How to island-hop in Greece

If there is a more tempting holiday proposition than ‘Do you want to go island-hopping in Greece?’, I have never heard it. But with the sheer volume of ferry crossings and the vast number of islands, it can be hard to know where to start. Add to that the desirability of these heavenly specks in the Aegean, with the ensuing summer crowds, and it becomes even more important to plan accordingly.

The great Greek writer Nikos Kazantzakis once wrote, ‘Happy is the man… who, before dying, has the good fortune to sail the Aegean Sea’. I have indeed had the good fortune to sail the Aegean Sea many times since I first fell in love with Greece in 2012. Allow me to impart what I’ve learnt along the way…

My top tips for island-hopping in Greece

1. You should include the big-hitters (Santorini, Mykonos, Crete, etc) for ease of arrival, and bucket-list purposes, but make sure you get out to the lesser-visited isles as well — you will be rewarded.

2. Even the tiniest islands can have airports, mostly to facilitate easy access for the Athenians who have homes there. Astypalia in the Dodecanese may only be 11 miles long and 8 miles wide, but it has its own airport (really just a runway that disappears back into nothingness once the tarmac ends). But Sifnos’s lack of an air hub only adds to its resolute exclusivity — yes, she’s harder to reach, but oh, is she worth it.

(Side note: I once boarded a boat bound for Sifnos in Piraeus at 1pm and it didn’t depart until 7pm due to high winds, meaning we didn’t drop anchor at Kamares port until close to midnight. I hushed my deep-seated Londoner impatience by mimicking the families on board, who were playing cards and queuing for sandwiches and snacks from the kiosk on board. I pictured the London equivalent of being trapped on a Tube for six hours and the grumbles that would erupt. We can learn something here.)

3. Journey times by boat vary wildly, so be careful which vessel you book. Yes, there are high-speed hydrofoils nipping between the islands, but the chance of vomiting on board these increases greatly, so it can be a false economy. The bigger ships chart a much more leisurely course. En route to my sister’s wedding in Paros in 2012, I left London Heathrow on a 6am flight and arrived on the island just before midnight. Yes, I could’ve reached Australia in that time, but how I enjoyed the slow voyage, the frappés (and fags, I was young) on deck, the transition into salty sea dogs with salt in our hair and faces, channelling Zorba and his Boss. I appreciate that in the fast-paced 2020s taking the slow voyage might seem impractical, but life is about the journey as well as the destination.

4. You don’t have to travel very far from Athens to experience the Cyclades — the closest Cycladic isle to the capital is Kéa, reached in less than half an hour by private One&Only-branded, James Bond-worthy speedboat, or an hour via mortal ferry from the Athenian port of Lavrio to the town of Ioulida.

5. Each island has its own thing going for it. Though the landscape of parched earth, bright bougainvillea, hilltop choras and whitewashed buildings are similar across many of the Cyclades, they each have their own character and identity — even industry in some cases, such as Santorini’s prosperous caper hustle, or Naxos’s potato trade. Even if you started your exploration of the Greek islands as a child, you’d likely never get to all of them, so do a bit of research to see which one might suit you best.

6. Ferry travel is not glamorous. I once met an Italian hotelier in Capri who told me he sails the Aegean every summer in his yacht and have never felt more sick with envy in my life. While some luxury hotels do of course have private boats that will whizz you on to your next stop, these transfers, though priceless for speed and lack of hassle, don’t come cheap — pushing €1,000 per trip.

7. Technology has made it easier to island-hop, but this makes me wistful and nostalgic for the old days: getting to the port hours before to find the office to collect your ticket; rerouting to another island on a whim and just finding a B&B owner with a sign at the port; the old ports themselves, many now replaced by bigger docks that can berth cruise ships. But, today, the ease of itineraries being mapped out and booked online, with in-app tickets and QR codes, can’t be underestimated.

