Help with 13-Day Cycladic Itinerary

Your trip looks do-able if you are OK with a loong ferry ride at the End. Folegandros has no airport... and no bookings on the large open-deck ferries where you can walk around during extended journey, such as to Piraeus (the Athens port). There is ONE ferry dail to Piraeus, the large & stable rserved-seat CHAMPION Jet leaving 3: 30pm -- arr 8:10 (those thse are often delayed). No need to book from home... book before leaving Santorini if u like. I suggest going on the 6th or even the 5th -- Folegandros is really all about the beautiful high town (Chora), the beaches are, meh, and I'm not sure about boat trips. I highly recommend this hotel - https://www.anemousahotel.gr/en/article.php?cat=2 -- which was a huge bargain a few years ago in May. I had a fine 3 days on Foley because friends were teaching in the Gymnasium (H.S) there & they drove me around... but island itself isn't a showstopper.

From my many stops at Santorini (because of Newbies who insist), I hve found the BEST place to stay is FIROSTEPHANI ... it's at the north fringe of Fira town - away from the hubbub, but walkable to all attractions, bus transport etc... and has Many Cliffside hotels with FAB views at Much less $$ than overpromoted OIA. Best way to enjoy OIA is, on 2nd day early, book taxi 7:30 to go there, you'll have 2+ hours to stroll its lanes & enjoy high views & photograph in peace, before invasion by Cruise Mobs AND tour groups (yes there are also large groups coming via ferry/plane). When they cram-jam the streets, you escape by bus, go see museum, or (nobody does this) climb up the heights of Ancient Thira overlooking hte beach. Do NOT go to Oia for sunset - crowds pack the caldera walls, no fun ... Lovely dining in Firostephani, or there are wine-tastings at wineries with a view.

NAXOS has everything even tho alas, it's been "discovered." Still, it's a big big island... rent a car & get awy to hillside villages. its beacjes are fme. if you stay away from the new plague of (illegel) 4-poster Sunbeds in high season yuk.

Thanks for the reply! Would it be better to do Naxos then Folegandros and end on Santorini to not have that long ferry at the end? Or should we swap out foley for Amorgos or sifnos?

We are planning a trip to Athens, Naxos, Santorini. We may also return to Athens and drive to Nafplio for a few days before flying home (we are coming from Seattle). - We have 2.5ish weeks to play with in May 2026. It's just my husband and myself, two very active 59/60 year olds. I was thinking of these islands as I want minimal ferry rides and to be able to fly to/from Athens and not take a very long ferry ride to or from Athens. A friend told me Amorgos is beautiful and chill, but not sure it will fit our travel plans. Would love others' insight relative to this and what myd5049 has asked. TIA!

Regarding ferries to and from Folegandros, there isn't just one ferry per day from Santorini.

On July 4th, for the Santorini-Folegandros route, you'll have the Dionisios Solomos ferry at 9:00 AM, the legendary traditional ferry that has operated 365 days a year for many years on this Western Cyclades route. It will be at the dock in the morning, having remained moored overnight in the port of Santorini. It has exterior decks, just like the Blue Star ferries.

You'll be in Folegandros a little before noon.

https://youtu.be/QYPfpAAqP98

There will also be at least one Seajets, but it departs later in the afternoon, and the tickets cost twice as much (€84).

However, for the Folegandros-Piraeus on July 8th, you will have at least one Seajets to return to Piraeus during the day, as well as the Dionisios Solomos, but this one leaves Folegandros very late in the evening. It's true that it does take almost 5 hours to return to Piraeus; personally, that wouldn't bother me.

A 4.5-hour ferry ride is perfectly manageable and doesn't really matter when it comes to going exactly where you want to go.

LM
You probably should open your own thread to ask your question. Having said that you have a decent plan already. I would suggest when you arrive in Athens you book a flight to either Santorini or Naxos. You will need 2 to 3 hours to make a connecting flight. Getting to your first island as soon as possible will give you time to relax and recover from jet lag.

My choice would be to fly to Santorini and spend your first couple of days adjusting to Greek time. Santorini is a great destination as long as you manage the crowds. You might want to consider staying in Firostefani. Its a village about a 15 minute stroll into the main town. Its just far enough from all the tourist activity to be reasonably quiet.

Of course you could do Naxos first but I suggest Santorini because of ferry logistics. The first two ferries of the day depart to Naxos at 8:30 AM and 9:50 AM and take about an hour and a half. If you do Naxos first the ferrys depart Naxos at 10:30 and 11:45AM. You will lose more than half the day by making the ferry hop from Naxos to Santorini.

For fun here is why you made a good choice in choosing Naxos.
https://www.flickr.com/photos/stanbr54/albums/72177720329571437/
https://www.flickr.com/photos/stanbr54/albums/72177720318406428/

Thanks Stanbar- we were planning on taking a flight straight to Naxos from Athens when we arrive. I believe there’s an airport in Naxos

Yes there is an airport on Naxos. Both Sky express and Olympic fly that route. Both are good reliable airlines.

