Island-hopping through the Cyclades in Greece is truly the sort of trip you’ll want to have done at least once. Think white villages with blue domes, hidden beaches, cosy tavernas, spectacular sunsets and ferries that take you from one beautiful island to the next. As far as we’re concerned, this is island hopping in Greece at its very best. During this three-week tour, we visited Santorini, Milos, Sifnos, Paros and Athens. Each destination had its own unique atmosphere. In this blog, we share our full itinerary for island-hopping around Greece, including practical tips, ferry information, accommodation and our personal favourite islands.
General information on Greece
Are you working on a travel plan for Greece? Then check out our tips for the best travel period, daily budget and transport to and in Greece. You’ll find all the information about Greece here.
What is the best itinerary for island-hopping through the Cyclades in Greece? (2–3 weeks)
During our tour of Greece, we chose a route that took us past Santorini, Milos, Sifnos, Paros and Athens. As far as we’re concerned, this is the perfect combination of stunning natural scenery, charming villages, beautiful beaches and a quintessentially Greek atmosphere. It is precisely because each island feels completely different that island-hopping through the Cyclades remains incredibly varied.
We recommend allowing at least two to three weeks for this itinerary. Three weeks will give you plenty of time to explore several islands at a leisurely pace without constantly being on the move. You can relax on the beach, discover lovely restaurants and still see plenty of each island. Personally, we found that much more enjoyable than catching the ferry every two days. Short on time? No problem. You can easily skip one or two islands or spend a little less time at each destination. Do you have more time? Then islands such as Naxos, Ios, Mykonos or Folegandros make for lovely additions to your itinerary.
Tip: we have written extensive blogs for almost all destinations on this itinerary, so you know exactly what to expect.
An example of our 3-week itinerary through the Cyclades
To give you a good idea of the pace of the trip, we’ve set out our itinerary through Greece below. This way, you can see exactly how many days we spent on each island and get a better idea of roughly how much time you’ll need whilst island-hopping.
Day 1: Flight to Santorini
Day 2: Santorini
Day 3: Santorini
Day 4: Santorini
Day 5: Santorini
Day 6: Ferry to Milos
Day 7: Milos
Day 8: Milos
Day 9: Milos
Day 10: Milos
Day 11: Milos
Day 12: Ferry to Sifnos
Day 13: Sifnos
Day 14: Sifnos
Day 15: Ferry to Paros
Day 16: Paros
Day 17: Paros
Day 18: Ferry to Athens
Day 19: Athens
Day 20: Athens
Day 21: Return trip to the Netherlands
As you can see, we deliberately chose to take things at a leisurely pace. Especially whilst island-hopping, we enjoyed not having to spend all our time on ferries, checking in and lugging our suitcases about. We actually enjoyed some of the islands, such as Milos and Paros, so much that, looking back, we would have liked to have stayed there even longer. So do consider what suits your own style of travelling and feel free to adjust your itinerary.
Transport during your tour of Greece
Island-hopping through the Cyclades might sound complicated, but it’s actually incredibly easy to travel between the Greek islands. Almost all the islands are connected by ferries, and on the islands themselves you can easily hire a scooter, quad bike or car. It was precisely that freedom that we loved so much about this trip. One moment you’re boarding a ferry to a new island, and a few hours later you’re riding a scooter past hidden beaches and tiny Greek villages.
1. Travelling by ferry between the Greek islands
When island-hopping, you’ll mainly be travelling by ferry. There are several daily sailings between popular islands such as Santorini, Milos, Paros and Sifnos, and everything is well organised. However, we do recommend arriving well in advance, especially during the high season. Some ports can feel quite chaotic. You can book ferry tickets in various ways:
- in advance online via, for example, Direct Ferries or Ferryhopper
- on site at the port
- through local ticket offices on the islands
Tip: if you book a ticket via Direct Ferries, you’ll still need to have your official boarding pass printed out at a ticket office in the port. The confirmation email alone isn’t enough to board the ferry. The cost of printing an official boarding pass can range from €1 to €5.
