Finalizing places...

Sounds like a pretty good plan. You have been doing your homework.
I would suggest St George beach for your Naxos stay. It is actually part of Naxos town and is just a short stroll to the waterfront promenade of Naxos town.

There are lots of hotels many with sea views. St George is also quiet at night for sleeping.

On your way to Nafplio consider a stop in Corinth. You can see the canal and possibly a stop at Ancient Corinth and maybe drive up to Acrocorinth which is a huge fortress with 360 degree views.

From Nafplio you could consider a hour and a half drive to the last Byzantine city at Mystras near Sparti.

Those last two suggestions might be a bit difficult if walking is a problem but a drive by and a stop might give you a glimpse of some cool history.
Corinth Area. https://www.flickr.com/photos/stanbr54/albums/72157711755443483

Santorini deserves two nights and Firastefani makes a nice base. Do go to Oia (EE-ah) by 9a and plant yourself at the castle to get a sweeping view of the cave houses overlooking the caldera complete with two windmills. Afterwards, walk along the white cobbled path and window shop. You want to be out of Oia by 11a to avoid the bus load of cruise ship tourists.
The only thing I liked about Naxos was the ferry ride from Santorini through the caldera; Naxos is not a pretty island. There’s lots of traffic, it’s loud and you have to escape the city center to get away from the noise and gas fumes. I walked up to the castle twice to get away from cars honking their horns and motor scooters rushing by. Naxos is the ugliest island I’ve visited. There is one cute street with shops and a good restaurant but the merchandise consists of souvenirs, homemade jewelry and cheap clothes.
There is one good restaurant that opens at 6p. Unfortunately, my ferry back to Santorini left before then. If beaches are your thing go to Mykonos instead and check out the windmills too.
The Plaka is a fantastic area to stay. If you take a taxi in Athens make sure you ask how much before getting in. If the price sounds high then it is. I had problems with two cab drivers telling me I gave them a five when it was a 20. I jumped out both times and walked away.

This seems very well thought out, considering the complexities of meeting multiple people.

However, you might be hard pressed to get from Nafplio to Athens by 11 am to return the car. If you are determined, be prepared for very early departure. I can't remember how long it took us now but I know both ways, it seemed to take longer than it should have.

In contrast to Mary Pat, we loved Naxos. We spent four nights there and wished we had more time.

Wow, these are all such helpful responses. Thank you so much! :)

I am not sure if we are being trolled but I will take the bait.

We have been going to Naxos since 1996 and this is the first time I have ever heard Naxos described as "not a pretty Island" and "Naxos is the ugliest Island I have visited" and "There is one good restaurant that opens at 6p."

This poster arrived by ferry and experienced what is essentially the same for any Greek Island port. There are cars and trucks loading onto the ferry with hundreds of passengers swarming out and into the ferry. The result is an unbelievable chaos which is a wonder and a uniquely Greek island experience.

Indeed there are people, cars trucks and motorcycles along with hoteliers all crowded near the dock. However within 15 minutes that is all gone until the next ferry arrives. In between it is calm and peaceful on the harbour and waterfront promenade.

Naxos is a large island with a lovely waterfront, harbour, and back alleys full of Venetian era buildings and topped by a Venetian era Kastro.

Once outside the main town there are kilometres of good beaches, mountains with villages snuggled into the countryside, antiquities, some ruins and olive groves everywhere.
It is not possible to experience the whole island on a day trip ferry hop.

I am surprised to learn that there is only one good Restaurant on Naxos. By the way these establishments are called Tavernas and there are dozens that would fall in the "good" category and at least 15 that are often recommended as excellent.

Judge for yourselves. Here is what Naxos is like.

Around Naxos town 2022 https://www.flickr.com/photos/stanbr54/albums/72177720299959098
Back to Naxos 2022 https://www.flickr.com/photos/stanbr54/albums/72177720299940917
Trip around Naxos https://www.flickr.com/photos/stanbr54/albums/72157634605629689
Chalki and Vivlos villages https://www.flickr.com/photos/stanbr54/albums/72177720299950915
Naxos sunsets https://www.flickr.com/photos/stanbr54/albums/72157700728046481

Stanbr, that person who hated Naxos was apparently there for 5 hours at the most on an ill-conceived daytrip from Santorini ... her post indicates that she took the morning Championjet becase she mentions a view of Santorini.. and arrived about noonish. From her description, she never got out of the port town, or had a relaxed meal and knows little or nothing about the island OR its tavernas OR its beaches because she said " There is one good restaurant that opens at 6p. Unfortunately, my ferry back to Santorini left before then. If beaches are your thing go to Mykonos instead and check out the windmills too."

I am sorry that people go to ANY island with so little research beforehand, go for a few hours in the middle of the hottest month wander around a port town, and then post a reaction. THis will be forgotten tomorrow ... As the song says, let it go, let it go...

Hey Jan good to hear from you. For accuracy sake I checked the ferry schedules and there are now early morning ferries that do Santorini to Naxos in the morning with arrivals between 9 and 10 am. Thats a great improvement in the service.

