Santorini holiday from Ireland
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20 Top Tips For Island Hopping in Greece

My travel guide to island hopping in Greece has top ferry tips, the best sunset spots, and how to choose the right islands for the ultimate Greek island hopping holiday.

There are many ways to enjoy island hopping in Greece. The seven Ionian islands are a popular choice with many international flights to Corfu, Zakynthos and Kefalonia, as are the 12 larger islands in the Dodecanese, which include Kos, Rhodes and Simi. However, for the ultimate island hopping in Greece experience, it has to be the Cyclades.

The Cyclades are home to pretty white-washed villages in seaside towns and awesome cliff top locations, as well as crystal clear waters, and the famous blue and white Greek architecture. The Cyclades are synonymous with the iconic images of Greek island hopping holidays.

how to book a holiday island hopping in Greece
Klima, Milos

The name ‘Cyclades’ means circular islands (there are 220 in total), which refers to the islands forming a circle around the sacred island of Delos.

We visited Paros, Milos and Santorini over 12 glorious days. Our trip was packed with incredible experiences in stunning locations and I hope my guide to island hopping in Greece will help you plan a trip there soon.

How to plan the best island hopping in Greece vacation

1. Plan your trip in advance

How to plan a Greek Island hopping holiday to the Cyclades

Unless you are a student and have no time line to stick to, it is important to plan a Greek island hopping holiday in advance. Accommodation, flights and ferries are extremely busy during the peak summer months, so the earlier you book the better.

There are 33 inhabited islands in the Cyclades, so it is important to know how to choose the right islands to suit your holiday style and your budget.

You will find everything from the overpriced party islands of Mykonos and Ios, to the quieter, more unspoilt islands of Folegandros and Tinos. Islands such as Naxos and Paros are very family friendly, while Santorini and Milos are very popular with couples.

2. Choose a variety of islands for the ultimate Greek Odyssey

Sarakiniko, Milos
Sarakiniko, Milos

I am basing my choices here on an average 12 – 14 day holiday in the Cyclades. Three or four islands is about as much as I would visit on one trip, as you will need at least three nights in each. You may also wish to spend a few nights in Athens, depending on the time of year you visit – I would avoid Athens in July and August as it will be extremely hot.

Check the exact locations of the islands before you book. For instance Paros and Naxos are right beside each other and are similar in style. You can easily do a day trip from one to the other without having to stay in both islands –  the ferry time is 25 – 50 minutes depending on the vessel.

I would choose Paros OR Naxos and combine with one of the other more unspoilt islands such as Milos OR Foligandros, and possibly Santorini OR Mykonos if you want to see one the iconic Cyclades islands too. This allows you to see the more traditional islands as well as having some glitz and glamour thrown in!

Read: Santorini travel guide, where to stay and top tips

3. Allow at least 3 days in each island, and check ferry times before you book.

family holidays to Santorini

If you want to explore the islands properly you will need at least 3 days in each, and a lot more if you want rest / beach days.

During our visit, there was only one ferry per day from Paros to Milos which departed at 7pm. Similarly there was only only ferry from Milos to Santorini and it departed early in the morning. This meant that although we spent three nights in Milos, we had only two full days  – this wasn’t nearly enough time to explore Milos.

The moral of the story: Check the ferry times before you decide on how long you are going to spend in each island.

4. Stay in Naousa, Paros

Naoussa is the picture perfect Cycladic town. With white-washed buildings, beautiful paved streets and vibrant bouganvilla on every corner, it is an Instagrammer’s dream. It is also home to a stunning harbour that is lined with countless restaurants and bars with outdoor tables at the waters edge.

Naoussa is the place be seen in Paros and it attracts an upmarket crowd looking for a lively but classy night scene. It is renowned as being a foodie town too, so you can expect some top class restaurants here. I loved the buzz and overall glam of Naoussa, its a stunning spot – don’t miss it.

Family holiday in Paros

You can drive around Paros in 90 minutes, so three or four nights would be ample here, although I would happily stay longer. It is home to many more pretty white washed villages, such as Marpissa and Lefkes, as well as traditional fishing villages such as Piso Livado.

There are some great sandy beaches in Paros too, including Kolymbithres which is just outside Naousa, and  Golden Beach, a longer wider beach close to Marpissa.

Sunset in Parikia, Paros

Parikia is the capital and the main port town. It is much bigger and busier than Naoussa, although it also has a pretty old town. While it may be more authentic than Naoussa, it didn’t have the same wow factor for me.

