere is warm and wonderfully unhurried.

Rock Jumping in Ammoudi

Follow the coastal path from Ammoudi Bay and you’ll reach one of Santorini’s most beloved adrenaline bursts, a cluster of rocks and a tiny island chapel surrounded by deep, glittering blue. Swimmers gather here to cliff jump into water that feels both cool and electric. We had the best afternoon cliff jumping here with the boys.

Island Catamaran Tour

Seeing Santorini from the water is like reading the island’s story written in layers of volcanic rock. Our catamaran tour glides you past steep caldera walls, hidden coves, red and white beaches, and geological formations shaped by ancient fire. You stop to swim in warm, mineral-rich springs and in bays where the water is impossibly clear.

The Athenian House, Imerovigli

Perched high above the caldera in Imerovigli, The Athenian House offers one of the most romantic dinner settings on the island. White walls, candlelit tables, and views that make conversation pause mid-sentence. As the sun drops behind the cliffs, the sky turns blush pink then fiery orange, and the lights of the caldera begin to twinkle.

The food is refined modern Greek, it wasn’t as good as I had hoped (for the cost) but the view here is spectacular!

Anhydrous Winery

Wine tasting at Anhydrous Winery is where Santorini’s volcanic terroir comes alive. The wines are crisp, mineral-driven, shaped by sun and salt and ancient soil. Tastings unfold in a serene, stylish setting, each pour revealing something new about the island’s character. The star is Assyrtiko… bright, bold, and unmistakably Santorini.

It’s the perfect pause between adventures, calm, sensory and wonderfully grounding.

TWB Tips for Santorini

• Getting around: Walk Oia early, explore Ammoudi by foot, and book transfers for sunset dinners. For full island freedom, rent a quad or car.

• Best time to visit: Late May–June and September–October for warm seas, soft light and gentler crowds.

• Must-do moments: Rock jumping at Ammoudi, a sunset catamaran, and one slow dinner overlooking the caldera.

Zakynthos

Emerald water swirling around limestone arches, hidden coves, tavernas perched above endless sea, and the iconic shipwreck resting on the whitest sand you’ve ever seen.Zakynthos is an island made for dreamers and sea-lovers… wildly beautiful, impossibly photogenic, and best explored by boat, car and a little curiosity.

Blue Caves

Carved into the island’s northern cliffs, these arches and grottos glow from within, lit by refracted sunlight that paints the water shades of jade, turquoise and electric blue. Arriving by boat is magic as you glide through narrow passages, the hull glowing neon beneath you, the cool shadow of the caves shifting to brilliant light as you move. Come early for the clearest colour and the quietest seas. This is a place where the island feels ethereal.

Shipwreck Beach (Navagio)

The most photographed location in Zakynthos, and one of the most striking in all of Greece. By boat you arrived to a perfect crescent of blinding white sand, vertical limestone cliffs rising like a fortress, and the rusted skeleton of the famous shipwreck resting in the middle like a relic from another world.

You can also view the beach from above at the (very busy) viewpoint which reveals a spectacular palette: sapphire sea, ivory cliffs, and at sunset, the cliffs blush pale gold and the beach looks almost painted. Worth the hype? Absolutely. But be prepared to be patient, it’s a place everyone wants to see.

Xigia Beach

Xigia smells faintly of sulfur, but don’t let that scare you, the mineral-rich spring that flows into the sea here is what gives the water its luminous, milky-turquoise glow. Sheltered between cliffs, the cove feels small and intimate and the added bonus is the water leaves your skin soft. Swim early morning when the sea is calm and the colours the most intense. Bring water shoes as the pebbles can hurt your feet!

Cameo Island

Cross a wooden bridge above crystal water to a tiny island that feels plucked from a postcard. Cameo is all about romance: the white draped canopies fluttering in the breeze, the little pebble beach, the sound of gentle waves echoing around you. Perfect for a slow afternoon swim or a golden-hour drink when the light softens and the sea turns a warm silver-blue. Stay long enough and the island glows under sunset, a photographer’s dream.

Mizithres Beach & Viewpoint

At the southern tip of Zakynthos, two towering white rock formations, the Mizithres, rise dramatically from transparent, impossibly blue water. The beach below feels untouched, a slice of Ionian wilderness only accessible by boat. Its very easy to rent a boat yourself in town and visit this beautiful beach.

From above, the viewpoint is breathtaking: white cliffs falling away into a gradient of blues so vivid they hardly seem real. This is Zakynthos at its wildest and most dramatic.

Where to Eat: Tavernas with Heart & Sunset Tables

Nobelos Restaurant

Nobelos in is one of those rare places where you arrive for a meal and end up staying for the atmosphere. Perched above crystal-clear water in Agios Nikolaos, this family-run spot blends elegance with the kind of laid-back island charm that makes Greek summers unforgettable. Expect organic, locally sourced dishes, beautifully prepared seafood, and flavours that celebrate the island without trying too hard. Come for lunch when the water glows turquoise below you, or linger at dinner as the sky folds into pastel pinks. Nobelos is slow, soulful dining.

