My husband and I are going to be in Greece for five weeks starting in early September. We are going to Athens for three nights. Then we are heading to Naxos for five nights and Santorini for three nights with our 34 year old son. We plan to do a little island hopping using Naxos as our home base while we are there. After that we are hoping take advantage of the fact that we don't have to rush home and slow down our pace and enjoy some more island time. We want to do some exploring/hiking and enjoying beautiful scenery and good food. We are also trying to avoid renting a car if possible, but are open to some car rental (or bikes or scooters). There are so many islands to choose from it's hard to know which ones to prioritize. Any suggestions?
There's something I don't understand about your itinerary that makes it difficult to answer.
From the way you describe it, your itinerary begins in Naxos and then continues to Santorini.
After Santorini, do you want to return to Naxos a second time as a starting point to travel to other islands?
Normally, you should start in Santorini, then go to Naxos. From Naxos, there are quite a few options, but certainly not using Naxos as a base. You'd have to change the island you're staying on.
If your itinerary begins with Naxos before going to Santorini, you'll have to travel to other islands from Santorini without returning to Naxos.
Thank you for clarifying.
We were planning on taking day trips to other islands using Naxos as a home base so our son can see a few islands for the week he is with us, then going to Santorini. After Santorini we are not planning to go back to Naxos, but we are looking for other islands to visit. Is this an illogical order to do things in?
Yes, illogical. LIsten to suggestions.
You can take organized boat tours to other islands from Naxos, but you won't be visiting these other islands; you'll just spend a short time there (and a lot of time on the boat).
So, no "exploring/hiking and enjoying beautiful scenery and good food" as you suggested in your initial message.
It would be even more difficult using ferries, whose schedules and routes aren't designed for this type of tourist trip.
The Greek islands shouldn't be seen as attractions in a theme park. They are inhabited places, each with its own history, culture, landscapes, villages, food, etc. It's not just a port and its surroundings where you stay for a few hours.
So, if you want to visit other islands, you'll have to do what everyone else does: take a ferry and change the island where you stay, meaning find accommodation on the other island.
It's simply the principle of island hopping, and it's perfectly suited to what you want to do since you have plenty of time available.
That said, going to other islands will depend on which island you're leaving from.
Ferries have itineraries that you need to know before saying "I want to go to this island." Sometimes it's impossible.
Here, for example, are the ferry departures from Naxos on September 5th:
https://gtp.gr/greekferries_searchresult.asp?Code=EGRSKY56&AskDate=22%2F7%2F2025&IsDep=True
And the departures from Santorini on the same day:
https://gtp.gr/greekferries_searchresult.asp?Code=EGRSKY22&AskDate=5%2F9%2F2025&IsDep=True
You can change the dates.
I hope my answer isn't too disappointing, know that it's just to help you.
I think I may have already disappointed you in a previous post when you wanted to save time by avoiding the ferry. :)
Thank you for your detailed response. I got bad information from other sources that told me to use Naxos as a home base for several nights and “island hop” from there without having to worry about luggage and changing sleeping arrangements. Based on your helpful information I think I will change my cancellable reservations and book three night in Naxos and two in Paros. My big concern at that point in my trip is making sure my son has a good time.
My main question on my earlier post was what islands does this forum recommend for after I leave Santorini and my son heads home. I’m hoping to avoid the crowds and have a relaxed island experience.
From Santorini, a good option is to head to the western Cyclades. The ferries take this route:
Santorini - Folegandros - Milos - Kimolos - Sifnos - Serifos - Piraeus (with variations depending on the ferry).
I've been to all of these islands, so I can't tell you which one would suit you best. It all depends on what you're looking for. You can find an overview on the official Greek tourism website
https://www.visitgreece.gr/islands/cyclades/
That said, it's still not clear to me.
You say you have 5 weeks to spend in Greece, but Athens 3 nights, Santorini 3 nights, Naxos 3 nights, and Paros 2 nights make 11 nights, not 5 weeks.
Considering what you plan to do, here's what will happen, for example, with these two nights in Paros:
DAY 1: You will spend the morning of Day 1 checking out of your accommodation in Naxos, then going to the port, waiting for the ferry, and traveling by ferry to Paros.