It is the best place to watch the sunset though, with plenty of bars and restaurants lining the seafront. You can prebook bars for sundowners too. We pre booked Evinos cocktail bar and there was no minimum spend.

Make sure to set aside a day to visit to Antiparos. You can catch the ferry from Parikia but it is much busier and harder to park here, plus the journey time is longer – circa 30 minutes.

I suggest going from Pounta where there is a shorter 7 minute crossing. Antiparos has a pretty town to explore – similar to Naoussa, but less busy, and a beach just 8 minutes walk away from the harbour.

TOP TIP: Walk a few minutes past the first beach to Fanari Beach Club. You can enjoy a fabulous lunch here in a gorgeous setting and get two loungers for €20 by the waters edge. Don’t forget to bring your swimwear!

5. Milos is a must

Milos may not have the chic resorts that Paros has, but its stunning fishing villages certainly make up for it. Mandrakia, Klima and Firopotamos are all breathtaking, and each have Milos signature Syrmata or boat houses. You will find some great seafood restaurants here as well as stunning sea views.

Top Tip: Arrange your day so you can visit Medusa Restaurant in Mandrakia. They don’t take reservations so the wait time in the evening is extremely long, but you can get lucky with short wait times during the day.
Mandrakia Milos

There is so much to see and do in Milos, everywhere we went had a different vibe. It is one of two volcanic islands in the Cyclades – Santorini being the second.

The hilltop town of Plaka has a more traditional Cycladic feel, with white washed buildings and cobbled stone streets and is the best place to watch the sunset. However, I found the best place to visit in the Cyclades was Sarakiniko, or Moon beach as it is more commonly known.

cliff jumping in Sarakiniko, Milos - a must visit on a Greek island hopping holiday

This incredible beach looks like a lunar landscape, with layers of white rocks and caves in striking formations. The beach was formed by erosion and fossil layering of volcanic rock by wind and waves.

As well as a small cove beach there are numerous rock bathing areas, and thrillseekers will love jumping off the rocks into the sea. Get there for sunset if you can, the sun setting on the white rocks is spectacular.

One of the other top things to do in Milos is to visit the south west coast of the island, which is only accessible by boat. You can skipper your own small boat for a half or full day, without a licence.

I planned on visiting Kleftiko and even booked a self drive boat in advance ( which is recommended in high season ) but I had to cancel it as we didn’t have enough time. These are great value at €150 for a half day!

I suggest spending at least four nights in Milos.

View boat hire

6. Mix it up – Combine luxury hotels with traditional boathouses or Airbnbs

Boathouses for rent in Milos

Luxury hotels are part and parcel of staying in islands such as Santorini or Mykonos, but in islands such as Milos, where there is so much to see and do, you won’t be in your accommodation as much, so a luxury hotel is not necessary. If your budget allows, try to stay in one of Milos’ Syrmata or boathouses, it is part and parcel of the Milos experience.

Naoussa is THE place to stay in Paros so if budget is an issue, I would choose a cheap hotel here or close by, rather than a luxury option in one of the less appealing resorts.

Where to stay in Santorini: We made the mistake of paying a small fortune to stay within walking distance of Oia where we could see the iconic sunset in the evening. However, the crowds were so intense in August we never got to see it – despite spending four nights there!

where to stay in Santorini

If I was to return I would choose the pretty hill top town of Imerovigli. This has the typical Santorini vibes with a pretty white-washed village, but without the crowds. If you want to see Santorini on a budget, then opt for the beach resorts of Kamari or Perissa.

Read: Santorini travel guide, where to stay and top tips

TOP TIP: Choose a self catering accommodation half way through your trip. You may fancy a night in after all the travelling, especially if you have a late ferry. Get a local take-away and use the washing machine too!

7. Fly where you can

flights to Greek Islands from Athens

You know the small ferries that you see in the movie Mamma Mia? Well don’t expect to see them island hopping in Greece! Any romantic notions you may have of sitting out on deck with stunning ocean views – forget them.

Most likely you will be sitting on a seat in a packed row that resembles a bad flight experience, with poor air conditioning and no access to the outside decks. I have some top ferry tips for island hopping in Greece at the bottom of this post.

While the ferries are extremely efficient and in most cases the only way to travel between the Cyclades, if you have the option to fly, do it! There are direct flights from Athens to the popular islands such as Mykonos, Santorini, Paros, Naxos, Milos etc, and there are direct flights from international airports, to Mykonos and Santorini – including direct flights from Dublin to Santorini.

