The Lesser Cyclades & Amorgos: Island Hopping Through Greece’s Hidden Gems
This 18-day Lesser Cyclades island hopping itinerary covers Naxos, Iraklia, Schinoussa, Koufonissi, Amorgos and Santorini by ferry. Best time: May-June or September. Highlights: the legendary Express Skopelitis ferry, sunrise over the Aegean from Iraklia, Schinoussa’s fava beans, Koufonissi’s coastal caves, and Amorgos—home of The Big Blue. No car rental needed.
Note: This trip took place in June-July 2015. While the islands themselves remain timeless, specific prices, accommodation availability, and ferry schedules may have changed. The Express Skopelitis continues to serve these islands—some things in Greece are eternal.
The Lesser Cyclades hide in plain sight. Clustered between Naxos and Amorgos, these tiny islands—Iraklia, Schinoussa, Koufonissi, Donousa—rarely feature in travel brochures. Yet they offer everything the famous Cyclades promise, distilled to its purest form: golden beaches, whitewashed villages, crystal waters, and a pace of life that the 21st century hasn’t quite reached.
What makes this route special is the Express Skopelitis—a small ferry that has connected these islands for generations. Stepping aboard feels like joining a family; by the end of the trip, you’ll recognise the captain’s wave and understand why this boat appears in documentaries about authentic Greek life.
What Makes This Itinerary Special
The Express Skopelitis Experience
This legendary small ferry is more than transport—it’s an institution. The Skopelitis family has been sailing these waters for generations, delivering mail, supplies, and passengers to islands that larger ferries overlook. The short crossings between islands (sometimes just 10 minutes) mean you spend time on islands, not travelling between them.
Islands That Time Forgot
Iraklia and Schinoussa remain gloriously undeveloped. No cars on Iraklia. No crowds on Schinoussa’s beaches. These are islands where accommodation owners meet ferries personally, where taverna menus feature vegetables from the garden out back, and where the only traffic jam is cows crossing the road.
Naxos: The Perfect Launchpad
The largest of the Cyclades offers mountain villages, ancient temples, and the iconic Portara before you even reach the smaller islands. It’s the perfect introduction—or return—to Cycladic life, with excellent bus connections and accommodation options.
Koufonissi: Boutique Beauty
Of all the Lesser Cyclades, Koufonissi has become the most “discovered”—but don’t let that put you off. The island remains small enough to walk in a day, the coastal caves are spectacular, and the Chora retains its character beneath the boutique additions.
Amorgos: The Big Blue Island
Made famous by the 1988 film The Big Blue, Amorgos feels like coming home if you’ve ever dreamed of Greece. The clifftop Chora, the windmills at sunset, Le Grande Bleu café in Katapola—this island delivers on every romantic Greek fantasy.
Designed for Slow Travel
This isn’t a whistle-stop tour. The route allows 2-4 nights on each island, time enough to find your favourite beach, discover the best taverna, and watch the ferry patterns from your balcony. Slow travel reveals more than rushing ever could.
The Route at a Glance
Route: Santorini (transit) → Naxos → Iraklia → Schinoussa → Koufonissi → Amorgos → Santorini
Duration: 18 days (June-July 2015)
Transport: Blue Star ferry from Santorini to Naxos, Express Skopelitis between Lesser Cyclades and Amorgos, ferry to Santorini
Best Time: May-June or September for perfect weather without peak crowds. July brought the Greek referendum during our visit—fascinating historically but banks had withdrawal limits.
Who It’s For: Those seeking authentic Greece beyond the postcards, island hoppers who prefer small ferries to mega-ships, beach lovers, walkers, anyone drawn to places where Greek life continues unscripted
Throughout this post, you’ll find links to excerpts from my travel diary. Feel free to click through and follow the journey exactly as it unfolded.
The Island-by-Island Itinerary
Day 1: Santorini Transit to Naxos
Flying into Santorini rather than Athens made logistical sense—though I don’t love Santorini in high season. The plan was simple: land, taxi to the port, catch the 15:30 ferry to Naxos. Simple plans in Greece require flexibility. The pre-booked taxi was late, then disappeared entirely. A replacement taxi driver took those bad-boy bends to Athinios port like a man on a mission. We made the Blue Star Delos with minutes to spare, collapsing on the deck with tea and views of Santorini’s caldera receding behind us.
Two hours later, Naxos appeared—the Portara silhouetted against the evening sky, the Kastro climbing the hillside, and Marcos from Hotel Panorama searching the port for guests who’d already walked up the hill themselves!
Getting There: Fly to Santorini. Taxi to Athinios port (approximately 20 minutes, pre-book). Blue Star ferry to Naxos (approximately 2 hours).
