Island Hopping in the Cyclades - Everything you Need to Know!

Enchanting, whitewashed villages, bluer-than-blue seas and mouth-watering cuisine. The reality of Cyclades island hopping lives up to your dreams from alluring travel magazine covers. The stars of the show, such as Santorini and Mykonos, draw gasps from visitors spellbound by the sights of blue-topped churches and historical windmills dotting photogenic landscapes.

However, lesser-known islands are just as breathtaking with diverse personalities that ooze charm. From swimming at the best Cyclades beaches to hiking ancient trails and diving volcanic underwater worlds, you’re spoilt for choice with exciting activities no matter which islands you visit. And when it’s time to dine, get set for taste bud explosions with produce unique to each island plus, your favourite Greek classics.

Understanding the Cyclades

Decorating the Aegean Sea, the Cyclades Islands in Greece encircle the sacred island of Delos. In Greek mythology, the god of the sea Poseidon turned nymphs into the paradise havens that now attract millions of visitors every year.

Among the 33 inhabited islands and islets, the most recognisable feature is the whitewashed, cubic-shaped architecture adorned with accents of blue and topped with pink bougainvillaea.

As a centre of a Bronze Age culture, ancient ruins pepper landscapes and grace museums. Among rulers including the Crusaders, it was the Venetians in the Middle Ages that left a noticeable mark across many islands with castles and fortresses, along with Byzantine-era churches and monasteries.

From folk festivals for patron saints to sleepy fishing village displays of octopus drying in the sun, traditions still flourish and captivate visitors.

Planning Your Island Hopping Trip

Ready to turn Greek island dreaming into reality? Here’s everything you need to know to plan your trip.

Best Time to Visit the Cyclades

Balmy beach weather in the Cyclades during July and August ensures that the summer months are the most popular time to visit. Other than occasional, strong Meltimi winds, skies are blue and sun-drenched seaside resorts bask in average temperatures of 27°C.

The high season is calling your name for glamorous parties on Mykonos and buzzing vibes across capital cities and beach towns. They generally hit full swing in late June. Expect higher prices for hotels and crowds at popular attractions, so book early.

If you’re looking to avoid the peak season crowds, plan your trip for April, May, September or October. In my opinion, these are the best months to visit, as you’ll avoid the notorious winds that can ruin lovely beach days, and although still busy in places, you’ll also avoid much of the mass tourism.

Spring delivers wildflowers across grassy hills as nature wakes up, with mild temperatures in the low to mid-20s. For many, September is the best month to visit. It’s still warm enough to swim, and if you’re a hiking or mountain biking fan, there’s less chance of scorching sun on spectacular coastal trails.

As October moves into November, cool, cloudier days arrive, but average maximum temperatures of 18°C are still pleasant for adventure activities. While hubs of activity remain on some larger islands, December, January and February see many resorts close as the colder, damp weather sets in.

You’re rewarded with the cheapest prices in the winter months, and thoroughly local vibes. By the end of March, warmth seeps through winter’s chill and the tourist season arrives again.

Choosing the Right Islands for You

When it comes to Cyclades travel, you could close your eyes and point at a map with no fear of going wrong in terms of finding paradise. When budget isn’t an issue, choose first based on your interests.

Santorini, Mykonos and Ios are among the most visited, for good reason. Along with dazzling scenes of volcanic calderas and ravishing beaches, exciting shopping, dining and nightlife options join a wealth of activities. Hotels range from decadent luxury to traditional and rustic.

Prices reflect the popularity, so choose lesser-known or smaller islands to get more for your money, and if you prefer a slower pace. For example, laid-back Sifnos is a gourmet heaven with villas tucked into terraced hills, spectacular hiking trails and unspoiled sandy beaches to enjoy without so many overpriced menus.

All of the islands mentioned here are accessible via direct flights or ferry connections from mainland Greece, and each other. To fly straight in, Santorini and Mykonos have international airports.

