“Greece just has a way of making you feel alive and at home at the same time.”

So says self-employed hair stylist and content creator Siobhan Dodd from Sevenoaks in Kent, who spends the winter months carefully planning every detail of her next summer holiday – providing an escape from the short days and cold nights of January in the UK.

This time, it took Siobhan, who studied the classics at school and has been hooked on Greek mythology ever since, two months to plan her 12-day island hopping adventure around the Cyclades, visiting islands many have probably never heard of – one of which has just 150 permanent residents.

Travel fan Siobhan explained: “I usually start dreaming up destinations and playing with itineraries during January, most often on a Sunday morning in bed, instead of reading the papers.”

Siobhan lives with partner Al, a musician, and they’ve been together for 12 years. She also has 20-year-old son, Xander, whom she says comes and goes (mostly with a bag of washing) while he’s at university!

Siobhan (pictured above in Iraklia) explained what she loves about Greece and opened up about her recent trip with Al. She said:

I’ve had a fascination with the Greek islands since I was a teenager and I absolutely love planning holidays, especially island-hopping adventures. I think I find as much joy in the planning as I do in the travelling.

I work long hours – usually six days a week – so my holidays are something I really cherish. I think it’s really important to try and strike a work/life balance, whenever possible. Holidays are essential, not just to rest and recharge, but to learn about new places and cultures. I absolutely love discovering different foods, local traditions and the history behind each destination.

Plus, there’s the added advantage of being able to step away from the daily routine and see the world with fresh eyes, even just for a little while. It always leaves me feeling inspired, grateful and somehow a little more me!

Favourite holiday destination

I have so many places that I love that it’s hard to choose a favourite. They all have different meanings for me and they each evoke different emotions. Summer means Greek islands, spring probably a European city break and for autumn/winter, it’s got to be the Caribbean for a dose of sunshine, sea and reggae!

My love for Greece

The first Greek island I visited was Rhodes, when I was 21. Since then, I’ve travelled to 18 Greek islands (so far), including 11 in the Cyclades. I’ve also been to Athens several times.

Greece is a country I keep going back to and each trip just adds to the love I already have for it.

Greek island hopping

I’ve recently returned from an island-hopping adventure around the Cyclades islands of Greece with Al. We flew from London Gatwick to Santorini on the 30th of June and began our trip from there, travelling between the islands by ferry.

We spent three nights in Naxos, followed by two nights on the tiny and tranquil island of Iraklia. Then it was on to Paros for three nights (we spent a beautiful evening on its tiny & beautiful neighbour, Antiparos) before heading to Ios for the last three nights. We finished up with a final 10 hours back in Santorini before catching our flight home.

It was the perfect mix of discovery and downtime. Each island offered something a little different and we loved every moment of it.

Where are the Cyclades islands?

The Cyclades is a group of islands in the Aegean Sea, south of Athens and north of Crete. They’re known for their distinctive, picture postcard architecture. Think whitewashed houses and blue-domed churches, as well as stunning beaches.

There are around 220 islands in the Cyclades – some just being rocks poking out of the sea – with the most popular being Santorini, Mykonos, Naxos, Paros, Ios, Milos and Syros. Just 33 of the 220 are inhabited.

Planning your island hopping trip

I honestly get almost as much enjoyment from planning the trip as I do from going on it! I always plan and book my holidays myself and never use a travel company.

With Google at my fingertips, I can find everything I need, from flights, to ferry schedules to hotels. It means I can tailor my trip exactly how I want it!

Getting to Greece:

We flew from London Gatwick directly to Santorini, which was our starting point, flying with Easyjet, with a flight time of just over 3.5 hours (cost: £155.55 each for return flights).

From there, we travelled between the islands by ferry and, with the help of the Ferryhopper app, it was all surprisingly easy to organise.

You can see all the routes, timings and prices in one place with Ferryhopper and you can book your tickets in advance. The ferries themselves are reliable (they occasionally run late, but the app will always notify you, if so). Hopping from one island to the next became part of the fun.

I booked all of our ferries in advance. I like to have things organised, especially when travelling between islands. Using Ferryhopper made it really easy to map out the route and timings, and booking ahead gave me peace of mind that everything was in place.

It also helped avoid any last-minute stress or changes, especially during peak season when ferries can get busy.

The longest ferry crossing was from Santorini to Naxos, which took two hours. We could’ve taken a faster ferry, but sometimes it’s lovely to take the slower ones so that you can sit on deck and just take it all in.

The ferries cost anything from €8 up to €40, per person, per trip, depending on how long the journey was and also which line we took. The slower ferries for example, are considerably cheaper.

 

What’s so good about island hopping?

I simply love the freedom it gives you. And yes, you can set a budget if you need to – or not…that’s the beauty of it. You can make it work for you!

Gone are the days of me staying in hostels (I’m a bit long in the tooth for that now), but that doesn’t mean I need luxury everywhere I go. If I discovered a tiny island with only the most basic accommodation, I’d still happily stay in it. It’s all part of the adventure.

