Island Hopping in the Cyclades

Island hopping in the Cyclades, the most famous island group of the Greek islands, is a dream. Visiting just one of these gorgeous, iconic places with unique architecture and an astounding richness of heritage and history is an unforgettable experience. But how to choose which one to visit? It’s a tough choice and a hard conundrum.

That’s why many don’t limit themselves to one island in the Cyclades. They choose them all and go island hopping from one stunning destination to the next!

Island hopping in the Cyclades is so popular that it is considered a vacation category all on its own, which requires its own preparation and knowledge of what to expect and how to organize it in order to make unique, precious memories and experience the Cyclades at their best.

This guide is your perfect starting point for designing your own amazing island hopping in the Cyclades. Learn all you need to create your best vacation yet!

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A Guide to Island Hopping in the Cyclades

When is it best to go island hopping in the Cyclades?

Summer is the obvious and optimal choice for island hopping in the Cyclades. During summer, which is also the high season for tourism, you will get full access to all services, amenities, and venues available. That means you will also be able to reach every island in the most efficient way possible.

Summer in Greece roughly begins in May and ends in late September. The sea is warm enough to swim around June and stays that way throughout. So, any month within that range is technically good for island hopping in the Cyclades.

However, on a practical level, there is a summer month you should avoid at all costs, and that is August. August is the peak of the high season, so everything will be more crowded and more expensive, and competition for seats or places in boats or venues will be high. Beyond that, though, there is one more element that August has which is best avoided: the weather.

The Cyclades are notorious for their winds, and especially the meltemia. They are seasonal northern winds that are quite strong and can significantly affect your experience since they frequently cause ships to remain bound to the port.

As you might have guessed, meltemia are especially prevalent in August! So, your best bet is to avoid August altogether and increase your chances of low, pleasant winds while you go island hopping.

Characteristics of the Cyclades’ islands

There are a whopping 220 islands in the Cyclades, but of those, 15 are the largest and most inhabited ones. In general, the Cyclades are iconic for their architecture and the arid landscape that clashes with the deep blue of the Aegean Sea.

In all the Cyclades, you will find the whitewashed, smooth sugar cube houses that tend to cluster together and form picturesque, stone-paved winding paths. They have brightly colored doors, shutters, and splashes of pink and green against the white as bougainvilleas grow everywhere in manicured, large clay pots. There are several churches, too, white with blue domes and impressive bell towers.

Beyond that, each island has some unique features that it doesn’t share with any other. Here are the most significant ones:

Syros: Syros is the capital of the Cyclades and is famous for its 20th-century opulence and artistic grace. There are gorgeous neoclassical buildings, from mansions to administrative ones, to explore and enjoy. There are also beautiful, unique churches you won’t find elsewhere in the Cyclades and a lot of history and tradition to immerse yourself in.

Santorini (Thera): Easily the most famous of the Cyclades, Santorini is best known for its volcano. There are gorgeous views from the caldera, alien landscapes and dramatic beaches of black volcanic sand or red and yellow hues, excellent wine, and of course, the most gorgeous sunsets you can find.

Mykonos: Mykonos is synonymous with a wild nightlife, extremely expensive tastes, and gorgeous beaches. If you love a high-octane night out, this is the island for you! The same goes for lounging on the beach or engaging in water sports.

Delos: This is the famous sacred hub of the Ancient Greek world. It’s a UNESCO world heritage site, and it’s forbidden to stay overnight. Treat it as the largest open-air museum in the Aegean, and enjoy its archeological sites for a few hours.

Andros: This is the calm, fun, family island where you can enjoy beautiful museums and lovely beaches. There is also somewhat richer vegetation than most of the Cyclades. It’s just an hour away from Athens, so that it can be a great entry point for your island hopping.

Tinos: Tinos is the island of the Virgin Mary. Known for its pilgrimage site of the church complex reigning over the island’s Chora, you will get deep traditions, great food, and some of the most picturesque villages you can find here. Tinos is famous for its marble craftsmen and sculptors and its pigeon houses, so make sure you get to see both!

Paros and Antiparos: Paros is yet another cosmopolitan island that offers excellent nightlife but also many activities for families, beautiful beaches, and pretty impressive heritage and traditions. Get on the only ferry that can take you to Antiparos and its vibrant nightlife, calm daylife, gorgeous beaches, and impressive cave.

Naxos: This is the largest of the Cycladic islands, known for its stunning Venetian castle, lush history, immaculate sandy beaches, and great food. Visit several gorgeous villages, and don’t miss out on the giant Kouros statues you’ll only find here!

Amorgos: This is where you will find wild beauty, gorgeous beaches, and breathtaking views of nature at its best and wildest. If you’re up for exploring and hiking, this is the island for you.

