Island Hopping in the Cyclades – The Perfect Greek Island Itinerary

Updated on April 19th, 2024

If you are planning your first trip island hopping in the Cyclades, Greece then this is the guide for you. After visiting the area 6 times, here are my highlights of the best way to see 4 very different islands (Santorini, Paros, Naxos & Milos) as well as get the most out of a day in Athens.”

Where?

Athens, Paros, Naxos, Milos & Santorini
Cyclade Islands, Greece

Why?

Island hopping in Greece is my favourite way to spend 2 weeks in Europe. I love it so much, I have been 6 times! Although I have studied a number of different archipelagos in the region, I always come back to the Cyclades Islands. In my opinion, these are the best islands to visit in Greece. Here I give you the chance to see 4 very different islands & dip your toe into the history of Athens. All in one 14-day trip! I recommend 2 days in Athens & then 3 at least on each of the islands. Greek Islands travel is easy due to regular ferry services from Athens & between all the Cyclades islands. Here, I give you the itinerary I used on my last visit in 2018.

Island Hopping in the Cyclades – The Perfect Greek Island Itinerary

Getting Around

If this is your first experience of visiting the Greek Islands, then please check out my First Timer’s Guide. It gives you all the details on when to go, how to navigate the ferries & more information to help you choose the perfect islands for your trip. To follow this travel guide I recommend you fly into Athens & out of Santorini. The first stop, Paros is 5 hours on a ferry from Athens.

See also: First Timer’s Guide to Greek Island Hopping

Athens

I started in Athens for a 36-hour whistle-stop tour. The main objective was to see the Acropolis. If you choose to start your Greek Odyssey here, I have a few top tips:

• Go early to avoid the crowds & the heat. Also, take advantage of this by getting the perfect photos before all the people catch up with you!
• Don’t take a tour & you can have the place almost to yourself, at least initially.
• Wear shoes with a good grip. The marble floors can be lethal!
• The Acropolis Museum is highly recommended & was the only thing we actually regretted not doing for our whole trip. If in Athens & you have enough time, please visit. I have it on good authority that you won’t be disappointed!

Where to stay?

We chose to stay in the Plaka district of the city. This is only a short distance from the Acropolis & if you are lucky you will get great views. There are also plenty of choices for bars & restaurants in the area.

There are loads of fantastic tours in Athens, Greece, here are a few of the most popular you can choose from:

Booking.com

Paros

The first stop on our Greek Island-hopping itinerary was Paros. We came to Parikia on a large passenger ferry from Athens which was an experience in itself. As a foot passenger, you wait on the car deck as they slowly lower the gate. From there you get your first glimpse of the island with its iconic windmill. We chose to stay in the picturesque port town of Naousa which was a 15-minute taxi ride away.

When we arrived in Paros, one of our priorities was to spend some time relaxing on the beach & there were plenty of options to choose from.

Monastiri Beach

Monastiri is a 10-minute boat ride away. It is very picturesque, with hiking trails & an archetypal blue-domed church. The water is crystal clear & it is sheltered from the wind. This makes it a popular choice among tourists & locals. Make sure you take a walk to the church for some beautiful photo opportunities!

Santa Maria Beach

The next day we took a recommendation & got the bus to Santa Maria. We had been told to head for ‘Small’ Santa Maria. However, as we got off the bus & didn’t see any signs, we ended up at ‘Big’ Santa Maria instead. It was very busy & packed with very expensive sunbeds.

Also recommended:

Lageri Beach is a nudist beach but comes highly recommended as having a lovely atmosphere. Apparently, you don’t have to fully strip to take your place on the sand!

If you have transport or would like to go further afield:

Lefkes is a village in the centre of Paros which is picturesque & worth a visit for exploring its traditional streets.

Golden Beach is supposed to be lovely but is a much longer bus journey to get to.

