Greek Island Hopping: The Cyclades Edition
Island hopping through the Greek Islands is arguably on most people’s travel wish lists, and for good reason. Whether you’re travelling with family, a group of friends, planning a dream honeymoon or simply in need of some solo time - there is an island for you! But with over 200 inhabited islands to choose from, the challenge comes in picking the right one, or combo, to suit your tick-list.
Over the past few years I've been doing a bit of a deep dive into the Cyclades Islands and, as the title suggests, it’s this group of Greek isles that this post is dedicated too. I’ve chosen to explore this region not only because it’s the group of islands I tend to get asked about the most - thanks to its big hitters Santorini & Mykonos - but also because each year there seems to be a new hotspot and I’m struggling to tear myself away. Why break tradition when somewhere works so well? At least that’s what I tell myself.
Before I get carried away with my take-aways for each island, I thought it might be helpful to share my insights on a couple of questions that get asked the most when I have guests enquiring about Greek Island Hopping…
Which island or combination of islands should I book?
Knowing which islands to combine can very much come down to logistics. However, the one rule that I live by is ‘the extra hop is always worth it’. If you’re dependent on ferries, then some careful route planning and timing logistics will need to be considered. But, if you’re looking to travel by private boats or by helicopter, then your options and the order of which islands you visit really opens up.
The other main thing to consider is how many islands you want to fit in? For some, the idea of packing and unpacking multiple times starts to feel more like a chore than a holiday. If that’s you, then you might want to pick just one or two islands. Other guests get itchy feet and love the variety of being on the move, and so three islands (or more) might be right if that's you.
Getting the wrong island fit is something that I’m very aware of, which is why all of my recommendations and itinerary ideas are completely bespoke.
How do I know which hotel(s) I should pick?
This is another question I get asked a lot when working on Greek itineraries and the answer is always the same, ‘it’s very much dependent on you, and what you’re looking to get out of your holiday’.
If you’re a lover of boutique hotels, then there are many great options across every island and so it’s more a case of pinning down the islands I think will be the best fit depending on the kind of things you’re looking to do, plus the type of setting and location you’re looking for. However, if you’re very much more of a high-end luxury, full service resort kind of guest, then it’s more about uncovering what you want from an island and paring things that way. Odera on Tinos, and Gundari on Folegrandos (two hotels on a lot of people’s radars), both have that ‘wow’ view and beautiful setting, but only one might be right for a certain guest and not the other because the islands they’re located on are so different.
Essentially, there is a skill to match you with the perfect property and overall holiday experience, and that’s where I come in…
My personal favourite islands to date...
Sifnos
For me Sifnos is a haven for guests who love stylish boutique hotels.
My all out favourite is Nòs which I love for the interior design and the short walk over to Pelicanos restaurant (a must try!). I also have a soft spot for Verina Astra which has views to die for. The island also has an amazing food scene, so is perfect for travellers who love great (albeit often low-key) restaurants. As well as the aforementioned, Cantina & Omega 3 are another couple of favourites, plus some excellent local tavernas - which I like to keep under wraps specifically for Papillon guests.
Side note: Sifnos is developing quickly, with many new boutique boltholes opening year on year, so my advice, get a visit booked before it becomes too busy.
Koufonisia
Koufonisia is (for now) a true under-the-radar island. It’s the one for guests who are looking for that total ‘away from it all’ experience.
You’ll find some wonderful sandy beaches and great local dining options. Tourists aren’t able to rent cars on the island, so once you arrive you can truly switch off and relax. You won’t find any major hotels to speak of, with the exception of the super special Eros Keros - where you’ll be welcomed with open arms by the wonderful and kind owner, Anita.
Side note: I hear on the grapevine that new hotels are coming, which in a lot of ways make me sad because I would love this island to remain a ‘secret’. So take my advice and go now!
Folegandros
A tiny island with dramatic cliffs and insane sunsets. The island's chora (main town) is one of the most beautiful in the Cyclades and perfect to wander around for a morning coffee or late afternoon shopping trip.
When staying on Folegandros I always recommend a boat trip, followed by lunch at Papalagii, plus a visit to Anemomilos for sunset drinks after the strenuous walk up to the famous Church of Panagia - you can also stay here for a more low key option (Anemomilos, not the church, just to be clear).
Gundari is without question my top-pick of hotels on the island, in fact it’s where I'm en route to visit as I write this. The pool suites here are next level and the views are incredible - get it on your wishlist!
Antiparos
Antiparos stole my heart for many reasons, but the wild beaches have got to be up there as one of the pulls for a visit. The chic boutiques and brilliant dining options also help. But then again, I do have guests that set sail for the island simply for a stay at the gorgeous The Rooster hotel and/or their recently opened sister property The Beach House. I know I’ve told you not to pick an island simply because of a hotel, but this might be the exception to that rule.