We usually bought our tickets one or two days in advance at the harbour itself. Personally, we found that the best option because it gives you a lot of flexibility during your trip. Sometimes you might want to stay on an island a bit longer, or you might decide on the spur of the moment to move on sooner. What’s more, tickets at the harbour were sometimes just a little cheaper than online.
Tip: are you travelling during the high season? If so, be sure to book your ferry tickets online in advance. Popular routes between Santorini, Paros and Mykonos, in particular, can fill up quickly during the high season.
2. Hiring a scooter, quad bike or car on the islands
On almost all the Cyclades islands, you can easily hire a scooter, quad bike or car. As far as we’re concerned, this really is the best way to explore the islands. Especially on islands such as Milos and Paros, you’ll come across hidden beaches, viewpoints and small villages along the way that are almost impossible to reach by public transport. We usually hired a scooter or quad bike because it’s cheap and gives you plenty of freedom. Especially outside the larger towns, we loved simply driving around without a plan and stopping wherever we fancied.
Would you like a bit more comfort, or are you travelling with other people? In that case, a hire car is often a better option. This is particularly true on larger islands such as Paros, or if you have a lot of luggage.
Tip: Do you want peace of mind or to be properly insured? If so, we recommend booking a car in advance via SunnyCars. We personally like this because all insurance is already included, so you won’t have to worry about extra costs or unexpected claims whilst you’re on the road. What’s more, they can ensure your car is ready and waiting the moment you arrive at the port. It doesn’t get any easier than this!
3. Public transport on the islands
On many islands, local buses also run between popular beaches, harbours and villages. This works particularly well on Santorini and Paros. However, we found that you have much more freedom with a scooter or car, and it’s easier to discover the quieter spots.
What’s more, buses in Greece aren’t always on time, and during the high season they can get quite crowded. They’re fine for short journeys or a day at the beach, but for complete flexibility, we’d personally always opt for our own transport.
Our itinerary through the Cyclades in Greece
As far as we’re concerned, the Cyclades are one of the most beautiful places in Europe for a round trip. On this trip, you’ll hop from island to island, discovering a completely different atmosphere each time. From the white-washed streets of Santorini and hidden beaches on Milos to quiet villages on Sifnos and lively promenades on Paros: no two islands feel exactly the same.
As we deliberately chose a mix of popular and quieter islands during our trip, this itinerary gives you a comprehensive overview of the Cyclades. In this blog, we’ll also share some extra tips on alternative islands, hidden gems and handy stops that you might want to add to your itinerary. And to be honest? Even after three weeks, we felt we were still a long way from having seen everything. But that’s precisely what makes island-hopping in Greece so much fun: you always have a good reason to return to these beautiful islands.
1. Santorini
Our trip began in Santorini and, to be honest, it feels quite special to spend your first few days in Greece here. Chances are you’ve already seen Santorini hundreds of times on Instagram or Pinterest you may have seen. Still, we thought it was even more beautiful in real life.
Here you’ll find narrow streets, white houses, churches with blue domes and viewpoints from almost everywhere overlooking the famous caldera. There’s a truly special atmosphere on the island, especially at sunset. Yes, Santorini is touristy. But at the same time, it’s simply a place you have to see at least once. What many people don’t realise is that Santorini is more than just Oia or luxury hotels. You’ll also find black sand beaches, lovely hikes and quiet villages where it’s much less crowded. We therefore strongly recommend staying on the island for at least a few days.
Curious to find out what you can do? Then take a look at our comprehensive blog featuring the most beautiful sights on Santorini.
Where to stay:
- Oscar Hotel: Simple and affordable accommodation close to Fira. Don’t expect luxury, but you can expect tidy rooms, a lovely swimming pool and a great base from which to explore Santorini.
