Three Week Itinerary Help mid September

That should work, though I would personally prefer to save Crete for its own exclusive trip (and would not bother with Hydra since you have so much island time). I would also look at incorporating at least one flight into your plan. Most recommend flying to your island destination on arrival day. You can then work your way back to Athens via ferry.

Valedelphia is correct -- Athens LAST ... here are oft-repeated reasons from us "Greece vets":
• After transatlantic flight you're tired/jetlagged, NOT ready to cope with whirl of sightseeing in a busy world capital, in a completely new country where you don't even know the alphabet
• It's better/more fun to recharge, reinvigorate in slower-paced beautiful place... an island
• Sept Weather better for isles - also they start "closing down" in Oct, while Athens becomes more vibrant.
• A few days on isles helps u learn "how Greece works," so at end you'll be savvier to explore the big city
• With immersion in Greek culture a few days, famous Athens landmarks will resonate so much more!

With 3 weeks, the sensible sequence. minimizing transit time, would be:
• CRETE - 6 Days - Fly immediately to CHANIA (2 days); suggest Imbros Gorge. rent car, drive S then NE end outside HERAKLION for Knossos (take bus into city for Museum & dinner, bus back to car - drop it at Herak pier before 9 am Ferry)
• SANTORINI - 3 nights (I recommend staying on cliff-edge Firostephani to avoid crowds; walkable to Fira, bussable to Oia
• NAXOS - 3:15 Blue Star ferry (open deck view) -- 6 DAys - stay on St George beach adjacent to Port town - beach, ruins, food, sunsets! one-day car rental? If u r there before end of Sept, there are day-excursions to Mykonos/Delos.
• DELPHI - fly ATH, drive Delphi in aft, see museum, stay 1 night, Ruins in AM, return to Airport; uber to Hotel
• ATHENS - 4?5? days Sightseeing relaxed pace.

Thank you so much for these tips! Is it a hard drive from Athens to Delphi?

Unfortunately our flight gets in after the ferries are done for the day, which is why we were going to do Athens in the beginning of our trip, and then fly back from Crete the day our flight left. I guess we could just stay over night the first night and leave for the islands first thing in the morning? So then it would look like:
Day 1 arrive Athens 7:00pm; dinner and sleep-1 Night
leave for Mykonos , next day, stay 3 nights, with day trip to Delos
leave for Naxos stay 5 nights
leave for Santorini stay 3 nights( Is this too much time here?)
leave for Crete stay 5 nights
fly to Athens stay 3 nights and 1 in Delphi?

Do you think this would be a better trip?

I just looked at flights to Crete from Athens. There are at least 2 flights available on Sky Express and Aegean/Olympic that depart around 9:30 in the evening. Both are to Heraklion. You will have no problem making that connection. I would do that rather then overnight in Athens.
That was a dummy booking on September 15 Just guessing your actual dates.

I am going to suggest that you re order the plan and start with Crete then ferry to Santorini, Naxos and Mykonos. For 2 reasons. There are flights that allow you to get to Crete on day of arrival. Secondly the ferry system works most efficiently from Crete to the Cyclades Islands. If you plan to ferry from Mykonos that is the turn around point for the ferries and they do that in the afternoon so you get to your next island much later in the day.

It would help us help you better, if there was a specific date Of Arrival - is that a problem?

I still feel the Crete-first approach works a bit better, for several reasons ...
(1) by good date choices, you might be able to land in Santorini for weekend - much less cruise-ship mob scene
(2) the ferry FROM Santorini TO Crete goes only to Heraklion & arrives just before dark, whereas the ferry FROM Heraklion TO Santorini arrives just before Noon.

ALso, I do take exception to 3 days on Mykonos (!!) are you into super-luxe shopping?? -- Chanel, Hermes, Cartier, Hugo Boss, DKNY, etc etc etc - over 100 such.. if that is your taste, i recommend Rodeo Drive instead. Also up to 8,000 Cruise-ship shoppers cram into Mykonos town some days. PLus, Mykonos-Naxos ferry no fun, small enclosed cabin, bumpy in Autumn weather, vs large, open-deck. smooth-sailing Blue Star from Santorini-Naxos. Appreciate explanation for this preference. The day-excursion from Naxos I mentioned gives you over 3 hrs on Delos, plenty to cover its highlights.

As to Crete-First approach -- nobody was suggesting a long ferry ride upon arrival. Thinking about 7 pm arrival, I checked flight options on this handy Aegean/Olympic link - https://en.aegeanair.com/plan/book-a-flight/ -- ATH - CHANIA for any day sept 14-15-16-17... has a 22:45 flight (10:45pm ), 50 mins duration only... If this doesn't work for you, there's a pleasant local overnight option. -- a FREE shuttle to nearby AVRA Hotel, for a bite to eat & early bedtime, then zip back (FREE) to Airport next AM & get 8 am flight to Chania. (OR if you like to spend $$$ u can stay at Sofitel at the airport). Either flight would start you off in a gorgeous place (CHania is most beautiful Old TOwn in Crete, 2nd most beautiful Old TOwn in all of Greece).. and a surrounding NOt invaded by cruise-ship armies.