The best time to go island hopping

We deliberately decided to go before the school holidays broke up. We enjoyed cloudless, blue skies in early July, beautiful long, sunshiny days, with temperatures hovering in the lower 30s, with the cooling of the Meltemi winds. In a word…the weather was perfect!

Now that I’m no longer tied to school holiday dates, I try to avoid them whenever I can. Plus, this makes travelling slightly cheaper and a whole lot less busy.

Saying that, Santorini was super busy, but then it always is. With its international airport and cruise ships arriving daily, the crowds are pretty much a given.

The other islands we visited on this trip (those only reachable by ferry and not on the cruise ship circuit) were much quieter. Some were blissfully peaceful, with quiet beaches and a much slower pace. It was the perfect balance.

Our island hopping itinerary:

Days 1-3: We flew from London Gatwick to Santorini, where we had three hours. That gave us enough time for a little lunch before catching a ferry to Naxos, where we spent three nights

Days 4-6: From there, we headed to the tiny island of Iraklia for two nights of total peace and quiet

Days 7-9: We then moved on to Paros, which I always enjoy, for three nights. Paros has just the right balance of pretty villages and great food and perfect sunsets. Mind you, you could argue that every Greek island has the perfect sunsets!

Days 10-13: After that, we spent three nights in Ios, which surprised me in all the best ways. It was much calmer than I expected and really beautiful.

We finished the trip with a final short stop in Santorini, catching up with friends before flying home. It was a really lovely mix of islands – each one different and all of them memorable in their own way.

Greek island details:

SANTORINI: this island still has me. I’ve known it for years and somehow I still find my way back to the corners no-one else looks for.

Santorini facts: unashamedly beautiful, iconic Santorini is the largest island of a small, circular archipelago and is the southernmost member of the Cyclades, with an area of approximately 73 km² (28 sq mi) and a population of around 16,000.

Siobhan says: Santorini is stunning, without a doubt, but it’s also buzzing with tourists and cruise ships, with a busy, bustling vibe. It’s a place full of energy and beauty, but it can also feel quite hectic!

It can also be more expensive. The busier the island, the more expensive it’s likely to be, as a general rule. For example, an Aperol Spritz in Santorini would set you back around €12, whereas in Iraklia it was €8, and the other islands, somewhere in between.

Iraklia (and some of the other smaller islands) are a world apart from beautiful, bustling Santorini, but I love both. The pace slower, the beaches quieter and the sense of peace and calm was incredible. It felt like stepping into a completely different world. Both have their charm, but sometimes you just need that quiet, untouched escape.

Where to stay in Santorini: we were only here for a few hours, but we always stay at The Homeric Poems (above) in Firostefani (my favourite hotel). Rooms approx €450 per night in peak season.

 

 

NAXOS: open-hearted and generous, with wild and beautiful beaches and the prettiest old town. The food alone is unforgettable.

Naxos facts: the largest island in the Cyclades, it has around 9,000 inhabitants and, according to Greek mythology, the young Zeus – the Greek god of war and thunder – was raised in a cave on the island.

Where to stay in Naxos: we stayed at the gorgeous Argo Boutique Hotel (above) in the main town (15 minutes’ walk from the port ). Cost: £150 per room, per night.

Where to eat in Naxos: The best restaurant we ate at in Naxos is called Irinis, which serves organic produce. It is typically Greek and utterly delicious. The complimentary slices of milk pie and orange pie were heavenly. The price for our meal for two was around €45, including wine and beer. We ate there every night for the three nights we were on Naxos.

 

IRAKLIA (above): quiet and unapologetically itself. No performance, no polish – just deserted beaches, endless sea, sky and stillness. And oh, so very quiet! We stayed for just two nights, but how I wish we’d had longer.

Iraklia facts: now with just 150 inhabitants, in the mid-1890s, an archaeologist discovered an ancient inscription banning goats from the island – with the penalty for introducing them being death! However, by the 20th century, the island was largely uninhabited – other than by goats – earning it the name of ‘goat island’!

Iraklia is still off the beaten track, so the crowds haven’t arrived yet! The prices reflect that too.

Siobhan says: As a hairstylist, I spend my days up close and personal with people and, as much as I love them, sometimes, I just want to go somewhere away from people – somewhere I can hear my own thoughts and recharge my batteries!

Iraklia is the perfect escape. It’s a tiny, beautiful island with serene turquoise waters, quiet, empty beaches and a pace of life that lets you breathe. It’s peaceful, untouched, and offers the kind of calm that resets your soul. A place where you can simply just be!

Where to stay in Iraklia: we stayed at the perfect Cosmos Studios, 300 metres from the port and about 1,000 metres from Livadi Beach. Cost: £88 per night, per studio.

Where to eat in Iraklia: in Iraklia it has to be Syrma Taverna, which has beautiful views and delicious food. I had the best beetroot salad ever. It was so lovely that we literally stayed here all day. Price wise, it was around for two €40 for dinner.

 

PAROS: fun, pretty and slightly busier than Naxos, but without the crowds of Santorini. It’s a bit like stepping into a Mamma Mia set, especially Naousa. Think pink bougainvillaea, blue shuttered windows and music drifting down whitewashed lanes.

