Thoughts on 2+ week Greece/Island Itinerary

You're being fooled by the tourist brochures. It's impossible to see all these places in such a short time.

Corfu is in the Ionian Islands, Rhodes in the Dodecanese Islands, Santorini and Naxos in the Cyclades, Crete in another location, Olympia is in the Peloponnese at the other end of Greece, an 8-hour round trip from Athens.

There are no flights between the islands, you'll have to go back via Athens.

Except for a few rare exceptions involving overnight ferries, there are no ferries between the different island groups.

The maximum you can see in 12 days (not including arrival and departure days) with a fairly busy schedule, being optimistic and optimizing your itinerary is, for example: Athens + One site in the Peloponnese + One island in the Cyclades (or Crete).

Jo-Lui (as usual) is so perceptive ... please take her advice! (BTW, you get best advice when you say (1) WHERE you're coming from -- from Western US or Canada, it's much longer/more exhausting journey and (2) WHEN in October -- 1st 2 weeks vs last 2 can vary a lot for weather & "open" island facilities). Besides the limits she mentioned, ferry skeds in Cycladic islands v limited AND fast-ferries often affected by rough seas (either cancellations or seasickness). BTW your 1-day allotment for Peloponnese means you have yet to look at a map.

IF you say "2+" I take that to mean involving 3 weekends -- i.e. landing by noon on a saturday, and 2 weeks later, leaving Sunday AM. This gives you 14.5 days. -- and I recommend Oct 4-19. Here are 2 feasible itineraries to research:
(1) Day 1 FLY afternoon to CHANIA Crete for 5-6 days; from HERAKLION fly FRI am to ATH, Rent car, Drive to NAFPLIO in Pelops for 4-5 nights... Return Car to Airport, final 4 nights in ATHENS
(2) DAY 1 Fly Afternoon To SANTORINI for 2 nights - Large BLUE STAR ferry (2 hrs) to NAXOS (4 nights) Fly AM to ATH, rent car drive to NAFPLIO for 4 nights, return car to airport, final 4 nights in Athens
I've done a version of each, with newcomers, and it can be enjoyable & unrushed, IF there's good planning; if you're not up for details, consider using an Athens-based travel agency (Fantasy travel and Dolphin Hellas are often recommended on these travel forums). They are used to dealing entirely online with N. American travelers. They can handle the logistics of transport & hotels for an independent-travel visit for you ... leaving you the pleasant job of deciding on activities and dining.

Crete, the southernmost point of the continent, stays warm longer, and is likely all the island you'll ever need.

I agree with Janet and JoLui. With your current itinerary, you will be spending way too much time getting to places and not actually seeing and doing.

To give you an idea, with Janet's help, I planned an awesome trip to Greece for 16 nights. Our itinerary was: Santorini (3 nights); Naxos (4 nights); Nafplio (5 nights), and Athens (4 nights). You have 2 nights less than us and an additional location. Too much time traveling and not enough time seeing. You need to think about how long it takes to get from place to place. Our itinerary was so easy: a 2-hour ferry ride from Santorini to Naxos; then we flew to Athens Airport where we picked up our rental car and drove 2 hours to Nafplio. Then drove to Athens Airport where we returned our car and took a taxi to our Athens hotel.

Want to add that we really enjoyed our 3 nights on Santorini. We spent one day exploring Fira, Firastefani, and Oia, and then on our second full day we rented a car to explore the island. Visited the Akrotiri archaeological site, Red Sand Beach, and Black Sand Beach. The caldera, of course, is beautiful and stunning, but there is more to Santorini than just the caldera.

Congrats on your 25th!

On our first trip to Greece (your age +/-), we did the following and had a wonderful, self-drive, trip:

Arrived to Athens (from NC) and drove directly to Delphi - 1 night
Visited Delphi, then drove to Meteora - 3 nights
Drove back to Athens/Piraeus, ferry to Sifnos- 4 nights
Ferry to Milos - 3 nights
Flight to Athens - 3 nights

We loved Sifnos, but Meteora was the highlight of the trip!

Only one night for the Peloponnesean peninsula which is filled with amazing antiquities? It needs much time. And Santorini is the only place we didn’t like of all the islands. We could not wait to leave there with its crowds and it was cover the top touristy.
Why Corfu??
Remove Corfu and Santorini.
More time on the Peloponnesean Pen staying in Napflio .
Add Crete( using all the days you allocated Santorini and Corfu, 6 nights.)

