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Help with itinerary for 2 weeks in Greece May 2023!

Everyone has been so helpful with our first trip to Europe (Rome, Paris and Amalfi Coast in 2019), then to Portugal this past May. I've read a lot of the Greece forum already and there are so many options.
We would be flying from Toronto May 19, for 12 nights in Greece, flying home June 2nd. We could stay 14 nights if we need to.
We enjoy walking, local towns, eating at local restaurants and finding great coffee at local cafe's. We love being on or near the water, but don't need it to be a beach vacation where we swim and sun. We don't like touristy areas, loud nightlife and partyting. Saying that, I know that Santorini and Mykono's are very touristy, but lots have said it's a must see if you are going to Greece. I've read to land in Athens and fly to the first island same day and end in Athens for 1 or 2 nights which suites us fine. I know RS suggests starting with the quietest place first to get over jet lag and end with the busiest place. We are not opposed to renting a car, we did this in Amalfi just fine and Portugal along the Silver Coast. We prefer to stay in accommodations with a balcony and kitchenette over a hotel, when possible, unless it's a night or two then a hotel is fine.
Thanks in advance,

Posted by
3135 posts

I would advise you to choose either Santorini or Mykonos, but not both. Instead, choose one or two other islands close by so your time in transit is limited to a few short hours, instead of taking a whole day, such as Santorini to Rhodes. Santorini has much more to offer in terms of things to see and do, so my recommendation would be Santorini, Naxos or Paros, and Milos, a nicely diverse 3-island experience. I like Paros, and from there you'd also have the option of a daytrip to neighboring Antiparos, a charming little island just a short shuttle ferry ride away. If you opt for 14 nights you give yourselves ample time to enjoy the islands before you return to Athens for your last days.

Posted by
1398 posts

I predict you will be very annoyed at yourselves for not using the extra 2 days. A transatlantic flight really deserves a full two weeks.

I see you have been doing your homework. Indeed experienced travellers to Greece generally recommend getting to your first island immediately on arrival in Greece. You need a 2 hour window to catch a connecting flight. If you are on Air Canada book your flight to your first island on Aegean and because they are both Star Alliance you can do it on one ticket. That puts the responsibility on the airlines to get you to your destination.

With 2 weeks you might want to consider flying to Crete. Its huge about the size of Vancouver island and it has enough interesting things to see and do to keep you busy for a month. It has Venetian era cities with ports and old towns areas where you can get lost in the maze of period back alleys.

I would suggest you look at Chania. Its our favourite.
Return to Chania 2022

Lots to do in the surrounding countryside. as well.

You can spend 11days in Crete and then fly back to Athens for 2 or three days.

Good stuff from Lee. While Santorini is a tourist hot spot it certainly is beautiful. Its worth 2 or 3 nights. With careful planning you can manage the crowds and have a very enjoyable time.

The Santorini Naxos combination is a good one. Naxos in many ways is a mini Crete with a lovely main town with an old market area all topped off with a Venetian Era Kastro. It has great beaches, mountain villages for hiking and exploration, some antiquities and local population who are happy you chose to visit their island. Naxos can be done quite nicely in 7 to 10 days.
Here are some images of our 15th visit to Naxos in May 2022
Around Naxos town 2022
Back to Naxos 2022

Posted by
64 posts

Thanks Lee, good advice. I was thinking Santorini. I didn't know about Milos, it looks beautiful. I think we will stay for 14 nights in Greece, it's a long way there, so why not enjoy a full 14 days. Which island would you suggest we fly to after landing in Athens? I've also read it is really nice to boat up to Santorini, especially at night. RS recommends going to the quieter place first to get over jet lag, which I do get.

Posted by
64 posts

Thanks Stanb! I have been following along your trip reports and all of your beautiful pictures. The flight from Athens to Crete would give us a 6 hours layover waiting to fly out. I don't think that is doable for me, too long in the airport. Perhaps they will have more flight options closer to 2023?

