This blog was actually inspired by a client who got in touch last week asking about some of these islands. It reminded me of some of my own experiences in the Greek Islands. To be fair, Santorini and Mykonos get a lot of attention. They are basically the Kardashians of the Greek islands: glamorous, always in the spotlight, and sometimes a little too busy for their own good. Lovely, yes. Relaxing, not always. I can attest to this. 

If your idea of a great holiday is a bit more low-key, a bit more authentic, and a lot less “queueing to photograph the sunset with 3,000 strangers”, then Greek island hopping on some of the lesser-known islands might be exactly what you are after.

This is my take on a more relaxed, more characterful way to do the Greek islands. Think shorter ferry hops, smaller harbours, better tavernas, and the smug feeling that you have found somewhere that still feels like a secret.

Let us start with Poros. This is a great one if you love the idea of an island but are not thrilled about a long ferry journey. It is close to Athens, so it works really well at the start or end of a trip. Poros is green and hilly, with pine trees tumbling down towards the sea, small beaches, and a pretty harbour where the cafés and tavernas seem perfectly designed for long, lazy evenings. You can head out on a small boat trip to swim in quiet bays, paddleboard on calm water, or pop over to the Peloponnese for a hit of ancient history. It is the sort of place that eases you gently into holiday mode.

Paros gives you the classic Greek look without the full Mykonos circus. Whitewashed houses, cobbled lanes, blue shutters, bougainvillea everywhere, and a nice balance between buzz and laid-back. There is plenty going on in places like Naoussa and Parikia, from bars and restaurants to low-key nightlife, but it never tips into full party island territory. The beaches range from well-organised stretches with sunbeds and beach clubs to smaller coves where you can just turn up with a towel and a good book. You can add in things like wine tasting at a local vineyard, a lazy boat trip, or some windsurfing if sitting still for more than 10 minutes sounds like a personal challenge.

Then there is Folegandros. If you have ever said “we want somewhere quiet, like really quiet”, this is where I start to get excited on your behalf. Folegandros has a dramatic, cliff-top main village with views that are frankly ridiculous. Little squares, lantern-lit tavernas, white churches perched high above the town, and a pace of life that makes even the Greek mainland look rushed. Days here tend to follow a simple routine: breakfast with a view, a wander, a swim from a small beach or rock platform, a siesta, then a slow evening with good food and even better scenery. There is a walk up to the Church of Panagia that rewards you with one of those sunsets that ruins all future sunsets for comparison.

Sifnos is where I send food-lovers and people who like their holidays to come with a bit of substance. The island has a big culinary reputation, but it does it quietly. This is not flashy fine dining, more “how is this chickpea stew somehow the best thing I have eaten this year”. You will find gorgeous little villages, walking trails between chapels and hilltops, and tasteful, low-rise hotels that feel more like homes than resorts. You can join a cooking class, take a guided hike, drop into a ceramics workshop, then finish the day with your feet practically in the water at a taverna in Platis Gialos or Vathi. It is chic, but relaxed with it.

Antiparos often flies under the radar, which is exactly why I like it. It sits close to Paros, but has a quieter, slightly more “if you know, you know” feel. The main village has a stylish but unpretentious vibe, the beaches are beautiful without being overdeveloped, and it works brilliantly as a few-night stay as part of a wider itinerary. Think gentle mornings, dips in the sea, long lunches, then evenings that somehow stretch on without you noticing the time.

There are a few other islands that slot nicely into a less obvious route. Naxos is great for families and anyone who wants big sandy beaches, a relaxed town, and some inland villages and ancient sites to explore. Serifos has a rugged, slightly wild beauty and a hilltop village that looks like a film set. Milos brings volcanic landscapes, vivid cliffs and some of the most interesting boat trips in the Cyclades.

The beauty of island hopping is the way you can stitch these places together. A relaxed 10 to 12 night trip might look like Athens, then Paros, then Sifnos. If you want something more romantic, you could start with Athens, head to Folegandros for those wow-factor views and quiet evenings, then move on to Sifnos and finish on Paros. Families might prefer Athens, then Naxos, then Paros and Antiparos for a mix of beaches, boat days and low-stress exploring.

Behind the scenes, there is a bit of logistics involved: ferry schedules, the right routes, sensible transfer times, and choosing hotels that match your style, budget and tolerance for steps, hills and “characterful” roads. The good news is you do not have to be the one obsessing over timetables or working out whether you can realistically get from that afternoon ferry to that late-night flight. That is where I come in.

What I love doing is putting all the pieces together so your holiday feels seamless: choosing islands that suit how you actually like to travel, lining up the ferries, arranging the transfers, and suggesting those little extras that turn a good trip into one you end up talking about for years. It might be a private sunset sail, a cooking class on Sifnos, a wine tasting on Paros, or simply making sure you are in the right place on the right night to catch the best sunset.

Greek island hopping does not have to mean backpacking and shared bathrooms. It can be as comfortable, stylish and laid-back as you want it to be, with just enough adventure to keep things interesting.

If you like the sound of Poros, Paros, Folegandros, Sifnos, Antiparos or any of the other islands I have mentioned, I would be very happy to design a trip around you: your dates, your budget and the way you actually want to spend your time.

Get in touch and let us start planning your own, slightly smug, very relaxing Greek island-hopping escape.