Recommended Islands

What are the best islands in the Cyclades for you? You’re spoilt for choice.

NAXOS

The largest island in the Cyclades is dotted with Venetian palaces and fringed with stunning beaches. Meander through lush countryside amid wildflowers on the way to enchanting hilltop villages.

In Naxos Old Town, alleyways beckon and historical architecture houses boutiques and cafes. A seafront promenade tops it off, with views of the Temple of Apollo. Fill your picnic basket with bakery goodies from Naxos Old Market before traversing the network of hiking trails.

One winds up Mount Zeus, the highest point in the Cyclades and steeped in mythology. With an archaeological and a folk art museum, traditional Apiranthos is a culture vulture’s dream, complete with houses made from marble and the 9th century Church of Agia Kyriaki.

If you like a tipple with tradition, visit Halki village to sample the local kitron liqueur distilled from the leaves of citron trees.

Hire a bike to cycle from Naxos Town to Agios Prokopios Beach, where watersports and volleyball are framed by lagoon-like water. Nearby, Agia Anna Beach has a fishing village vibe with rocky outcrops to explore and beachfront tavernas to chill out in.

Lined with cliffs peppered with cedar trees and not much else, Aliko is the perfect place to escape the crowds, and claim your own patch of golden sand.

PAROS

Paros blends all the magic elements of islands in the Cyclades, with something for everyone topped with bougainvillaea and sparkling Aegean views. Sink into island life at sleepy fishing villages or shop and sip exotic cocktails in the capital Parikia, and charming Naoussa.

History takes centre stage at the Venetian Fortress of Naoussa and the Asklepion of Paros. You’ll see the tradition of mining companies at the Paros Marathi Marble Quarries.

Hilltop Lefkas is as pretty as a picture with whitewashed streets and quaint restaurants. From here, hike the historic Byzantine Road through olive groves to Prodromos village.

Coastal trails abound, from a stroll around Parikia Bay to the network at Paros Park Nature Reserve. Set out across the island on foot or by bike to idyllic villages, including Marpissa on the hill above popular Piso Livadi beach.

Speaking of which, from kitesurfing to paddle boarding and diving, Paros beaches deliver the action. Head to Chrissi Akti or Pounda Kite Beach for windsurfing. If you prefer floating, submerge in the calm bay of Santa Maria Beach.

Don’t expect to put the camera down at Kolymbithres Beach, where granite rock formations create idyllic, sandy coves.

IOS

Are you ready to party? Ios rivals Mykonos as the summer party destination, from beach clubs to trendy bars dotting cobbled streets. That said, there’s plenty more to define this pretty island.

The lovely Church of Panagia Gremiotissa overlooks Chora, with the characteristic blue dome and bell tower. Next to it is the Venetian castle, with views across the cube-shaped buildings on the hill slopes. Get happily lost among the labyrinth of laneways and follow your nose to traditional bakeries.

Embark on a history-hopping adventure at Skarkos, a Bronze Age excavation from which items such as pottery and tools are displayed in the Archaeological Museum of Ios. Legend has it that the famous poet Homer took his last breath at The Tomb of Homer, surrounded by ancient ruins. Visit the 16-century Agia Theodoti church resting above the Temple of Apollo ruins.

You’ll find party central at Mylopotas Beach, a breathtaking arc of golden sand and turquoise water. It’s easy to stay all day and night, with sunbeds and watersports to enjoy before legendary beach bar parties with celebrity DJs. Jump in the water from either side of the sandy stretch that separates tranquil coves at Instagram favourite, Manganari.

SANTORINI

For many, Greek island hopping isn’t complete without what’s often called the jewel of the Cyclades. The cliffs studded with whitewashed villages and sunsets over the caldera live up to a world-famous reputation and make it one of the most popular destinations in the world.