On booking Agean flight with Air Canada, is this something you can do online? I tried and can't find it, or do I need to call to book both flights? I know you love Naxos, what would you say is the difference between Naxos and Paros? If we want to do 3 islands, with Santorini being one of them, which other two would you suggest so we get a variety?

Posted by
2058 posts

On booking Agean flight with Air Canada, is this something you can do
online? I tried and can't find it, or do I need to call to book both

It is too early to know what the possible flights will be, in particular because of the codeshare between Aegean and Air Canada.

That said, I looked on the Air Canada website. There are quite a few possibilities with the Air Canada-Aegean codeshare.
For example on May 19, 2023 there are several Toronto-Santorini flights while Aegean does not offer them.
There is a departure from Toronto at 7:15 p.m., arrival ATH at 11:45 a.m., departure for Santorini at 1:30 p.m., arrival Santorini at 2:20 p.m.

Air Canada does not offer any other option with the islands of Milos or Naxos, although this should be possible.
Aegean does not offer either but they specify that the schedules are not yet published.

So don't rush into flight reservations before this fall

Posted by
1178 posts

There are numerous Greek Islands other than Santorini & Mykonos which are always hyped by glossy travel magazines and travel agents.

May will probably not be as crazy as high season but who knows what 2023 will bring. If by all reports 2022 has already been packed with tourists. You may want to consider if that's what you want to deal with.

There are many other islands that can offer beautiful scenery, lovely villages, beaches, more traditional atmosphere without the cruise ship crowds and high prices if you do a bit more research.

There are fans for and against the Big Name Islands but in the end do what's best for you.

If you want more info on other Greek Islands check out this website:

Posted by
2058 posts

We prefer to stay in accommodations with a balcony and kitchenette
over a hotel, when possible, unless it's a night or two then a hotel
is fine.

With the exception of Santorini, which is a special case, the majority of accommodation offers on the islands are studios or apartments, often with a kitchenette. There are also Cycladic houses and villas, sometimes with private pools.

If you start looking on specialized sites such as booking, Airbnb, or search on Google Maps you will have no difficulty finding this type of accommodation.
Most of the time these are family businesses or individuals.
Cleaning, change of sheets and towels are provided, additional services such as transfer from or to the port or laundry washing are often possible and free.
You will just have to do some shopping to prepare your breakfast.

I have been traveling the Greek islands for 30 years, I have known the small 15 square meter studio and the large villa with swimming pool and private beach but I have never spent a single night in a hotel.

Posted by
2599 posts

In 2018, we made our first trip to Greece and stayed in Santorini (3 nights), Naxos (4 nights), Nafplio (4 nights) and Athens (3 nights). It was a wonderful combination of sites that were different from each other and yet reasonable from a travel perspective. We rented a car for part of the time on each of the islands and at Athens airport when we flew back from Naxos. We returned the car to the airport after visiting Nafplio and took the bus into central Athens. We stayed in apartments everywhere but Naxos. We had a group of seven and the apartments located where we wanted to be were not big enough.

We absolutely loved our trip and would recommend this itinerary. We returned to Greece this past May and focused on Crete, spending 11 nights there.

Posted by
64 posts

Thanks BethFL,
I do like the sound of your first itinerary. I'm having the same struggle as I did with our first trip to Europe. So much to see and realizing we can't see it all in one trip. So deciding where to go is the hardest part. I'd like a bit of everything on each island. How would you compare Crete? Some have suggested flying to Crete from Athens, then ferry to Naxos/Parol and then Santorini.

Posted by
64 posts

That is great advice for Air Canada direct to Santorini. I think Stanbr also mentioned this option.

Posted by
2599 posts

We absolutely loved Crete but then we have loved almost everything in Greece. We were there for 11 days and did not come close to seeing the island. For first time Greece visitor, I would be more inclined to do itinerary more similar to what I did in 2018. It is nice to get the variety by staying in different kinds of places. If you are interested in a third island in addition to Santorini and Naxos, you might look at Amorgos which can be reached by ferry from Naxos. I haven't been there but I have been intrigued by others' adventures.

