Cyclades Island Hopping - Advice Requested !!

Before listing islands, you should know that there are established ferry routes, and you can't necessarily travel from any island to any other without considering these routes. If you're choosing Sifnos or Folegandros in the western Cyclades, you can forget about Tinos since they don't have the same ferry routes.

Paros and Tinos can also be difficult to reach by ferry from Sifnos/Folegandros, and the same is true in the opposite direction.

Ios and Santorini are somewhat different, as they are served by several ferry routes: one through the western Cyclades and another through the central Cyclades (Paros/Naxos).

I've been to all the islands on your list (except Ios), but it took me several months in total. So whatever the length of the stay, you have to know how to limit yourself and not want to go to too many islands. Traveling from one island to another takes up a good part of the day, including check-out, getting from your accommodation to the port, waiting for the ferry (which isn't always on time), the ferry crossing itself, the transfer upon arrival, and check-in.

Based on all the activity priorities you've established, I don't see how you could complete them in just three nights on an island (two full days). On your first day of arrival, you won't be able to do much besides get used to the surroundings and explore the area. You'll only have two days to do everything you've planned. On the evening of the second day, you'll need to pack your bags to be ready to leave for the port the next day.

Renting a car is often the only way to explore an island efficiently. Otherwise, you're dependent on buses, their routes and schedules. Tinos, for example, with its many small villages, is difficult to visit without a car and without wasting valuable time waiting for a hypothetical bus.

To summarize my advice: The best thing you can do is:

1. Take a map and check the location of each island to establish a more or less coherent itinerary.

2. Check on Ferryhopper that there are ferry connections between two islands.

3. Try to stay at least 4 full days on each island. With 3 weeks, minus the 4 nights in Athens and Santorini, you could, in my opinion, visit a maximum of 3 islands to fully enjoy them.

Hydra, being outside the Cyclades in the Saronic Gulf, should be considered separately.

To add to JoLui's comments, Koufonosia is kind of an outlier as well, in that in your list, you need to take a small ferry from Naxos, then return to Naxos to head elsewhere. When we went (from Mykonos, then Santorini after Koufonisia) timing of the ferries meant we had to stay a night in Naxos either on the way there or back (don't exactly recall). For the Greek islands, it is almost very literally that even though you can see an island in the distance, you just can't get there from where you are, or doing so can mean going back through Piraeus to get there (short of hiring a private boat to take you).

Tinos, Mykonos, Paros, Naxos, Ios, and Santorini are all pretty much on the same route. Koufonisia is as indicated above. Folegandros and Milos are accessible from Santorini (or Piraeus), Sifnos is probably in that mix, but when I looked at going there, I had problems figuring it out with the central Cyclades.

Flying back to Athens from Santorini would mean maybe backtracking if you do the Western Cyclades, you might look into flying back from Milos.

Common advice as always...figure any travel day mostly lost, figure no fewer than 3 nights on any island (unless it is a night to wait for a next day ferry), understand that ferries are fickle regarding wind and storms, so flexibility in lodging (able to cancel or reschedule) is wise. Fast ferries sound great, but much more fickle than the slow ones. Allow at least one night in Athens before flying home, even planes are subject to wind and storms.

JoLui and Paul,

Thank you very much for the wealth of information and advice.

Please keep in mind that there is an important reason that I posted a significant number of islands...
I was hoping that experienced travelers to Greece ( like yourselves ) could help me narrow down my choices ( to 3 or 4 )..

My wife and I have a wealth of travel experience, but not pertaining to Greece.!

Could you help me in that regard ??

Thank you and Cheers !

Matt

gdmplc66. I know that answers to requests like yours often include "you can't do that," "you won't have enough time," etc., which initially generate disappointment and frustration. These answers shouldn't be interpreted as obstacles to travel, but rather as ways to help you plan your trip.

Understanding the constraints of ferry travel between the islands allows to narrow it down to what's feasible within a given timeframe. Given that there are roughly 20 islands worth visiting in the Cyclades, choosing 3 or 4 islands for a 3-week trip shouldn't be difficult once you're aware of these constraints.

