Rough Greece Itinerary: Feedback, please

-Does the itinerary make sense as far as the chronology, driving distances, etc?

There is no ideal itinerary, and everyone can suggest another itinerary that they have done (like starting basically in Nafplio) but this is in my opinion a doable and not too ambitious itinerary.

In the Peloponnese you start by going to the furthest (Kardamyli) to gradually come back towards Athens, which can be smart but which implies a rather busy day of travel from Naxos to Kardamyli via Athens airport (on 8/31). Note that the last part of the trip between Kalamata and Kardamyli is on a particularly winding road in a mountainous environment.

And there is the very interesting and not well known Archaeological site of Ancient Messene on your way

https://greeking.me/blog/greek-mainland/ancient-messene
This is also why you could stay one more night in Kardamyli in Mani which is a superb region if you like nature. (1 night shifted from Nafplio)

Despite its undeniable photogenic side, I found Monemvasia uninteresting because it's like a theme park, without any local life other than that dedicated to tourists. This is the place where I regret having wasted my time staying there for 2 nights. A few hours would have been enough.

On the other hand, between Monemvasia and Nafplio, if you take the route along the coast via Leonidio (which is a little longer) the road is very scenic
https://maps.app.goo.gl/XZhNnBYdeYMf7RoS7

and there are plenty of nice places to stop like here:

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

-Is the Grotta Hotel in Naxos a good choice/location?

Why not?
But I am always surprised when I read this kind of sentence "enjoying the ambiance and locals" and to see that it is always the same 2 or 3 hotels that are chosen in Naxos.

Naxos is the largest island of the Cyclades with hundreds of possible places to stay, and despite this, everyone whatever their preferences, goes to the same place in Naxos town or its immediate surroundings, where there are the most crowds and where the beaches are invaded by people and sunbeds to the point that you can hardly see the sand anymore.

I must not have the same idea of ​​"enjoying the ambiance and local" :))

Go with your itinerary. There is no perfect. Why ask here to begin second guessing yourself and juggling suggestions into your plan. Do you think you could be so wrong that your Greece visit will be a downer?
Free yourself from the tyranny of the perfect trip and the limitless possibilities that will arise in the suggestions.
You can handle planning your own trip.

You have picked the usual tourist destinations for Greece which is fine but there are many other islands and parts of the mainland that may offer more enjoyment "taking our time and enjoying the ambiance and locals" elsewhere.

If you have your heart set on Santorini & Naxos then go for it but expect more crowds and higher prices especially Santorini.

Naxos is large enough to find more traditional areas to enjoy.

I also found Monemvasia another tourist hot spot, very pretty but definitely tourist oriented.

Five nights in Nafplio is not too many as it's a perfect base to explore the entire Argolis/Corinthia areas which are filled with archeological/historic sites, mountains, beaches, villages and lots more.

Check out https://visitnafplio.com/ to see what those areas have to offer.

The 9 days you have planned for the Peloponnese will only give you a taste of what it has to offer. It has just as much as any island and a lot more.

I've been there 3 times and planning again for 2025.

I would recommend some type of navigation system for driving. I use Google Maps and works very well albeit with a few "hiccups" here and there.

The best guide for the Peloponnese is the Cadogan Guide with more info than any other guide. Although last published in 2010 it's still the best. Available from abebooks or ebay.

If interested check out my Peloponnese trip report with photos from another website.

https://www.tripadvisor.com/ShowTopic-g189483-i1277-k14200587-Peloponnese_Trip_Report_Sept_25_Oct_12-Peloponnese.html

In the end do what's best for you and regardless of where you go.

Grotta hotel gets very good comments on travel threads. Never heard any complaints. It is close to Naxos town however there is one thing you need to know about Grotta. It is high up on a hill so great sea views however in the evening you have to walk up that unpaved path in the dark. A flashlight would be helpful. If mobility is an issue you might want to consider a different hotel.
For fun this is an album of Naxos town in the evening.
Naxos at night2024 https://www.flickr.com/photos/stanbr54/albums/72177720318406428/

Have you booked your hotel in Santorini? It is spectacular but can be very busy. If you look for a hotel in Fireostefani it has great Caldera views but it is just far enough from Fira the capital that cruise visitors do not venture that far so it is more quiet. You can time your visits to Fira before the cruisers arrive and after they depart in the evening.

We loved Monemvasia. Some of our Greek friends tell us it is one of there favourite places to take a short vacation. It is an old walled village with a ruined fortress at the top of the rock. The hotels are restored period rooms. Our bathroom had a gun port in the wall.
Sleeping in a period room inside a 14th century walled village is a real treat.