- Ifestia Hotel: A small, modern hotel in the charming village of Firostefani. The rooms are stylishly furnished and some offer stunning views of the caldera.
- Villa Manos: One of the better budget options in Santorini. This family-run hotel is situated close to Fira and boasts a lovely swimming pool, spacious rooms and a peaceful atmosphere. Ideal if you want to explore Santorini without paying top dollar straight away.
- Aethrio Sunset Village: A charming hotel in the heart of Oia. Here, you’ll be staying within walking distance of the famous sunsets, cosy restaurants and the iconic white streets for which Santorini is renowned.
Journey time from Amsterdam to Santorini: approximately 3.5 hours by plane.
Read also: 10x The best Instagram photospots in Santorini, Greece (with map)
Read also: Island hopping in Greece? Here's how to plan a round trip!
2. Milos
After Santorini, we travelled on to Milos, and this island ended up being an absolute favourite of the whole trip. Milos feels completely different to Santorini. It’s quieter and less crowded, even though it’s popular. The island is volcanic, and you can see that everywhere in the landscape. The most famous spot on Milos is without a doubt Sarakiniko Beach, a white rocky landscape that almost looks like the moon. But honestly? Milos has so much more to offer than just this well-known spot.
It was the small fishing villages in particular that we loved. Places like Klima, Mandrakia and Firopotamos still feel truly authentic. Milos also has an incredible number of beautiful beaches with crystal-clear blue water. Some beaches can only be reached via dirt tracks or by boat, which makes it feel even more adventurous. We also found Milos to be an ideal island to explore by scooter or quad bike. Along the way, you’ll constantly come across hidden beaches and viewpoints. Want to find out more? Then take a look at our blog with the best sights on Milos.
Where to stay:
- Captain Giorgantas: A lovely and affordable place to stay in the charming harbour town of Adamas. From here, it’s an easy walk to restaurants, shops and the harbour, where many excursions set off from. Ideal if you want to stay in a central location on Milos.
- Santa Maria Village Resort: A comfortable hotel with a large swimming pool and spacious rooms, close to Adamas. Thanks to its central location, you can easily explore the most beautiful beaches and villages on Milos.
- Chaido Studios (Tripiti): A small-scale accommodation in the charming village of Tripiti. Here, you’ll be staying amongst the white houses and narrow streets for which the Cyclades are famous. A great choice if you’re looking for an authentic atmosphere and a peaceful base from which to explore Milos.
- Maistrali Hotel (Provatas): A simple but charming hotel within walking distance of the peaceful beach at Provatas. Thanks to its location right by the sea and its relaxed atmosphere, this is a lovely place for travellers who want to enjoy the sun, the beach and some peace and quiet.
Journey time from Santorini to Milos: approximately 5 hours by ferry
3. Sifnos
Sifnos was perhaps the biggest surprise of this trip for us. This island is far less well-known than Santorini or Paros, and that is precisely why we recommend it. Don’t expect any major attractions or famous Instagramspots here. Sifnos is much more about atmosphere, tranquillity and authentic Greek island life. You’ll find hilly landscapes, small white villages, walking trails and cosy tavernas where you can while away the hours.
What struck us most of all was how relaxed everything felt here. There’s certainly some tourism, but the island doesn’t feel overcrowded at all. What’s more, Sifnos is known as one of Greece’s best islands when it comes to food. You’ll find lovely restaurants and traditional Greek dishes everywhere. Want to find out more? Take a look at our comprehensive blog featuring the best places to visit in Sifnos.
Where to stay:
- Margarita Karidi Studios: Affordable and centrally located accommodation in the charming village of Kamares. The rooms are simple but comfortable, and thanks to its location close to the harbour, restaurants and the beach, this is an ideal base from which to explore Sifnos.
- Nival Boutique Hotel: A modern and charming hotel in Apollonia, the lively heart of Sifnos. Here, you’ll be staying within walking distance of cosy tavernas, shops and bars, whilst at the same time enjoying a peaceful and comfortable setting.
