Ferry Questions and Island options for short stopovers

If we opt to take an overnight while in Santorini ; Folegandros looked a good option. Close by and dramatic scenery with a much less touristy vibe. Timing wise despite the short distance only way to do it is with an overnight stay.

Also had interest in Andros which is much closer to Athens than Santorini but not finding a good way to make that work. No airport in Andros and is not exactly on the way via ferry.

Santorini is the most hyped of the Greek Islands, many love it others avoid it.

Lots of islands that have outstanding scenery without the high prices and hordes of tourists.

Late August won't help to avoid the numerous daily cruise ships docking off of Santorini.

There's more to Athens than just the tourist sites. It needs a minimum of 2 days with 3 better to fully experience the city.

Lots of options for islands but regardless of where you go late August will still be High Season.

My favorite three islands are:

Amorgos
Chios
Tinos

Tinos is the closest and a real gem of an island. https://tinyurl.com/y6w5ncb8

Chios is furthest away and has a airport. https://tinyurl.com/ycgkrqza

Amorgos has no airport so it's a long ride but worth the effort. https://tinyurl.com/y7bqwfma

It's really not worth the effort of an overnight stay on any island or even a few hours.

Naxos and Paros are good options and can be accessed from either island.

Late August is not my 1st choice but cannot change the dates now

I understand the love / hate feeling with Santorini ; is a place we want to see at some point regardless.
Not adverse to crowds. In my opinion, there is usually a good reason why so many people want to see a place.

For this trip not getting an authentic Greek feel/experience is ok with us as this is not a trip to Greece but a trip to Italy with Greece being added as a multi-day stop over if you will.

Could extend Athens but have heard very mixed feelings about the city and honestly tend to think we will love Santorini despite it's negatives and not really care much for Athens other than the main site.

That is just a guess but heard from many that they just wanted to get out of Athens and to the islands as soon as possible.

This may be wildly incorrect but I get the sense Athens is like Naples and Santorini is like Positano. And we love Positano despite it's flaws and fine skipping Naples despite all that it offers. Just to give insight into our likes/dislikes.

Unfortunate that you mention none of the islands are well suited for a single overnight. Would think that would be something of interest for many of course if we had weeks for Greece would stay a few days on another island but sometimes you want to maximize what time you have. To again bring up a comparison to Italy, the island of Capri is a great "day trip" island in my opinion so was hoping there might be something with similar type of situation to be well suited for such a short stay.

Appreciate the reply and really enjoyed your gallery of images.
I will look up the islands you mentioned but am fairly limited by a.) only staying one night and b.) trying to make logistic sense of it knowing that Santorini is the main place in Greece we are going.

Thoughts on the ferry actually being enjoyable??? and a part of the vacation itself or is it just boring for 90% of the time and am better off saving the time by flying?

I did some digging on the ferry times and stops and looks like Syros would be one that works logistically best for us as an on the way stop if going via ferry.
If staying there one night and taking the ferry is a good plan vs. skipping other islands and fly to Santorini would still be the main debate.

The times are a little better than even Paros and Naxos I think ; though those are also 2 : "on the way" choices, Mykonos another and a little more complicated but Folegandros being the last one I think that still can be done with extra nights added to Greece.

I don't understand why you want to stop one night on an island on your way to Santorini.
Stopping for a few hours on an island (and staying there only one night) is of no interest.
Moreover, apart from Delos which is an uninhabited island and an archaeological site, there is not really an island on your route where you can take a day trip.

The comparison with Capri is not quite appropriate. Ferries are not designed for excursions but for travel between the islands and Athens. Apart from tourists, it is the usual means of transport for the inhabitants of these islands.

In fact the only perfect island for a day trip is Santorini itself where many cruise ships arrive and thousands of cruise passengers go to this blue and white shopping center every day. They leave a few hours later, happy and exhausted...

If you want to go to Santorini, go there. No need to stop on the way.

From Athens (at the port of Piraeus) if you take a conventional Blue Star ferry on which you can move around and walk around the various decks, the crossing will take approximately 7 hours.
It will be 5 hours with a Seajets Worldchampion Jet type Highspeed ferry, but there is very little possibility of going on the outside deck. (nothing to sit in, lots of wind) The cabin style is more like an airplane cabin than a boat.

From Santorini to Catania there is to my knowledge no direct flight, you must have a stopover, maybe in Athens.

I just didn't know Jolui

Have researched a decent amount online but some things you have to ask to get clarity.

Santorini - Catania ; Wizz Air flies direct and is very cheap. Not every day but they do fly this route without stops at least through Sept.
Our Italy trip is from Catania to Bari ; so there is also the option of flying Santorini direct to Bari and doing the Italy portion in reverse available. From Santorini you can fly direct to both, just not every day.

Basically want to go to Santorini and will be in Athens to start.
When I planned out our days, I see 1 day that we could definitely use for something be that one more day in Athens (not really of interest), 1 more day in Santorini (fine but likely not necessary and lodging there is pricey where I plan on booking), so that got me thinking why not visit another island for that 1 day. I don't have multiple days that I can spare.
With Wizz Air only flying on certain days I can not move that "extra" day to get to Italy sooner either.

Hopefully that answers the why.