Spend your days hiking to ancient ruins, sipping wine at enchanting vineyards and taking selfies with blue-topped churches. It’s little wonder this is a favourite honeymoon island (my own included!).

To soak up the best views, set out on the Fira to Oia hike. You’ll cross through the beautiful towns of Firostefani and Imerogvigli, with Skaros Rock a highlight for ocean panoramas.

In the postcard village of Oia, admire the famed, blue-domed roofs and whitewashed walls as you weave through tiny, steep streets. Finish the day with a blazing sunset at Oia Castle. History buffs make beelines to Akrotiri to delve into the ancient ruins of the Minoan site, nearby Red Beach dazzles with soaring red cliffs.

Stroll on the backdrops of Mesa Vouno and black sand at Perivolos and Perissa beaches, then hit the beach bars. Work up an appetite swimming out to the Agios Nikolaos Islet at Ammoudi Bay, after walking down more than 200 steps from Oia. Then, gorge on lobster linguine and fried calamari at seaside tavernas – you can bypass the walk back up with a taxi.

SIFNOS

Fancy sinking into the slow rhythm of Greek island life? Sifnos might be the Cyclades island for you. Pockets of wilderness and the scent of herbs join a renowned culinary scene where you’ll dine with your feet in the sand. Wherever you look, you’ll likely spot traditional windmills and whitewashed chapels.

The capital town, Apollonia, is built across three hills. Meander through narrow streets for tavernas and lounge bars with low-key nightlife. Nearby Artemonas is the spot for patisseries serving hot loukoumades to enjoy after a visit to the house of poet Ioannis Gryparis. Discover clifftop Kastro, an open-air museum with medieval remnants and cobblestone alleys.

A long stretch of golden sand fronts Platis Gialos, the ‘go to’ beach on the island for sunbeds and beach bars within steps of crystalline water. For fantastic views, visit the hilltop monastery of Panagia you Vounou. Sailboats stop in the sheltered bay of Vathy, a coastal village that’s home to local potters and scrumptious seafood tavernas.

MILOS

Bronze Age ruins and boutiques combine with fishing villages and museums in Milos. The port town of Adamas is the hub, with a maritime museum and elegant waterfront restaurants to enjoy after a boat tour to nearby sea caves.

Pollonia offers similar delights framed by swaths of sand and shallow water that is popular with families. Inland Plaka brims with folklore and history amid narrow alleys atop the island’s highest hill.

See the Ancient Theatre of Milos in whitewashed Trypiti, resting beneath the impressive Agios Nikolaos church. In nearby Klima, colourful boathouses called syrmata decorate the waterfront, hosting a smattering of accommodation options and souvenir stores.

A gorgeous photo opportunity awaits at Mandrakia, where a viewpoint perfectly frames boathouses lining a curved bay. And you can’t visit Milos without witnessing the ethereal volcanic landscapes at Sarakiniko.

Settle in at a beach town to spend lazy days swimming, eating and snoozing by the sea. Palechori’s sunbeds and watersports keep everyone happy, as does Provatas Beach with rocky outcrops for snorkelling.

Explore the Papafragas cliffs while staying at Pachena, where serenity reigns beneath tamarisk trees on the edge of transparent water.

ANDROS

Dive into the maritime traditions of the northernmost of the Cyclades islands – when you’re not diving beneath azure water yourself, that is.

The main town (Chora) is known as a domain of wealthy shipowners and renowned Greek captains. As you admire medieval and neoclassical architecture along narrow streets, pop into museums, including the Archaeological Museum of Andros. More history awaits at the Frankish castle built on an islet and accessed via a 13th-century stone bridge.

Along with history buffs, this is an island for hikers. Lush valleys and mountains present waterfalls and streams dotted with ancient landmarks. Signposted trails take you to ravines and villages, along with swoon-worthy beaches.

For seclusion, trek to the blue-green waters of Achla Beach overlooked by a chapel. Tis Giras to Pidima Beach is the magazine cover stretch, with towering cliffs and a rock formation to explore just offshore.

