Please debug this possible itinerary

You need to understand that every change of location eats up half a day, sometimes longer than that if you are island hopping by ferry.
Slow down and take the time to really explore your destinations. Logistics are important on a Greek trip.
Many of us recommend getting to your first island the day you arrive in Athens. Getting over jet lag on an laid back island is way better than facing all the activity and crowds of Athens.
Here is what I would do.
On arrival in Athens find a connection flight to Santorini. It certainly deserves 3 nights. It is close to Naxos so you can ferry there.
Naxos is a great choice. You can easily spend a week there and not see the whole island. Naxos also has excursion boats that go to Delos then Mykonos on day trips. That means you can experience these destinations without having to pay the price of a hotel in Mykonos which is known for being an expensive destination.

Now return to Athens for 4 nights before your return flight.

As for Bugs, I'd have to call Terminix to handle the bugs in this ... and no there is nothing to add -- but much to skip. But Let's get started, because we Do want you to have a successful (and Realilstic) Greece adventure. FIrst: for best help we need to know WHEN. Advice for May or September is far different from Late June thru Labor (heat, crowds, $$). Plus, you only have 13.5 days, IF you arrive by noon, otherwise 13... and for such short visits, most "vets" recommend 2 islands - maybe a day-stop for fleet of foot, and at least 2 full days in Athens. Also, while nice to start AND end in ATH, your time is too short - it takes precious hours to go Into/out of Central Athens & check in/out Twice. ... If you choose flights that arrrive before Noon, we recommend a short flight to Isle #1,.. much nicer to get over jet-lag in lovely, slower-paced isle vs bustling world Capital.

You need places where scooters work, and selective ferry travel (a scooter challenge). You apparently favor scenic & famed ancient sites vs shopping & beaches. So here goes -- To Skip: • Mykonos (daily cruise mob scene, little history) •Delos (paths V difficult for scooter, ferry prob) • Tinos (not a daytrip for u 3). More time in Naxos, 2.5 days max in Santorini. Your plan sequence should be (1) lock in flight logistics (including local); (2) know skeds for suitable ferries, Only then (3) book suitable hotels (free-cancel provision). I hope u are ready to act, because getting well-located hotels, w elevators or main-level accoms, will make trip much more do-able.
(NOTE: I've hotel options at each stop, but share later, because R. Steves has word-limit on postings.

ITINERARY OPTIONS
Day 1 - Arr ATH (Airport) before Noon - 2pm FLIght CHANIA; stay elevator hotel on OLd Harbor
Day 2-3 - Explore CHANIA plus half-day tour of area Highlights (12-psgr mini-bus- excellent) - transfer to Herak for night 3
Day 4 - 9 am Hi-Speed to SANTORINI arr noon; stay in FIRA Day 3 & 4
Day 5 - Hi-Speed Ferry to NAXOS arrive noon. Seaview hotel at Fringe of Port town, level walk/wheel to highlights
Day 6 - 7 Continue Exploring Naxos via car rental
Day 8 - AM flight to ATH.. Car rental by noon -- Drive to MOST beautiful Old-Town in all Greece, NAFPLIO, on tip of peninsula, surrounded by sea, near THE most famed ancient sites -- and only 2 1/2 hrs from ATH airport on modern scenic highway. See links below For photo highlights & superb website. NAfplio Old-town is virtually car-free, all flat lanes to stroll & explore. Best hotel i s right on seafront, 3 floors With elevator & balconies (but a challenge to book!)
Day 9 - 10 - Explore Nafplio & area
Day 11 - AM - return via coast road to Corinth Canal then to ATH by afternoon check into hotel before dinner.
DAy 12 - 13 - 14 -- Athens Sightseeing; for Acropolis, you qualify for disability elevator, but advance booking & constant re-check is vital (and crossed-fingers because it often isnt running). Either boook pvt Guide or use R Steves excellent FREE audio tours)

NAFPLIO LINKS -- http://www.visitnafplio.com/ https://www.flickr.com/photos/visitnafplio/sets/72157626483407223/

Ha ha ... Stanbr & I almost always answer the same posts, with the same advice! The only difference is that he gives the big picture and leaves you to fill it in , while I always somehow wander down into the weeds... My lengthy screed was due to thinking about the dumb details that can slow up the fun, like stairs in h otels & ancient sites, and walkways too bumpy for scooters..