Shopping

In Naousa, the shopping was some of the best we saw in terms of quality & variety. Be prepared that the island is not cheap. However, they have an excellent choice & you can spend hours getting lost among the narrow streets … spending a small fortune!

Where to stay?

Naousa is a small port village & I would recommend staying close to the centre if you can. Wandering the maze of streets in the evening & eating by the water is part of the quintessential Greek Island-hopping experience. Make sure to book your restaurant if you are visiting in peak season.

Booking.com

For more details, head to What to do in Paros for 2 days.

Naxos

Next on my list of islands to visit in Greece is Naxos. In comparison to Paros, Naxos is less expensive & also has some of the best beaches in the Cyclade Islands (in my opinion).

Sunset at Portara (Apollo’s Temple)

This is a must-do in Naxos & so close to the port that you can see it as you come in on the ferry.

Dusk is a great time to visit so you can see the sun go down behind the temple. If you do go at this time though, expect to have competition. It is breathtaking & well worth the effort.”

Agios Georgios (St Georges) Beach

The beach is within an easy walk from the port & the town. We loved it here so much that we barely moved for 3 days & it was great to catch up on a bit of reading!

Hire a car/ATV/moped & go exploring

In previous years I have hired an ATV & used it to explore the island. Naxos is the biggest & most fertile island in the Cyclades so it is well worth hiring your own transport & heading to the centre, particularly at dusk where the light makes it look even more beautiful.

Old Town (Old Market Shops)

As with all the islands, one of the most fun evening activities is to get lost in the maze of streets in the old town, in particular going deep into the Old Market Shops. There are some amazing jewellery stores & my favourite, locally made pottery shop – Morfes Workshop.

Plaka Beach

Plaka Beach is less busy but with restaurants & a pleasant excursion if you have your own transport. The buses also go there from the terminal at the port.

Where to stay?

We stayed in the Iliovasilema Hotel which was a great location in the main town of Chora, between the port & Agios Georgios Beach, with a pool.

Booking.com

For all the details, check out 21 Best Things to Do in Naxos

Milos

In my opinion, Milos is one of the best Greek Islands to visit. We arrived in Milos at night but were staying in the port town of Adamas which meant a flat, easy walk to our hotel.

Sarakiniko Beach

We had been told that this is a must-do when visiting Milos & I couldn’t agree more. We got the bus from the main square & it felt like we were walking on the moon. Sarakiniko is nicknamed “Luna Beach”.

The beach is made of volcanic white rock which has been eroded by the wind & waves. It literally looks like you are walking on marble.”

Take a couple of hours to explore, swim, relax & marvel at the beautiful rock formations. Be aware that there is limited beach & no shade. Make sure you have your camera as this spot is stunning!

Plaka

We got the bus to this picturesque, inland village. Our first stop was to climb to the Kastro, a church on top of one very dominant hill. My advice is to get there early & go straight up. This is partly because you can avoid intense heat & too many people. However, it also stops you from looking at it for a long time & talking yourself out of the climb! It looks way worse than it actually is! The views from the top are well worth the effort as you can take in the whole island from here.

Trypiti

From Plaka, we walked via the windmills of Trypiti. On closer inspection, they are all converted into houses. Some are available to rent which struck me as an opportunity for a unique experience, check out  Aera Milos for details.

Klima

Klima is a hot 30-minute walk downhill from Plaka. If you choose to brave the walk, please bear in mind that coming back up is a challenge (we hitched!).

Klima is a collection of gorgeous fishermen’s cottages. The houses are all painted brightly, with the sea lapping against them. It’s very picturesque & with a welcome restaurant in the centre for some shade & a chance to cool off.

Round Island Boat Tour

This was the 2^nd time I’d visited Milos & my second boat tour. I can report that not all are created equal! This time we opted to go with Eleni Sailboats & I would highly recommend the company. It was owned by the same family business as our hotel & clearly nurtured in the same way to make the experience special. The tour was €90 per person (cash only), payable on the day.