Also, Crete doesn't have the whitewashed houses which most people think of when they think of Greek Islands. Chania is prettier than Irakio but the ferries leave from Irakio so would have to get to Irakio if you flew into Chania which is several hours away. I think that makes Chania a bit more difficult to do as part of a multiple island itinerary unless you are going to spend more than a few days on Crete.

Posted by
64 posts

Thank you everyone for all your responses.
I get the impression that Santorini is the most beautiful island. If that is true, then i feel like if we go there first, the other islands will not compare (kind of like when we went to Lisbon and were disappointed because it didn't compare to Rome (I wish I had the heads up on that first). And on our second cruise, it didn't meet up to our expectations from our first get my point.
Should we end there instead of start there?
Which island would we do first, and would flying back to Athens at the end be best? I prefer less travelling, so even if flying is more expensive, to me it is worth it. Just like flying direct instead of stopover's.

I'm leaning toward (not in any particular order) Santorini, Naxos, Milos or Paros and Athens. It sounds like Crete is too big to stay for only 5 nights.
We have 14 nights and only 2 nights in Athens on our way home.
Which would I do first, and would flying back to Athens be best? I prefer less travelling, so even if flying is more expensive, to me it is worth it.

Posted by
2599 posts

Well, I would do Santorini first as we did because beautiful but is the least authentically Greek. We did not really notice the latter, having never been to Greece, but would have after visiting a couple other islands. But honestly, logistics should probably dominate. Naxos and Milos are in opposite direction from Santorini (as I recall) so may be better to do one of them first and Santorini in the middle. On the other hand, there are many more flights to Santorini so the logistics of coordinating with an international flight may be much easier if you start with Santorini. We flew back to Athens from Naxos and I think both Milos and Paros also have airports.

Posted by
2058 posts

Just as BethFL suggests, I think a good solution for you would be to start with Santorini. From mid-May you will not only have the possibility of going through Athens (with one ticket), but also several possibilities of having a Toronto-Santorini flight via a European city served by Aegean or via Frankfurt or Munich with Lufthansa which is also a member of Star Alliance.

After two (or even three) nights in Santorini you will have 7 or 8 nights left before leaving for Athens.
So going to 2 islands is quite possible, it all depends on your way of traveling and your lifestyle.

There are dozens of possible combinations, but taking into account the easyest ferry routes, from Santorini you can do:

  • Amorgos - Naxos

  • Naxos - Paros

  • Paros - Milos

  • Milos - Sifnos

  • Paros - Sifnos

Here are websites that will allow you to form an opinion on these 6 islands:

Posted by
11 posts

Have you think of Corfu and Paxos island?They are at the Ionian Sea. Corfu has a lot of beautiful places to explore and in Paxos you can have more relaxed time with beautiful beaches (Antipaxos) and nice atmosphere.

Posted by
1398 posts

We have been away. This thread has certainly been informative. My thoughts. You are correct 5 nights in Crete is not efficient nor sufficient. After a transatlantic flight, (actually flying from Toronto you are doing about a half transcontinental and then a trans Atlantic fight) you will be rather fatigued when you land in Athens. We always get to our first island on that day just to get it all over.
Santorini is absolutely spectacular. The moment you arrive, the excitement will give you a boost just long enough to look around, find a place for dinner then crash. Next morning you will be very happy that you arrived the night before and you can start your Santorini experience refreshed.
That has been our experience.

I think the Santorii Naxos combination is excellent. You get all the vibe of Santorini then a more laid back Greek experience on Naxos.
Naxos can be done in 5 days, a week is better and you still will not see it all with 10 days. If you do want a third island while we really like Milos, Paros is a much more efficient logistical sequence with Naxos.
You are going to love this trip. You will be planning your next visit on the flight home.

