Need help deciding between Sifnos or Naxos for Greece trip in September
 

Hi there,
My partner and I planning a trip to Greece in September for two weeks. Nothing is booked or confirmed at all, but the tentative plan is to fly into Athens from Toronto, then head straight to the islands (visiting Athens on the way back for a couple nights). We've narrowed the island selection down to four, but think we need to cut the list down to three given our tight time frame:
- Santorini
- Milos
- Naxos
- Sifnos

We for sure want to visit Santorini and Milos and are now struggling to decide between Naxos and Sifnos. I'm reading forum after forum and keep switching my preference as both seem great. We're interested in Naxos because being a larger island it seems like there is more to do and things to see. I want to see Sifnos because I just keep reading about what an awesome place it is in terms of being a quieter but still exciting island with great beaches, good hiking and amazing food.

We are in our 30s - 40s, like to do a mix of super 'touristy' things but also happy to spend a day just wandering and exploring a city or town. Enjoy some outdoorsy-ness like beaches, the water, and hiking but aren't looking for intense physical activity. Love good food, good wine, and exploring markets and shops (less for the shopping itself and more just for the experience and people watching). We like some museums and visiting culturally and historically significant sites like ruins and churches, but wouldn't say that is the main priority. Nightlife in form of clubs are not really our scene, but definitely appreciate places with a lively vibe in the evening for a late dinner and night cap at a low key bar. Ultimately, we are looking for this trip to be a nice combination of exciting fun activities and excursions (e.g. visiting a winery, taking a sailing day trip) and just relaxing and hanging out (e.g. reading a book on a beautiful beach). Would be up for renting a car if it would facilitate exploration of and transportation to harder-to-reach areas, but generally would be happy to stay somewhere where we can walk or take local transit--I don't necessarily want to have to rent a car on every island.

All that said, would you recommend Naxos or Sifnos as a complement to Santorini+Milos? Haven't done extensive research yet on the transportation between islands but both seem to be relatively easy to combine with Santorini + Milos? We'd probably do Naxos-Santorini-Milos or Santorini-Milos-Sifnos.

Another question I have--which may or may not factor into the recommendation for the above--is about when we should travel. Thinking either the 8th - 22nd of September or 15th - 29th. Will it make much difference pushing out the trip by a week? I've read a couple places that prices (on accommodations, excursions, etc.) start to drop after mid-September, so if that's true that would be a potential incentive to push it out a week--plus I'm thinking crowds might start to thin out later in the month. However, I'm concerned with pushing it out too late into September as I'm wondering about whether the weather will start to cool off near the end of the month and whether there is a risk (though this seems unlikely) that things might start to close down as the season comes to a close.

Any suggestions on island selection + trip timing would be very much appreciated! (And any other suggestions, tips, advice, words of wisdom welcome as well -- at this stage we haven't got anything nailed down so are totally open.)

Thanks all!

I haven’t been to Sifnos, but I loved Naxos. Have you seen my trip report? You might find some useful information – check posts 109 and following.
https://www.fodors.com/community/eur...greece-1460735

Enjoy!

Sifnos is on the same Western Cyclades ferry route as Milos, while Naxos is on the Central Cyclades route. Travelling between the two ferry routes sometimes means long ferry rides on a small catamaran. I wouldn’t combine Milos with Naxos for that reason.

Since you want to head straight for the islands that probably means a flight, and Santorini, Milos, and Naxos have airports while Sifnos does not. The airports at Naxos and Milos have short runways, so are served by small turboprops.

You could fly straight to Santorini on a jet, then go by ferry to Milos, Sifnos and Athens in that order. If you want to combine Milos and Naxos it would be best to fly to either of those islands first, then ferry to Santorini. There are good ferry connections from Santorini to both Milos and Naxos, so if you put Santorini in the middle you avoid the long catamaran ride.

Thanks kja for directing me to the right section of your trip report :) I'd seen it but hadn't managed to read through the whole thing yet so that is super helpful.
Heimdall -- that's what I'd planned to do so thanks for affirming that we were on the right track with respect to itinerary. If we pick Naxos, we'd go straight to Naxos then Santorini then Milos then back to Athens. If we choose Sifnos then we'd do Santorini - Milos - Sifnos then to Athens. Do you have any thoughts or preference on Naxos vs. SIfnos?

Hi Eggbert, glad we are thinking along the same lines. I’ve been to Naxos several times, partly because it’s so easy to reach from my favourite island, Antiparos, but never been to Sifnos. Many people love Sifnos, and I’m told it has great hiking and some of the best cuisine on the islands. Sifnos is very popular with Greek visitors, but takes a little more effort to reach.