Yes both Olympic and Sky express fly that route. Both are reliable. Since Naxos has a short run way they use prop airplanes. Never had a problem with either airline.

What’s a prop plane?

you're kidding, right? I realize you are babies (37) but surely you have seen movies made before 1980. The plane engines hve big long things in front that whirl around.

HA! Now I get that that was an abbreviation for propeller!

Sorry for not being clear. The aircraft have propellers, they are not jets.

All good Stan! We have Janet a nice laugh 😂

Just to clarify, in case you were thinking of flying in an old clunker from the 1950s, the ATR turboprops used by Aegean and Sky Express do indeed have propellers, but they are still state-of-the-art jet aircraft.

And they're very fuel-efficient. A flight from Athens to Naxos with an ATR 600 consumes less kerosene than 10 minutes of taxiing on airport taxiways in a Boeing 747.

https://www.atr-aircraft.com/aircraft-services/aircraft-family/atr-72-600/

This thread is making my head spin. ;)

Better than Trip Advisor these days, Stanbr, which deletes any kind of fun posting for the reason "determined to be innappropriate by the Trip Advisor Community" -- the wisdom of AI, employed to save staffing costs. Hurrah for Rick Steves, long may he wave!

Re your two or three nights in Athens, that means one or two days there. I would suggest that you save Meteora for another trip, and spend your time in Athens. There's more than enough to see in Athens for the amount of time that you have.

Agree with janet regarding Trip Adviser which now relies on AI (ask Ollie) about travel forums.

A lot of posts have been deleted for no apparent reason by AI about algorithms thinking a bad word or phrase makes it "inappropriate"

Even worse a complete thread is closed for no apparent reason!

Another thing I like about this forum is that you can go back and edit a post numerous times unlike TA which limits changes to just a few minutes and then you are out of luck!

Hurray for Rick Steves!

I’m back with a follow up question my friends. Our departure for Athens state needs to change due to childcare restrictions, so I think I need to adjust my trip a little bit. We now are going to arrive in Athens on July 2
With the new date if I were to keep everything as it is right now, there would be five cruise ships in Santorini when we would get there. When I originally planned the trip, Santorini only had one cruise ship scheduled, and one day had none on the schedule yet.

So this is what I’m thinking: I can arrive in Athens and go straight to Santorini, and then continue on to Naxos and Sifnos as originally planned, just switching up the order. If we do Santorini first, then we get to Santorini on that day with the no cruise ship, and the one cruise ship.

Option two would be to cut out Santorini altogether, and possibly add Meteora instead to use up the two days I was planning on spending in Santorini. If I were to do that, then the order I was thinking would be Landon Athens, flight to Naxos immediately. Possibly just stay on Naxos the whole time, then back to Athens for Meteora and Athens and fly back to New York City. This would just cut Sifnos out altogether. I want to be mindful of only having 14 days and making sure that I’m not overpacking the trip with the travel days. Does Sifnos offer a lot of of the same things that Naxos is already offering.

No, do not add Meteora to your itinerary... that's for people who have loong holidays, and/or for those who have visited Greece before. Even stanbr, who's had many long trips for 20+ years, didn't get around to it for quite awhile. Adds too much travel during 13 days. Instead, Do Santorini FIRST ... when you land, allowing 2-hr layover, fly straight there, and as Stanbr says, stay in Firostephani... we've both tested this successflly many times. Great hotels at rimside w caldera views, handy to Fira town (15 min stroll along rim) but away from hubbub... AM of day 2, splurge & get 8 am taxi to OIA, and u can enjoy it for 2 hrs, before tour armies invade. For sunset dinners Remvi cafe in Firostephani has fab views, no crowds. TIP: since u are in July, reserve Santo hotel NOW! Use this link - https://www.booking.com/city/gr/firostefani.html - and pvt prowser page to avoid cookies. Some good choices - Hotel Mylos, Sunset Hotel - places w pools: Blue Dolphins, Mill Houses, Villa Ilias, Agndadema Apts. Stick to the 2 nights - it's really mainly about the view.

NO do not skip Sifnos ... It is a treasure, with great beaches, history, stunningly beautiful hillside villages ... and not yet totally discovered (and ruined) by the ugly rich. Every day I've spent there has been a discovery, and a joy... I ache to return. Please go before it changes. PS: I stay up on the hillside, lovely places in 3 linked villages - Apollonia- Ano Petali - Artemonas -- and take good bus network to Platy Gialos & Vathy beaches ... but u can rent car as well. The port town of Kamares has many fans, but its busy-busy main road circling whole town bothers me & to me it feels closed-in wedged into corner between 2 high hills, that's just me. I love outlook from hillside down to vally & out ot sea. DO go.