What to know before you go island-hopping in Greece

Transport If you don’t have the luxury of a friend with a yacht, the ferries will have to do. There are several operators, including Blue Star and the smaller, swifter Seajets fleet. Most arrival towns have a car-hire office right by the port, so you can pre-book or pick up a vehicle or moped as soon as you disembark. To get to the remote beaches, hilltop or coastal towns, and to see the island fully, a car is highly recommended.

How long to spend island-hopping It’s easy to select a handful of islands located near each other, with shorter ferry crossings, and see them all in around a week, but I would recommend at least three nights on each landmass to really see it properly.

Weather conditions The Cyclades’ famously blustery Meltemi wind can rage even in high summer, with the draughtiest spots being Tinos and Mykonos. It’s still warm in the sun, of course, but be sure to batten down the hatches (and car doors, parasols, etc).

Your secret weapon The Ferryhopper app will be your friend. Even as the most determined techphobic elder Millennial, I swear by it. It allows you to book multi-stop routes on various dates with ease, shows you all the options, and then stores your QR codes for boarding in one place. Ferryhopper also issues timely updates to announce changes and delays to your journey before anyone else.

When to go The Cyclades are now so busy, the ferries are heaving even in early May. Greek Orthodox Easter is typically when many hotels open. The weather can still be changeable with many places not open for the season yet by then; but consider April — or wait until after the summer crowds have dispersed and travel in October.

Know before you go It can be hectic when the ferry ramp comes down and the hordes start to board — wheelie suitcases are essential for smoother embarkation. You will then just leave it on the luggage racks in the boat’s garage so be sure to remember where you put it.

3 Greek-island itineraries

Itinerary 1: Rafina (Athens) – Andros – Tinos – Syros

Ideal length of stay At least three nights on each island.
Best for Fewer people, wild landscapes, gourmet travellers.
Don’t miss The vineyards on Syros.

Stop 1 Many travellers touch down in Athens and head straight to mega-port Piraeus, but for certain islands, the Athenian port of Rafina facilitates more efficient ferry crossings. From here, the fastest journey south to Andros takes just 50 minutes. Andros is wilder than some of its glossy counterparts, with a mountainous coastline, waterfalls and springs forming its landscape. It might seem unlikely, but this island is known as Little England, a relic of its shipping heyday when its magnates opened London outposts and brought English governesses to the island, and built a school, hospital and a retirement home on the square. Continuing this nautical theme, Onar Andros — set on protected wetlands and a wilderness — started out as a holiday home for its ship-broker owner, but he generously decided to share it.

Stop 2 Tinos (fastest crossing time, 40 minutes), an isle of good food, devout pilgrims and almost-impossible-to-reach beaches. One of Pnoēs Tinos’s three self-contained, two-storey suites will be the perfect base for exploring the island’s mountain villages, gourmet restaurants and vineyards, and dovecotes.

Stop 3 A 15-minute ferry ride away is Syros, the Cyclades’ erudite elder, home to the University of the Aegean, a refined cultural calendar and grand, colourful neoclassical villas. Aristide Hotel, at the edge of the main town Hermoupolis, is one such mansion, restored by its dedicated owners, with a gallery’s worth of artworks and a much-lauded restaurant. Or check in to Castro Hotel Syros, also in Hermoupolis, built in 1857 for its Italian owner, now with a spa in the cellar. From Syros, fast hydrofoils will get you back to Piraeus in under three hours, or you can head to Mykonos for your flight home.

Itinerary 2: Mykonos – Paros – Antiparos – Naxos

Ideal length of stay Two nights on Mykonos, three nights on Paros and Naxos, and a night or two on Antiparos.
Best for Partying and peace.
Don’t miss Attempting kite-surfing between Paros and Antiparos.

Stop 1 Thanks to its international airport, Mykonos is a popular jumping-off point for multi-stop itineraries. And though it is undoubtedly busy, it still has some quieter corners away from the party scene. Rocabella is ideally placed on Agios Stefanos, five minutes by car from town when you want to be in on the action; or try bright-white sanctuary Myconian Ambassador above Platis Gialos on the island’s south-west coastline.