Naxos has great beaches, interesting inland villages, and a beautiful chora (main town) which is a joy to explore in the evenings. On logistics alone I would recommend Naxos, because it has an airport and among the best ferry connections with Athens.

I have been to both islands repeatedly (Naxos 13 x Sifnos 5 x) and love them both ... the time of year is determining factor IMHO, Naxos has larger permanent population so will be vibrant year-round, Sifnos may be emptying out more in September. Also, don't forget Naxos is a highly agricultural islands.... inland and in the hills, many many farms, livestock, veggies galore (it's the biggest supplier of greece's FAB potatoes), and of course VINEYARDS, so in September there are some wine festivals in hill towns. You can inquire about such at the store on the harbor "crescent" that specializes in Naxos-only products. The young women clerking there are up on whatever events are around.

Hello Eggbert,

I've been to both islands. Each one has something different to offer. Sifnos is very charming but it is not that touristy and might be a bit "empty" at that period. Sifnos is great is you are looking for exquisite cuisine, as it is considered a foodie island. It is also known for its hiking trails and has more than 350 churches scattered around... Sifnos has also a great tradition in pottery. If you are looking for more sightseeing then Naxos could be a better much. Check out Portara, the Temple of Demeter, the 2 Kouros statues. The Venetian Castle in the old town of Naxos is beautiful, you'll travel in time... Plenty of good places for food, great local products like potatoes and vegetables. They also make their own trademark cheese. Naxos is also famous for its mainland villages like Filoti, Apirnathos and Halki. Numerous beautiful beaches as well... In my opinion if you are looking for beaches and more things to do then Naxos is the one to pick. If you want just to relax then head to Sifnos, romantic and serene but with not much to do around since it is the end of season.

8th - 22nd of September sounds a lot better. Don't forget that the longer you wait the more likely it is to start raining. Greece has great weather but sometimes September can be tricky.

Thanks everyone for your super helpful input!
From the feedback, sounds like Naxos is the way to go here and perhaps we will leave Sifnos for the next trip :) It's also pretty telling that kja and Heimdall you've both been to Naxos (but not Sifnos) and travelerjan you've visited Naxos 13 times vs. 5 times for Sifnos.

anniesweetiepie, thanks also for your input on the dates. I think I was leaning towards earlier in the month to ensure we have good weather -- but was thinking if prices (of accommodation, activities, etc.) were significantly lower later in the month we'd consider pushing it out. I did just a quick random check on some places on airbnb and looks like there often is a bit of a drop in the second half of the month, but not so significant that I think it's worth pushing out our trip. Rain would be a downer so want to avoid that if we can :)

Travelerjan, love the idea of the wine festivals in Naxos! Will try to research that a bit online first before we go--do you happen to know the name of the store (maybe they'll have someone resources...)?

Finally, two transportation-related questions. What do you all think about renting a car? I'm thinking Naxos and Santorini it likely will be useful to help us get around and explore, but can forego the car in Milos? If we can get around without one i'd prefer that but will definitely rent a car if it will help.
And I know it's super important to work out the logistics of travelling between the islands before we book accommodations. Does anyone have any specific sites that they prefer for ferry information? I've seen a few that have been recommended (e.g. https://www.seajets.gr/en/and https://www.ferriesingreece.com/ and https://www.gtp.gr/RoutesForm.asp)

but would love to hear your thoughts if you have a solid recommendation.

Thank you! So excited for the trip now that we've settled on our destinations. :)

I wonder if you took the wrong message from the fact that I visited Naxos, but not Sifnos -- what I meant was that I can't comment on Sifnos. That said, I definitely loved Naxos!

Whether to rent a car on any island depends, I think, on what you want to do. As noted in my trip report, I rented one on Santorini primarily because I had very little time there and seeing Akrotiri was a priority. I would NOT rent from that company again -- ever!!! I also rented a car for one day on Naxos, and doing so met my needs well. I didn't feel the need to have it for any longer; YMMV.

For the ferries, you might check rome2rio.com and then click through to the actual ferry company web sites to which it directs you.

Oh I just meant that clearly we couldn't go wrong with Naxos if everyone had chosen to visit that island -- not to take anything away from Sifnos though.

Flights have been booked! Now just to determine how many days to stay in each place. I think we will spend 4 nights in Naxos, 3 in Santorini, and then it's a toss up between spending 4 nights Milos/3 nights Athens or 3 nights Milos/4 nights Athens. Will do a bit more research to figure out what we're interested in doing in each place.

Appreciate everyone's help planning thus far :)