Another memorable photo opportunity awaits at Tourlitis Lighthouse. Perched on a narrow, rocky islet with stairs winding up to its white door, it looks like a backdrop for an ocean-themed fantasy.

There’s no shortage of water sports and boat trips to help you explore. Wrecks and blue holes greet divers, while sunset cruises combine sightseeing to the Gavrionissia Islets with nature’s fiery show.

TINOS

Just a short ferry ride from Mykonos and its international airport, Tinos is easy to add to your Cyclades island-hopping itinerary. It’s famous for the Miraculous Icon of Virgin Mary at Panagia Evangelistria church and, along with religious significance, the island is a firm favourite on the foodie trail. Gastronomic experiences revolve around slow, farm-to-table cooking and delicious cheeses.

Drift from beach to beach to find an idyllic slice of paradise to suit you. Kolympithra is popular with two sandy stretches to choose from, the clear blue water you expect and sunbeds and snacks on hand. Savour fresh seafood after a swim at Panormos Bay and discover the boho vibe under tamarisk trees at neighbouring Rochari Beach.

Nature needs no adornments at Pachia Ammos, with rolling dunes and shallow water for family-friendly swimming. When you’re exploring Tinos town, Agios Fokas is within walking distance with beach bars and views of Renia Island.

Wander the cobbled streets of Chora and you’ll stumble upon lovely fountains and charming shops. A visit to Pyrgos, the marble village, brings you to the Museum of Marble Crafts and the Giannoulis Chalepas Museum.

You’ll discover that village hopping is just as delightful as beach hopping in Tinos. See Dio Choria’s whitewashed houses with colourful trimmings and sample wine in Falatados.

MYKONOS

If you love glamorous beach parties, Mykonos is among the best islands to visit in the Cyclades. Overlooking the town, iconic 16th-century windmills set the scene for endless photo opportunities.

None so popular, perhaps, as the Little Venice area with colourful Venetian buildings and romantic restaurants stretching over the water. Head into the maze of streets in Chora to shop till you drop and taste your way around tavernas.

At the old port of Mykonos Town, drift between churches, cocktail bars and museums. Check out an array of boat tours, including to nearby Delos. The heritage-listed island is known as the birthplace of Artemis and Apollo, with ancient ruins including the House of Cleopatra and the Ancient Theatre of Delos.

Back on Mykonos, keep history hopping at the monastery of Panagia Tourliani and inland villages such as authentic Ano Mera.

Choose a beach to suit your mood. When you’re up for a party, Paradise and Super Paradise present glitzy beach clubs to enjoy between watersports. Join the jet-setters at Psarou Beach, where turquoise water laps white sand dotted with plush sun loungers.

Families flock to Ornos Beach for all the bells and whistles of a resort town, and peace is found among the natural backdrop of Fokos Beach.

SYROS

Cyclades tours to Syros transport you into cultural traditions and festivals, including the International Classical Music Festival of Cyclades. Ermoupoli is the charming capital (and also the capital of the Greek Cyclades islands), with a grand town hall, the Apollon theatre and historical captain’s mansions overlooking the Aegean. Walk to the top of the hill for breathtaking panoramic views after exploring the whitewashed lanes of Ano Syros (upper town).

Life’s a beach at Azolimnos, with a calm, sandy bay and tavernas for stuffed cuttlefish after scuba diving tours. If you can fit more in, head to the casual fish restaurants of Kini, where villas dot the hillside and spectacular sunsets are renowned.

There’s plenty to do for families with kids at Finikas. The coastal village revolves around a scenic harbour filled with bobbing fishing boats unloading your dinner while you play on sports courts and build sandcastles.

Delve into history at the ruined settlements of Chanlandriani and set aside plenty of time to admire Poseidonia. The traditional village is adorned with neoclassical houses and lush, manicured gardens once home to the island’s wealthiest families. Named after Poseidon god of the sea, it’s in the same bay as Finikas with shady Voulgari Beach between villages.

