Mainland loop and island hop. Please advise.

Hoping to one day retire and do the same, so I am wondering if you planned some longer stays to be included (like the week in Naxos), would that reduce the feeling of "too long?" Your plans look pretty good--of course there are things you are missing, but it's a nice overall plan.
Making it two trips adds so much airfare costs to the plan that I would have a hard time with that (though in the big scheme of things, I guess it all balances out)--but if you did, I would do mainland in May/June and islands September into early October for sea warmth.
Another random thought--keep one trip as the Peloponnese/Athens and islands, and make a second trip northern Greece plus some islands (maybe just Crete).

Regarding the mainland, I know it's necessary to define stopover locations, but don't make the mistake of confusing the must-sees in travel guides with these stopover locations.

Places like Olympia, Monemvasia, and Delphi aren't necessarily places to stay overnight, but rather places to visit, where the visit can be as short as 3 hours. And if you do as I usually do and carefully study the route to take between two stops, you might discover tons of places to spend time, enough to turn a two-hour drive into several days.
Greece isn't just a series of must-sees; there are hundreds of things to discover in between (I'm taking advantage of the fact that you have a lot of time to try to convince you and, if necessary, transform your tourist side into a traveler)

I see you've only considered the Cycladic islands. Since you enjoy nature and hiking, you could add Kythira to your Peloponnese itinerary.
It's easy to reach in a 2-hour ferry from the ports of Gythio or Neapoli (a 45-minute drive from Monemvasia).
See some photos:

https://photos.app.goo.gl/fq4yiQ4Jz4FpFqWL8

Regarding the "islands" section, if you're traveling in May, you may not have daily ferries between two islands in the Western Cyclades (Milos-Sifnos-Folegandros), or you may have ferries that run very late in the day. It's worth considering.
But otherwise, your itinerary is pretty good. I could add a few more islands and ask why you're only going to the Cyclades, but I'll refrain.

It's up to you to see how many days you spend on each island, knowing that you need at least four full days on an island, even the smallest ones. Santorini can also be worth four days if you're not just following the crowds of tourists who are short on time.

If it's at all possible try to get to the island of Kythira as it's a wonderful island that doesn't get the hype of the Big Name Islands.

It's do able from the Peloponnese and gives you a chance to experience a more traditional island without hordes of tourists (off season anyway) and probably even during high season.

Lots to see including lovely villages, archeological/historic sites, secluded beaches, easy walking and more challenging hiking routes but offers something for everyone.

Check out my trip report with photos:

https://www.tripadvisor.com/ShowTopic-g319777-i11468-k14565904-Kythira_Trip_Report_Sept_28_Oct_3-Kythira_Attica.html

Thank you all for your responses! I do appreciate what you experienced travelers have to say and I consider it all when finalizing a trip.

@valadelphia - I am looking forward to your retirement so that you can travel when you want for however long. :-) I do agree with you. I think a longer, more restful stay in the middle of travel, especially a long road trip, could be helpful. We usually take Rick's advice and have a 'vacation within a vacation', but the trip was already pretty lengthy compared to our travel in times past. Even when I built in 'relaxing days' we hiked for hours. That just means I'll have to keep traveling and tweaking. :-) By the way, I do like your thought of northern Greece plus Crete as a separate trip. That looks interesting!

@JoLui - Thanks for your comments and questions. I completely agree with you that, to me, it looks like Olympia, Monemvasia, and Delphi are more suited as places to visit rather than stay the night. Having just come off a 5-week road trip in Central Europe, my husband and I definitely studied and focused on what there was to see between the point to point places. On travel days, our habit was to have a leisurely breakfast, check out by 10a, and meander to our next stay, arriving late afternoon/early evening. That's why we like our next stay to be, ideally, 2 hours away. Whether it's the countryside, a gorge hike, a castle, an abbey, or a scenic mountain pass, we enjoy the in-between as much as the locations of the stays themselves. Perhaps I need to find better stopover locations in this case. For example, I would love to see Delphi on the way to Meteora, but that's a very long drive on our arrival day. We won't drive more than 3 hours on arrival day. Ideally, two.

You asked why only the Cycladic Islands? I kept reading that it's best to travel in the same island group for ferry planning purposes. I will take a look at Kythira! Thanks, tommyk5, for mentioning that island as well.

All in all, I do want the Pelonponnese road trip to be our priority and I can certainly make tweaks to that loop at this point as well as not see every island on my current hop. My husband has told me before that even though every place has something different to offer they can start to all look the same to him. I think that comment came after I took him to most of the white towns in southern Spain. ;-)

Please keep your comments coming and I'll follow up! Thank you!

..my husband and I definitely studied and focused on what there was to
see between the point to point places

Whether it's the countryside, a gorge hike, a castle, an abbey, or a
scenic mountain pass, we enjoy the in-between as much as the locations
of the stays themselves.