Travel Tip: Pre-book the taxi but have backup plans. Allow buffer time—Santorini port queues can be chaotic in summer. I ALWAYS book overnight stays on Santorini for my clients – I’d never put them through that stress!
→ Arrival on Santorini and a Mad Dash to Naxos
Days 1-5: Naxos
Twenty years had passed since my last visit to Naxos, and the island had changed—more development along the beach strip, more boutique shops in the Chora. But climb into the Kastro quarter and time slows. The marble doorways of Venetian mansions, the winding alleys, the views from our rooftop terrace at Panorama—these remained.
We took the organised bus tour with Zas Travel—a revelation. The ancient olive press at Damalas, the Kitron distillery at Halki (tastings included), mountain villages where old men played backgammon in the square. Our guide Irene and driver Yiannis knew every corner of this island.
The beaches of Agios Prokopios and Agia Anna showed the development that locals worry about—sunbeds stretching further each year. But catch the bus to Stelida, walk the quieter stretches, and Naxos still delivers that Cycladic magic.
Getting Around: Excellent bus network from the port to beaches, villages, and mountain destinations. Organised tours available through Zas Travel.
Where to Stay – My Personal Recommendation: Hotel Panorama, Naxos Town – Situated just below the Kastro with spectacular views over the port and Portara. Marcos and Irene are wonderful hosts. The rooftop terrace at sunset beats fighting crowds at the Portara itself.
Where to Eat:
• Metaxi Mas – Pretty taverna in the streets below the Kastro
• Sto Ladoxarto – Harbour views for the final evening
Don’t Miss: The Portara at sunset (or view it from Panorama’s terrace), Halki village and the Kitron distillery, the ancient olive press at Damalas, exploring the Kastro’s Venetian architecture, Agios Prokopios beach.
The Reality Check: Naxos is the largest of the Cyclades—you can’t see everything in four days. The beach strip has developed significantly; the mountain villages remain authentic.
Onward Travel Connection: Express Skopelitis from Naxos to Iraklia.
→ Ancient Olive Press, Mountain Villages and Crashing Waves
Days 6-8: Iraklia
Stepping onto the Express Skopelitis for the first time felt like joining something special. This small ferry—almost a large boat—has connected the Lesser Cyclades for generations. The crossing to Iraklia took minutes, not hours.
Iraklia has no pretensions. Michael from Hotel Aiolos met us at the port and drove our bags up the hill while we walked, taking in the first views of an island that would steal a piece of my heart. The hotel sits on the hillside with panoramic views across to Schinoussa and the scattered islets between.
I set my alarm for sunrise and wasn’t disappointed. Standing alone on the hillside as the sun peaked over Schinoussa, fishing boats chugging out of the harbour below, cockerels crowing—these are the moments travel is really about.
Agios Georgios Beach offered golden sand, tamarisk shade, and ferries to watch. No sunbeds, no beach bars—just crystal water and the occasional sea urchin to avoid.
Getting There: Express Skopelitis from Naxos (short crossing). Check schedules—the Skopelitis serves multiple islands and times vary.
Getting Around: Walking. No bus service or taxis existed in 2015—accommodation owners provide port transfers when ferries arrive.
Where to Stay – My Personal Recommendation: Hotel Aiolos – Hillside location with the best views on the island. Michael’s cooking at the restaurant uses vegetables from the garden. The climb up the hill is worth every step for those sunrise views.
Don’t Miss: Sunrise from the hillside (set that alarm!), Agios Georgios Beach, dinner at Aiolos with garden vegetables, the walk down to Livadi Beach, simply doing very little.
The Reality Check: If you have mobility issues, the hilltop hotels require steep walking. Accommodation near the port offers easier access. Iraklia is for those seeking genuine relaxation—don’t come expecting nightlife.
Onward Travel Connection: Express Skopelitis to Schinoussa (approximately 10 minutes).
→ A Walk to Panagia and Livadi Beach
→ Sunbathing, Sunrises and off to Schinoussa
Days 9-11: Schinoussa
Three nights on Schinoussa wasn’t long enough. This island—small enough to walk in a day, flat enough to explore easily—delivered everything I’d hoped for and more.
Georgios from Grispos Villas met us at the port with the hotel bus, driving us over the hill to accommodation overlooking Tsigouri Beach. The room was spacious; the terrace views, spectacular; the restaurant downstairs, a fish taverna where Georgios displayed the morning catch on ice for you to choose.
Walking to Chora (also called Panagia) revealed a village of whitewashed simplicity. The church of Panagia Akathi protects a rare icon where Jesus stands beside Mary rather than sitting on her lap—many local women are named Akathi in honour. At Deli Restaurant, we ate the famous Schinoussa yellow fava beans with modern Greek flair. The walk to Psili Amos beach via Messaria village took us through agricultural landscape, past abandoned windmills, to a small taverna where the owner pointed from our omelettes to his chicken hutch—the freshest eggs we’d eat all trip.