We flew to Athens and waited for a connecting flight to Paros, rather than take the ferry. We then travelled by ferry from Paros to Milos and onwards to Santorini, before flying home directly from Santorini. This meant we only needed to take two ferries, although we visited three islands.

Crete, whilst not one of the Cyclades islands, is easily accessible from Santorini and is another island offering international flights if you want to avoid additional ferries.

Chania in Crete is served regularly by Ryanair and is a beautiful area with lots of pretty towns and beaches. Aer Lingus announced a new service to Heraklion in Crete for 2024. This would be a great way of combining Crete with the Cyclades and limiting the number of ferries.

Read: Top things to do near Chania

TOP TIP: Most of the internal flights within Greece have higher airfares that include seat selection and checked baggage in the cost, but some include airport lounge access too. We had a four hour wait in Athens but because we chose a higher / inclusive fare, we were able to use the business class lounge with complimentary drinks and snacks. The cost was only €30 more expensive than the cheapest fare.

Cycladic Air have a small schedule between the islands, Paros to Milos and Heraklion in Crete being the most popular choices, but in most cases the ferry will be the only option between the islands.

8. Check in online as early as you can

Cyclades Islands, Greece

Internal flights and ferries in Greece are like buses and are regularly overbooked. Check in online as early as possible for flights – you are less likely to be bumped off if you have checked in online.

9. Call local car hire companies

car rental in the Cyclades

I recommend hiring a car if you want to explore the Cyclades properly. While public buses are available, if travelling during the hot summer months, waiting for a public bus is not ideal.

Parking is generally free and accessible in most islands, with the exception of iconic resorts like Oia in Santorini where you need to pay if you want to be close to the town centre.

I had mixed results renting cars when I was island hopping in Greece. Simply Rent a Car in Paros were a pleasure to deal with, and inexpensive, however, Milos Rent A Car charged me three times more than the local rate.

Average prices in high season are €50 – €70 per day for an average car. If you are being quoted more than that, I suggest calling local car rental companies to check prices, or ask your hotel or accommodation host to recommend a local company to deal with.

Regardless of which car rental company you choose, make sure to take out car hire excess cover before you leave. You will pay €2.99 per day if booked in advance – we were quoted an average of €14 per day locally.

Read: 12 Top tips for renting a car abroad

10. Pre book port transfers

Mandrakia, Milos

Ports can be a little intimidating if you are visiting for the first time. You will see countless people touting for business, from taxis and buses to organised excursions. You will probably arrive feeling a little stressed from battling the queues to reclaim your luggage on the ferry, and it is the ideal place to fall for an overpriced transfer.

If you have port transfers prebooked, either through your hotel or via a transfer company, it will make the whole experience less stressful. You will likely see someone standing with your name on a placard, and off you go!

Check GetTransfers Check Hoppa Transfers

11. Avoid Mykonos and Santorini in July and August if possible!

Our Greek Island hopping holiday was in early August – one of the busiest times of the year. While crowds were minimal in Milos and respectable in Paros, they were far from pleasant in Santorini.

The crowds in the busy resort of Fira during the day – mainly due to it being the cruise ship entry point, and Oia at night time – due to its iconic sunset, were something I had never seen before in my 33 years of travelling!

Santorini crowds for sunset

The best time to go island hopping in Greece is May and September. The islands are less busy, and the meltemi (dry northerly winds) are not around to upset your tummy on the ferries.

If you want to go island hopping in Greece in July or August, I recommend you avoid the busy islands of Santorini and Mykonos, unless you are happy to see the sights at 9am in the morning…

FYI most restaurants, bars and ferries close during the winter.

12. Pre book restaurants and excursions in advance

pre book restaurants for sunset if island hopping in Greece during the summer

Greek island sunsets are some of the best I’ve seen, and places like Santorini are commonly listed as the best places in the world to watch the sunset.  If you want to avoid the ridiculous crowds in Oia, pre book a nice restaurant to watch it.

However, be prepared to pay a hefty price! In many cases you will be asked to pre-pay a minimum amount to guarantee a view, but I’m guessing at this point your Greek island hopping holiday has cost you a small fortune, so make sure you book at least one sunset dining experience! I can highly recommend Sunset Taverna in Santorini, but there are many more great options.

TOP TIP: If you don’t want to pay expensive dining prices, check sunset bars. In most islands there are cocktail bars with sunset views that you can pre book, with a much lower minimum spend.