Ios: Ios is famous for its party culture, but there’s a lot more than the admittedly fantastic parties you can enjoy there. There are a lot of archeological sites to visit, impressive churches, and some of the most gorgeous beaches you can find.

Milos: Milos is a gorgeous volcanic island not unlike Santorini, but with half the crowds and half the prices. Explore beautiful beaches and a unique mining history that will carry you back to the 19^th century.

Kimolos: Famous for its ability to have you relax and kick back on its beautiful beaches, Kimolos is a quiet island that features a pretty imposing, impressive Venetian castle. Explore Kimolos’ astounding Chora and get to know the locals like you’re part of the family.

Sifnos: This island is gorgeous and has a bit of everything. You will find beautiful beaches, picturesque villages, gorgeous views, and excellent food. Perfect for flexible vacations.

Serifos: Like Milos, Serifos has a strong mining tradition. But what it’s really known for is the beauty of its beaches.

Kythnos: If you go to Kythnos, make sure you enjoy its hot springs and lush landscape. The island is considered off the beaten path, though it is unexpectedly close to Athens. Perfect if you’re looking for authenticity.

Kea (Tzia): Known for needing a car to be explored well, Kea is a deeply culturally attuned island. There will likely be many events for you to experience after a day at the beach or exploring one of its picturesque villages.

Small Cyclades: This is a cluster of small islands near Naxos named Koufonissia, Schinoussa, Donousa, and Iraklia. They are known for being gorgeous, pure, and perfect for relaxation, swimming, and recharging. Though they retain their unspoiled character, they are quite popular, so make sure you book in advance.

Anafi: This island is remote and famous for its free camping culture. If you like camping, this is the island to go to. Enjoy laid-back fun, gorgeous sunrises, and excellent views.

Sikinos: Known for its unspoiled character and wild beauty, Sikinos is for anyone looking to relax, reflect, and enjoy authentic food.

Folegandros: This is an island that is remote and wild but becoming swiftly popular for its traditions, hiking paths, secluded beaches, and cool nightlife.

Where to begin island hopping in the Cyclades?

There are so many amazing Cycladic islands that it can be overwhelming to choose where to begin island hopping! While there is no single right answer to the question, there is a rule of thumb you can use to decide not only what your entry point to the Cyclades should be but also which islands you should add to your list.

Look at the map of the Cyclades first. You will find that they are roughly clustered around Syros, which is why their name is “Cyclades,” meaning “circle.” If you visit during summer, you can be quite assured that all the islands that are geographically close to each other will also be interconnected. So, your best bet in choosing an entry point would be first to decide which islands you want to visit.

If you want a full range experience of the islands, Andros is a great entry point as it is so close to Athens, and then you can go along the line south to Tinos, Mykonos, Syros, and more.

If you’re interested in the highlights, Santorini is a good entry point, and then you can visit Mykonos and go from there.

If you want to experience the wildness of the Small Cyclades, then Naxos is where you want to go first.

Study the map, see where there are airports, and be clever about planning your hopping to be between as closely located islands as possible.

Which Cycladic islands have airports?

There are international and domestic airports in the Cyclades. Here is a list of where is what:

Islands with international airports in the Cyclades

• Santorini (Thera)
• Mykonos

Islands with domestic airports in the Cyclades

• Naxos
• Milos
• Syros
• Paros

If you are abroad, you can fly into the Cyclades directly in Santorini or Mykonos, but keep in mind this is only practically feasible on a consistent basis in the summer.

You might want to check the following: Greek islands with airports.

Ferry service and ferry types in the Cyclades

Airports aside, the main way to go from one island to the other in the Cyclades is by ferry. There is more than one type of ferry, and you should choose wisely depending on your available time, budget, and tolerance of sea travel. The three main types of ferry you will find in Greece are:

Standard ferry: This is the most frequent type of ferry and by far the most reliable one, even in turbulent seas. Ferries usually also carry cars and have three classes of seating. They are also the slowest-speed ferries, with “high-speed” ferries mitigating that a bit. You can usually buy refreshments on a ferry, though expect prices to be a bit steep.

Hydrofoil: You might hear these being called “flying dolphins.” They are small ferries that have the highest possible speed. They only have aircraft-type seats and no other amenities beyond a toilet. They can be difficult for people that get seasick easily, and they can’t sail in rough weather. Hydrofoils are an excellent choice for quick transport between nearby islands.

Catamaran: This is the ideal mix of the previous two types. You might hear these being called “sea jets” or “sea cats.” They have high speed and more luxurious seating with more amenities. They can be the most expensive of the three, but that depends on the season and the route.

During the summer, ferry service is at its best, with several ferries per day serving each route.