My suggestions are not off the cuff -- based on 13 trips to GReece 1999 - 2019, multiple visits to all places mentioned.. both solo, and with numerous "newcomer" travel companions... so I really do know what works, in terms of sequence & length of stay.

PS - forgot about your delphi query... you can check the route on Michelin Planner -- https://www.viamichelin.com I like it better than some over-optimistic onlilne guides. It's 2 hrs 39 minutes from Airport -- over half that time is on modern divided interstate-type highway, then modern smaller highway... last 1/2 hour is gradual climb into the higher elevation but not steep or super-curvy. Quite pleasant. Rooms on the DOWNHill side of Hotels give stunning view down mountain, thru olive groves to setting sun on the sea.

Thank you so much! I really appreciate your help with this. You are so helpful, I hope you don't mind me picking your brains about this.
I rechecked our flights, and we will be arriving non-stop from Newark at 4:05 PM on September 20th. It looks like Aegean Air has a flight from Athens to Chania at 6:00pm so that might work? Hoping that is enough time to go through customs and such.
We depart from Athens on October 11th at 5:35pm, so it makes so much more sense to start in Crete and not to have to worry about catching a flight from Crete and making our return flight home.
New itinerary:
9/20, EWR to ATH, ATH to CHQ; stay in Chania
9/21-24 Chania-Imbros Gorge,Botanical Gardens, Beach-rent car
9/24-26 Heraklion Area-Knossos
9/27-9/29 Santorini
9/30-10/5 Naxos-day trips to Delos and Mykonos; or 2overnight in Mykonos -1 full day in Delos?

10/6 fly from Naxos to Athens Delphi
10/7-10/11 Athens

A few More questions,
Would we pick up a car to drive to Delphi at the airport?
How much time do you need at Naxos airport before a flight?
Many thanks again!

HAve sent you pvt message.

That is the flight I flew to Chania in May but it was on one ticket. Two hours will be tight. Are you checking luggage? I would not as you will have to wait for your luggage as well.

The planes to the islands are small and unless you travel really light, you will have to check your luggage for the flight to Crete.

There is another flight that night but much later. My connection was even tighter (one hour but with luggage checked all the way through) so I checked. There are different classes of tickets on Aegean. I would buy the one that includes luggage and allows you to change the flight without penalty. This is the most expensive option.

In 2018, my husband and son flew from Newark to Athens. I met them at the airport. I had already figured the airport out. They had a 90 minute layover and had to check bags. We had enough time to pick up some food before boarding.

You can rent a car at Athens airport. We have used Athens Car Rental twice.

For Naxos airport, you don’t need to be there very much ahead of time. Our hotel supplied transportation and they thought we were nuts for wanting to go as early as we did. They were right. We checked in and then had to sit outside because only people on next flight can go though security!

You have so little time in Naxos it would be a shame to leave there without really seeing much. If you want to take the day excursion which gives you 3 hours at Delos plus 3 hours in Mykonos. That will give you time to wander Mykonos town. It is very pretty but expensive. The day trip gives you the experience but not the costs of a stay in Mykonos.

Here are some recent images of Naxos
Around Naxos town 2022 https://www.flickr.com/photos/stanbr54/albums/72177720299959098
Back to Naxos 2022 https://www.flickr.com/photos/stanbr54/albums/72177720299940917

I forgot part of your question. Athens airport is very easy to navigate particularly if your connecting flight is all on one ticket. If not you have to pick up your bag then go to passport control. That process probably will take 30 minutes. There is no costumes just walk out the door that says nothing to declare. Go upstairs one floor to Departures level. Re check your bags then go through security. On our return trip the Athens airport was absolutely full and security only took us 19 minutes. They are very efficient in moving people through the airport. Almost 2 hours to get that done will give you enough time to try out your first glass of Greek beer.

Thank you very much for your kind responses. I will check with a different airline to see if there is a better flight, or maybe just to be safe book the later one. If we have 7 nights on Naxos, maybe we will just take a day trip and do Mykonos and Delos. We could have 7 nights on Crete, 3 on Santorini, 7 on Naxos and 1 in Delphi, and 3 in Athens.
I appreciate all your suggestions!

Re:Crete. Give most of time there to Chania . You can use it as a base to visit Western Crete. Take a bus or drive to Heraklion to visit Knossos and the Archeological Museum which we did as a day trip from Chania.