A few other islands (that I’m sure are on your radar)...
Paros
Paros is an island that has changed so much since my first visit 5 years ago. It’s great for foodies, has incredible villa options and a great hotel scene that’s constantly evolving. I like to think of Paros as a new alternative to Mykonos - still a lively night time scene but not as ‘party party’ as Mykonos can be. Guests have some fab beach club options such as Monastiri, and for restaurant recommendations, I love Siparos for dinner and Barbarossa for a buzzy vibe in Naoussa port.
Milos
If you’re looking for an island that stands out from the crowd - from a scenery and landscape point of view - then look no further than Milos. Arriving here feels like landing on the moon, in the most beautiful of ways. It’s perfect for exploring by car or on foot, there are some fab hiking trails. It also has a great dining and up & coming hotel scene - my pick would be the villas at Skinopi Lodge, simple but ‘escape from the world’ perfect.
Naxos
As one of the biggest islands of the Cyclades, and with flights direct from Athens, Naxos makes a great hub to both explore and venture on from. It pairs well with both Paros and Koufonisisa.
Because of its size, the island offers great experience both inland and on its shores. Guests will find gorgeous quintessential Greek villages dotted across the island, as well as some amazing dining options. Admittedly, it’s been a few years since my last visit so I’m definitely due another but with many locals labelling it amongst their favourite islands to visit, you don’t need to take just my word for it.
Tinos
Tinos may have Mykonos as its closest neighbour but the vibe couldn’t be more different. It’s much more laid back, rustic and a visit here is all about exploring local villages and getting lost in nature. Newcomer Odera has put this island on the map to international tourists, however, despite this being the kind of hotel you’d expect to see on Mykonos or Santorini, the atmosphere is most certainly different - the only thing shared are the stunning views.
The Cyclades classics...
I won’t be doing a deep dive into Santorini or Mykonos because I feel like they get a lot of airtime already and I probably wouldn’t be able to expand too much on what you already know, but here are a couple of my thoughts…
Mykonos
It goes without saying that Mykonos has built up a bit of a reputation as being the glitzy party island - full of designer shops and bougie beach clubs. However, it’s an image I think they’re looking to change somewhat and proof of this can be found in stays at the beautiful Kalesma or Cali Mykonos, both chic escapes away from the chaos. Plus an experience like Rizes, a beautiful island farmstead, takes you away from the stereotypical image of the island.
Santorini
Despite attracting the crowds, I do really love Santorini, it’s such a unique place and there’s a reason it’s such an iconic Greek Island. As long as you’re ‘in the know’, there are ways to avoid the crowds and the masses. A stay at Canaves Epitome is a dream and I love it for its caldera views, the fact that its touching distance from Oia, yet also far enough away to feel like you can fully recharge and relax. While in Santorini, lunch down at Ameni is also a must! The team are such characters, while the food and setting are also perfection.
On the Cyclades wish list...
The islands of Serifos with a stay at Perma Serifos, and Kimolos, staying at The Windmill are very much in my plans for next year. Both places come highly recommended by a lovely Greek travel friend of mine and I feel that they would be great additions to the portfolio. Then there is Kéa, an island of rugged, natural beauty. It’s conveniently located close to Athens, home to the stunning One & Only Kéa which opened last year and has been getting rave reviews from Papillon guests.
A special mention to...
Athens
Athens itself is having a bit of a moment, and I’m here for it. Not only is it a gateway to the islands, but the history is fascinating, the culinary scene is exploding and the hotel options are great. Two of my top favourites are: The Dolli for the ‘wow factor’ - think Acropolis views, the comfiest beds known to man and even Steamery steamers in the room (yes I have been known to judge a hotel by its electrical appliance offering). Then you have Shila, which is complete opposite, a boutique hotel that I can only describe as granny chic, but please don’t be put off by that description, it’s charming, lovely and authentic. Perfect for guests looking for a more low-key city stay.
A pre or post stay in Athens also works perfectly for anyone who wants to twin city and beach without taking to the seas. The Athens Riviera is a short drive away, with many incredible resort options, including Four Seasons Astir Palace and One & Only Aesthesis.
For our US clients, a few nights in the capital is almost a given. However, with direct flights to many of the most popular Greek Islands, guests from the UK often forgo a stop in Athens, which is a great shame - I can only hope sharing my thoughts might change this for future trips.
Sign off…
Writing this has made me want to look into flight immediately - I hope it’s had the same effect on you. Even though this was a deep dive into The Cyclades, I want to reassure you that I design trips all over Greece and work with incredible partners across the breadth of the country, so if you’re keen to explore other areas, do get in touch!