- NOS Hotel & Villas: Right… this hotel is definitely not within our budget, as it’s one of the most luxurious places to stay on the island, situated close to Kamares harbour. Think stylish suites, a stunning swimming pool and a modern Cycladic design. An ideal choice if you want to treat yourself to a little extra comfort during your tour.
Journey time from Milos to Sifnos: approximately 2 hours by ferry
4. Paros (+ Antiparos)
Paros is one of the most popular islands in the Cyclades and, to be honest, we realised straight away why. The island offers a perfect mix of charming villages, beautiful beaches, lovely restaurants and a lively atmosphere, without ever feeling overly crowded. We particularly loved Naoussa. This fishing village is full of narrow streets, cosy terraces and charming little boutiques. We also thought Lefkes was beautiful – a traditional mountain village where it feels as though time has stood still. What’s more, Paros is ideal if you want to fit in a few days at the beach during your tour. You’ll find plenty of lovely beaches scattered across the island.
Day trip to Antiparos
From Paros, it’s really easy to take a day trip to Antiparos. The ferry journey takes just a few minutes and you can even take your scooter on board. Antiparos feels even more peaceful than Paros and has lovely little beaches and cosy tavernas. We’d definitely recommend it if you want to experience the quiet Greek island life a bit more.
Want to find out more? Take a look at our blog featuring the best sights on Paros.
Where to stay:
- Argonauta Hotel: A charming and welcoming hotel in the heart of Parikia. Here, you’ll be staying within walking distance of the harbour, cosy restaurants and the narrow streets of the old town. Ideal if you want to stay in a central location and make the most of the atmosphere of Paros.
- Parilio Hotel: Perhaps the most beautiful boutique hotel on Paros. This stylish five-star hotel is renowned for its minimalist design, excellent service and peaceful setting. A dream destination for couples seeking luxury, tranquillity and a unique experience.
- Parian Lithos Residence: A stylish, small-scale accommodation where traditional Cycladic architecture is combined with modern comforts. The spacious suites, peaceful setting and stunning views make this an ideal spot for travellers seeking relaxation. At the same time, you’ll be just a short distance from the charming villages, beaches and sights of Paros.
Journey time from Sifnos to Paros: about 3 hours by ferry
5. Athens
We ended our trip in Athens, which we actually thought was the perfect way to round it off. After weeks of island-hopping, it’s nice to see a completely different side of Greece for a change. Athens is busy, chaotic and lively, but at the same time incredibly impressive. Of course, a visit to the Acropolis and the Parthenon is a must, but the city has much more to offer than just history.
It was precisely the lively neighbourhoods, rooftop bars and local restaurants that made Athens so enjoyable for us. There’s a really lovely atmosphere in the city, especially in the evenings. What’s more, Athens is an ideal starting or finishing point for a tour of the Cyclades, as virtually all the ferries converge here.
Where to stay:
Where best to stay depends mainly on what you’re looking for. Do you want to be right in the thick of the action, would you prefer to stay amongst the locals, or would you rather be within walking distance of the Acropolis? Below, we share our favourite neighbourhoods and places to stay.
Accommodation in Psiri
Psiri is undoubtedly one of the nicest neighbourhoods in Athens. Here you’ll find street art, cosy cafés, local restaurants and a lively atmosphere reminiscent of Berlin. What’s more, the Acropolis is just a 15-minute walk away.
- Ederlezi Boutique Hotel: A charming boutique hotel right in the heart of Psiri. The rooms are stylishly furnished and, thanks to the peaceful courtyard and rooftop garden, it feels as though you’ve escaped the hustle and bustle of the city for a while.
- City Circus Athens: One of Athens’ most popular places to stay. It combines the atmosphere of a cosy hostel with the comfort of a hotel. Ideal for travellers who enjoy meeting other people without compromising on comfort.