By the way, I have this map that may give you some ideas .. (Take your time)

https://www.google.com/maps/d/edit?mid=1HzqyEorKrUZxc5LjPjlvG2utnKof78E&usp=sharing

@JoLui - Thank you for that map! I've had a good time studying it and I'm sure it will come in handy on our road trip. More studying to come, I know!

So, with your help, I feel like I've settled a few things in my mind and want to run my latest questions by you. I am happy with a mainland road trip first, followed by 2-3 Cycladic islands. I think this would be a well-paced, good first introduction to both historic and 'postcard' Greece. Crete and other islands will have to wait but it's pretty evident that there will be a next time. So, with that in mind, how does this look for a trip early May to mid-June?

For the Peloponnese (and in drive order, I think...revisited so many times):
Nafplio (4-5 nights)
Dimitsana (2-3 nights)
Pylos (3 nights)
Kardamyli (3 nights)
Gytheio (3 nights)
Athens (3 nights).

My questions are:
(1) Should we stay a night or two in Olympia or take a day drip from Dimitsana? (We like the mountains and hiking which is why I chose Dimitsana.)
(2) It seems fairly easy to see Monevasia from Gytheio, but it's still a 2 hour drive. Would a stay in both make more sense?
(3) The drive from Gytheio or Monevasia back to Athens is fairly long. Can I do better with my routing?
(4) And my burning question still....Do I keep Delphi and Meteora in the mix? We do love mountainous scenery but that is a long drive at the beginning or end of our trip. Still, I've seen videos on both and have read comments. Both locations look like they are worth the drive time. If so, would you place those locations at the beginning or end of our Peloponnese trip?

In Athens we'll return the car and probably fly to Naxos (7 nights), then ferry to Folegandros (4-5 nights), then ferry to Santorini (3-4 nights), then fly back to Athens to stay overnight before flying home. I'll have to study the ferry schedules to see which order works best. It will feel good on the islands after all that driving on the mainland. Thanks for your feedback. I sincerely appreciate it.

(3) The drive from Gytheio or Monevasia back to Athens is fairly long. Can I do better with my routing?
Both Nafplio and Dimitsana are easy drives back to Athens, and Nafplio is such a great place to start (we drove there on arrival after a flight from the east coast), so maybe put Dimitsana last?

While they are not in the same league, Dimitsana did give me a slight "monasteries in the sky" fix that sufficed until I get back and visit the north. And in the same vein, Nemea served as a fair replacement for Olympia (which was not on my list). Hard decisions!

1) Should we stay a night or two in Olympia or take a day trip from
Dimitsana?

I think it's up to you. Personally, I would try to avoid staying overnight in Olympia, which has nothing to offer.

We did this trip in the opposite direction and found a place to stay for one night in Kakovatos, about 40 minutes from Olympia. At the Ostria Hotel, we don't usually stay in hotels, but this one was suitable for one night. It's right on the sea and a large beach, and most importantly, we avoided the tourist traps of Olympia.

https://maps.app.goo.gl/G1obxGZL6G1WGF287

In your itinerary, this would be a 2.5-hour drive from Dimitsana, split into two separate journeys since you're stopping in Olympia, and the next day, approximately 1.5 hours to Pylos.

(3) The drive from Gytheio or Monemvasia back to Athens is fairly
long. Can I improve my routing?

Same principle as I explained in a previous message: don't focus on the "must-sees" to find a place to stay. It's only about an hour's drive from Gytheio to Monemvasia. Leave Gytheio and stop to visit Monemvasia, then head further north along the coast.
For example, consider Kiparissi, 1.5 hours from Monemvasia, at the family-run Hotel Avra

https://maps.app.goo.gl/J4Lkiz5XwXrKNz3s8

or a little further north in Leonídio

https://maps.app.goo.gl/N6FSSnsBzuwfxFEUA

(4) And my burning question remains... Do I include Delphi and Meteora
in my itinerary?

As they say, "you can't have your cake and eat it too" , avoiding long car journeys and visiting Meteora, combining the two isn't possible. But it's your trip, you choose.

Fly to Naxos (7 nights), then ferry to Folegandros (4-5 nights), then
ferry to Santorini (3-4 nights), then fly back to Athens.

Traveling in this order will be complicated. Folegandros is a small island in the Western Cyclades, and Naxos is in the Central Cyclades. At best, you'll find a small Seajets catamaran operating within the Cyclades from Naxos, which will take hours and stop at 3 or 4 islands before dropping you off in Folegandros.

