Hello!

My husband and I will be visiting Greece Sept 20 (our arrival day)- October 1 (departure day). We are going to be flying in and out of Athens. Our plan as of now is:

Sept 20: Arrive in Athens and immediately take flight to Santorini. Stay in Santorini
Sept 21: Santorini
Sept 22: Santorini
Sept 23-28: Ferry to different nearby island. Currently considering Naxos, Paros, Sifnos, Milos, Folegandros...even thinking about just picking one town in Crete. However open to anywhere really, even if it means taking a short flight. We want to choose one island and stay there for 5 nights instead of hopping around.
Sept 28: Ferry to Athens ideally vs. fly (though are not opposed to that based on island we choose). Stay in Athens
Sept 29: Athens
Sept 30: Athens
Oct 1: Depart from Athens

We are a youngish couple who have never been to Greece before and love beautiful/unique hotels with ocean views, charming villages we can walk to that have a good mix of locals/not crazy touristy, nice beaches to hang out at one day and a couple sites to see that we can walk to during the day, and great tavernas we can eat at. We're not looking to go crazy at night but the idea of staying in a taverna with live music and ouzo until midnight sounds great. (Not interested in the club scene) We also don't want the town to feel like it's shutting down/too quiet. We are also really hoping to do a boat tour around whichever island we choose where we can swim near caves, etc.

As seems to be the case with most people we are really having a hard time deciding which island is best for us. Any advice would be much appreciated!

Thanks!

Some of the smaller islands in your shortlist will be getting very quiet by the end of September, and that could be a good or bad thing depending upon your point of view. Sifnos, Milos, and Folegandros will be quieter than Naxos or Paros. The other thing to consider is getting back to Athens at the end of the trip. Both Naxos and Paros are on the Santorini - Naxos - Paros - Piraeus Blue Star ferry line, which has the most dependable and comfortable (especially in rough seas) ferries. Most ferries in the western Cyclades (e.g. Folegandros, Milos, Sifnos) are smaller catamarans. Naxos and Paros both have airports, as does Milos.

If you choose Paros you may be able to find a boat that will take you to the sea caves at the southern end of Antiparos. One of these is Captain Ben Antiparos Lazy Day ? Daily cruises from Antiparos and Paros Greece ? Boat trip arround the island , which has a new boat this year. There are other boats offering day trips, some of them listed in the Polos Tours website: https://polostoursparos.com/daily-cruises/

We combined Santorini with Paros last June. On Paros, we stayed right outside of Naoussa at Saint Andrea Resort which was perfect. The cab into town was about a 5 minute drive and there were so many restaurants and bars to choose from in Naoussa. We visited a different beach each day and did a day trip to Antiparos. My trip report is posted here: Greek Islands & Athens Trip Report: 11 Days in June

Thank you Heimdall! I will look at those boat options, they sound great!

northfork280: That sounds like a great combo as well. Did you enjoy Santorini and are you glad you did it? Could you walk from your hotel in Paros to sites as well or is everything on Paros mostly a drive?

HappyTrvlr: Thank you! Second vote for Paros.

northfork280 I just read your wonderful trip report. Honestly Santorini does sound magical and sometimes I feel like a lot of people dismiss it (hence my wondering if you loved it, but you clearly did!). It's a bucket list place for me. I have two additional questions for you if you don't mind!

Santorini: We are planning to fly here immediately after we land in Athens (we arrive fairly early so if all goes well with weather would arrive in Santorini around lunch). We are planning on spending three nights only (the first would be that dreaded jet lag night) but your trip report has me wondering if we should add an extra night for 4 nights total. We could either remove a night from our second island, or a night from Athens (currently planning on three). Would you take a night away from Paros or Athens if you had to choose?

We loved Santorini - it is truly magical and a place not to be missed. It's a tough call re adding another night since it means taking a night away from Athens or Paros. I would probably split it up evenly between the two islands (4 nights on each) and 3 nights in Athens, if I understand your itinerary. That will give you plenty of time on both islands to relax and to see everything you want to.

On Paros, we weren't able to walk to any sights from our hotel. We had a rental car and used that to drive to the different beaches each day. We also took our rental car on the ferry to Antiparos for our day trip so that we could explore that great island. At night, we took a taxi into town arranged by our hotel. It was never an issue finding a taxi to take us back to the hotel at the end of the night.

northfork280 That sounds like a good plan, thanks for the advice!
Heimdall They definitely lean towards Naxos over there! I feel like we've seen so many photos and videos of both islands and something about them doesn't pull us in, but of the two Paros seems to be the winner to me. I had seen that T&L survey however and it also made me lean towards Paros, mainly b/c it was a reader survey vs. an article with one editor's opinion. All in all it seems like we can't go wrong with any of the Greek Islands since at the end of the day, we will still be in Greece enjoying it all. Antiparos did seem super intriguing to me as well! It seemed a bit like the best of both worlds.

Some other islands I can recommend are Amorgos and Tinos with Tinos being an unexpected gem and Amorgos is truly lovely. September will find those islands far less crowded with tourists, the weather still nice and prices for accommodations lower.

Lesvos is also another great option and I'll be going there this October.

I'm not sure if you can get to all those islands I recommend from Santorini but it may be worth looking into.

Heimdall I will def. check it out, thank you!!
crazyh I had looked at Tinos and agree it looks really interesting. Do you prefer Amorgos, Tinos, Lesvos vs. smaller islands like Sifnos?

LAG:

Sifnos & Milos were the first 2 Greek Islands we went to many years ago and it was everything and more we could have wanted in Greek Islands. Sifnos was especially wonderful and it would be an island I would go back to. Milos was lovely but Sifnos had more to offer.