Accommodation in Plaka
Plaka lies at the foot of the Acropolis and is perhaps the most atmospheric neighbourhood in Athens. Here, you can stroll through narrow streets lined with flowers, stairways, tavernas and historic buildings.
- Cityzoe Athens Suites: A modern boutique hotel with comfortable rooms, a charming patio and a roof terrace overlooking the Acropolis. A perfect base from which to explore Athens.
- Kimon Hotel Athens: Simple yet affordable accommodation in a prime location in Plaka. Ideal for travellers who spend a lot of time out and about and want to stay in a central location.
Accommodation in Monastiraki
Monastiraki is the bustling heart of Athens. Here you’ll find charming squares, markets, rooftop bars and many of the city’s most famous sights within walking distance.
- Muse Urban Suites: Modern, spacious flats with a fully equipped kitchen and an excellent location close to the underground station and Monastiraki’s central square.
- 360 Degrees: A popular hotel right on Monastiraki Square. The highlight is undoubtedly the roof terrace, where you can enjoy a magnificent view of the Acropolis.
Journey time from Paros to Athens: about 4.5 hours by ferry
From the port of Piraeus, it’s just a few minutes’ walk to the metro station. From here, you can easily travel on to the city centre or Athens Airport.
Please note: you can easily get from the city to Athens Airport as there is a direct metro and train service. However, please bear in mind that you will need to buy an Airport Ticket. A standard 90-minute ticket is not valid for the journey to and from the airport, but only within the city itself.
Alternative itineraries for island-hopping in Greece
Greece has much more to offer than just the well-known Cyclades islands. Precisely because each archipelago has a completely different feel to it, you can tailor your itinerary entirely to your own preferences. Are you looking for more nature, quiet beaches, charming villages or, on the contrary, lively islands? Then these are some lovely alternatives for your tour of Greece.
1. The Ionian Islands (greener and more tropical)
Are you looking for more nature, green mountains and clear blue water? If so, the Ionian Islands are probably a better fit for you than the Cyclades. These islands lie off the west coast of Greece and have a completely different feel to them.
A lovely route: Corfu → Lefkada → Kefalonia → Zakynthos
Zakynthos and Kefalonia, in particular, are renowned for their stunning bays and white beaches. Personally, we think this is a brilliant route if you’re looking for more nature and that road trip vibe.
2. The Sporades islands (quieter and less touristy)
Would you prefer to get away from the crowds? Then the Sporades are a brilliant choice. Here you’ll find lush green islands with pine forests, quiet beaches and a much more relaxed atmosphere.
A lovely route: Skiathos → Skopelos → Alonissos
These islands are perfect if you love nature, walking and small villages. What’s more, they’re far less crowded than, for example, Santorini or Mykonos.
3. Adding extra islands to your Cyclades itinerary
Would you like to follow the Cyclades route but not our exact itinerary? That’s no problem either! You can easily extend your Cyclades itinerary to include other or additional islands such as:
- Naxos: perfect for hikes, beaches and traditional villages
- iOS: a friendly atmosphere with lovely beaches and a lively nightlife
- Mykonos: luxury hotels, beach clubs and lively evenings
- Amorgos: more rugged, quieter and ideal for walkers
Frequently asked questions about island hopping in Greece
1. What is the best route for island-hopping in Greece?
For your first island-hopping trip, we’d definitely recommend the Cyclades. We found the combination of Santorini, Milos, Sifnos and Paros particularly perfect, as each island has a completely different feel to it. But whether this is the best itinerary for you is something only you can decide!
2. Which Greek islands are the least touristy?
Sifnos, Amorgos and some of the Sporades islands still feel a lot quieter than popular destinations such as Santorini or Mykonos. Especially outside the high season, you can still discover the real, authentic Greece here.
3. How much does island hopping in Greece cost on average?
The cost of island hopping in Greece naturally depends on the season, the islands you visit and how luxuriously you wish to travel. On average, you can expect to budget around €75 to €150 per person per day, including accommodation, transport between the islands, food and activities.
