Itinerary and when to schedule flights to/from Athens, Santorini, and Naxos

I would most definitely fly direct to Athens and straight on to Santorini...and leave Athens for the end of your trip. I am not certain given the pandemic but I think BA had a direct flight to Santorini from Chicago seasonally....don’t know if that flight will return.

I would want to be back on the mainland minimally 2 nights before flight home. Also.... I think Athens deserves several days or more.

Sometimes with flight schedules there is no way to do this, but it is ideal to get to an island the day you arrive, then return to Athens for the end, for however many days you want there. If you just want to see the Acropolis, a day is enough. I personally think Athens is underrated as a city, but I totally get why one would minimize time there in order to have more time elsewhere (we only get the vacation days we get). That was what I did, my reasoning was also that I like to go to places multiple times, so I fully intend to revisit Athens.
So, if you can arrive in Athens in the morning and get on a flight to the island that day, go for it! Others can advise on the best amount of time to have in between flights, but I'd feel okay with about three hours.
This lets you avoid having to split time in Athens and also may give you an extra night on an island.

Looks fun to me! You may want to consider adding a day to Athens. I've never been to the latter (unless you count the ferry stop where you don't get off the ship) but have to both Athens and Santorini. IMO it will be difficult to enjoy and appreciate what Athens has to offer (Acropolis, Agora, 2 major museums, tourist zone and other ruins, food, vibe, etc.) in less than 2 days. You might also consider going straight to the islands after landing in Athens (especially if you land in the am rather than late evening) and then covering Athens at the end of your trip. Also, Santorini is beautiful but you can't explore the entire island in less than 2 days. Perhaps you would enjoy your trip just as much by staying in either Naxos or Santorini in order to cut down on the time/rigors of travel and provide yourself more time to relax and more thoroughly experience one place rather than quickly visit two. Regardless, you'll have a great trip!

Thanks.

My incoming flight arrives in Athens at 9:00 p.m.

I think I'd rather spend the first night in Athens upon arrival than arrive in Santorini close to midnight. I would like to enjoy my Santorini hotel, view, evenings, dinners, when I'm there. Ditto for a possible first stop Naxos.

Then I ask myself: fly out to the islands in the morning, or just see Athens first since I'm already there? I do want to see some of Athens this trip, but the highlights will do. I would love to return in the future.

The last night in Athens is just planned as a pitstop/dinner for my flight the next morning. So I don't mind arriving later in the evening from Naxos.

Is there a particular reason you all suggest saving Athens for last?

Not to burst your bubble but with just 8 days I think you'll be spending more time getting from Point A to Point B than you would like.

Athens deserves more time. There's more to the city than just the tourist sites/sights.

Would you consider just one island?

If so I would pick Naxos because it has a lot more to offer than Santorini. It's larger, more villages, spectacular mountain road through the interior, beaches, archeological/historic sites, centuries old Byzantine churches, great food and lots more.

In addition it will be a lot cheaper!

Flying to Santorini and return flight from Naxos will save time but still reduces your time on both islands having to pack, unpack, settle in, etc.

However, if Santorini is a must I guess you can devote the time to get from one island to the other but time is very valuable on holiday especially with only 8 days.

It is just what everyone strives for (some people really dislike one-night stays, etc.), but if your arrival and departure times don't make it ideal, then don't sweat it!
I like to have one stay of four nights somewhere, but if you are good with the night allotment, then I don't think you can improve upon the plan. Maybe look at your Athens wish list and see if you'd feel comfortable moving a night to Naxos?
I found getting to and from the airport from the city by taxi was easy, but you might want to schedule to avoid rush hour traffic.

People advise you to do the islands first because ferries, flights, weather and now add covid are unpredictable. You don't know if a ferry or flight you had counted on will simple not be running. You don't want to get stuck on an island when you are trying to get home.

As others have said, with only 8 days perhaps it would be wiser to do just 1 island along with Athens. My MIL really liked Naxos.

We all have different criteria and while I might do things differently, there’s nothing really wrong with your plan. I do think you need a realistic mindset, so know that you will not have a full half day for Athens on your partial day by the time you need to return to the airport, check in, and fly. And that’s fine if that is the time you have. In answer to your main question, I would choose to arrive in time to be at my new location before dark. On Sept 10, you might choose to overnight closer to the airport. I haven’t done this but some regulars have and on other threads have recommended places.

Traveling between places on 3 of the 7 days you have there is to me a killer pace.