13. Embrace the Gyros and Greek’s local dishes


Dining out in the Cyclades can be expensive, especially in islands such as Santorini, Mykonos or Paros, so embrace the local dishes while you can.

Gyros are a typical Greek fast food option and consist of a pitta wrapped around chicken or pork with vegetables, sauce and chips. They are similar to kebabs, and trust me at €4 – €6 each, they are a great value option for lunch on the go!

Some of my personal Greek favourites for restaurant dining are Prawn Saganaki – a hot prawn dish in tomato sauce with Feta cheese, Feta Cheese with Honey in Phyllo (filo pastry),  and of course, no trip to Greece would be complete without having a traditional Greek salad ❤️.

14. Book a sunset cruise

The Cyclades are one of the best places in the world to watch the sunset, and watching the sunset while sailing is the ultimate experience.

Most islands have various options to choose from and usually dinner and dinks are included the cost, so its a win win – you can avoid the overpriced sunset dining options!

We booked a private sunset cruise in Santorini and I can highly recommend it. It was expensive, but it was the highlight of our stay in Santorini.

TOP TIP: If travelling with a group or family, it may be worth it to pay the extra for a private cruise, however if travelling as a couple there are many more small group options which are more reasonably priced.

15. Pack light, but bring a colourful wardrobe and surf shoes!

The colours of the Cyclades are pink, blue and white

Island hopping in Greece is by nature a holiday where you will be packing and unpacking regularly, so my advice is to pack light. If travelling during the summer months the most you will need is a cardigan at night time, although temperatures were so warm in August, I didn’t need one at all.

However, vibrant pink Bouganvilla lines many streets, and pretty churches with blue domes are everywhere, so pack some blue and pink items if you want your photos to pop. And don’t forget surf shoes for those must visit stoney beaches.

TOP TIP: Check if your hotel or Airbnb provides beach / pool towels and toiletries to cut down on carrying unnecessary items.

Ferry tips when island hopping in Greece

16. Choose your ferry company wisely

ferry tips for island hopping in Greece

It goes without saying that you will need to use ferries when island hopping in Greece, so make sure you choose the ferry company wisely. Fast ferries such as Seajets have no outside access. Blue Star Ferries have a longer journey time but the overall experience may be better if you are able to sit outside.

It is important to note that the Cyclades islands are notorious for being windy during the summer months, so crossings can be rough – make sure to pack tablets if you are prone to it sea sickness.

Top Tip: Generally speaking, the larger and slower the ferry, the more stable, so you are less likely to feel seasick.

17. Use Ferryhopper to book all ferries

use ferryhopper to book ferries when island hopping in Greece

Ferryhopper is the best website to use for Greek island hopping holidays. It is the Skyscanner for ferries and lists all ferry companies operating on that route. You can book easily on their website and their App is good too.

Once you download the app you can save all your ferry bookings in one place. You will be prompted to check in online and it shows all the information you need in advance. You can also track your ferry in real time, and see if it is on time or delayed.

Search here

18. Book business class on ferries

top tip when island hopping in Greece - book business class on Seajets ferries

Pay the supplement for business class on ferries. I thought this seemed a bit extravagant, but believe me, on our trip from Milos to Santorini, it was the best €20 I ever spent! Delays and unscheduled stops are common, so when our 90 minute journey time turned into 3 hours – I was delighted I had paid to upgrade.

The business class lounge is basic, but you will get a nice comfortable chair in an air-conditioned room and will possibly have an ocean view too.

19. Get there in plenty of time

The harbourmaster runs a tight ship (excuse the pun).  We witnessed people being left at the boarding point simply because the ferry wanted to leave on time – they were told to wait for the next one, which incidentally, was not for another 3 hours.

Arrive at least 30 minutes before the ferry is due to depart and get in line. The Ferryhopper app will track your ship in real time so you can see if it is on time or delayed. If it is delayed there are usually coffee shops or tavernas close by where you can relax until 30 minutes before arrival.

20. Bring snacks

A 500ml bottle of water in most of the Cyclades islands is 50cent, on Seajets, a 300ml bottle is €3.00. The prices on board for drinks and snacks is exorbitant, so bring plenty with you.

I hope this post will help you plan a holiday island hopping in Greece. It is a wonderful experience and I am already planning a return trip to see more of the Cyclades.

While every effort is made to ensure accuracy, prices and experiences are subject to change. Some of the links in this post contain affiliate links, where I receive a small commission if a booking is made, but at no additional charge to you.

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