During our trip, we noticed that accommodation and ferries, in particular, can make a big difference to your budget. If you’re travelling in May, June or September, prices are often considerably lower than in July and August. Furthermore, islands such as Santorini and Mykonos are generally more expensive than, for example, Sifnos, Milos or Naxos.
For a two-week tour, we recommend allowing for a total budget of around €1,250 to €2,000 per person, excluding flights. If you opt for small-scale hotels, local tavernas and regular ferries, you can travel much more cheaply!
4. Can you book a last-minute island-hopping holiday in Greece?
Yes, that’s usually fine outside the peak season. We often book last-minute ourselves, and that can sometimes save you a lot of money. Accommodation and ferries in particular are often still readily available outside July and August. Check out WeFlyCheap: last-minute deals to Greece.
5. Which is better: Santorini or Mykonos?
That depends entirely on what you’re looking for. We found Santorini more impressive in terms of views and atmosphere, whilst Mykonos is popular for its beach clubs, luxury hotels and nightlife.
6. What are the most beautiful beaches in the Cyclades?
Personally, we thought the beaches on Milos were the most beautiful. Sarakiniko Beach in particular, and the hidden coves dotted around the island, were truly special.
7. Do you need a car or a scooter whilst island-hopping in Greece?
Not necessarily, but we do recommend it. Especially on islands such as Milos and Paros, you’ll discover far more hidden spots if you’re travelling by scooter, quad bike or car.
Are you planning to hire a car? If so, we recommend booking a car in advance via SunnyCars. We personally like this because all insurance is already included, so you won’t have to worry about extra costs or unexpected claims whilst you’re on the road. What’s more, they can ensure your car is ready and waiting the moment you arrive at the port. It doesn’t get any easier than this.
8. What is the best ferry company in Greece?
During our trip, we mainly used Blue Star Ferries and Zante Ferries. Both worked very well. We often found Blue Star a little more comfortable for longer routes.
9. Is it easy to eat vegetarian or vegan food in Greece?
Yes, absolutely. Especially on the popular islands, you’ll find more and more vegan cafés, healthy brunchspots and vegetarian restaurants. What’s more, many Greek dishes are vegetarian by nature.
10. When is the best time of year for island hopping in Greece?
We personally found May, June and September to be the best months. The weather is lovely and warm then, but you largely avoid the extreme heat and crowds of July and August.
11. Is island-hopping in Greece suitable for beginners?
Yes, the Cyclades are the perfect choice for your first island-hopping adventure. The ferries run regularly, the islands are relatively close together, and you’ll find accommodation and restaurants everywhere. Worried you might forget something on your trip? Download our Free packing list for trips to Europe!
12. Do you need to book ferry tickets in advance?
During the high season, we would definitely recommend this, especially for popular routes such as Santorini ↔ Paros or Mykonos ↔ Santorini. Outside the high season, you can often book at the last minute without any problems.
Island-hopping through the Cyclades in Greece
As far as we’re concerned, island-hopping through the Cyclades is one of the best ways to discover Greece. It’s precisely the variety between the islands that makes this tour so special. One moment you’re strolling through the white-washed streets of Santorini; a few days later, you’re riding a scooter past hidden beaches on Milos or enjoying a leisurely lunch in a small village on Sifnos. No two islands feel the same, which means you’ll never be bored for a single moment on this trip.
And to be honest? We can totally see why so many travellers keep coming back to Greece. And there’s a good chance you’ll feel exactly the same after this trip. Because even after three weeks of island-hopping, we felt we were still a long way from having seen everything. We hope this itinerary helps you plan your tour of the Cyclades. Do you have any tips or questions of your own? Feel free to send us a message via Instagram. Thanks to you, we might just discover a new Greek island for our next trip.
If, after reading this blog, you still have any questions about this route or the destinations, please feel free to send us a message via Instagram or e-mail us at info@thousandtravelmiles.nl.
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