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Itinerary Help: 9 Days, Greek Islands, in late August 2020

Hi there. I've thoroughly confused myself planning and replanning my family's trip to the Cyclades in late August 2020. I'm usually very decisive when planning but the optionality in the Greek islands universe is making me a little crazy. Hoping some clear-headed soul will have some advice for me. Here's our situation:

-Traveling with 2 teenagers, both of whom are experienced, hearty, and adventurous travelers. Love food. Love wandering around interesting places. Love swimming. Very active.
-We have nine nights to spend on the islands
-Parameters: we will be leaving for the islands from Athens and heading home from Santorini.
-None of us has ever been to the Greek islands, thus the final stretch in Santorini just to take a look before we head home.
-We aren't excited about crazy crowds, so we're definitely avoiding Mykonos and Ios, since we're already going to Santorini.
-Also trying not to spend more than 3-4 hours at a time on a ferry.
-At the moment, the itinerary looks like this:

August 21: Ferry to Sifnos
August 22: Sifnos
August 23: Sifnos
August 24: Ferry to Folegandros
August 25: Folegandros
August 26: Folegandros
August 27: Ferry to Santorini
August 28: Santorini
August 29: Santorini
August 30: Fly home from Santorini

So, here's what I'm wondering: Too much hopping around? Too much redundancy between Sifnos and Folegandros? Should we swap one of those for places for Paros or Naxos, and if we do, which one would we lose? Which one would we take instead? And if we make this change, how would this impact the ferry situation?

Any insight would be welcome and appreciated. Many thanks in advance.

Posted by
78 posts

I visited Santorini, Folegandros, Milos, and Sifnos last summer. If I were to do 3 of the 4, I'd definitely include Milos. It's the best for beaches of the four IMO and if you are worried about Sifnos & Foley being too similar, then skip one and do Milos instead. I'd probably skip Foley with teenagers, but really all the islands are great and you'll love where you go.

Milos does have crummy public transportation compared to the others so rent a car if you go there. Definitely do a boat tour one day in Milos.

Milos is on the same ferry line between Sifnos and Folegandros.

Posted by
2418 posts

I agree that teens will get bored on Folegandros... it has an absolutely beautiful high town (Chora), but nothing to do but look at the beauty... and the beaches are just OK. I would substitute another place

• Milos .... it has 22 beaches! And you can do a fab island-rim cruise ... avoid the 50+ passenger "party boats" and choose a catamaran -- there's one that holds about 10, and another with 14 capacity. We chose the latter... were happy with it, it was big enough it could go under sail most of the time even tho quite windy -- smaller boats have to drop sail & go under motor, not what one wants. The drawback: you'd need car rental at least part of the time, because bus schedule is fairly lame even in High Season. Most of the restaurant choices & night life is in Adamas, but the beach there is n.g. In high season, more choices of where to stay

• Naxos -- I think this is the ideal island for families like yours (or anybody, truth be told). Excellent bus network, so your teens can be (safely) independent - just have cel phones & make them check in periodically. You can do without a car except for a day to whirl arond the whole islnd. Since you're in high season, stay out on Plaka Beach, & bus in to Port Town for some evenings ... but Plaka has 2-3 really swell restaurants. See if you can book rooms at Three Brothers out there. Friends of mine do 3 nights in Plaka, 3 nights at St. George beach... because the latter is directly adjacent to port town, a 10 minute walk along the water. Naxos beaches have water sports like Kayaking, wind-surfing etc... the Port Town is fasinating, lovely mazy lanes leading up to high town and Kastro (medieval fortress) ... outstanding tiny museum, best in the Cyclades ... There are good tours that take u all around the island on small bus for €23, a good buy -- and stop at top of island at noon for lunch/swim oppty. The trick is, to find a good ferry sked from Sifnos to Naxos -- but in August, there should be a run allmost daily. And there are TWO good ferries from Naxos to Santorini -- the ChampionJet at about 10:45 gets u there around noon, and the BLUE Star 1 pm - 3:15 or so.

• SANTORINI --- if you get the Champion-Jet, you'll have half a day on the island, Day #1 - for wandering fira town, sunset dinner. Then on Day #2 yank your teens out of bed early to go to OIA by the 8 am bus, before the cruise mobs invade and cramjam every lane, and leave OIA by 10:30 or so -- go see Fira museum, admire the view, pick a restaurant for sunset dinner (NOT in OIA). Black grit beaches will not appeal to your bunch after Sifnos & Naxos or Milos ... so decide if you really want to spend the whole next day on Santorini, amid Gigantic crowds. You say on day #4 "fly home from Santorini." How can we know if that's feasible, when you don't say where "home" is. If it's in Europe, maybe. If it's N. America, you cannot chance having a morning flight to ATH to connect with a flight to US/Canada the same day.. what if there's a delay a mechanical problem cancelling your domestic flight? I advise going back to mainland the afternoon before -- where u would stay (central Athens, or one of several places near airport) depends upon the time of your flight on Aug 30. We cannot give best advice without key info.

Posted by
2 posts

Thanks for these fantastic thoughts thus far. Based on your feedback, sounds like we should lose Folegandros in favor of Milos or Naxos. The question is which! They both sound fantastic. I feel like I'm never going to want to leave.

As for the departure home, we're already booked on a flight out on August 30th back to NY via Milan. The flight to Milan leaves mid morning and we'll be there for a day or two before heading back to the states. Should we be worried that we won't be able to get out on that flight? I just assumed that if it was cancelled, they'd find a way to get us to Milan. Perhaps this is naive, though even in India we managed to finagle flights to where we needed to go!

All this said, now that we've looked at Milos and Naxos, my husband wonders: should we toss Sifnos and just go to Milos and Naxos? I told you I find this confusing. Only reason to stay with Sifnos/Naxos or Milos/Santorini is because the ferries are more manageable than Milos/Naxos/Santorini. Athens to Milos is almost 5 hours vs. Sifnos which is 3. Am I right?

Grateful for your input.

Posted by
2418 posts

If your flight is direct from Santorini, no problem. The danger comes when someone plans to fly from an Island to ATHENS, and there make a connection to N. America. If u are going to Milan & onward, it is that airline's responsibiity to see that you get to Milan.

I cannot make the decisions for you about which Islands. If you only have 9 days, you need to choose 3 islands (and as I said, cut your time in Santorini by a day -- the endless photo-promo of that place obscures the fact that it isn't for swimmers/active teens). I would suggest FLY to Milos, then ferry to Naxos, then ferry to Santorini. The ferry website gves 2020 schedules, but all are not posted yet. If you use THIS ferry website - - and Roll Back the calendar to August 2019, you will see what the typical ferry skeds are for Milos-Naxos ... about 3 daily.

Posted by
1082 posts

My young adult children loved Santorini but loved Naxos even more. I have not been to the other islands you are considering.

On Santorini, they all jumped off the cliff into the sea (I went in but did not jump) below Oia. We also hiked between Oia and Fira and took bus back. We spent three nights in Santorini and that was about right. We went hiking and then took bus back to Oia where we were staying and went down to go cliff jumping. The second day we rented cars (there were 7 of us) and visited Akrotiri and some other sites on the island.