I was so blown away by the beauty of Milos that I have dedicated 2 whole blog posts to it:

Milos Boat Tours – How To Choose The Perfect Milos Sailing Tour For You

What to Do in Milos – 21 Incredible Reasons to Visit

If you would like to book your perfect Milos experience, check out my personally curated list of activities HERE.

Where to stay?

We stayed in  Hotel Eleni, very close to the port in Adamas. I could not recommend it highly enough. The hotel is run by Eleni herself who is the most adorable, enthusiastic & helpful person you could wish for at reception! Apart from a lovely clean room, and a great outside terrace, the breakfasts were amazing (a huge array of options for only €7.50 per person).

Booking.com

Santorini

Santorini is one of the most famous Greek Islands & as such the perfect final stop in this Greek Island itinerary. The ferry into Santorini is an experience that doesn’t really do justice to the beauty of the island.

Sunset in Oia

Oia is a must-visit in Santorini, especially for the sunsets but don’t expect to be alone! It feels like everybody in the whole of Greece is amassing for the descent of the sun once you arrive in Oia. For the best spots & ‘front row’ make sure you arrive early. When we were there sunset was around 8pm & people seemed to be ‘in situ’ from 6.30pm. If you’re hoping to get a sunset view with your drinks or dinner, then definitely book ahead. It may happen every day but in Oia, the sun gets applauded as it disappears over the horizon!

Fira to Oia Walk

This is a 10km walk along the edge of the caldera & I couldn’t recommend it highly enough. It took us 3 hours, mainly because we stopped a lot to take photos as the views were spectacular. My advice is to start early – we left at 7.20am to avoid the main heat & the sun in our eyes all the way. We were very grateful we did this as we arrived in Oia at 11am with the crowds & heat building.

If you are planning to do the walk, then I would also check the weather. We went on a cloudier day which was perfect. It’s a moderate walk with some hills but make sure you also wear sturdy shoes as there are some parts where you walk on ash & gravel. Flip Flops would be challenging but that said I did it in my Birkenstocks & was fine, if a little dusty!”

For all the details you need to tackle this walk check out my in-depth post on the hike from Fira to Oia.

Cinekamari

Named as one of the Top 10 outdoor cinemas in the world, & a snip for €8. The films start at 9.30pm but the doors open at 8.30pm to allow you time to settle, buy your cocktails & snacks. If it’s a new or popular film then I would advise arriving early as the capacity is only 185. We saw Mamma Mia…it was perfect!

Kamari Beach

This is a black volcanic coarse sand beach, a short bus ride from Fira. Most beaches on Santorini are black sand (except Red Beach of course!). As a result, the sand gets very hot. I would, therefore, recommend hiring a bed & keeping your flip-flops on when you go for a swim. There are rocks by the water so if you get to the sea & back with your dignity then you have my utmost respect!

Santo Wine

For our final night, we booked a sunset slot (7.30pm) for a Wine Flight Tasting Session at Santo Wines. You can get the bus for Perissia & ask the driver to stop. The view, as everywhere in Santorini was spectacular & another angle again on the caldera & the sunset. A perfect way to end a perfect Greek Island Hopping experience!

If you would like to book your perfect Santorini experience, check out my personally curated list of activities HERE which includes food & wine, hiking, sailing, and e-bike tours.

Where to stay?

We stayed at Sweet Pop Hotel which was an oasis just steps from the madness of the main square. It has very funky décor, small but functional rooms & a pool to relax by during the day. The staff were all very friendly & helpful with recommendations.

Booking.com

Where Else?

You can take boat tours around the caldera that take you to volcanic springs & the White Beach (which I have never done). You can also take an excursion to Red Beach which unfortunately we didn’t get time for on this occasion.

Here’s some videos of some new Islands that I visited in 2022. Hydra, Syros, Tinos, Anti-Paros and Parakia

For everything you need to plan your visit, check out my Ultimate 2 Day Santorini Itinerary.

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