Orizontes Restaurant Skybar

Perched above Agios Nikolaos, it dishes up Mediterranean flavours with a side of sweeping Ionian blues. The vibe is luxe and the food is really good. Highly recommend.

Keri Lighthouse Restaurant

Perched high above the sea near the Keri Lighthouse, this restaurant is all about panoramic views and sunset magic, looking down onto beautiful Mizithres. Golden cliffs, deep blue sea, and a sky that turns from orange to lavender as you dine. It’s one of Zakynthos’ most unforgettable spots for dinner, fresh fish, crisp wine and the endless horizon.

Diakofereiko Restaurant

A traditional Greek taverna that’s been preparing food since 1680, with the comforting feeling of being fed by someone’s yaya. Expect hearty portions, slow-cooked dishes, beautiful local ingredients, and genuine warmth. It’s the perfect contrast to the island’s dramatic coastal scenery, a place where time slows and the food tastes like home.

Perfect Pairings: Beach → Meal

• Blue Caves → Nobelos A scenic morning exploring northern coves followed by a relaxed dinner with sea views.

• Cameo Island → Keri Lighthouse Restaurant

  Enjoy the magic of Cameo then toast the sunset from one of the island’s best vantage points.

• Xigia Beach → Diakofereiko Swim in mineral waters, then warm up with comforting Greek classics.

TWB Tips for Zakynthos

• Getting around: You must rent a car! Access to many of the island’s most beautiful places are remote, accessible only by winding roads.

• Boat days: Some of Zakynthos’ most iconic places (Mizithres, Shipwreck Beach, Blue Caves) are best seen from the water. Book a small-group or private boat for the dreamiest experience.

• When to go: Late May to September offer the best warm weather and seas. July–August can get very busy!

Kefalonia

Emerald bays wrapped in pine forests, villages painted in soft pastels, beaches that shift from sapphire to turquoise depending on the sun, and a gentler pace that sinks into your soul. Kefalonia is the largest of the Ionian islands, but despite its size, it still feels wonderfully unhurried, an island of dramatic coastlines, storybook towns and water so clear it sparkles like glass.

In the back streets of beautiful Assos, Kefalonia is a dream.

We only had 2 short days here and I cannot wait to go back and explore this magical island more!

Myrtos Beach

Myrtos is Kefalonia’s crown jewel, an arc of pure white pebbles tucked beneath towering cliffs, where the sea glows in shades of electric turquoise that almost don’t seem real. Standing at the viewpoint above, you’re met with a sweeping panorama of luminous water, wild, rugged coastline and the dramatic curve of one of Greece’s most celebrated beaches. This was easily one of my favourite spots to swim in all of Greece. It can be hard to find a car park so be early!

Myrtos is iconic for a reason… breathtaking, cinematic, unforgettable.

Assos Beach

Assos feels like stepping into a watercolour painting. A tiny horseshoe-shaped bay wrapped in pastel houses, gentle hillsides, and bougainvillea tumbling down stone walls. The beach is intimate, lined with a scattering of tavernas and fishing boats swaying lazily in the harbour.

A place for slow swims in clear, calm water, for wandering the village lanes with an ice cream in hand, for sitting beneath the shade of an old olive tree and letting the quiet charm of the bay sink in. Pure Kefalonian serenity.

Fiskardo

Fiskardo is Kefalonia’s polished little gem, a pastel-hued harbour village that feels more like a painting than a place. Venetian-style houses line the waterfront in shades of peach, lemon, and seafoam, and you'd not be mistaken toi think it looks a LOT like Italy which is not too far away as the crow flies. Yachts bob in the marina, tavernas spill onto the promenade and bougainvillea seem to bloom almost everywhere.

Ammos Beach Bar & Restaurant

Perched along the southern coast, Ammos is the kind of place that captures the spirit of Greek summer in a single afternoon. Soft sand, umbrellas swaying gently in the breeze, music drifting through the air, and the scent of grilled seafood mingling with sun lotion and saltwater.

Ammos Beach Bar & Restaurant serves fresh, vibrant dishes that taste like sunshine, crispy salads, juicy fish, cold wine, and Greek classics with a coastal twist. Spend the day swimming between courses, or arrive late for cocktails as the sky turns peach and the water glitters. It’s relaxed, beautiful, and effortlessly joyful, the sort of beach spot you never want to leave.

TWB Tips for Kefalonia

• Getting around: Rent a car, the island is large, rugged, and full of scenic drives.

• Where beauty meets calm: Myrtos for grandeur, Assos for charm, Ammos for an all-day, sea-salty, sun-drenched escape.

• When to go: Late May to September offer the best warm weather and seas. July–August can get very busy!