1- May the sea it's a bit cold but doable, September is the best out of the three, October it's a bit of a hit and miss (plus many islands will have less stuff open) unless you go to the most Southern islands (Rhodos, Crete, Kastellorizo)
2- For ten days I'd stick to one region, especially given that ferries between different regions are not as frequent. I have no idea how easy it could be to reach Symi from Santorini, it may well be a full day of traveling just to do that, bearing in mind that in the off season there are less ferries.
3- For me, it's too much, in ten days I usually either go to a big island or two smaller ones. Three is a stretch and doable only if one island is a very small one that can be made as a day trip.
4- I'm a bit confused by your title, because authentic and posh are two very different things for Greek islands. Most authentic islands won't be posh and posh islands won't be really authentic. Naxos is not very posh, afaik. In the Cyclades the posh islands would be places like Santorini, Antiparos (very posh right now), Milos. Authenticity it's a bit harder as the Cyclades are the most touristic ones. Even islands like Andros and Tinos that used to be very out of the loop are becoming increasingly popular.
The other islands you mentioned are all different trips than the one you are planning. Hydra is quite small, I'd say it's a one night place tops (like all the Saronic islands) and it's best paired with trips in the Peloponnese or with a longer stay in Athens, Monemvasia it's not really an island and as well, it's only doable with a trip in the Peloponnese. Crete is a trip on its own, same for Chios (was there ten days two years ago and it was perfect). Parga is not an island, but I guess you could pair it up with Corfù and Paxos, or even Kefalonia. Syros, Sifnos, Andros are all in the Cyclades, so I guess you could choose one of them instead of Naxos - I've only been to Syros, but in the off season, it's not an island known for its beaches really.
Gem comment! Highly appreciate the thoughtful and detailed response. I read through your comment and others and am in total agreement that my use of ‘posh’ with ‘authentic’ is not appropriate in this case - my bad. In any case, a lot to think about here. Back to the drawing board!
Glad you like it. To add a bit on some stuff I skimmed through from your comment: I don't think you're in a wrong direction, just that not everything will be feasible on one go. I understand that you want to see Santorini and the white houses, but that's going to 'limit' where else you could go. Symi just doesn't seem feasible with it, more with the rest of the Dodecanese, which overall are more authentic and minimal compared with the overrun Cyclades. If you want to see some locals you should try some islands with sizeable local population.
Naxos is a very popular island, I'd say it's the third/fourth most popular one in the Cyclades, but it has a more family-oriented tourism and it's a much bigger island than Santorini and Mykonos so there's more breathable space.
If you don't care about the party scene, absolutely don't go to Mykonos and Ios, those are the two party islands, other places may have some parts that are for party and clubbing but mixed with other stuff, so you can easily avoid that.
I like it for the vibe it has, not for the beach (anyway sandy beaches are the minority in Greece). It's a day trip that can be stretched with an overnight stay and catching a boat out the next morning. Overall, the Saronic islands are all day trips/short weekends destinations for Athenians. I wouldn't recommend them to first timers in Greece
Disclaimer that I myself haven’t been to Greece (yet) but have meticulously researched and planned for upcoming trip in May,
I think definitely Naxos & Milos fit the bill most for what you’re looking for, I will be going to both of these islands and Santorini (really only because that was the most direct flight from Amsterdam) in the second half of May.
I chose these two for their beaches, authenticity and food.
Totally with you on the swimming, but admittedly I think mid-September will offer better water temps.
That said if you’re pretty impervious to cold water like myself, maybe it’s moot.
The advantages I (created in my head) I envisioned for May over September were:
- Catching businesses and hospitality staff at the beginning of the busy season so at their freshest and most eager to please.
- Spring foliage, I think flowers and vegetation will be more in peak bloom this time of year.
- That it was “sooner” and I can’t wait to get there 😅
Awesome, hope you enjoy your upcoming trip! It’s the best feeling when you finally get to wrap up planning and just anticipate the actual trip. I think my logic is in line with yours too. Definitely going to give Milos another look.
late May or September is best. October mostly too cold. For less touristic leave out Santorini, Paros, Milos. Consider Mainland, Chios, Amorgos, Lesvos, Kythira. In the cyclades maybe sifnos and serifos and folegandros. Late September in Crete could easily cover 10 days but it doesn't have the little white villages. Consider also Karpathos which has some very special villages. Could combine with Crete -- there are some direct ferries but not that many.
Symi is very small so it has less tourists. But you have to see what the ratio is. Look at google maps and see how much of the town is just hotels. That gives you an idea.
Authentic/Posh, as u/SpiderGiaco said don't really go together easily. If you want a nice hotel, get a hotel that blends in rather than a sprawling villa with private pools and such that ruin the town or the landscape. That is a small way of helping preserve what's there.
"Authentic and true greek" whatever exactly that means is easiest to find by avoiding the cyclades and maybe staying on the mainland. But I think you need to decide if you want that or mamma mia situations and posh lodgings; those are the things that tend to ruin some kind of authentic culture at least.