Are those earlier ferries ones with a small open back-deck, so passengers can glimpse the cliff briefly as they leave? I am aware that Blue Star diehards say that ONLY a Blue Star gets the full extended view, but hey! there are compromises involved...and the Blue Star doesn't arrive Naxos until about 5:30pm. (PS: Am pleased that u r glad to see me back but... I've been here all summer... it's you that went gallivanting and are now back on forums)

I did not take note of which ferries were on the early morning run just interested that the transfer can be done earlier. The last time we did the run out of Santorini I timed it. We we cleared the outer ring of islands in 14 minutes. While the Blue Star certainly has a better view through the caldera the fast ferry route is still pretty special.

Yes we have been parked at the seashore for the past 2 months. Poor internet connection, so I have been missing in action but we are back now.

It seems that in September the first 2 daily ferries at 10:15 am and 12:10 pm for Naxos are the Power Jet and the World Champion Jet. Both have an open back deck (no place to sit) The "Power" deck is much larger than the "World Champion" but more exposed to the wind.

Either way, I don't like either of them.

The World Champion Jet had a turbine problem last week, it was moving at 25 knots, no faster than the Blue Stars.

I haven't even thought about getting from Santorini to Naxos but it sounds like there are multiple ferries as an option...which one is the best? I can't say that we'll be in a hurry so doesn't have to be early, although we are early risers and checking out of hotel, that would probably be nice BUT I really would like to see better scenery vs not...

We are planning a Greece visit (May2023) and after reading this post and another recent post ("2 weeks in May 2023"), I find that our itinerary is looking very familiar to yours, too. We probably will do 4 nights in Naplio...but otherwise looks the same. And...we settled ont his itinerary based on the feedback on these posts from those experienced Greek travelers. It sure helps...I know I have more research to do, but wow--you really make a difference. Thank you!

Naxos was one of our favorite islands, so don't be dissuaded by the previous poster. We spent one day on a private tour which was terrific! Our guide stopped at various spots and there was minimal walking. Our experience on Sea Jets (Power Jet) was good and arriving in Naxos by mid morning was ideal.

To complete what janet and stanbr said, I confirm that Naxos is a beautiful island. It's the largest of the Cyclades and therefore has very diverse landscapes. There is everything to satisfy all kinds of travelers and activities. Beaches, villages, ports, sports activities or hikes. Good restaurants, many accommodation options of all categories, authenticity, etc. etc.

I'm going to be a little harsh and I don't like to argue but I think the person who denigrated Naxos said bul...it.

Regarding ferries from Santorini to Naxos , you have 2 main choices...each with advantages & drawbacks: For both, you can just purchase ticket at any handy Santorini agency the day before.

(A) CHAMPION JET -- "fast ferry: about 800? psgrs + cars; dep 10:15 arr about noon? ADVANTAGES - (1) early arrival allows complete halfday on island. (2)all-reserve seats, can arrive dock about 30 mins before departure (3) easy luggage stowage at entry to seating area, few steps (4) small open back deck for standee view of cliffs on departure. DRAWBACKS - (1) 2x cost of the B Ferry (2) v limited outside deck oppty (3) confined to seat for 2 hrs, limited view

(B) BLUE STAR - Reg Ferry; cap 1800?psgrs/250 veh; dep3:30-arr5:30pm ADVANTAGES - (1) Lower cost (2) 2 large back decks w seating (unreserved) for 2 hr "mini-cruise" enjoying sun/sea (3) nice "big ship" experience; can walk decks, aisles etc DRAWBACKS (1) arrive late aft - less time, if your sked only allows short Naxos stay (2) open back decks are up 2 flights (3) unreserved deck seats means in busy season, a scramble to snag them (4) u must leave large bags stacked on vehicle deck.
STRATEGIES for B.S. -- Arrive pier early, get seats right by exit of "psgr pen" at "head of line" -- when psgrs allowed to board be Brisk-- Entering vehicle deck, YOU tend to luggage, send teenager sprinting up to open deck to snag 2 prime seats.

Sorry u only allotted 3 nights to naxos! Is it poss. to leave the Aft of Sept 21? Really once u've seen the Famous Caldera View, that's the Main Santorini Thing... terrain is difficult for longish walks, crowds are a challenge. But I suppose all plans are set. Have fun!