On your trip back to Athens when you get to Corinth take the time to drive up to Acrocorinth there is a huge ancient fortress up there with 360 degree views of the surrounding countryside. I love fortresses that you can drive up to.
Corinth Area. https://www.flickr.com/photos/stanbr54/albums/72157711755443483
Peloponnese, Mani and Monemvassia. https://www.flickr.com/photos/stanbr54/albums/72157711323535897

Thanks very much for the input. The links with specifics of how I can improve the trip are especially helpful and appreciated.

I like the idea of adding a night to Kardamyli.

stanbr: Your photos are incredibly beautiful. I have seen them on different threads, and they are what gave me the final push to get off my butt and plan the trip. :-)

There are plenty of hotels in Kardamyli, but if you don't know which one to choose I can recommend the Vardia hotel.
It's just a little outside of town (there's a short walking path to Old Kardamyli) There is a beautiful view of the city and the sea, and the breakfast is excellent. The studio type room with fully equipped kitchen is a little expensive (€100) but very nice.

https://www.vardia-hotel.gr/

https://maps.app.goo.gl/bgNM1yW2UBNjo1Sh9

As a free bonus I would add the Platanos tavern, in the nice little village of Thalames, on the way from Kardamyli to Monemvasia

https://maps.app.goo.gl/v2s3CywkxNQ5PFQN7

Many of your Nafplio day trips could be seen en route from Nafplio to Athens, so that may help consolidate a bit.
We planned to visit Mystras in between Nafplio and Kardamyli, which can also save time, but we ended up doing it as a day trip from Kardamyli for weather reasons.

We went to Athens for 2 nights, then went by plane to Santorini for 3 nights and I wished I had stayed an extra night. There was a lot more to see and do in Santorini than I anticipated and we rented a car there. Took a plane back to Athens after and went to the Pelopenese for 3 nights but did not have time for Monemvasia. 2 nights In Napflio was good. The archeological site of Mycenae was close to it and very good to see. Hope this helps. By the way, we went to Milos on another Greece trip and paired it with Meteora. Both are spectacular.

Hi Lisa,

It sounds like you’ve put together an exciting itinerary! As someone who has lived all my life in Santorini and Athens, and who has visited Naxos, Monemvasia, and Nafplio multiple times, I’d love to share some insights to help fine-tune your plans:

Santorini (3 nights):
Three nights is an excellent choice for Santorini, especially given your arrival on a Friday and departure on Monday morning—this timing helps you avoid peak cruise traffic. While Santorini gets a reputation for being overcrowded in high season, my experience suggests otherwise; many other Greek islands can feel busier during this time.

I highly recommend booking a private tour or wine tour in advance, as availability can be limited. VIP Santorini offers fantastic services for private tours and airport/port transfers, and they’re a reliable choice for making your stay seamless.

Naxos (6 nights, Grotta Hotel):
The Grotta Hotel is a wonderful choice! It’s known for its warm hospitality, beautiful views, and convenient location. However, six nights might be a bit too long for Naxos. I’d suggest reducing your time here to about five nights and allocating the extra day elsewhere (more on that below).

Athens & Beyond:
Spending six days in Athens and its surroundings is a great plan! Athens provides ample opportunities to explore history, culture, and culinary delights. With a rental car, you can also easily explore mainland highlights. If you have any flexibility, I’d suggest adding 2–3 days to your itinerary, allowing for a visit to Meteora—an awe-inspiring site with monasteries perched on towering rock formations. It’s truly one of Greece’s most remarkable destinations.

Nafplio (5 nights):
While Nafplio is a charming and relaxing base, five nights might feel too long unless you’re planning to move at a very slow pace. I’d recommend four nights instead, allocating an additional night to Athens or another region, like Meteora.

General Tips:
Driving Distances: Your driving itinerary makes sense, though be prepared for long drives, particularly between Athens and Kardamyli or Monemvasia. Allow for breaks and enjoy the journey, as the scenery can be spectacular.
Activities and Tours: For Santorini, I recommend a catamaran cruise or a visit to the Akrotiri archaeological site. In Athens, a guided Acropolis tour is a must. For Naxos, consider a food tour or a visit to the mountain villages like Apiranthos. In Nafplio, day trips to Mycenae and Epidaurus are highly recommended.
Lastly, if you need a reliable travel company, I’ve worked with Xenon Travel in Athens and can vouch for their excellent service. Let me know if you have specific questions or need more suggestions. Your trip is shaping up to be unforgettable!

Thank you! This is very, very helpful.