Posted by
15686 posts

I spent 2 weeks on the islands in October. I started in Chania (absolutely loved it), then 2 nights in Heraklion to see Knossos and the archaeology museum and get the ferry to Santorini. Even at the tail end of the season, Santorini had 1 to 3 cruise ships docked there on each of my 3 days there. Lots of crowds. Naxos was also great, you can take a day trip by ferry to Mykonos , with Delos if you're interested in archaeology. The beaches were beautiful.

I'm surprised Janet hasn't chimed in yet. She is our super-maven on Greek islands. You can look at some of the other Greece threads to find her posts and even PM her. She has posted recently. At her recommendation, I stayed in a tiny apartment, perfect for 2 (twin beds), with a small balcony overlooking the beach. I had a glass of local wine each evening at sunset. magical.

Posted by
3363 posts

Here I am Chani ... have been busy last few days helping a local (Philly) couple get their trip organized -- I was spurred to action because was impressed that the Husband had undertaken the work of research & arrangements; good man!

Luckily, while I was busy, my friend stanbr did the work; we like same place, same vibe, same timing - in May everythings open, water swimmable, islands not overpopulated (except of course Santorini). We also think itinerary should be ONE direction. And 13 days or so limits you to a few options:
• FLY ATH then CRETE (CHania) - 6+ days (car) & Ferry from Heraklion to SANTORINI (3 nights?) - Fly ATH (3 days/nights)
• FLY Air Can Alliance - 1st stop SANTORINI (3 nights) - NAxos (6 nights) ATHENS (3 nights)

Lodgings? since u r thinking way ahead, many great sea view options ... CRETE = in Chania Old Town , many kitchenette studios on/near the no-cars Theotokopoulu Street... NAXOS - In May, Ag.Giorgios beach adjacent to Naxos POrt town, is just pleasantly populated, 15 min stroll to all attractions, many "studio units" wih seaview balconies. Beach is shallow at edge its a quick bus ride to outer beaches (I love Plaka) for long swim-days. Stanbr's stunning pix show why these 2 isle remain our faves, tho I've only racked up 13 visits to his 15.

Giving Santorini a try? (mainly because cruisy friends will ask if you've seen it!). Again, obey stanbr: plan well. Instead of FIra or Oia, stay in FIrostephani, ALSO rimside, w great caldera views, easy walk to Fira, no taxis/car needed, BUT overlooked by tour groups so it's relatively serene. Oia?? visit at 8 AM! You'll have 2 hours to wander & photograph. When cruisers/tour busses come, you go. Strategize ... enjoy Famous View... then head to Naxos.

Posted by
64 posts

Thank you all so much!!!
We have landed on flying into Athens, then a connecting flight to Santorini for 3 nights, then ferry to Paros, Antiparos and Naxos and back to Athens for a few nights. We also decided to do this trip just my husband and myself instead of with our daughter.
I posted a new topic for our trip with our daughter and are looking at France and Italy. We've been to Rome, Paris and Amalfi, so thinking south of France and Provence, and maybe Florence, Tuscany and one other place in Italy.
We have 14-16 days in Europe, not including flying time.
If you would like to comment, I am really lost for an intinerary for this type of trip.
Thank you,

Posted by
996 posts

My only experience with Greek islands so far was Crete. I only gave myself 2 nights and 3 days on Crete, which is not enough time to see it properly. My trip to Greece was 13 nights on the ground, one night on the plane on the way there. I stayed in Nafplio; Heraklion and Chania on Crete, Delphi, and Athens. I could have skipped Crete and gone to Olympia in Western Greece. Most travelers to Greece probably see at least Athens and then there are so many other potentially worthwhile places - you could spend the rest of your time on Islands or all on the mainland. Maybe post a supposed day-by-day itinerary and we'll see if we can suggest if it logistically is doable.

Posted by
3363 posts

PLease clarify that the 14-16 days in Europe you mention are solely for you and your husband in Greece -- and NOT part of some other hugely ambitious trip involving France & Italy. The Greece destinations you mention can be enjoyed very well by you two in 2 weeks -- but not in 5-6 days as prelude to two countries in a week! (eek)