Are you flying to Athens on Turkish Air via Istanbul?

I also agree with the idea to do all you Athens days at the end to reduce the moving around and eliminate the stress of getting to Athens for the flight home

It's really very risky to plan to fly back to Athens late in the day when you have a transatlantic flight home you must catch the very next day. If you miss the flight home, you'll have to pay a pretty penny for a last-minute, one-way replacement ticket. It sounds as if your arrival time in Athens is so late that flying immediately to an island may not be possible. If that is the case and you're stuck with spending the first night in Athens, I'd recommend just crashing somewhere near the airport and taking a morning flight to Santorini the next day. (Do allow a full night's sleep, though; it appears that you have a very long outbound itinerary, and you need jetlag recovery time.) You should be able to drop off your luggage at your Santorini hotel and start sightseeing before check-in time. Given how expensive Santorini hotels are, at least this tactic has the advantage of giving you more time on that island for the cost of two hotel nights.

I, too, think you are overestimating the amount of sightseeing time you'll have after discounting the time needed to pack up, check out of a hotel, get to the ferry port or airport, travel to your new destination, find your way to your new hotel and check in. With two hotel check-ins (probably) required in Athens, you are in effect going to 4 destinations in 8 days, and that is really not a great idea. Greece, of all countries, is a place to relax and enjoy the environment, not a place to rush back and forth to airports and ferry ports.

I would encourage you NOT to attempt sightseeing in Athens after an exhausting journey, arriving at 9 pm. Instead, I suggest you take a shuttle (it's free 24/7) 25 minutes to Hotel Avra, have a small snack and CRASH. Then the next AM you can shuttle BACK to Airport & catch an early flight to Santorini. Here are my experience-proved reasons for Athens last:

(1) With only 7 actual days, every hour is precious, and going into ATHens twice takes valuable time
(2) you'll be too exhausted for a sightseeing marathon in a busy city; instead, recover & re-energize on the islands
(3) this way you learn "how Greece works," thus can navigate Athens
(4) after even a few days of culture & ancient sites, famous Athens landmarks will resonate SO much more.
(5 this approach puts u in Santorini on the weekend, when there are fewest cruise & package-tour mobs

With this approach you could arrive Santorini 10 or 11 am on Day #2. I recommend staying Firostephani because of Ideal location; walkable to Fira town along cliffside path, but bypassed by tour groups. Also, do sunset dinner there or in FIra vs. OIA, due to those crowds. At 8 am Day #3 taxi or bus to OIA, have 2 hours to enjoy its views before the 10 am invasion of tour throngs. IF you are an archeology buff you could stay a day longer to explore Akrotiri etc, but if you are there mainly for the caldera view, why not check out and get the 3:15 ferry to Naxos on day 3 (Sept 5)? Stay in St. George beach, because u get a beach experience yet a 15 min walk to the port town attractions. You'd have an evening & 2 full days, and on Day 6 (Sept 8) fly Aegean to ATH on either a 9:50 or 10:35 flight. Only ONE trip into ATH (1 hr, flat-fare taxi €38) and 2.5 full days for sightseeing. Cruelly short visit, but the most efficient logistics, minimizing travel time ... only faster way to get around in the Aegean is a magic carpet & those are scarce lately.

Should have mentioned that Hotel Avra is in nearby Rafina, and the only proviso for the free shuttle is that you must sign up for it at the same time you book a room... that's so they can schedule its availability. Also, it's important for you nail down those crucial domestic flights before you book any rooms -- one can always find another room, but cannot magically find an airplane.

Thanks so much everybody.

I am now adding one more day to my trip to give me more flexibility.

Your suggestions are great.

We went to Greece in 2019 and arrived at the Athens airport around 9:00 pm just as you are scheduled to arrive. We stayed at the Sofitel Athens Airport Hotel the first night which worked out very well since we were very tired. It is just across the street from the Athens International Airport so we could easily walk over. The Sofitel has a wonderful restaurant for dinner and breakfast. Then the next morning we flew to Santorini, so that we could arrive in daylight and enjoy the day. We stayed 3 nights in Santorini and loved it. We also went to the Akrotiri Archaeology site and ruins on Santorini. That was just the right amount of time for us. Then we went to Athens for the remaining days of our trip, and we were able to enjoy the Acropolis and sites there after being well rested on the island. I would recommend saving Athens for the end of your trip. You will have a fabulous time!