Thank you Janet for the thorough answer about the ferries. That really helps a lot! My son and I are very small people so I feel confident we can work our way to getting a good spot LOL
My plans are not set in stone so I may look into cutting a night out of Santorini and use it for Naxos instead...thank you for the suggestion :)

I really hope you can add to Naxos! There's SO much more for energetic teens to do & see there! Our ACE photog on these forums, Stanbr, has wonderful photo Albums that I suggest you share with son:

Trip Around Naxos - https://www.flickr.com/photos/stanbr54/sets/72157634605629689/
Naxos Town - https://www.flickr.com/photos/stanbr54/sets/72157632094558042/
10 Days in Naxos - https://www.flickr.com/photos/stanbr54/albums/72157656336387898/page2

if u had 3 full days on Naxos (arr aft S21 - stay 22-23-24) .. u could have 3 eventful days, maybe like this:
S 22- explore Town & Kastro (castle) AM, beach afternoon, town evening - book a Next-day -bus tour
S 23 - https://www.naxosbustransfer.com TOPS - mountains, ruins beaches, a noonday swimstop "Naxos Highlights Tour"
S 24 - Bus to FAR beach like PLaka?? Ask to stop@ Aegean Land (free sunbeds when U buy snacks) - walk to Arch sunset
... Naxos is family-friendly, lots of young teens, St. George beach at Flisvos sports center has Windsurfing, kayaks etc.
ENJOY ...

her post indicates that she took the morning Champion jet because she mentions a view of Santorini. and arrived about noonish.

I took Seajets on Jul 19 that departed Santorini’s dramatic Athinios Ferry Port at 8a arriving in Naxos at 9:35a. My ferry back to Santorini departed at 5:50p arriving at Athinios at 7:15p. I then jumped on a shuttle that dropped me off at my villa in Akrotiri and saw a gorgeous sunset on the way.
I know everyone likes this island but I was extremely disappointed with the castle district; it wasn’t much and run down. There was an old unfinished church facade I liked but the one in Montepulciano is more impressive.
I then headed back down into the town and forgot I was on an island. It was loud because of the many motor scooters and cars; there’s lots of traffic in Naxos.
I walked the port twice and liked it then visited two beaches and neither made me want to hang out as a good beach does. There was nothing magical about this island. I admit that places of business are recuperating after COVID, so for those of you who were there before COVID, you probably did have a different experience.
Before I left, I ate dinner away from pier that was the worst meal I tasted in GR. I couldn’t eat it and it featured all the foods that are grown on this island.

Stanbr, you are a gifted photographer but your photos exaggerate Naxos good looks. I did find a path (lane) that finally woke up around noon where four merchants opened their inexpensive shops selling hand-made jewerlry, souvenirs and cheap dresses with a restaurant nearby that offered good views. Your photos make it look way better than it does.
I Googled Images of Naxos Town and thought “how beautiful” and that’s why I went. Naxos does not look like your photos.

Sorry Mary Pat all the photos were taken in Naxos, so in fact that is what anyone can see there. I am sorry your expectations were not met. Annoying things can happen anywhere one goes and that can leave a bad taste even when many other people absolutely love the same place. There are a few places in Crete and Paros where we were totally disappointed but that has not cause us to trash the whole island. Sometimes stuff does happen.

Opposing viewpoints should be relished here, even if we disagree with them.

As a sidenote, when people have questions regarding the Cyclades, they
are most often answered by people who love them and people who have
returned for many years. This does point to an inherent bias worth
mentioning.

Amen, AMann!

Just to add my two cents, my husband and I visited in May and were a bit underwhelmed with Naxos Old Town. We did not think it was ugly, but we were just not as enchanted with it as others seem to be. I wonder if we had this reaction because we had just come from Santorini (we stayed in Ouia), which we thought was absolutely stunning. We spent five nights in Naxos and had the time to explore some ruins, the mountain villages and two gorgeous beaches (Plaka & Aliko) and we felt like this is where the beauty of Naxos lies.

Interesting that the last poster was underwhelmed by Naxos Town in comparison to Oia in Santorini ... because Oia is not a real town, it is a postcard, a calendar page, an internet video. For many months a year it is essentially closed down & unoccupied. By contrast, Naxos Town year-round is the main town of an island with a large permanent population -- with elementary AND high schools, a hospital, sports teams, major supermarkets, industries etc. Off-season its waterfront tavernas still have plenty of patrons -- who are mainly locals, who love to dine out. So the town isn't picture-perfect in every corner, like Oia, but is more real.

We spent 4 nights in Naxos last May and absolutely loved it. Maybe May is quieter than July, but we didn't experience an excess of noise, cars honking, or motorbikes. Yes, Naxos Town is lively, but it's a "nice" and invigorating lively. And we loved Naxos Town! So beautiful! We have awesome photos! They are real, not fake.

For anyone visiting Naxos, I highly recommend renting a car for at least one day to travel around the island. The day we did this was one of the best days of our trip. We visited the Temple of Demeter, the villages of Chalki and Apeiranthos, and the seaside fishing village of Moutsouna on Moutsouna Bay, where we had one of the best fresh seafood meals of our trip. And then visited the small fishing village of Apollonas and enjoyed ice coffees on the beach.

We stayed at the Hotel Palatia on St. Georges Beach. It was quiet. Never any problem with noise.

For restaurants, we had delicious meals at Meltemi and To Elleniko; great lunches at Avaton 1739 and Yialos; and a delicious breakfast at Soulatski.

The only restaurant we were disappointed in was Elizabeth's Garden.