First Time Greece x 4 weeks

Here's a planning resource you might not have encountered yet. I think your timeline is good. I suggest two or three locations, Athens being one of them. Then maybe a smaller mainland city like Nafplion, and an island less crowded than Santorini or Mykonos (Naxos gets a lot of love in this forum but I haven't been there). I'm sure you'll hear soon from several people who know much more about Greece travel than I do.

That is an awesome resource!! Thanks!!

For this trip, it would be nice if we could simply rent an apartment
or small house (only the 2 of us) for the entire 4 weeks and use that
as a base to visit other locations

Just like in Italy where you have probably not visited more than 20% of the country in 3 weeks, in Greece you will have to make difficult choices.

Even if you only want to visit a small part of Greece, the configuration of the country with mainland regions far from each other and around 200 inhabited islands divided into 6 groups of islands also far from each other, does not allow not this kind of project (1 base for 4 weeks)

But for example you can spend 2 weeks on islands, in this case you could choose 2 or 3 islands from the same group with accommodation on each island, then the other 2 weeks on the mainland. Again, in the mainland a single base is not possjble even if you have a car, which is essential.

Finally, plan at least 3 days in Athens.

Goal timeline, late Sept/early Oct 2024 (is a different time better?
we are flexible)

Late Sept/early Oct is an excellent time to visit Greece, if not one of the best.

Here is the official website for tourism in Greece:

https://www.visitgreece.gr/

And that of Athens:

https://www.thisisathens.org/

After tons of reading and suggestions from others, a plan is slowly coming together for 5-6 weeks in Greece!
We will fly in and out of Athens from the U.S. (west coast).

Ferry to Naxos (Cyclades Island Group) for about a 2 week stay.
- This seems like a good choice early on in our trip (the last 2 weeks of September) as the weather will still be warm enough to enjoy the beaches and the warmth of the island.

Then some form of transport (still researching) up north to Alonnisos (Sporades Island Group) also for about a 2 week stay.
- The weather is getting cooler into October but this isn't the warmest region anyway as it is in the North Aegean.

Back to Athens for another 1-2 weeks.
- The worst of the Athens crowds will be gone in the second half of October allowing us to enjoy the tourist sites a bit better.

What are your thoughts and suggestions about this as a possible itinerary? We are considering a sailing (crewed) excursion for 3-5 days on one of the smaller sailing vessels (10-20 people) sometime during our stay, probably early based out of Naxos?

I don't know what led you to choose Naxos, with around 2 weeks Crete would have been a wiser choice, but why not.

Spending 2 weeks on Alonissos, this small island of 2500 inhabitants is an original idea, I hope you know what you are doing.

Alonissos has no airport and can be reached by ferry from the port of Volos, 350 km north of Athens. The other option is to take a flight Athens → Skiathos then a ferry Skiathos → Alonissos

A private sailing with a skipper is possible if you can afford it, it is generally at least 800€/day, fuel, meals, and drinks not included, probably a little cheaper in October if the weather allows you to sail.

We don't know anything about the islands, so NO we don't know what we are doing, that is why I am here for advice :)
I do know we like to experience the quieter cultures of places we go. Trying to avoid any island that has cruise ship stops. Naxos and Alonnisos seem like a really nice quiet island.

My last visit to Naxos, just before Covid was in late September and I can guarantee that it was overrun with tourists throughout the Naxos Town area and the beaches from Agios Georgios to Agios Prokopios. It's now even worse.

So if you are looking for a quiet island, Naxos is a very bad choice. In the Cyclades Islands it is the 3rd most frequented island by tourists (tied with Paros) the 1st and second being Santorini and Mykonos. The 5th being Milos.

If you eliminate these 5 islands (and generally those that have an airport) there are more than 15 other islands to visit in the Cyclades.

In 2023 Naxos was also in the top 5 "Sun & Sea" favorite tourist destinations in all Greece and is a destination for some (small) cruise ships of 200 to 500 passengers until late September. In fact, as you can see, if you chose Naxos, it is not by chance.

That being said, it is a big island, and if you stay away from Naxos Town and its surroundings you will find quiet places.
However, and to stay only in the Cyclades I can suggest quieter places:

Amorgos

https://amorgos.gr/

Sifnos

https://sifnos.e-sifnos.com/

Tinos

https://tinosecret.gr/en/

Folegandros

https://www.folegandros.gr/en/

Kimolos

https://www.gokimolos.gr/en/

The last two, Folegandros and Kimolos being small islands, I do not recommend that you stay there for more than a week

As for Alonissos, I have never been there, but I will not be very far next September, somewhere in the "quiet" islands of the North Aegean Sea.

Now it's up to you.