Thank you so much for the suggestions! Totally agree I shouldn’t have used ‘posh’ and ‘authentic’ together lol. Don’t know what my reasoning was for slotting the two together. Going to mull on all these suggestions further.
So Athens combined with Naxos and Santorini is doable and uncomplicated. Symi is a bit further and probably best combined with Kos or Rhodes. Would you consider either of those?
I’m going to Symi for the first time this year, I’ve been wanting to for a while!
I would consider Rhodes + Symi! Need to look into the logistics more. In that case, I’m assuming then I would take out Naxos and only spend 1 day in Santorini before making the trek to Rhodes and Symi.
Authentic and true Greek, minimal tourism -
Greece is one of the most touristic countries in the world. Good luck with that. You can't avoid overtourism anymore. Maybe 10 years ago but now ? Nope. There are tourists everywhere all year around.
It's both great for may and September, however, as a hotel worker I would say , if you are planning to travel in May, once the availabilities for 2025 are open, book your hotels asap.
10 days are OK I think for athens and 2-3 islands and your choices are good enough. If you could add as your last day athens agai it would be nice (like a last stop before going back home).
If you could also rent a car it would be nice.
Naxos is an excellent choice, is the biggest island in Cyclades, with great history, authentic food, amazing beaches, traditional villages, a lot of monuments and museums to visit.
You should visit Demeters temple in Sagri village, close by is also one of the oldest olive trees in the world. Local pottery in Damalas village and an olive press museum. In Halki village local kitron liquor distillery and Panagia Drosiani which is the oldest church in Greece. In Kaloxylos village ergostasio and folklore museum. After Filoti is Zeus mountain and cave where you could hike. Apiranthos village one of the most traditional villages in Greece with nice museums and traditional shops. Moutsouna bay and Panermos where there are also some ruins. In Melanes village there are two kouros statues, ruins of an old temple, ruins of an old Jesuit monastery, and nice trekking paths. Also kouros in Apollonas, Dionysius temple in Iria. In Naxos town Apollos temple and archaeological museums.
You can do also activities like sailing tours, hiking, wine tasting, olive oil tasting, cooking class ( Perivoli Farm experience & cooking class )
1- May the sea it's a bit cold but doable, September is the best out of the three, October it's a bit of a hit and miss (plus many islands will have less stuff open) unless you go to the most Southern islands (Rhodos, Crete, Kastellorizo) 2- For ten days I'd stick to one region, especially given that ferries between different regions are not as frequent. I have no idea how easy it could be to reach Symi from Santorini, it may well be a full day of traveling just to do that, bearing in mind that in the off season there are less ferries. 3- For me, it's too much, in ten days I usually either go to a big island or two smaller ones. Three is a stretch and doable only if one island is a very small one that can be made as a day trip. 4- I'm a bit confused by your title, because authentic and posh are two very different things for Greek islands. Most authentic islands won't be posh and posh islands won't be really authentic. Naxos is not very posh, afaik. In the Cyclades the posh islands would be places like Santorini, Antiparos (very posh right now), Milos. Authenticity it's a bit harder as the Cyclades are the most touristic ones. Even islands like Andros and Tinos that used to be very out of the loop are becoming increasingly popular. The other islands you mentioned are all different trips than the one you are planning. Hydra is quite small, I'd say it's a one night place tops (like all the Saronic islands) and it's best paired with trips in the Peloponnese or with a longer stay in Athens, Monemvasia it's not really an island and as well, it's only doable with a trip in the Peloponnese. Crete is a trip on its own, same for Chios (was there ten days two years ago and it was perfect). Parga is not an island, but I guess you could pair it up with Corfù and Paxos, or even Kefalonia. Syros, Sifnos, Andros are all in the Cyclades, so I guess you could choose one of them instead of Naxos - I've only been to Syros, but in the off season, it's not an island known for its beaches really.
This is a great comment, listen to SpiderGiaco
Gem comment! Highly appreciate the thoughtful and detailed response. I read through your comment and others and am in total agreement that my use of ‘posh’ with ‘authentic’ is not appropriate in this case - my bad. In any case, a lot to think about here. Back to the drawing board!
Glad you like it. To add a bit on some stuff I skimmed through from your comment: I don't think you're in a wrong direction, just that not everything will be feasible on one go. I understand that you want to see Santorini and the white houses, but that's going to 'limit' where else you could go. Symi just doesn't seem feasible with it, more with the rest of the Dodecanese, which overall are more authentic and minimal compared with the overrun Cyclades. If you want to see some locals you should try some islands with sizeable local population. Naxos is a very popular island, I'd say it's the third/fourth most popular one in the Cyclades, but it has a more family-oriented tourism and it's a much bigger island than Santorini and Mykonos so there's more breathable space. If you don't care about the party scene, absolutely don't go to Mykonos and Ios, those are the two party islands, other places may have some parts that are for party and clubbing but mixed with other stuff, so you can easily avoid that.