Booking tickets for island hopping in the Cyclades

Ferry tickets

In most cases, even during the summer season, you won’t have trouble finding a ferry ticket to any chosen destination. However, there are exceptions to the rule depending on occasion and time (e.g., in mid-August, tickets to Tinos may be hard to find due to the annual pilgrimage there). To be 100% sure, book your tickets at least a month or two in advance.

The best way to book your tickets is through Ferryhopper, where you can find all the routes and options available on a single site, including a price comparison. There is also a capacity to completely plan your island hopping ticket needs there and book everything in advance.

Click here for the ferry schedule and to book your tickets directly.

Or enter your destination below:

Starting points

If you are using a ferry to go to the Cyclades, then you will be leaving from Athens’ ports or from Lavrio. For northern Cycladic islands, your most efficient choice is Rafina, as it is the shortest distance. From all the others, Piraeus is where you will be leaving from. If you want to start from Kythnos or Kea, then Lavrio is your best option.

To cut down on time, many choose to fly to the first island of choice and then use the ferry service. Mykonos is a great hub for its surrounding northern Cycladic islands (e.g., Tinos, Syros, Andros), and Santorini is excellent for the southern ones (e.g., Small Cyclades, Ios, Milos, Folegandros).

You can also opt to fly to Paros, which is quite central, and use the ferry service for a wide range of islands (e.g., Naxos or Sifnos). The ferry trip from island to island is often under an hour, so a combination of plane flight and ferry can do wonders for your time management!

Flight tickets

For booking plane tickets, Skyscanner is a great equivalent to Ferryhopper, with price comparisons, efficient flight specification filters, and a capacity to design connection flights if you need them. Unlike ferry tickets, flight tickets can and do get sold out quickly, so book well in advance.

What is the best way to go island hopping in the Cyclades?

When it comes to island hopping in the Cyclades, more is not necessarily better. Depending on how many days you have to go island hopping, you should be prudent and not overload your itinerary with more islands than you can handle.

Handling an island means being able to get there, have a rest, have time for meals as a baseline, then also have time for exploration of the island highlights before you need to hop to the next. If you don’t allocate time for rest, relaxation, and meals, you will end up being overworked and overstressed and unable to enjoy any island you visit.

That’s why it’s best to allocate around two days per island at the absolute minimum. If the island is big or has many things you want to visit, then add more days accordingly. It’s best to go island hopping on two or three islands and remember them well with a ton of experiences on each than go to five islands and only remember how stressed you were going from one place to the other, with every other experience being a blur.

To give you a general idea, if you have a week, you shouldn’t plan for no more than two, at most three islands, depending on where you want to go.

Balance your budget not by what is necessarily the cheapest but by what is the best value for money: a plane ticket might look expensive compared to its ferry counterpart, but it might save you half a day of travel!

What are the best Cycladic island combinations for island hopping?

Depending on your interests and the type of vacations you prefer, you might enjoy some Cycladic islands more than others. Here is a grouping of the islands per vacation theme. This doesn’t mean that you should only pick islands from a single grouping, though!

Depending on your interests, you might want a varied selection or a single style: perhaps you only want to relax and enjoy great beaches, but you might also want to visit museums or hit the bars after sundown. Use the grouping to choose the best combination for you- always trying to pick the islands that are closest to each other or can be accessed by a flight and ferry combo.

The islands are in alphabetical order:

For beautiful beaches: Andros, Donoussa, Folegandros, Ios, Iraklia, Kythnos, Koufonisia, Milos, Mykonos, Naxos, Schinoussa, Serifos, Sifnos, Sikinos

Picturesque villages: Amorgos, Folegandros, Kimolos, Milos, Naxos, Paros, Sifnos, Sikinos, Syros, Tinos

History, archaeology, museums: Andros, Delos, Koufonissia (Keros), Milos, Naxos, Paros, Santorini (Thera), Syros, Tinos

Night life: Ios, Mykonos, Paros-Antiparos

Food adventure: Milos, Naxos, Paros, Sifnos, Tinos

Wild, authentic, remote: Anafi, Folegandros, Ios, Kimolos, Serifos, Sikinos, Small Cyclades

What are some popular island hopping routes in the Cyclades?

Here are some of the standard island hopping routes in the Cyclades. Have a look but never forget to make sure these islands are the best fit for you and for your time!

• Mykonos – Syros – Paros – Naxos – Ios – Folegandros – Milos
• Paros – Naxos – Iraklia – Schinoussa – Koufonisia – Amorgos
• Tinos – Mykonos – Naxos – Paros – Ios – Santorini
• Kythnos – Serifos – Sifnos – Kimolos – Milos
• Andros – Tinos – Mykonos – Naxos
• Syros – Mykonos – Naxos – Ios – Santorini

Remember, sometimes it’s best to use these as inspiration while you make your own unique itinerary!

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