I guess I am niave for thinking the boat ride might be a nice way to see the islands for a first timer to Greece; and I guess it could be just not sure it is when doing so for 7 hours. Which is one reason why I thought why not break it up into 2 rides so we would not be captive on a boat for so long if we stopped for a night in the middle of the journey.
In a perfect world it would be interesting and scenic to come into the various ports along the way, but the reality may be quite different. The plane from Athens to Santorini is MUCH faster and costs roughly the same so would only take the ferry if I thought it would be enjoyable.
The only ferries I have ever taken have all been very nice and add to the overall experience (at least when the weather co-operated). Taken many ferries locally as I live near to Martha's Vineyard, Nantucket, Block island, Provincetown so often take a summer ferry at least once a year. I would never fly even if the cost was equal to these locations as we enjoy the ferry experience. But these are 1 hour or 2 hour at most ferry rides.

The island of Syros seems to be a stop that could make sense for less than 24 hours. The town's colorful houses on the water's edge and the main old town streets seem very much of interest along with a church or two that could be visited. All points of interest on this island appear to be very close to the ferry port, which is ideal if a short stay.
I can take a ferry journey for this to be on the way to make the otherwise 7 hour ride to Santorini in 2 rides of roughly 4 hours each.

If it doesn't make sense to bother with the ferry at all ; than flying and adding one more day to Santorini is what I would do instead ; probably doing some kind of boat excursion to the volcano area.

Santorini-Catania; Wizz Air flies direct and is very cheap

Indeed Wizzair flies on Sundays in September.
I hope it will go well for you as this low cost Hungarian airline is ranked among the worst airlines in the world.
Note that the checked baggage surcharge can double the price of the flight without checked baggage.

The island of Syros seems to be a stop that could make sense for less
than 24 hours

As for the stop at Syros, why not. It is the administrative capital of the Cyclades but it is not where you will see white and blue houses and windmills.

Seajets confirmed last week the Wordchampion Jet schedule for 2023:

Everyday: Piraeus - Syros - Mykonos - Naxos - Ios - Santorini

So you can get there from the port of Piraeus in about 2 hours with the Wordchampion Jet which leaves in the morning around 7:00 a.m. or with a Blue Star ferry which leaves around the same time but takes more than 3 hours to reach Syros .

The next morning you can take the same Wordchampion Jet (around 9 am) and you will be in Santorini around noon. (after passing through Mykonos, Naxos and Ios).

BUT! You can stop for example in Naxos instead of Syros. In this case you could find a traditional ferry going from Naxos to Santorini because, except not yet published modification in 2023, there will be no traditional ferry in the morning from Syros to Santorini.

I give you these leads but I remain convinced that a one-night stop on an island is useless

BTW I have already taken the small ferry that goes to Martha's Vineyard ( a long time ago) , it's different from the Greek ferries. The ones you could take are carrying over 2000 passengers and over a hundred cars/trucks

Not expecting much from the flight just hoping they stay in business and don't make schedule/route changes!
Otherwise I am easy to please with these budget airlines. Have used Ryan Air a handful of times plus others that are similar.

I always buy all of the extras on these type of budget carriers, priority boarding, extra legroom seats, carry on bag, check in bag and yes the 25 euro fare becomes an 85 euro fare but that is still far less than any better rated carrier is going to be.
Of course no seat back entertainment nor food and drink free on board but for short flights is not a bother for me.

Yes, the ferry ideas you outlined is what I had in mind and meant by it not being out of the way to stop in Syros, would prefer the slower Blue Star when possible.
Syros looks much more Italian than the other islands ; which is maybe what caught my eye, lol.
The harbor where the boat goes into/out of looks very much like Procida (a small island in Italy) with the colorful houses built on top of each other with a church dome dominating the skyline.

It at first glance just seemed more "doable" in a day than larger Naxos or Paros would be.

The check-in / check out for just a 1 night stay with luggage in-tow is definitely in the back of my mind but it seems like it may give us a little more taste of the Greek Islands than the flight directly to Santorini and one more night there would overall.

It's up to you !

All ports in the Cyclades islands are relatively similar.
(However be aware that the port of Piraeus covers a quays length of approximately 3mi)

Yes, in a way, Syros with its neoclassical/Venetian architecture may be reminiscent of Procida, but you'll get more of the "Greek island vibe" as people imagine it in Naxos than in Syros.

Anyway, if you stick with your plan to take the ferry, you can watch this advice video made by an American expat living in Athens:

https://www.youtube.com/watch?v=S8iuG1gVsvQ

We love Greece and have been there several times. We have never “ wanted to get out of Athens to get to an island. ” We have enjoyed our time in Athens with it’s many significant site. We have been to nine of the Greek islands including Crete and there is only one we won’t return to, Santorini. You have to go once and then decide if you ever want to return there. It looks like Greece but doesn’t feel like it.
We love the Peloponnesean Peninsula and especially the beautiful small city of Napflion.
We also enjoy Athens.

I get it and totally understand how the crowds and touristy nature of Santorini could easily be the exact opposite of what many want and feel in-authenitc or fake. As you say, it is a place you have to see once and then you can decide if you care to ever return.
That is how I feel about it and as I mentioned this is not for us a Greek holiday but an Italian one with a start of Greece and Santorini is at the top of my must sees for Greece.

I personally think we will enjoy it but will use our time wisely, I will be up before dawn walking around while others are asleep and enjoy the views of the caldera from the cliffs. Mid day we will try to avoid the masses ; that method seems to work well in similar tourist hot spots.

Venice seems comparable, where the busy areas really no longer feel like Italy as it has toured into a Disney like town ; I actually really did not enjoy it in the day time but at dawn and at night after dinner it was magical!

On vacation we generally like to avoid the cities (unless a purposeful city vacation) ; and seek out natural beauty / larger villages which is why I think Athens will not have that much appeal to us but certain we will be in awe of the historical sites.