When I read the itinerary planned by chablis1935, I realized they really needed some "debugging." :)

Luckily, Stan and Janet are here to help.

I'll add a few remarks, mainly to confirm that there's far too much island hopping in this itinerary. In my opinion, in two weeks, active and fit travelers can visit two islands and Athens. Anything more is neither reasonable nor worthwhile.

It's also important to specify the travel dates, especially regarding the weather and temperatures. In Greece in July/August and until mid-September, temperatures can sometimes exceed 105°F.

Why take a day trip to Tinos? You need at least five days to visit Tinos, which is particularly interesting for its many small villages nestled in the mountains. With mobility issues, I don't see the point.

For many years, most savvy Europeans have gone to Mykonos to experience this kind of atmosphere and to see movie stars or showbiz personalities. So, going to Mykonos is a good idea if that's what you're looking for:

https://youtu.be/dMpaksY4sTE

The others are either cruise ship passengers or uninformed visitors who believe that Mykonos is the only place where they'll see whitewashed houses and blue domes.

It's also worth mentioning the exorbitant prices in Mykonos, which is one of the most expensive places in Europe.

So, forget Mykonos and Tinos (even though I love Tinos), it will free up some days for other places.

And if you want to see Delos, you can do so on a day trip from Naxos.

Janet, Stan & Jolui, sorry for my tardy reply. I'm retired so I don't have a great excuse. I fly fish a...lot and after an early start & a full day of it I'm ready for dinner and bed :). But I love it!

What each of you shared is bringing Greece a little more into focus.

There are 3 of us. Nita and I are 70 & son Joe 43. Joe has a light disability called Fragile X which gave him a slightly lower IQ but you'd hardly know it if you met him. Nita has long dreamed of enjoying Santorini. For the three of us its mostly about hanging out and enjoying the architecture, the culture, the food & wine and amazing landscapes & vistas. For Nita that mostly means sitting on hotel or rental porch & gazing at the sea along with ideally some cooking & eating some fresh whole fish. We are not partiers, nor shoppers. We only enter a shop if lost :). We do get a kick out of outdoor food markets and finding groceries & wine. And seeing ancient ruins & monuments. We dined up a side street about 2 blocks but had a decent view of the Parthenon. Our greatest joys in Europe are trying to live like a local. We rarely stay in hotels unless its the only option. We do a lot ABNBs since there are 3 of us and we love to cook. Our adult son Joe and I are very mobile and physically fit so we both love wandering around a quaint village in the evenings when the lighting really shows off the patinaed architecture. We all love eating in quaint little restaurants.

We are a bit leary of Athen's "energy" & crime but hate to pass it up at the same time. Crowded anything has little appeal for us. We were in Rome for 3-1/2 days just after the Pope died. Our rental was near the Parthenon in the heart of the old city so we can handle big cities if its worth spending time there. We're far more at home in small villages. I tend avoid driving in Europe and prefer trains & buses as our main way to get around. Especially high speed trains. I'm a bit queasy about the ferries unless the seas are smooth and I can see land:). That said, seeing the islands from the sea might be fun. No one will ever get me on a boat where I can't see land for more than 30 mins :). No cruises for us!

We don't have any time constraints so we can spend (at least) 3 night plus everywhere and like that pace. I'd likely skip the day trip idea and skip Mykonos if its too busy. We love the Bourne Identity movie though and the ending w/ Marie & Jason in cool bike shop setting in a Mykonos harbor with the windmills on the horizon. But were not 20 something partiers.

I see us going in April May or super late Sept - October time frame. Pros and cons?

Thank you all again and hope you can give me more advise knowing our time frames and our preferred laidback travel lifestyle.

Craig
Twin Cities MN

No one will ever get me on a boat where I can't see land for more than
30 minutes :).