But since we're not in your shoes, it's difficult to say whether you'll like this island or not. So, to keep it short, I'll just mention one route, deliberately leaving out Tinos, Paros, Naxos, and Koufonissia.

To summarize, the western Cyclades accessible from the port of Piraeus are, in the order of the ferry routes: Kythnos - Serifos - Sifnos - Kimolos - Milos - Folegandros and Sikinos. Not all ferries necessarily call at all these islands, and some ferries continue on to Ios/Santorini.

Therefore, it's a trip you can study by looking at what each island has to offer.
Given your preferences, I would focus on Serifos - Sifnos - Folegandros. This makes for a fairly varied mix of landscapes and atmospheres. But be aware that there won't necessarily be a ferry every day to go from one island to another. This needs to be checked on websites like ferryhopper or openseas.gr.

You should also consider the possibility of ferry cancellations due to bad weather, technical issues, or strikes. In that case, you could be stuck on an island for an indefinite period. Booking accommodations with flexible cancellation/modification options is a good idea.

Serifos isn't on your initial list; So see if it appeals to you. The island is mountainous, so a car or motorcycle is highly recommended given the rather limited bus network and the limited access to the southern beaches and the northern part of the island beyond Chora, the capital.

https://www.discover-serifos.com/en/

Sifnos is a hiker's paradise and the quintessential Cycladic island (whitewashed houses, blue domes, beaches, and everything you see on postcards). Its bus network is excellent. The main bus hub is roughly in the center of the island, where the capital, Apollonia, is located. The south of the island has charming seaside villages, and the ancient capital, Kastro, is a must-see. Sifnos is well-known among food lovers. At the end of September, a gastronomy festival is held there.

To find accommodation and other information about Sifnos, check out:

https://www.roomsinsifnos.com/

The website is managed locally.

Folegandros is also quite mountainous and very peaceful. Its main areas to stay are basically Karovastasis (the port) and Chora (the main town) in the middle of the island.
It's more of an island for walks and hikes than for spending time on the beaches. This might be why it's on your list. Transportation in Folegandros is basically limited to a bus from the port to the capital, hence the need to enjoy walking.

https://www.folegandros.gr/en/

Once in Folegandros, you'll be ready to head off to the crowds of Santorini; it will be a whole different world.

How flexible are you? I am more or less suggesting the same thing all the time and I know it is not for everyone, but maybe it helps you to make your decision: As you have about 3 weeks of time and it is mid September to early October, I would not stick to a schedule, but just decide on your first island and one of two routes. You can adapt to ferry cancellations, delays and most importantly, stay 2 days longer if you love it at one place. I know, there is always the fear of missing out when skipping an island, but just enjoying one or two more days at a place and get to know it better, is so worth it. Especially if you are into getting to know some locals, on small islands they will know you personally if you stay there for more than 3-4 days ;-)

It was already mentioned before, so it may seem a bit repetitive, but I also see two possible routes (and I will stick to routes where jet ferries are mandatory), note that the listing order is intentional:

1.) Western Cylades: Sifnos, Milos, Folegandros, Ios, Santorini

There are plenty of islands in between, where you could also stop, if you want to (Serifos, Kimolos - also possible via day trip from Milos, Sikinos). Ferries are not going every day, but several days a week

2.) Central: (Tinos, Mykonos), Paros / Antiparos, Naxos, (Koufonosia), Ios, Santorini

You could either start this route via Tinos or Paros. Koufonisia could be done in one of two ways (without an extra night on Naxos), either directly when arriving with the morning ferry in Naxos or after a Naxos visit if there is an evening ferry to Ios / Santorini. This is valid for all the other small cyclades as well, as they are on the same route of the Express Skopelitis.

Ferries do not need to be prebooked at this time of the year and accomodation can be found online even on the day of arrival, giving you maximum flexibility.