Getting There: Express Skopelitis from Iraklia (approximately 10 minutes).
Getting Around: Walking. The island is relatively flat and compact. Accommodation owners provide port transfers.
Where to Stay – My Personal Recommendation: Grispos Villas – Overlooking Tsigouri Beach with an excellent fish restaurant. Georgios and family provide warm hospitality. Highly recommended.
Where to Eat:
• Grispos Villas Restaurant – Choose your fish from the ice display
• Deli Restaurant, Chora – Traditional Greek with modern presentation; try the famous fava beans
• Taverna O Nikolas, Mersini Port – Breakfast with harbour views
• Taverna To Petrino, Messaria – Farm-fresh omelettes
Don’t Miss: The walk from Chora to Psili Amos via Messaria, Schinoussa’s famous yellow fava beans, Tsigouri Beach, the church of Panagia Akathi, Taverna O Nikolas at the port.
The Reality Check: The Schinoussa Fava Bean Festival takes place in the first week of July—time your visit if you can. The island is small; three nights feels about right.
Onward Travel Connection: Express Skopelitis to Koufonissi.
→ Exploring the Landscape of Schinoussa
→ Leaving Schinoussa and on to Koufonissi
Days 12-14: Koufonissi
Koufonissi is the most “discovered” of the Lesser Cyclades—boutique in the pretty sense, as I wrote in my notes. But don’t let that put you off. The island remains small (just 26 square kilometres), the coastal walks are spectacular, and behind the chi-chi additions, a traditional village survives.
We arrived to find a wedding at St George’s Church—white ribbons fluttering from trees, an atmosphere of celebration in the streets. That evening, we followed posters to Aneplora taverna overlooking Parianos Bay, where Rebetiko musicians played from a boat in the middle of the restaurant.
Our visit coincided with Greece’s referendum on EU bailout terms—the famous “Oxi” vote. Television news showed the drama; on Koufonissi, life continued peacefully. We walked to Pori beach past farmers herding cows, discovered the Ksylompatis Caves, and nursed sunburn at Milos windmill bar.
Getting There: Express Skopelitis from Schinoussa. The ferry passes Keros—an uninhabited island with significant archaeological remains.
Getting Around: Walking. The island is flat and compact—you can reach anywhere on foot. A small bus serves the beaches.
Where to Stay – My Personal Recommendation: Hippocampus – Five minutes from the port with sea-view rooms. Sophia provides a warm welcome.
Where to Eat:
• Aneplora – Overlooking Parianos Bay with live Rebetiko music; tomato rissoles, octopus, meatballs
• Taverna Kalofego, Pori – Beach taverna for post-walk refreshment
• Bakery in Chora – Bougatsa for breakfast
Don’t Miss: The coastal walk to Pori and the Ksylompatis Caves, Aneplora for Rebetiko music, the walk past Parianos Bay, the windmill converted to accommodation, Finika Beach (though windy in summer).
The Reality Check: Koufonissi is windier than the other Lesser Cyclades—the eastern beaches face the open Aegean. The island has become more “boutique” but remains charming.
Onward Travel Connection: Express Skopelitis or conventional ferry to Amorgos (Katapola port).
→ Oxi Day on Koufonissi and a Walk to Pori
→ Koufonissi – A Coastal Walk to the Devil’s Eye!
Days 15-17: Amorgos
Amorgos feels like coming home—if your home were a clifftop Chora with windmills, sunset views, and cafés named after French diving films. This island captured imaginations when The Big Blue was filmed here in 1988; it captures hearts still.
We based ourselves in Chora, the beautiful hilltop capital at 400 metres elevation. The main square buzzes with taverna life; the windmills on the ridge opposite provide the island’s defining sunset image. One windmill still has its grinding stones intact—walk up at golden hour and understand why photographers come from around the world.
The bus to Katapola (the main port) took us to Le Grande Bleu café—a pilgrimage site for Big Blue fans where the film once screened nightly (or it did back in 2002!). The Monastery of Panagia Hozoviotissa clings to the cliff face above Agia Anna beach, reached by 300 steps and strict dress codes. We explored Tholaria village in the north, caught buses to Aegiali, and watched the magical rays of sunset paint the windmills copper and orange.
Getting There: Ferry from Koufonissi to Katapola. Bus from Katapola to Chora (frequent service).
Getting Around: Excellent bus network connecting Chora, Katapola, Aegiali, and the monastery. Walking within Chora.
Where to Stay – My Personal Recommendation: Panorama Pension or Panorama Rooms and Studios in Chora for atmosphere and sunset views. The hilltop location means cooler evenings and less wind than coastal areas.