Neighbouring Antiparos, a small island less than one nautical mile from larger Paros, is understated and quietly refined. It’s sophisticated, without showing off. Antiparos is very pretty and she knows exactly who she is!

Paros facts: It’s hard to imagine now, but during WWII, Paros was occupied by the Italians, then the Nazis, the latter imposing brutal rule from the beginning, including forced labour. Local opposition to the occupation was apparently led by 23-year-old Nikolas Stellas, who was publicly hanged, becoming a symbol of resistance.

Where to stay in Paros: we stayed at Kentra House, Parikia (above), which is hidden away behind the bustling port, with its own little roof terrace and resident cat! Cost: £140 per night.

Where to eat in Paros: our favourite place to eat on this leg of the trip was actually in neighbouring Antiparos, in a restaurant called Pantelis. The setting is beautiful – right on the water’s edge. This is a place where you’d like to stay forever. The food was delicious too, a little bit pricier, but definitely worth it. The total bill was around €60 for two.

Sadly, I can’t personally recommend anywhere in Paros as we had a succession of poor meals there this time, which was just bad luck, I guess.

 

IOS: youthful and beautiful, with stunning views, Ios feels like Santorini’s little sister! It’s busy, but with lots of quiet corners too.

Ios facts: the island has a rich history, with connections to the legendary poet Homer. The island is believed to be his burial place, although the exact location of his tomb is debated.

Where to stay in Ios: we stayed at the stunning Katerina Hotel (above), which is run by the most delightful family. It has echoes of Santorini, but with a charm all of its own. Cost: £156 per night.

Where to eat in Ios: my favourite restaurant in Ios was a place called Seven Eleven, situated in the main town of Chora, serving simple Greek cuisine. just how grandma used to make. It’s very reasonably-priced too, with dinner costing around €15-€20 each.

My favourite Greek island

Santorini will always have my heart! It was my first love – and you never quite forget your first but Folegandros (below) –  located between Paros and Santorini – is a close second. It has the same dramatic views and whitewashed beauty as Santorini, just without the crowds. It feels more untouched, more peaceful and more real, somehow.

And then there’s Iraklia, which probably ties for second, if I’m honest. It’s tiny and quiet, with the most beautiful turquoise water and a kind of silence you very rarely find anymore. It’s heaven on earth, truly.

There are definitely some islands I wouldn’t rush back to, but only because there are still so many I haven’t seen yet. That’s the real challenge…too many islands, too little time! There are a few I’d happily return to again and again if I could.

Plus, I’ve always found the Greeks to be the nicest, kindest and most generous people I’ve ever met. Some of my best friends are Greek and every trip just reminds me how welcoming and warm-hearted they are.

 

Travelling light with a backpack

Even as a content creator, with a love of clothes and shoes, I travel light. I love having the freedom of a backpack rather than a heavy and, let’s face it, cumbersome suitcase – especially when it comes to getting on and off ferries. I also love being able to start the holiday as soon as the plane lands, with no waiting around at baggage claim.

A game changer for me has been Easypack Pro packing cubes. They keep everything organised and make travelling so much easier. Honestly, I don’t know how I managed without them.

Also, I always pack at least one pair of Vionic shoes as, not only are they lightweight and fashionable, their orthotic insoles are incredibly comfortable and supportive, meaning you can them wear them dawn to dusk. That makes them the perfect travel companion and I have numerous pairs.

 What to love about Greece

Everything – absolutely everything.

The colours, for starters: the dazzling white sugar-cube buildings, those iconic blue domes and the sunrises and sunsets that live in your memory forever.

The food….oh the food!  The tomatoes, the aubergines and all the fresh, vibrant flavours.

Then there’s the history, the stunning landscapes and the warmth of the people. It all comes together to create something truly magical.

 

Island hopping travel tips

1. Pick an island… then pick another… and another… and just follow your dreams!
2. Don’t over-plan. Part of the excitement is discovering what each island has to offer
3. Give yourself time to breathe and explore. In my experience, three days  is a good amount of time to get the taste of a place
4. And, finally, always enjoy the unexpected -because that’s where the real adventure begins

Useful apps and websites for Greek island hopping

Here are a few of my go-to apps and websites:

• Skyscanner: I always check flights here and it’s is great for comparing prices and spotting the best times to book
• Ferryhopper: super easy to use and it’s fantastic at keeping you up to date with ferry alerts in the day
• Booking.com: again, very easy to use, with a great range of accommodation to suit every budget and the added bonus is that you get rewards through its loyalty programme too.

Where next?

My birthday is coming up in September, and this year I’ve decided to spend it in Greece… again!

I’m planning to explore some different islands this time. I have a few new ones (to me) on the table, such as Sifnos, Serifos, Amorgos, Koufonisia, Anafi and Sikinos. The possibilities are endless – and that’s half the fun. I will be travelling solo for part of the trip, with Al joining me midway through this Greek adventure.

Then in October, I’m heading to Antigua – one of my absolute favourite places.

I love the turquoise seas, the white sandy beaches and that unmistakable Caribbean vibe.

The world is meant to be discovered and explored. It’s out there waiting – we just have to take the first step and then go find it.

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