Thank you all for advice and input, very, very helpful.
We'll be coming from Minneapolis; regarding when, we'd like to celebrate our actual wedding date (10/7) somewhere special. The length of trip can be a little flexible, min of 14 days.
Based on the above and wanting to get a taste of many things Greece has to offer...one thought is taking a cruise as part of the trip, thoughts on: Athens (3), Windstar Cruise that goes to: Mykonos, Kusadasi, Patmos, Santorini, Monemvasia, Nafplio, Athens (4), fly to Crete (4), Athens-Mpls. I realize cruising won't let us truly see much of each island nor experience it's true essence...but it does provide an easier way to see more. Please let us know your thoughts...I'm currently in thw data gathering mode but learning a lot and truly appreciate your firsthand insight.

More doesn't always mean quality.

Most of the members here don't take cruises as they tend to be a "drive-thru" type experience and you'll end up on a boat more times than on land.

With 12 days of time you have to be more judicious on your use of time, especially travel time from place to place.

Crete is huge and deserves a lot more time than 4 days to get any type of sense of what the island is all about. You could split Athens with Crete and give yourself more time on Crete.

There are a number of other wonderful islands to choose from if you want an island(s) experience. You could do two islands (5 & 4 days) plus 3 days in Athens.

The Peloponnese is a wonderful part of Greece and has just as much if not more than most islands to experience.

Many recommend Nafplio with it's Old Town and a wonderful base to explore world class archeological/historic sites and it's close to Athens so you can either take the bus or rent a car to get there plus it would come in handy to explore the Argolis region.

The Argolis is a amazing area that has a lot more to experience than people realize.

You could do 3 days in Athens, 4 on 1 island and 5 days in Nafplio.

You want to spend you Athens time at the end of your trip. You'll be approaching weather changes which can affect ferries and flights from islands. In 2024 our flight from Rhodes to Athens was cancelled due to winds.
Or you can look to leave an island and connect to a flight home from AMS, FRA, ROM or another European airport.

I realize cruising won't let us truly see much of each island, nor
experience its true essence...but it does provide an easier way to see
more.

False. Even if it would be easier in some ways, you certainly won't see more since you'll spend most of your time on a boat and visit (or not) pre-defined places for a few hours.

I also saw that the cruise you're talking about costs from $12,000 for two passengers. With $12,000, we could easily spend a super five-month vacation in Greece. :))

We actually did our first Greece trip with a week on a cruise ship. We used that opportunity to scout out islands we would want to visit on subsequent trips.

When you say you will see more on a cruise, you mean, you will have the opportunity to spend a few hours on several islands. You have to stay on an island for a few days to have a significant experience and see more. That was the case for us on our cruise. We visited several different islands in a week and used that experience to choose which Greek islands we wanted to return to. We have returned to Greece 19 times since then.
All that to say its OK to have your first Greek experience on a cruise ship. Be prepared to catch the Greek bug that calls for you to return time after time.

We are also 60+ and having our first trip to Greece in October, mainly because I hate really hot weather and crowds so wish to avoid them as much as possible.

We have sixteen nights in Greece and then we end with five nights in Istanbul before flying home to Australia.

Unfortunately as others have mentioned, flying invariably involves returning to Athens, it is a nuisance, but the places we have picked are primarily my husband's choices and he really wants to visit so we will.

Much as we'd like to see the Polopennese pensinsula we have decided against it. Maybe we'll come back, who knows.

We are starting in Athens for four nights to see the main sites. Then we fly to Naxos for another four which should be relatively relaxing while there.

We will ferry to Santorini for three nights because I cannot come to Greece and not see Santorini.

Then it gets complicated. My husband very much wants to visit Rhodes and the more I have read about it the more I want to too. Unfortunately the flight does involve returning to Athens then to Rhodes. Never mind. We aren't into beaches and swimming, we live in Australia with some of the best of those on earth, so we will stay in the medieval old town of Rhodes for the history. We will also hire a driver a couple of times to visit Lindos, and other historical spots on the island.

I hope to make it to Symi for a day trip too.

Finally, it is on to Istanbul again via Athens, but at least there will be another five nights in one spot before returning.

I hope this gives you a couple of ideas.

Good luck with the planning.