This is a deal-breaker for the trip you're planning, you'll have to limit your trip to just 1 island, provided it has an airport.

A ferry from Crete to Santorini or Naxos to Santorini takes 1.5 to 2.5 hours, depending on the type of ferry.

There are no flights between the islands.

The only ferry trip you can take is between Paros and Naxos (30 to 45 minutes).

So what are you going to do?

At least your time frame for this visit is fine late April early May or Late September early October are less busy with tourist season slowing down. The Greeks are pretty fed up with tourists by the end of the season so a late April May time period is probably best as the tourist season is just starting.
I hope you are understanding Jo Lui , Janet and my concerns with your initial plan. Slow down, enjoy where you are. more hops make for a disappointing visit because of the time it takes to ferry from one island to the next one..

Thank you, Stan, we definitely want to "slow down and not feel rushed. We have the luxury as retires to dedicate all the time needed to amerce ourselves in each location. In May this year against the advice of many we spent 4 nights in Verona with no regrets. Many said only give it 2 nights, but we enjoy the little moments "wasted" in a spot rather than killing ourselves checking off museums and waiting in line to see X monument. We're happy to slow down and attempt to live like a local.

I'm not worried about the length of time it takes travel from point A to point B as I am making the travel less stressful and comfortable as possible. If there are good ways to reduce the stress & hassle of ferries, I'll pay more to get it. I don't love flying but I'll do it if that is best or the only way. We love high speed trains in first class but it sounds like that's not an option in Greece.

I'd be inclined to do something like this time wise...
4-5 nights in Santorini. Assume one side of the island is preferred for relaxing and seeing the best views from a rental or hotel?
5 nights in Naxos
5 nights in Chiana Crete.
3 nights in Athens.
In whatever order makes most sense like Athens last etc.

We stay in Florida's west coast in mid-January. We don't need nor want sun-bathing weather so we could go earlier in the Spring like start in March or April unless it's too rainy and/or windy. Would just want to be comfortable outside on porch looking out from Santorini with long pants and a sweater.

You are getting a better plan now.
For Santorini you want a hotel with a Caldera view. On our first trip on our first night we just sat on our balcony and watched the activity in the Caldera. It was mesmerizing.
Despite that great view there is more to do in Naxos so I would be tempted to do 4 nights in Santorini and add that night to Naxos.
Since Naxos is much like Crete in many ways, but it is much smaller so you can do more intensive destinations in Naxos in shorter time frames.
A few images of Naxos.
Naxos town 2024 https://www.flickr.com/photos/stanbr54/albums/72177720318203165/
Naxos 2025 https://www.flickr.com/photos/stanbr54/albums/72177720329571437
Trip around Naxos https://www.flickr.com/photos/stanbr54/albums/72157634605629689

Suggest that you find a nice cruise of t he Greek Islands along with a stay in Athens. It is much better than taking ferries.

Your itinerary is getting better and now's the time to strategize. Your decisions depend on 2-3 challenges... and one big advantages. The challenges are (1) wife's mobility, and Greece's over-abundance of stairs and lack of elevators in most places with best views. . It would help to know if she can manage 6-8 steps to an entrance, or must be carried for that. (2) ferry choices - your queasiness, and hurly-burly boarding & climbs for enjoyable open-deck ferries means an itinerary must have few & short high-speed sea transfers - which means your last itinerary doesnt work. Also (3) romancing about "live like the locals." Local life features endless stairs, and nobody to help you. On islands, you'll do best in smaller Hotels (10-30 rooms) with, IF lucky, rooms on street level... or else bigger places with elevator. A Must = locations near paved streets/paths usable by mobility scooter.