Where to Eat:
• Tavernas in Chora’s main square – Multiple options with sunset views
• Le Grande Bleu Café, Katapola – For Big Blue nostalgia
Don’t Miss: The windmills at sunset (walk up from Chora), the Monastery of Panagia Hozoviotissa (dress code: long trousers for men, skirts for women), Le Grande Bleu café in Katapola, the bus journey to Tholaria and Aegiali, the Gavros Tower museum in Chora.
The Reality Check: The monastery involves 300 steps and strict dress requirements. Amorgos is larger than the Lesser Cyclades—you need the bus network. Many places don’t open until June.
Onward Travel Connection: Ferry from Katapola or Aegiali to Santorini.
→ Amorgos – Tholaria, Aegiali and Katapola
→ Last Day on Amorgos and on to Santorini
Day 18: Santorini
Returning to Santorini after the Lesser Cyclades felt like culture shock. The ferry delay gave us an unexpected gift—one of the best free sunset views available, from the deck as we approached the caldera. The clifftop towns lit up like jewels as darkness fell.
We stayed in Pyrgos at Symphony Suites, away from the Fira and Oia crowds. A whistle-stop tour took us to Akrotiri—the “Pompeii of the Aegean”—and a sunset volcano boat trip provided the dramatic finale this trip deserved.
But I’ll be honest: after the tranquility of Iraklia, the authenticity of Schinoussa, the character of Amorgos, Santorini felt overwhelming. It’s magnificent, but it’s tourism’s version of magnificence. The Lesser Cyclades had shown me the alternative.
Getting There: Ferry from Amorgos. Allow buffer time for connections.
Where to Stay – My Personal Recommendation: Symphony Suites, Pyrgos – Away from the crowds, cliff-edge location, close to Santo Wines. Pyrgos offers Santorini atmosphere without Fira/Oia intensity.
Don’t Miss: Akrotiri archaeological site (the Minoan city preserved by volcanic ash), a sunset boat trip around the volcano, the view from the ferry as you arrive.
The Reality Check: July Santorini is busy—very busy. Cruise ships disgorge thousands daily. If you’ve just come from the Lesser Cyclades, the contrast is stark.
→ Arrival on Santorini: Let the Old Lady Sit Down!
→ Santorini – A Whistle Stop Tour: Akrotiri and a Sunset Volcano Boat Trip
Is This Trip Right for You?
This itinerary is perfect if you:
• Want to experience the “real” Cyclades beyond the famous islands
• Love small ferries and authentic Greek maritime culture
• Appreciate simple beaches without sunbeds and beach bars
• Enjoy walking and don’t need a car
• Want to eat vegetables from the garden and fish from the morning catch
• Seek islands where tourism hasn’t overwhelmed local life
Think twice if you:
• Need predictable, frequent ferry connections
• Want organised beaches with facilities
• Prefer larger hotels with extensive amenities
• Have mobility issues (some islands involve hill climbing)
• Need nightlife and varied evening entertainment
• Struggle with limited ATM access (check in advance during uncertain economic times)
A Note on Travelling in 2015
This trip coincided with Greece’s referendum on EU bailout terms—the famous “Oxi” vote. Banks had daily withdrawal limits; uncertainty hung in the air. Yet on these small islands, life continued. Tavernas served dinner, ferries ran their schedules, and the Aegean sparkled regardless of politics.
A decade later, the Express Skopelitis still sails. The Lesser Cyclades remain quieter than their famous neighbours. Iraklia still has no cars. Schinoussa still grows its famous fava beans. Some things in Greece are eternal.
Prices will have changed, some accommodations may have new owners, and Koufonissi will have become more “discovered.” But the essential character of these islands—the reason to visit—remains.
Final Thoughts
Eighteen days. Six islands. One legendary ferry. And memories that define why I keep returning to Greece. If I could speak to my younger self I’d tell her to slow down and not try to pack so many islands in on such a short trip.
The Lesser Cyclades taught me that the best Greek islands aren’t necessarily the famous ones. Iraklia’s sunrise—alone on a hillside as fishing boats chugged out to sea—remains one of my treasured travel moments. Schinoussa’s omelettes from chickens I could see from my table. Koufonissi’s Rebetiko musicians playing from a boat. Amorgos windmills turning copper and gold.
The legendary Express Skopelitis tied it all together—not just transport, but a character in the story. Boarding that small ferry, recognising the same crew, watching them deliver mail and supplies alongside passengers—this is Greek island life as it has been for generations.
Yes, Santorini was beautiful. Yes, the volcano boat trip delivered. But returning to Santorini after the Lesser Cyclades felt like returning to a theme park after experiencing the real thing.
The Skopelitis still sails. The Lesser Cyclades still wait. Go—while they remain the Greece that tourism hasn’t quite reached.