Dick above gave you the link that you need. A ton of great info there.

But, in a nutshell, I would land at ATH, jump into a car and drive a figure-eight\, first loop in Acadia and the territory north of the Gulf of Corinth and the second south.

It's interesting how these trips take shape. Sept-Oct is ideal, btw.

When I planned my first 30-day trip to Greece I had a flight in to Corfu and a flight home from Athens, and nothing else. I used that link and its corresponding Facebook group to do virtually all the planning.

I've been back four more times for a month since but that figure-8 out of ATH is the way to go.

So if you think Alonnisis may be too small, where would you recommend amongst those island for early to mid October?

I didn't say that Alonissos was too small, I said: " Spending 2 weeks on Alonissos, this small island of 2500 inhabitants is an original idea" because I am rather used to seeing people here who want to stay only 2 or 3 days on an island. And it's the first time that I tell someone that the time they want to spend on an island might be too long!

That said I don't know why you chose Alonissos, maybe you have a good reason to stay there for 2 weeks

I have already stayed 12 days on an island and I could have stayed 2 or 3 days longer but it was exceptional, even as a slow traveler.

We chose the island randomly by reading and looking, no real reason, lol... of course what we are after is not to try and see as much as we can. We want to relax and enjoy the culture of places we visit. It just seems that a few days or a week just isn't really enough to get a real feel for a place. That is why we were thinking 2 weeks in 2 different locales and then maybe 1-2 weeks back in athens before leaving. We are open to any and all suggestions!

Imagine that, wanting to visit the western USA, I would plan to stay 2 weeks on Vashon Island.

What would you say?

Point well taken, but then again, using your analogy... we will be spending a week or two in "Seattle" and another 2 weeks in Richland, WA... (lol)
But, you may be right, if we have 4-6 weeks, maybe it is better for 7-10 days in more areas?
So, here would be my next question as you are very insightful and thoughtful, thank you!!
Here is the scenario I ask of you
You are giving travel advice to your best friends (us!) and you realize their itinerary is very open for Greece.
Your friends enjoy learning about the hallmark locations of world history, but only for a few days at a time as they do not love big cities, crowds and hectic/touristy places.
Your friends are global travelers, the world is a big place, with many regions yet to visit and experience, so they may never get back to Greece.
Where would you advise them to go? About how long in each place to be an easy non-hectic pace on the trip. To let them see what they should see and yet not rush anywhere and still get a feel for the real culture.
(As an example-in Italy we spent 3 days in Rome, a slow big loop around northern Italy hitting all the iconic towns and cities... then finished with a week in a quiet bed and breakfast in the rolling hillsides of Tuscany an hour from any large town.)
I am anxiously awaiting your thoughts! :)

The first mistake you make (IMO) is to start with the details by choosing a small island at random.

Given that you have at least 4 weeks, are you ready to go to Greece without really planning destinations and an itinerary? (late September/early October you can find accommodation without having to book in advance if you avoid tourist spots)

Regarding the mainland, if you plan to go there, will you rent a car?

Regarding the islands, are you ready to travel 6 or 7 hours by ferry?

Here is a little story from 3 years ago in September, in Greece:

We met an American, John, from New Jersey, retired, who came to Greece for the wedding of his daughter who was marrying a Greek in Mykonos.

Since he couldn't stand the touristy and party atmosphere of Mykonos, after the wedding he wanted to escape Mykonos and asked what the opposite of Mykonos was.

He had no specific plan and was advised to go to the island of Kimolos. That's where we met him, in the middle of nowhere during a hike. Given that he was lost, had no water, couldn't find his smartphone, and didn't know how to get back to his hotel. we brought him back, and then we spent a little time together on the island (including my birthday party at the restaurant)

After 4 days since we had to go to Serifos, another island, we advised him to go to Sifnos, an island close to Kimolos. What he did.
Then we stayed in touch, he stayed on Sifnos for 15 days and made lots of Greek friends!

Are you ready to travel like John?

I hope other forum members will also have some advice for you.

By the way, I googled Richland, it's 65,000 inhabitants, (Alonisos is 2,500)

Richland is a farm town, so I was referring to a small totally different location than where the other two are... not actually staying in town! :) thanks again

Over the past 24 years, my husband and I have made 10 trips to Greece, each lasting about a month. We’re currently on week 3 of a 4-week stay in Crete.

I’ve been struggling with how to advise you on your first trip. I think a good first trip might be the “standard” Santorini, Naxos, Naphlio, Athens. This would introduce you to Greek culture & the transportation system.