Stop 2 A 40-minute ferry ride will take you to Paros, the Cyclades’ most cosmopolitan isle, with vibrant little towns, beautiful beaches and lots of tavernas at the water’s edge. Near Ambelas, a short drive from peak-chi-chi town Naoussa, Vione Paros has rooms with a view, some with a pool, too.

Stop 3 A chain ferry will get you from Pounta on Paros to Antiparos in less than 10 minutes, passing the kite-surfers enjoying the optimal conditions of this strait. You can head over for the day on foot and wander around the port town, which has shops selling all manner of ceramics, clothing and trinkets, and a few restaurants along the waterfront (though it’s worth heading by car to Captain Pipino’s on Agios Georgios). Or stay the night at The Rooster, making sure you arrive in time for sunset on its terrace, with a spa treatment and trip to its farm scheduled. For something a little more laidback, sister stay The Beach House has just a handful of old-school suites at the shore.

Stop 4 Return to Paros and then catch a ferry to Naxos (swiftest crossing: 25 minutes), the largest of the Cyclades, and the most fertile and Demeter-blessed, hence the potatoes. Stay at The View, high in the hills but close to the island’s old town and beaches; or ascend to Mount Olympus at Ayiopetra, with just five suites, each with stone walls and a terrace for admiring your surroundings. From here, return to Mykonos to catch your flight.

Itinerary 3: Santorini – Ios – Folegandros – Milos

Ideal length of stay Folegandros is tiny so a night or two will do, then two or three nights on each other island — a leisurely version of the itinerary could take a fortnight if you linger a little longer on Santorini and Milos.
Best for Spectacular scenery, from the blue domes and caldera of Santorini to the eye-popping geology of Milos.
Don’t miss A swim off the bright white rocks of Sarakiniko on Milos.

Stop 1 All the way down south in the Aegean, volcanic Santorini is a true must-visit-at-least-once destination — and it has an international airport to make trips here easier. The southernmost Cyclade is famous for its caldera, a type of crater caused by an eruption that took it from circular to croissant-shaped around 1600BC, blowing away Thirassia, its miniature islet across the water, and a few other crags of rock. Oia is its most iconic sunset spot, but Imerovigli is just as scenic. Stay a little away from the action at Noūs Santorini in the caldera-facing village of Mesaria, or opt for Iconic Santorini in Imerovigli to be close to island capital Fira.

Stop 2 The fastest ferry service from Santorini to Ios takes just 35 minutes. Ios is known for its lively nightlife — not for nothing was it once known as Ireland-On-Sea. These days it’s a little more tame, though the late-night bars and clubs are still there if you know where to find them. Stay at Liostasi for its idyllic setting, above the port and a 10-minute walk from the island’s chora. Or book Ios Grand Pool Suites to be close to Mylopotas, the longest beach on the island.

Stop 3 Travel from Ios to Folegandros in around an hour and a half. One of the more diminutive Cyclades, Folegandros is just eight miles long, with only one road traversing it. As a result, it feels blissfully trapped in time. Just up the road from the port, Anemi is a classic Greek-island hotel with most activity centred around the main pool. For a blow-out option, luxury-resort Gundari clings to the cliffs in the south-east.

Stop 4 From Folegandros, make your way to Milos — the boat ride should take an hour. Milos is incredibly geologically diverse, with spectacular landscapes such as the dazzling lunar-like beach Sarakiniko, colourful rock formations, caves, hot springs and fumaroles, and healthy mineral deposits making it a mining hub. Stay close to Sarakiniko at sunset-ready Domes White Coast Milos, or try to find the camouflaged villas of Skinopi Lodge, between main port Adamantas and Kilima. Either way, be sure to head to main town Plaka for hilltop sundowners. To catch your flight home from Santorini, return to the island by ferry — Milos to Santorini crossings with Seajets are two hours and 30 minutes long.

Sail on to Saronic isle Hydra, or stop over in Athens for a weekend break on the way home