If you replace Folegandros with Amorgos, it's much more easy and doable, and you won't regret going to Amorgos, the "Big Blue" island, especially if you enjoy hiking.

https://amorgos.gr/

Some pictures of Amorgos:

https://photos.app.goo.gl/sS5aZ6iajGEtrz1G8

Hi mcalico, I haven't been yet but you had commented on my itinerary question to which I have replied.
Your itinerary looks as good as any. I agree with some of the others that the journey from Monemvasia back to Athens is a bit tricky. I plan to visit on a day trip from Gytheio. I use Google maps a lot to calculate the travel time from A to B, but I found that in Italy, if I added 20 minutes to every hour, I came in pretty close to the actual time. With these winding roads, you'll want to adjust for that.
I ee that you have dropped Delphi from your original plan. It has added a lot of extra driving time to our "loop" but my gut keeps insisting that I have to go there. We shall see...
Question: are you picking up and dropping off your rental at the airport or in the city? Just wondering about the timing. I abhor those absolute time frames.

You asked what our final Peloponnese itinerary looks like on a different thread. I thought I would respond here. Realize that we have been to Athens and Nafplio and are not returning to them. We visited Nemea when we were in Nafplio which is lovely and uncrowded and decided against going to Olympia this trip.

1 night -Near Athens airport
3 nights-Pylos
1 night-Koroni
3 nights -Kardamyli
2 nights Areopoli
2 nights Gytheio
1 night Monemvasia
3 nights stemnitsa
1 night near Athens airport

And I am glad to know you enjoyed my Crete report. It is a fabulous place to visit. We went to Delphi and Meteora on the same trip to Crete.
Meteora is quite far from the Peloponese.

Hello, All! Beth and bap, thanks for sharing your feedback and itinerary! I share your joy and angst over trip planning. :-) And JoLui, I heard you when you said that I don't have to stay point to point exactly. I'll work on that. Valadelphia, I liked your comments on Dimitsana and Nemea. I know that leaving out Delphi and Meteora will make the trip much simpler and, so far, I can't seem to do that. But knowing I have something somewhat similar is helpful!

After looking at what you all said, I'm thinking along the lines of getting a rental car at the Athens airport and driving the opposite route I originally thought. Something like:

Athens airport to Nafplio (4-5 nights)
Nafplio to Gytheio (3 nights)
Gytheio to Kardamyil (3 nights)
Kardamyil to Pylos (3 nights)
Pylos to Dimitsana (2-3 nights)
Dimitsana to Olympia or further north to make drive to Delphi shorter (2 nights)
Olympia to Delphi or further north (2 nights)
Delphi to Kastraki (2-3 nights)
Kastraki to Athens (probably 3 nights if we don't stay at the airport, then only 1 night)

Islands:
We will make Crete a separate trip to avoid more driving. Probably go in September 2026 or the following May/June 2027. So our island hopping may look like:

Athens airport to Naxos (7 nights)
Naxos to Santorini (3-4 nights)

Maybe Paros. Maybe Amorgos. Maybe Folegandros which is my top choice, along with Sifnos, so far. Kythira will have to wait, I think, but I'm still thinking about it in relation to the Peloponnese portion of our trip. Is this starting to take shape logically? Thanks!!

I think your mainland loop looks reasonable with a few tweaks.

I am unsure why you would want to spend two nights north of Olympia in a town you are choosing to be a little closer to Delphi.

I also would also consider starting with the islands, fly back to Athens, rent a car, do your mainland loop, return car at airport, and then see Athens. This would save you extra nights at the airport.

You need to look at ferry schedules to see the feasibility of visiting the ones you list in one trip. They are all in the Cyclades but not necessarily very near each other. You may need to make some hard choices.

Starting with Nafplio, which is only about 2 hours from the airport via an easy route (80% highway), seems like a wiser decision than starting with Delphi. You'll be staying several days in Nafplio to visit the city and surrounding area and won't have to leave the next day and drive for 3 hours to Kastraki.

Unless you have a specific reason to do it this way, instead of the Pylos-Dimitsana-Olympia route, I would do Pylos-Olympia-Dimitsana (this shortens your driving time and allows you to take the coastal road between Pylos and Olympia). But it's up to you.

Regarding the islands, keep in mind that there aren't necessarily ferries every day from every island to every other one. Depending on the time of year, a ferry crossing may be impossible or only run twice a week.

Before planning your itinerary and booking accommodation, check http://www.openseas.gr/. You can enter an equivalent date in 2025 for your planned travel dates and see the ferry connections that have been operating this year.

See an example of possible routes from Paros to Folegandros in mid-September 2025:

http://www.openseas.gr/PAS/FOL/2025-09-10/2025-09-10/itineraries

You'll see that there are only 3 ferries per week, and by selecting the small Seajets "Superjet" ferry on Tuesdays (which is very uncomfortable, by the way) you'll see that it takes an extremely long route that passes successively through Mykonos, Naxos, Amorgos, Koufonissi, and Santorini before reaching Folegandros.

So think twice..