Our second trip was 3 weeks on just the island of Lesvos. We changed locations 4 times & saw all four coasts of the island. We ended up at a wonderful hotel where we made some lasting friends & ended up returning a half dozen times. We even made a visit to Pergamon in Turkey from Lesvos. Something like this might be good too, allowing you to experience different villages & scenery without the hassle of ferries & airplanes.

But another great trip took us through the Dodecanese island chain, island hopping from Rhodes to gorgeous little Kastellorizo to amazing Nisyros, with its active (but not erupting) volcano we could walk right into.

Yet another started in Samos, with a day trip to amazing Ephesus in Turkey, and included a visit to the Blue Zone island of Ikaria, the holy island of Patmos & little-known Leros where we found fabulous meals & an immaculately maintained cemetery of Allied soldiers who had died there during WWII.

Another month brought us back to Naxos plus its neighboring gorgeous Amorgos, quirky little Antiparos and lovely Milos with sunsets rivaling Santorini.

Then we discovered Crete! You easily could spend 4 weeks here — we’ve done it for three years in a row now..

So I guess I’m saying you can’t really go wrong. Do a little research & see what feels right for you.

Everyone has given me such good advice here that we have decided to change our vision of this trip.
As I was retiring we discussed what we wanted with our retirement travel.
1) Not hectic or rushed, not trying to jam everything in.
2) Try to stay somewhere for weeks or a month at a time to really relax and get a real feel for local life
3) Use that central locale where we rent a house or apartment, and take 1-2 days excursions to other areas.
4) Visit the big "tourist" attractions / history sites for at least a few days in each country we visit.
5) Be flexible to stay somewhere longer if we are enjoying it or leave sooner if not.

With those goals still in mind, Greece is unique in the world due to the vast number of islands and differences that is seen on them. So for this trip, it has become clear we need to change our travel plans for this particular trip.

Maybe we now change our plans to 4-8 days in each locale, but maybe choose those locales differently. I have been reading various travel itineraries and blogs about Greece, there is an infinite number of options. So now I am truely looking for a nice 4-6 week itinerary that lets us relax and still get a nice feel for the Greek life...

Good thinking, to adjust your approach based advice from "Vets" who really know Greece, and have know what works (I'm one; for decades I longed to see greece so had plenty of time to study up; upon retirement I went for a month -- and loved it so much, I have returned 12 more times, for trips of 15 - 24 days each). You are still in time to plan well and wisely for a great trip. Some thoughts:

• Reallstic to plan shorter stays. I recognise your "one-stop" plan -- people who've visited Italy try to impose same "template" on Greece -- where it just doesn't work. In Nothern Italy (Tuscany, Umbria), you can get apt in small or large town. Every day you can either drive or train 30 miles to a wonderful Different place, & return "home" by dinner time;; you can do that 5-6 directions. In most Greek islands, if you go 30 miles, you'll drown! On mainland, NO rail network; Good KTEL bus system but above 5-direction plan not at all workable. There's a reason we talk of "island-hopping." You stay in one for awhile, then "hop" to another. You still can get the flavor of a place ... and In Crete, you can spend weeks in ONE iland... its a country unto itslef. I've been to Crete 5 x, for 5 days each time, and after 2 days or so, would move on to next section... and still have nearly all the East half to explore.

• Let the calendar guide your itinerary --- Makes Sense to start with farthest-out places, and work your way back to Athens Last . By doing this, you'll be immersed in History & culture awhile, learn "Greek ways" and be savvier about Navigating a big bustling city for efficient sight-seeing, and its Famous Landmarks, and museum treasures will resonate so much more.

• Charlene's thought, with a "tweak." I suggest Starting Day 1 landing in Athens
(1) allow 2 hr layover get domestic flight (50 mins) to CHANIA CRETE Most beautiful Old Town of Crete, right on sea! delightful to explore --now has great half day mall-lgroup tours to olive farms & the like, or short group walks thru small villages. Don't try to "do " Crete -- bus or drive scenic N coast highway to o ther Big Town HERAKLION for Museum, Knossos, last night (day 6?)
(2) AM ferry to SANTORINI aarrive about Noon, stay at Rimside Hotel in FIrostephani (away from crowds) enjoy the View, that's what it's all about. Don't unpack. Next afternoon (day 8?) take 3:15 BLUE STAR ferry sit out o n deck for view & 2 hr "miini-cruise.
(3) NAXOS -- Alas our "dream Island" has been "discoovered" and now V-crowded midmay - early Sept ... but by now will be thinned out... Great ancient sites, dramatic inland scenery, fascinating port town, divine beaches... worth at least 5-6 days... once you get logistics locked in, we can recommend ideal hotel locations for w alking to town, on beach etc,
-(4)-- it's now about 15 days in -- you could do another island like ANTIPAROS here fore 3 days VERY restful -- and day-trip into PAROS itself on a c ute 10-minute ferry ... Antiparos evenings are enchantingl with August c rowds gone
(5) - FLY (40 mins vs 4-5 hrs on fery) to ATH AIRPORT . Travel to Magical NAFPLIO either on Rental car (much to see & stop f or en reoute) or on modern intercity KTEL Bus on scenic modern highway.,. just 2,5 hrs from Athens but a world away. This fab website -- http://www.visitnafplio.com/ - noncommercial, created by a Scandinavian expat -- tells all, where to go, what to see, where to stay etc. THE most beautiful Old Town n all GReece, on peninsula, surrounded by sea, center of more ancient sites than anywhere else... along with wonderful hiking paths, scenery, grape harvesting. 4-5 days will fly by... but you'll totally relax in seaside cafes with Greece's best sunsets. On my 1st trip, Nafplio was on impulse my last 2 days -- and now I return every time.
(6) ATHENS - do BIG stuff, then find little treasures (Melina Mercouri Foundation, LaLounis Jewelry Mus, the Pnyx! What joy.