Since then we have gone to many other islands and parts of the mainland and consider ourselves more in the line of a culture, history, archeological and Greek food lovers than over-the-top touristy islands. We travel off-season, October when the weather is still comfortable, the Aegean still warm for a dip, lower cost for accommodations and more importantly far less tourists. However everyone has their own opinion on what they consider a Greek Island and when they can go.

Amorgos and Tinos were outstanding islands and turned out to be exactly what we want for a Greek Island. Tinos was especially wonderful, even better than our research showed. It had the highest percentage of beautiful villages than any island we have been to so far. There is a road on the west end of the island that goes over spectacular mountains with beautiful scenery and vistas. Lots of out-of-the-way villages and beaches.

Amorgos is a wonder to behold, especially the spectacular Hozoviotissa Monastery. In addition St. George Monastery was also beautiful but on a smaller scale. There were numerous mountain villages, beaches, shipwrecks, mountains, archeological sites and much more.

Don't overlook Chios, another beautiful island with the magnificent Mastic Villages in the south, the one-of-a-kind abandoned mountain-top village of Anavatos and a history that is tragic but also impressive.

I am scheduled for Lesvos this October and it's another island that I am looking forward to.

There is more to Greek Islands than Santorini & Mykonos and even Naxos is starting to become more touristy than when we went several years ago but is still a good option.

You can check out my photos of Tinos, Amorgos and Chios below and decide if they are island to consider.
Amorgos::Too bad there isn't a way to send a personal message where I can provide more assistance.

crazyh Thanks so much for the breakdown! As of now we are leaning towards Sifnos b/c of the walking trails, ability to stay near Apollonia and Artemonas, and the look of their beaches (we actually prefer coves to long stretches of sand. We live in California near the beach so prefer different geography). It also seems to have some interesting food choices which we love. In re: to Tinos, do you think at the end of September when we are going places will still be open? Restaurants I've contacted in Sifnos seem to stay open until mid-Oct but am not sure about these other islands like Tinos and Amorgos. Is it easy to stay in Tinos near some of the action (so you can walk to a couple tavernas, etc.)? Naxos does seem to have a lot of what we want, but it just seems so big. Everywhere we want to go is spread out. We love to walk most places and I'm not sure if that would be possible there.

LAG: I was on Tinos in early to mid October and stayed in Tinos Town. Everything was up and running with many shops, markets and tavernas open so there were lots of options available. I assume September will be even better in Tinos Town and possibly you'll be able to find a more traditional village to stay in like Pyrgos which is lovely but at the far west end of the island. Tinos Town is centrally located and a great place to base yourself to explore the entire island and enjoy a day seeing the sights and get back for a night out in Tinos Town. I stayed at the Athos Studios in a quiet, residential area but just a short walk to the waterfront and all kinds of tavernas and shops.

Naxos is beautiful island, the largest of the Cyclades and has something for everyone. I stayed there for 9 days and could have stayed longer and I consider it one of Greece best islands with enough space to get away from crowds if you need to. I stayed at St. George Beach, just a short walk to Naxos Town but if you don't want to walk to far there is a nice town square with lots of options.

Amorgos was fully open in October and in fact most of the businesses in Katapolo where I stayed were open so again lots of options for services. I stayed at Porto Katapolo which is right across from the beach area with the owner speaking perfect English and has a large garden behind the studios where he'll let you pick all the produce you want for free! There are also mountain villages on the east side of the island which could be a good option

If I had to pick in order of where I would stay again it would be:

Tinos
Amorgos
Naxos

But I would also look into Chios and Lesvos, not to mention Kythira, Karpathos, Lemnos and Thassos, just to name a few.

One of the hardest things about going to Greece is where to go: Over-the-top Tourist-oriented islands or more traditional and "Greek" islands.

crazyh you are so right about the choices...there are so many and being a first-time visitor you feel like you are sort of blindly choosing. Walking around Google maps seems to help us at least get some feel for the geography of a town, and of course wonderful advice from commenters like you! Thank you so much for all your help!! We are going to investigate Tinos further. I hope to write a trip report when we get back.

LAG: Since I have been fortunate to go to Greece on a yearly basis and the number of places to choose to go dwindles making it a bit easy to make a decision since many of my "bucket list" have been visited but there are still numerous places I want to go to, so I understand the "difficulty" of making a decision but in the end the research is part of the fun and is always educational.

Check out some videos I made of villages on Tinos that I posted on another travel forum. I'm not a professional videographer nor do I have a high-end cam-corder but hopefully they will help with making a decision on Tinos:

https://www.tripadvisor.com/ShowTopi...th_Aegean.html

https://www.tripadvisor.com/ShowTopi...th_Aegean.html

I loved Naxos!

I'm glad I saw Santorini, but really only for Akrotiri -- I am among the few who found Santorini an otherwise overrated and overhyped place. That said, I was there in May, when it was thoroughly and unpleasantly overrun by tourists; it might be much more pleasant when you plan to go.

If you haven't already seen it, you might find some useful information in my long (but searchable) trip report:
With Gratitude for a Glorious Solo Month in Greece

We have just come back from our holidays in Crete and liked it a lot. The beaches are amazing and there are plenty of things to see and explore the only thing is that you have to make sure to choose a decent hotel, as many hotels put nice pictures and dont show the reality as such. In case you want an honest review of several resorts that we stayed in Crete, you can check out my videos on YouTube channel - Dadunikos Deda . There are 3 videos about Crete there and I will be happy to answer any questions that you might have