In Paros, you will go from the port to your accommodation and checkin in . It will already be 1:00 PM or 2:00 PM. You still have a few hours left in the afternoon to explore the surrounding area, and the evening to find a place to have dinner.
End of day 1 - 1st night in Paros
DAY 2: This will be your only full day, by the evening of Day 2 it will be time to repack your luggage to leave your accommodation the next morning.
End of Day 2, last night in Paros
DAY 3: Morning: check out of your accommodation and head to the port to catch a ferry to ???
Do you think this is compatible with your intention to "slow down, enjoy more island time, and do some exploring/hiking"?
Here's a map with what you can do and see in Naxos:
https://www.google.com/maps/d/edit?mid=1d7GZMjFODUlB8lf7EPSXQRwu-YXaKxw&usp=sharing
Take a look at Sifnos. Seems to meet all of your criteria. We loved it…but did have a car.
Here’s another thought; your son should really be back in Athens the night before his flight home (unless his trip home is on one ticket, starting on the island, connecting in Athens, then home).
So you might consider rearranging: all of you fly directly from Athens to Santorini when you arrive, then ferry to Naxos, maybe Paros, then ferry/fly back to Athens & spend your Athens time together. He flies home and you fly to … Crete!
I agree with JoLui that 2 nights on Paros will seem very short. I think it might be best to go back to your original 5 nights on Naxos. You may be able to take a day-trip to Mykonos & Delos, depending on your travel dates. Or you can find a boat in the Naxos harbor to take you sailing around the island. There’s lots to do on Naxos — if he’s into kitesurfing or jet skis, you can rent these & other water toys. You can rent a car for a day or two to explore the island and easily fill 5 days.
As for Crete — it’s a very large island that you could then easily explore for the almost 3 weeks you have left, without looking at ferry logistics. Lots of archeological sites, including Knossos, beautiful villages, the lovely port of Chania, amazing beaches, and a string of little villages along the southwest coast that would be a perfect ending to a busy trip. You could rent a car for part of the time and use buses or ferries for the rest. There are several Crete lovers on this forum who’d be happy to help you put this together.
And then the same advice for you — get back to Athens the day before your flight home.
Thank you for the insight. I appreciate it.
I would also recommend Sifnos and the Western Cyclades route in general if you have about 10 days available.
On this ferry route, you'll find, among others (in order from Piraeus): Serifos, Sifnos, and Milos.
In 10 days, you can combine Sifnos with Milos or with Serifos. Each of these islands has completely different characteristics.
Sifnos:
Note that the renowned Nikolaos Tselementes Gastronomy Festival is held annually in Sifnos; this year it will be on September 25th, 26th, and 27th. There's live music, traditional dancing, and of course, tastings.
https://sifnos.e-sifnos.com/what-to-do-in-sifnos/cooking-festival-in-sifnos.php
Serifos:
Milos
Kimolos, between Sifnos and Milos, can also be a destination on this route, but it's reserved for the island's 750 residents and visitors who don't want to be bothered by crowds... LOL
Sifnos. It’s a pretty chill island, has a fantastic food scene, and is a great place to unwind and get away from it all island hopping, to me at least, isn’t a way to spend a chill vacation. I’m speaking as one who lives on an island, leaves perhaps twice a year and then ends up going on vacation on Greek and Italian islands. We rarely island island hop. The exception was this year and last year. This year we went to Rhodes and Symi. Both are beautiful, both are very different from each other. Last year we went to Folegandros, another island I can recommend for its chill vibe, and then Milos, which isn’t, by any means, a chill island. It’s very touristy, although we did enjoy itt but perhaps that was because we were there in the second week of June. By the last day there seemed to be twice as many people as our first day. The choices are there. Many other commenters have given their suggestion. JoLui has given hers, and she’s more experienced in Greek travel than I am. Either you stay on one island for a couple of weeks, at the very least. Sifnos, for example, or Folegandros, or you ditch the chill vacation idea and spend it all island hopping, which can be very stressful and not a way to spend one’s vacation.