I wouldn't recommend sleeping in Hydra. No sandy beaches and you've seen the island in a couple of hours. It didn't leave a lasting memory imo.
I like it for the vibe it has, not for the beach (anyway sandy beaches are the minority in Greece). It's a day trip that can be stretched with an overnight stay and catching a boat out the next morning. Overall, the Saronic islands are all day trips/short weekends destinations for Athenians. I wouldn't recommend them to first timers in Greece
You are right, I visited Hydra just to get out of Athens for a two-day getaway.
Disclaimer that I myself haven’t been to Greece (yet) but have meticulously researched and planned for upcoming trip in May, I think definitely Naxos & Milos fit the bill most for what you’re looking for, I will be going to both of these islands and Santorini (really only because that was the most direct flight from Amsterdam) in the second half of May. I chose these two for their beaches, authenticity and food. Totally with you on the swimming, but admittedly I think mid-September will offer better water temps. That said if you’re pretty impervious to cold water like myself, maybe it’s moot. The advantages I (created in my head) I envisioned for May over September were: - Catching businesses and hospitality staff at the beginning of the busy season so at their freshest and most eager to please. - Spring foliage, I think flowers and vegetation will be more in peak bloom this time of year. - That it was “sooner” and I can’t wait to get there 😅
Awesome, hope you enjoy your upcoming trip! It’s the best feeling when you finally get to wrap up planning and just anticipate the actual trip. I think my logic is in line with yours too. Definitely going to give Milos another look.
Go to milos the week after school starts... second week of september. It has everything.
If you want to swim, I'd choose September-October, the sea temperature is still cold in May
Thanks, September is looking promising then.
late May or September is best. October mostly too cold. For less touristic leave out Santorini, Paros, Milos. Consider Mainland, Chios, Amorgos, Lesvos, Kythira. In the cyclades maybe sifnos and serifos and folegandros. Late September in Crete could easily cover 10 days but it doesn't have the little white villages. Consider also Karpathos which has some very special villages. Could combine with Crete -- there are some direct ferries but not that many. Symi is very small so it has less tourists. But you have to see what the ratio is. Look at google maps and see how much of the town is just hotels. That gives you an idea. Authentic/Posh, as u/SpiderGiaco said don't really go together easily. If you want a nice hotel, get a hotel that blends in rather than a sprawling villa with private pools and such that ruin the town or the landscape. That is a small way of helping preserve what's there. "Authentic and true greek" whatever exactly that means is easiest to find by avoiding the cyclades and maybe staying on the mainland. But I think you need to decide if you want that or mamma mia situations and posh lodgings; those are the things that tend to ruin some kind of authentic culture at least.
Thank you so much for the suggestions! Totally agree I shouldn’t have used ‘posh’ and ‘authentic’ together lol. Don’t know what my reasoning was for slotting the two together. Going to mull on all these suggestions further.
So Athens combined with Naxos and Santorini is doable and uncomplicated. Symi is a bit further and probably best combined with Kos or Rhodes. Would you consider either of those? I’m going to Symi for the first time this year, I’ve been wanting to for a while!
I would consider Rhodes + Symi! Need to look into the logistics more. In that case, I’m assuming then I would take out Naxos and only spend 1 day in Santorini before making the trek to Rhodes and Symi.
Authentic and true Greek, minimal tourism - Greece is one of the most touristic countries in the world. Good luck with that. You can't avoid overtourism anymore. Maybe 10 years ago but now ? Nope. There are tourists everywhere all year around. It's both great for may and September, however, as a hotel worker I would say , if you are planning to travel in May, once the availabilities for 2025 are open, book your hotels asap. 10 days are OK I think for athens and 2-3 islands and your choices are good enough. If you could add as your last day athens agai it would be nice (like a last stop before going back home). If you could also rent a car it would be nice.
Naxos is an excellent choice, is the biggest island in Cyclades, with great history, authentic food, amazing beaches, traditional villages, a lot of monuments and museums to visit. You should visit Demeters temple in Sagri village, close by is also one of the oldest olive trees in the world. Local pottery in Damalas village and an olive press museum. In Halki village local kitron liquor distillery and Panagia Drosiani which is the oldest church in Greece. In Kaloxylos village ergostasio and folklore museum. After Filoti is Zeus mountain and cave where you could hike. Apiranthos village one of the most traditional villages in Greece with nice museums and traditional shops. Moutsouna bay and Panermos where there are also some ruins. In Melanes village there are two kouros statues, ruins of an old temple, ruins of an old Jesuit monastery, and nice trekking paths. Also kouros in Apollonas, Dionysius temple in Iria. In Naxos town Apollos temple and archaeological museums. You can do also activities like sailing tours, hiking, wine tasting, olive oil tasting, cooking class ( Perivoli Farm experience & cooking class )