I agree with Janet, don't include Meteora in your trip, you'll spend too much time traveling so far up the mainland from the islands.

I also agree with her about Sifnos, which has managed to avoid overtourism thanks to a very strict local policy regarding new tourist developments. It was my first trip to a Cycladic island a long time ago (before cell phones). I have photos from that time showing that very little has changed in 35 years, except for the car and motorcycle models.
It was Sifnos that gave me the Greek island bug. It's incurable. :-)

Like Janet, I'm not a big fan of Kamares, the port. I stayed there, as well as in quite a few other places on Sifnos. But my favorite place is the village of Kastro. Probably too isolated for you. Apollonia and Artemonas are very beautiful villages and the hub of the excellent bus network that takes you to almost every part of the island.

But it's especially the numerous hiking trails that are worthwhile.

Now, the less pleasant part about Sifnos:

If you want to travel to Sifnos from Naxos, you'll encounter the usual difficulty of traveling from the central Cyclades to the western Cyclades. This is only possible with the small and very uncomfortable Seajets Superjet and Superjet2 ferries, which take a long detour around the islands and make quite a few intermediate stops. As a result, the journey takes about 4 hours. You'll arrive in Sifnos around 7 pm, and it will cost you around €100 per person (a bit pricey for seasickness).

The easiest way to get to Sifnos would be to leave from Santorini, just as you originally planned a Santorini-Folegandros trip.
From there, you can take the same ferries as for Folegandros, plus the traditional Anemos ferry operated by Aegean Sea Lines, whose schedule is not yet published.

Thanks so much for the input!! Would you say to to Santorini then Sifnos and completely skip Naxos, or would we do the order of Santorini, Sifnos, Naxos

I didn't say that, but simply that the Santorini-Naxos-Sifnos order isn't the best from a ferry travel perspective.

In (very) short, all the islands in the western Cyclades—Kithnos, Serifos, Kimolos, Sinos, Milos, Sikinos, and Folegandros—are connected by a ferry route that starts in Piraeus and ends in Santorini. This route doesn't go via Naxos or Paros.

Regarding Naxos and Paros, which are in the central Cyclades, the ferries take a different route that also starts in Piraeus and ends (sometimes) in Santorini.

Interconnections between these two routes are rare, and since Santorini is the common point of both, it's best positioned in the middle of an itinerary.

I suggest you check the Ferryhopper website.

Example for a Naxos-Sifnos trip in June

https://www.ferryhopper.com/booking/results?itinerary=JNX,SIF00&dates=20260617

By clicking on the "i" in the green circle, you will see the very convoluted route taken by the ferry.

Thank you! That “I” is extremely helpful. Is it crazy to do the morning Naxos to Paros ferry.

Stay in Paros til 5 pm (look for a luggage drop off) and take the 6 pm ferry from Paros to Sifnos. It looks like it’s 30 min from Naxos to Paros and only 55 min from Paros to Sifnos.

Yes, that's a good option.

To try several possible dates, on Ferryhopper select multi-destination instead of one-way. Define a departure from Naxos, Paros as destination 1, and Sifnos as destination 2, and set the same date for both.

However, I think you won't arrive in Sifnos before 7 PM anyway.

The port / town of Parikia in Paros is nice, and yes, you can leave your luggage while you wait for the second ferry. There are a few travel agencies and shops that offer luggage storage.

For example, here at Café Limani, which you'll see right in front of the ferry terminal:

https://maps.app.goo.gl/xj4GbjGbsNSNu1SGA
https://maps.app.goo.gl/xj4GbjGbsNSNu1SGA

At one point you had mentioned Amorgos — and I think it would actually be a good alternative to Sifnos, because of the logistics.

You would still fly directly to Santorini upon arrival, but from there it’s a short ferry ride (1 hr 15 min) to Amorgos. A few days later, another short ferry ride to Naxos. And from Naxos you’d have the option of ferrying or flying back to Athens, which Sifnos wouldn’t give you.

Sifnos is wonderful & I think it’s worth seeing — it was my first Greek island too. But for such a relatively short trip, I think you should avoid that long connection. Amorgos is a jewel of an island that I think you’d enjoy.

I agree with Charlene that Amorgos could be a better alternative considering the ferry connections.
A Santorini-Amorgos-Naxos itinerary also allows you to finish your island-hopping trip with Naxos, which has an airport.

And Amorgos, the island of the Big Blue, although very different from Sifnos, is splendid.

We’ve officially booked some airfare! Now looking at my Santorini flight

If I land from NYC in Athens at 8:10 AM can I take the Athens to Santorini 10:05 AM flight or should I do the 11 AM flight.

Two hours is doable but a bit risky.

If you're coming from a non-Schengen country, I would take the 11:00 AM flight.

It's better to spend an extra hour at the airport than to miss your flight by five minutes (which would be a no-show) and struggle to change your tickets or, more likely, have to buy new ones.