Planning Your Route

Cyclades island hopping routes are relatively easy to navigate with ferry rides and flights.

First of all, choose your favourite islands and work back from there. Unless you love a fast pace, seeing more islands over exploring the best of a few isn’t always a good option. Depending on what you’d like to do, determine how long to spend on each island, taking into account flight and ferry schedules.

If you’re limited on time, consider starting at your favourite island, hopping nearby and departing from a different island so you don’t double up. For example, fly into Santorini for three nights, take a ferry to Ios for three nights and onto Mykonos for three nights before flying from there back to Athens.

I’d recommend sticking to no more than three islands per 10-14 day trip, and spending at least 3 full days in each. Any more than this, and they’ll all blend into each other in your memories, and you’ll be spending too much time checking in/out of hotels, on ferries, or at the airport.

Transportation in the Cyclades

Choosing ferries or flights between islands is largely a personal preference. Here are the pros and cons.

Ferry Travel

There’s nothing quite like zooming between islands with the wind in your hair. Cyclades ferries are relatively inexpensive and popular, and the only way to get to some of the islands such as Tinos and Sifnos.

Choose from fast ferries and slower car ferries from Athens or between the islands. Ferryhopper is my preferred site to plan a route around the Cycladic islands.

Do be aware that ferries can sometimes be unreliable, especially in high winds or at busy times of the year, so it’s best to leave a little wriggle room in your schedule room for potential time changes. Booking the larger ferries, although slower in general, can sometimes pay off, as they’re more likely to still sail in windy conditions.

That said, I’ve personally never experienced any delays of more than an hour on my travels around the Greek Islands.

Air Travel

It pays to compare prices between ferries and flights, as travelling by plane can also be a cost-efficient option. It’s certainly often quicker, especially on the longer journeys. And Santorini, Mykonos, Paros, Naxos, Milos and Syros all have airports.

As international airports, it’s possible to fly directly to Santorini and Mykonos from other locations in Europe. On my most recent trip, I flew direct from Marseille to Mykonos, ferry-hopped around the Cyclades, and then flew from Milos back home via Athens to save time and avoid having to backtrack to Mykonos.

As the airports are small, you don’t normally have to check in too early either, saving you time for one last dip in the sea!

What to Pack for Your Island Hopping Trip

Arrive fully prepared for hot summers in the Cyclades with breathable fabrics like cotton and linen, breezy skirts and shirts, and plenty of sun protection. It’s a good idea to pack light for island hopping, so consider layers for cooler seasons and chillier nights. Pack a lightweight backpack for hiking, a quick-drying beach towel and a travel plug adaptor for your devices.

Of course, you’ll need a couple of glamorous outfits for the plush beach club scenes. Otherwise, it’s often best to leave valuables at home. Avoid those ‘just in case’ items as you’ll likely find everything you need on most islands – and you need space for souvenirs!

Somewhat contrary to what you’ll read elsewhere, it’s fine to travel with a wheeled suitcase instead of a large backpacking-style bag. The ferries have luggage compartments downstairs, and you won’t encounter too many obstacles.

If possible, opt for a bright colour or attach a unique luggage strap to differentiate your suitcase from the mass, as I’ve heard too many reports of people losing their luggage due to a case of mistaken identity!

Take a separate tote or backpack, so you can keep your valuables with you though. I love my Peak Design Travel Backpack for this purpose!

The islands of the Cyclades are living Greek island postcards that capture all your senses on arrival. Yes, the beautiful beaches are divine. But the slow-paced fishing villages, whitewashed alleyways dripping with bougainvillaea and warm hospitality in lively tavernas ensure your heart is firmly captured by the time you depart.

Island Hopping in the Cyclades: A Guide to Exploring Greece’s Beautiful Archipelago

Understanding the Cyclades