Thanks for your feedback, Beth, and for your questions. I'll share what my thinking was to see if it makes sense in reality. I mentioned "stay north of Olympia" because I appreciated what JoLui was saying. We didn't necessarily need to stay in a point-to-point location, rather we could stop, visit, and stay overnight elsewhere. I thought that my husband and I could spend a couple of hours in Olympia but continue driving towards our next destination (originally, Delphi) to cut the next day's drive time down.

My thinking for starting our travels with the mainland, rather than the islands, was to complete the more 'labor-intensive' portion of the trip (ie. driving and moving around) while looking forward to some restful island time. I do realize that we'll still be driving some on the islands but starting with a week on Naxos sounded nice after the Peloponnese - Delphi - Meteora - Athens portion of our trip.

JoLui - I'm encouraged that the route to Nafplio is 80% highway and a more logical way to start our mainland trip. I originally had the Pylos - Dimitsana - Olympia route because the drive from Olympia to Delphi looked a bit less complicated, but I do enjoy coastal drives so I'll tweak that route per your suggestion. Thank you. Perhaps our overnight should be Galaxidi instead of Delphi. Not much difference in drive time, really.

Whew...I have looked at ferry schedules from 2024 just to see what might be scheduled in the future. I see what each of you mean by hard choices and think twice. I pared down my initial 5 island Cycladic island hop adventure to 3 (leaving out Milos and Sifnos). I came to peace with that and thought I had it made with a Naxos, Santorini, Folegandros combo. As an aside, I do get motion sick easily so I would definitely fly to either Naxos or Santorini first, take conventional ferries to the other two islands, and fly back to Athens. It seems that my best bet for seeing Folegandros is to ferry from Santorini but then I'd have to return to fly back to Athens. If I want things to be super uncomplicated I know just to include Naxos and Santorini. But somehow, others seem to make it to Folegandros and I sure would like to add that island to the mix. Still, perplexed on that one.

Lastly, I always read not to schedule lodging before the ferry schedules come out to ensure that you can move from one island to another on specific days and, in my case, on specific ferries (conventional). How is that possible when the schedules may not come out until March or April before a trip starts in May/June?

Many thanks to the time and attention you have devoted to making my trip the best it can be. I sincerely appreciate it!

Okay, so you absolutely want to go to Folegandros, I get it! LOL

Regarding ferries.

It's important to know that the ferries are primarily intended to transport islanders, raw materials, and other goods destined for the islands, as they aren't self-sufficient. Therefore, there are established ferry routes that mainly connect the mainland to the different island subgroups. For the islanders' travel needs, there's also a route that connects (not every day) the islands to Syros, the administrative capital of the Cyclades.

Folegandros is part of the western Cyclades subgroup. The main ferry route to Folegandros starts in Piraeus, then goes to Kythnos, Serifos, Sifnos, Kimolos, Milos, Sikinos, Ios, and Santorini. Look at a map and you'll see the logic of the itinerary. The main ferry line for this route is operated year-round by the traditional (and almost legendary) Dionisios Solomos ferry:

https://youtu.be/QYPfpAAqP98

See its 2023 timetable:

https://drive.google.com/file/d/1buB4iBgXC36giH7ucRBi68cDx4WY11vB/view?usp=sharing

and 2024:

https://drive.google.com/file/d/1hh16piPMj6RJ1Eko4bV_NbJulGn2_o7_/view?usp=sharing

If you are prone to seasickness, this is the one you should take.

As for the other islands in the central Cyclades, like Naxos and Paros, you'll take a traditional Blue Star Ferry, which also serves Santorini.

In addition, there are some inter-island connections and other ferry services. Most of the time, these services only operate during the tourist season, and many are provided by Seajets fast catamarans.

These are the smaller Super Jet and Super Jet 2 catamarans, here's one arriving in Folegandros. (Don't watch if you're prone to seasickness.)

https://youtu.be/q9kwckiKFiw

How is it possible that the schedules may not be released until March
or April before a trip starts in May/June?

That's precisely why you should check the previous year's schedules. They change very little from one year to the next, and this allows you to see the frequency of the routes, whether there are ferries every day, two or three times a week, or none at all.

Anyway, there are also days when ferries are canceled due to bad weather, but you'll only know one or two days before, you'll just have to deal with it. It's happened to me 3 times in over 25 years of traveling in the Greek islands, you just need to be prepared for surprises and have some flexibility.

That's also why it's recommended to save your stay in Athens for the end of your trip, because you don't want to see your return flight leaving from Athens airport while you're stuck on an island... it happened to me too, a long time ago. :)

FYI If you are prone to motion sickness, do bring Dramamine from home. We ran into a ferry strike and ended up on a local boat on a windy day. Need I say more.

I understand you wanting to relax at the end but I still would do the islands first. It just is more efficient. It, of course, it is your trip!