Big advantage? No limit to dates or length -- So target BEST Weather, everything open, not crowded yet You can even pinpoin dates when Santorinii less jammed (Fri - Mon) MID-May is perfect... NO rain, not hot, swimmable water -- and sea is llike glass for the 2 short ferry ride ypu need. ) I suggest May 9 - 29th. Arrive ATH byearly aft SAT May 9 - fly Immediately to CHANIA, CRETE., 4 nights, 4 1/2 days 5th night stay in HERAKLION, above Ferry port. 9 AM May 15 - HIgh-speedt 1-level ferry 2.5 hrs to SANTORINI. Stay SANTORINI Nights of May 15-16-17-18 (in FIrostephani). AM May 19 10:30 high-speed ferry (open-deck part-way) arrive NAXOs @ noon. Naxos 19-20-21-22-23-24. MAY 25 am Flight to ATH. FLat-fee car service to Central Athens for 4 nights or ?? depending.
In each location, lodging recommends based on your needs/wants --

CHANIA, (1) Casa Veneta (no elevator) Has 1 ground-floor room - on Charming Flat FLagstone lane
(2) Porto Veneziano -- right ON the Old Harbor, all rooms have balconies w views... one of few elevator bldgs. Don't cook in Crete - that's for Naxos.
HERAKLION -- Hotel KRONOS (elevators)-- Has Sea view & looks down on Ferry pier...Right on seafront PRomenade leading to Stunning Fortezza, for your last Crete night. Has brreakfast buffet, good service but not $$ or swanky.

SANTORINI -- it is mandatory that you book accoms with few Stairs, & lodging that leads directly to a paved usable path/street usable w scooter. I do NOT Recommend OIA. Main town FIRA too crowd-jammed. I Suggest FIrostephani, Just on N. Fringe of Fira, away from hubbub, hotels & Pension on cliffside w stunning views, no crowds. My best tip for you has entry right off MAin Road, just 10 steps up... and rooms all open on huge terrace w stunning views. HOTEL SUNSET - https://www.sunsethotel.gr

NAXOS - Best location for you =edge of POrt-Town, St. George Beach. Seaside view AND sidewalks/street a 15 minutes stroll to a ll the town attractions. You want "studios" w BR/LR Kitchenette with PATIOs (No stairs!) However, these in Great Demand! ... Two such lodgings right ON Sands all units w front-facing patio or balcony. -- Studios Kalergis and Studios Thomais. Others right on or just off beach w no-steps accommodations and kitchenette facilities: Studios Panos, Diogenis Studios, and Summertime Studios. All viewable on booking dot com. URge you try for suitable booking ASAP, because families can book first-floor accoms waaay ahead. And its NO-RISK, either thru agency or direct, with free-cancellation up to 2-3 weeks before. Do not dither.

ATHENS - best location = SOUTH SIDE of the Acropolis, low-rise Old Building, car-free Promenade, lush greenery... Moderate hotels right in this area Include Airotel Parthenon and Hotel Phillipos, Hotel Herodion a bit up-scale. Booking dot com now also has many private apts for 3-4 days in same area, with ristk-free cancellation provisions.

Sightseeing strategies are for later due to RS word-limits.

Janet, thank you your advice is... awesome! Nita can do stairs. She does them every day in our home going up and down from our main floor to our lower level. 2 flts of 8 w/ a landing in between but she can do more. Our ABNB in Idaho in Aug had one long flt up to the 2nd floor master of at least 20 stairs. She's pretty good on stairs. Here risk point is walking hands free for more than a few steps. She mostly relies on a walker for walking any distance inside or her portable scooter.

Thanks Janet & all...

More to follow....
Best
Craig

Stair-ability very reassuring! See how important it is to give relevant details? It would also help to know if you guys can PUSH her powered-scooter a few yards to get from a small paved path to a proper sidewalk or Paved lane. Another thing; I hope you are not fixated on a triple room -- you'll do alot better looking at a double & single next door. or across the corridor. This also gives you 2 bathrooms.

In places like Naxos, a "bedroom studio" has ideal set-up: a BR + mainroom, witth a couch that's either fold-out or Daybed, plus a kitchenette, table & chairs -- PLUS table on balcony. The stairs-capability opens up a few more lodging options ... Balcony room in Naxos on that beach at Hotel Palatia. In FIrostephani, Hotel Mylos, right on road as mentioned, with all rooms hving caldera-view balconies... you could ask for the level with least steps (say that, rather than First-floor).