You’re right — there are an infinite number of options. And strategies for visiting Greece are very unlike most other European countries.

As you’re planning, try not to tie yourself in knots trying to fit a particular island into an itinerary. Save that island for another trip. Familiarize yourself with ferry routes. But don’t ignore cheap short flights, particularly for those long distances (ie Athens to Rhodes or Crete or Lesvos).

Feel free to come back here for suggestions as you’re fine-tuning your trip.

You mentioned 4-6 weeks ... if the latter, then you might think about starting Sept 10th or so ... depending on what your last island hops may be.. if you'd plan to go from Central Cyclades (Paros - Naxos) to Western Cyclades (Sifnos etc) those ferry schedules can thin out in late october and Sifnos not served by plane (yay!).

Janet explained the context perfectly.

What you were able to do in Italy is not possible in Greece.

In the islands, inter-island travel for a day is most of the time impossible, even within the same group of islands. Ferry schedules are not designed for this type of trip.

Going from one island group to another is also impossible most of the time without returning to Athens.

Her example Crete (minimum 10 days) + Cyclades (minimum 5 days per island) is a choice that you can make by having, let's say, 3 weeks.

This is one option among dozens of others.

As for the mainland, Peloponnese or other regions, the possibilities for day trips are even more limited than in the islands, even if you have a car. So what you could do would be a kind of "mainland hopping" by choosing a place and staying there for a few days, then going to another place, etc. etc.

Above all, all this requires time and research work.

I tell you this, but I also regret knowing that you are probably not going to spend 2 weeks on Alonnisos.
I would have been really curious to have feedback about such a stay :))

Janet lays out a very smart plan, I think -- not that you necessarily want to follow it precisely, but her strategy makes sense and she provides a lot of insight and detail. I was going to suggest Crete for part of your trip, since you have time to explore and it's rich in culture and history. And I was going to plug Nafplion, an absolutely charming small city with beautiful surroundings and lots of easy day trips to places like Mycenae, Epidavros, Nemea, and Corinth. It makes sense to keep Athens till the end. I think a week there is plenty of time to see the "big sights" and make some discoveries. The only downside is that it will tire you and you won't have time to recover in Greece -- but that's why getting home can be the final highlight of a great vacation!

I don't know how realistic it would be to try to fit in a short Aegean cruise, perhaps at the end to decompress after Athens. I don't mean a ferry to an island but rather a small ship that makes several stops, but where the real destination is the sea itself. If this appeals to you, you might want to look for a cruise line that doesn't just cater to Americans, so you can spend some time with people from other European countries. That can be enriching and fun.

With retirement, the world becomes your oyster. If you don't get this trip exactly right, take another one next year. Rinse and repeat..... ;-)

We recently returned from our first trip to Greece. We had been already around Crete. We took three weeks to drive around the Peloponnese. We stayed for 2-4 nights at various places. Your relax philosophy is right on. Because most towns are pretty small and not hustle bustle or even much of anything. I would say that Nafplio is the busiest of all the places we went. And that is a small town. Walk around it in 20 minutes. Climb the hill to the.castle for another excursion. Some places were so small, no one was about. Maybe 2-4 cats and a cafe with no one there, or the one guy drinking his one coffee for the afternoon. Valtesiniko. So, your relax is right there for you most of the time.
Peloponese might be a place for you.

Wow, there is so much to decide!! I guess we will go for about 1 week planned to different islands, if we really like someplace we will stay longer, which raises the question about availability in late Sept and the month of October. If we plan on doing the VRBO thing for most of it, how hard is it to find places for 2 last minute?