“I haven’t seen a single cloud since we got here”.
A week into our Greek island adventure, my new husband commented on the remarkable cerulean skies that dominate one of Europe’s most popular summer hotspots.
It’s true, the gorgeous shades of blue are everywhere: the sea is tinted deep aqua and of course, the famous domed churches contrast against whitewashed stone streets.
After two weeks island hopping the Cyclades, from the chilled beaches of Naxos to Paros’ chic boutiques, I can understand why visitors flock to the country for fresh food, iconic views and world-class sunsets.
So, I’ve put together a Cyclades island hopping itinerary of practical tips (based on our own travels!) to help you plan your own unforgettable trip.
Why the Cyclades?
The Cyclades are what most people picture when they think of your classic Greek island hopping adventure: whitewashed buildings, domed churches, vibrant bougainvillea and taverna tables spilling out onto the oceanfront.
There are around 220 islands in the Cyclades – with only 30 inhabited – so, while narrowing down your choices isn’t easy, you can plan so many different types of adventure in the region. One thing is guaranteed though: the perfect mix of iconic sights and off-the-beaten path charm. Plus, it’s easy to get around by ferry, making it ideal for a multi-stop adventure.
How to get to the Cyclades (and how to get around!)
Flights
Internationally, most people will fly into either Athens, Santorini or Mykonos to start their island hopping adventure. From Athens, you can also take a connecting internal flight to Milos, Naxos, Paros or Syros.
Naturally, the islands with airports are much busier with tourists than the others, so consider your travel preferences when putting together your itinerary.
We flew into Santorini then out of Athens, as this was the cheapest option on our chosen dates, so do your research if you’re on a budget!
Ferries
We booked all our connections on Ferryhopper, which makes it super easy to compare times and prices, which can vary between companies. They’re pretty easy to navigate but I’d recommend booking ahead in peak season for peace of mind.
For our two week Greek islands itinerary, the cheapest option tended to be Blue Star Ferries and Hellenic Seaways, with Seajets being the most expensive but much quicker for longer journeys.
Car hire
Hiring a car on each island, even just for one day, gave us so much freedom to explore at our own pace. While bus networks have varying levels of service across the islands I’ll talk about today, it’s definitely possible to explore this way, but you won’t see as much – especially with often-hourly services.
When is the best time to visit the Cyclades?
While summer is by far the most popular time to visit the Greek islands, I’d actually recommend visiting in April – May or September – October. Our late June trip was wonderful, but the heat was starting to kick up a gear!
Two week Cyclades island hopping itinerary overview
Santorini: 3 nights
The island that needs little introduction: Santorini sunsets overlooking the caldera are legendary and staying in one of Oía’s cave suites is a top item on many travel bucket lists.
It surprised us in a few ways too. More on that in my blog post (coming soon!): 7 things that may surprise you about visiting Santorini.
Great for: those who’ve heard the hype and want to experience it for themselves.
The highlights
- An early morning visit to Oía, before the crowds and the cruise ships arrived.
- Sunset in Pyrgos with panoramic views of the entire island.
- Dipping our first toe into the Agean at Perissa beach.
- Exploring the ancient city of Thira.
- Stepping back in time with delicious food at Traditional Kafeneio Megalochori.
Naxos: 4 nights
Honestly, Naxos felt like the most authentic ‘popular’ island in the Cyclades. Something about it made me relax the instant we arrived and while it’s still popular on Greek island hopping itineraries, it’s bigger, greener and perfect for a few days of exploring historical sites and visiting some wonderful beaches.
Great for: families, hikers and beach-lovers.
The highlights
- Sunset at the Temple of Apollo: VERY busy but an undeniably beautiful, unique spot.
- Hiking up Mount Zas – said to be where Zeus was given his thunderbolt! I’ll be writing a whole post on this soon.
- Exploring the fig-scented streets of Filoti and Chalki.
- Spotting a turtle swimming just off Plaka beach – although head too far down on the left hand side, and you might encounter some slightly more cheeky sights!
- Sunbathing next to an abandoned hotel at Hawaii Beach.
Paros: 3 nights
Paros is a midway step between Santorini and Naxos: the beaches are nicer than Santorini but the Chora (or old town) has inherited some of its grown up boutiques and delicious fine-dining. This was the island that surprised me most on our Cyclades island hopping itinerary.
Great for: a boujee girls trip!
The highlights
- Taking a day trip to small yet stylish Antiparos.
- Enjoying the best meal of our entire trip at Apollon Garden Restaurant.
- Window shopping in Chora.
- Exploring Naousa’s unique fishing village-meets-party vibe.
Milos: 4 nights
The TikTok island of the moment, Milos is definitely growing in popularity and while it still retains a certain authenticity thanks to its smaller towns, the higher prices indicate it’s well on the way to becoming one of the Cyclades’ big hitters.
This is an island where you’ll particularly benefit from having a car or taking a boat trip.
Great for: a romantic escape.
The highlights
- Sarakiniko Beach’s lunar landscape: it’s popular but totally unique.
- Sunset at Plaka Castle – although don’t be fooled that it’s still a local-only spot!
- Exploring the Ancient Theatre and Catacombs.
- Taking a boat trip to Kleftiko.
Final thoughts on our Cyclades island hopping itinerary
It’s impossible to scratch more than just the surface on a two week trip to the Cyclades. Each island has its own unique charm and this is really the minimum time you’d want to spend on each without feeling too rushed.
We didn’t hit the smaller, less touristy islands and in hindsight, I wish I’d made space for at least one in our itinerary. However, it’s also impossible to choose which island I’d have skipped out on!
My best advice would be to think about your own travel style. Do you like plenty of accommodation options, organised trips and ticking off iconic sights or are you one to avoid anywhere busy and head out into nature? If you’re choosing the latter, I’d head to some of the many smaller, beautiful looking islands in the area, like Sifnos, Koufonisia, Folegandros and Donoussa.
During our trip, we got the perfect balance of sandy beach days, historical sites, micro adventures and most importantly, unforgettable meals at every spot we sat down. I hope this guide helps you to plan a trip that’s just as special.
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