Greece Itinerary…please help!

Allow at least 2.5 hours of connecting time in Athens to take a domestic flight to an island.

Since all islands where you want to go to have an airport, you don't have to start with Santorini.

If you want to enjoy the islands where you will stay, I do not recommend that you go to 4 islands + Athens in two weeks.
Not only because each trip from one island to another takes a good part of the day, but also the more you do island hopping the more risk you take in the event of bad weather, strike, breakdown which would cancel the ferry you have to take.

3 nights in Santorini, 5 nights in island #2, 5 nights in island #3, and 2 nights in Athens would be wiser.

Milos is the least easy island to reach, it is the only one among those where you want to go that is located in the Western Cyclades.
To go to Milos from the other Islands the ferries are mainly small catamarans ferries which only operated in high season for tourists.
They are often delayed and if the sea is rough you will have a very bad time. These are the first to be canceled in the event of a bad sea

Ferry crossing time:

Santorini ↔ Naxos or Santorini ↔ Paros: 1.5 to 2 hours - 4 to 5 ferries / day
Naxos ↔ Paros: 30 min at 45 min - - 7 to 8 ferries / day
Santorini ↔ Milos: 2:30 to 5:30 - 1 or 2 ferries / day
Naxos or Paros ↔ Milos: 2h30 - 1 or 2 ferries / day

The 2 main types of ferries are either traditional ferries like Blue Star Ferries or fast catamaran like Seajets.

Note that the price of Highspeed seajets can be 3 to 4 times more expensive compared to traditional ferries

Not much I can add to JoLui's response.
I will however outline what you can expect at Athens airport. On arrival you will pick up your luggage and proceed to passport control. Next go to the exit door go through the one that says Nothing to Declare. You will be in the public area of arrivals. Next go up one floor (stairs, elevator or escalator) you will be in the departures area.
Both Sky Express and Aegean/Olympic allow you to check in 48 hours before your flight. You can go to the airline counter to drop off your luggage or you can find the machine where you print you own luggage tags. As I recall there is a drop off place where you put you bags then you go to Security and you are in Departures. Athens airport is very efficient, chances are you will have time to stop and enjoy your first Mythos beer before your Next flight. Generally this process needs about 2 hours.

United airlines is a member of star alliance as is Aegean/Olympic. In the event of delays, If you book your flights on one ticket Aegean has to get you on the next available flight.

Thank you SO much...this is very helpful advice!!!

Any suggestions to this proposed itinerary:

Flight arriving @ 10am into Athens. Fly to Naxos at 12:30pm
Naxos - 5 nights @ IRIA Beach Art Hotel
Paros - 3 nights @ Avant Mar Hotel
Santorini - 3 nights at Hotel Stella Roca a Mar
Athens - 3 nights at Emporikon Athens Hotel
Flight departing @ 11:45am

Just ready to book Island air from Athens to Naxos and Santorini to Athens...does it make sense that the total airfare for the 2 flights for 2 passengers is 750 Euros on Aegean Air and 343 Euros on Sky Express?

Any restaurant recommendations at these locations, and/or other special activities/sights?

Thank you so much! Karen

This itinerary is entirely doable,

does it make sense that the total airfare for the 2 flights for 2
passengers is 750 Euros on Aegean Air and 343 Euros on Sky Express?

About the flight ATH→Naxos:

On September 30, the Sky Express ATH→ Naxos flight at 12:30 p.m. (2 passengers in Sky Enjoy fare / 23 kg of checked baggage) cost €303.98.

It's €177.98 the next day, are you sure you will arrive on September 30 and not October 1 local time?

With Aegean (or Olympic, these are the same prices) the first flight available on September 30 is at 3:45 p.m. In ComfortFlex rate (2 passengers / 23kg checked baggage) the cost is: €333.98 .

It's also cheaper the next day: €293.98 with the 1:25 p.m flight on October 1

Also note that given that the runways of Naxos or Paros are not long enough, these flights are operated by small ATR Turboprops (42 or 72 passengers). If you have cabin baggage, their maximum size must be: 55cm x 40cm x 23cm

We ARE arriving on October 1st, and when shopping the air on both airlines, I get this:

Sky Express (with Luggage)
10/1 12:30 Athens to Naxos AND
10/12 4:35pm Santorini to Athens
The total for both is 418 Euros

Aegean (with luggage) (Business Class is cheaper!)
10/1 1:25pm Athens to Naxos AND
10/12 4:35pm to Athens
The total for both is 610 Euros

ANY reason we wouldn't choose Sky Express with this 200 Euro difference?

Thank you! Karen

Sorry, I understood that you were only talking about the ATH→Naxos only and not the two flights My fault!

Sky Express often has more interesting prices than Aegean/Olympic

Both companies offer the same service and are good airlines. Aegean is often more in demand, which is probably why the prices are a little more expensive. By booking on Aegean you will fly on Olympic which is its domestic subsidiary. (you can book the same flights with: https://www.olympicair.com/en )

There must be very high demand, there are already some flights already sold out in October and it is only February. I've never seen that before! I'm afraid you won't be alone in Santorini and Naxos, even at the end of peak season :-))

Honestly I don't understand why Business is cheaper than Economy.
I've never seen that either...

In any case, the Business Class on the Airbus A320 operating on the Santorin-ATH flights is the first 4 rows but the seats are the same. You are just closer to the exit.

Thank you so much for all of your help and suggestions!

So far we have booked the following (all fully refundable at this point)! Any suggestions would be appreciated. I know all of them are a bit pricey, but it's our Honeymoon and we want to be sure of a great place and room. Still open to feedback if we can do better!

Naxos: IRIA Beach Art Hotel (5 nights)

Paros: Avant Mar Hotel (3 Nights) I was swayed by the beachfront location with Lounge chairs and umbrella!)

Santorini: Hotel Stella Roca a Mare (3 nights)

Athens: Emporikon Athens Hotel
(how easy is it to get to Hydra from here?)

Any restaurants near these places that you loved?

Thank you so much! Karen

You would have to go to the port to get to Hydra. I would not do it as you will have already visited three islands. Three nights is a good amount to spend in Athens.

Our favorite restaurant in Athens was Mani Mani. We had a group of six and everyone loved their food. You should make a reservation, although we just called day of.

Just wanted to be sure you know IRIA Beach Art Hotel is located at Aggia Anna which is a village on the west coast. It is a delightful place but is a 6 km bus or taxi ride to Naxos town which is the centre of activity on the island.

Iria Beach hotel is, as Stanbr says, a little far from Naxos Town, this is not necessarily a disadvantage. Personally I find that the further you go from Naxos Town the better...provided you have a car. If you don't rent car you will be dependent on bus schedules or rare (and expensive) taxis. Up to you.

In Paros, where I often go, the Avant Mar Hotel is in Naoussa. It's the most expensive and touristy village on the island, but for a honeymoon it is certainly perfect. Moreover, it is the favorite place in Paros for honeymoon planners. And there are quite a few high-end shops selling jewelry, clothing, etc. So a great place to take your new husband ! (tell him not to forget his credit card).

The disadvantage is that the Avant Mar Hotel is a little far (10 to 15 minutes walk) from the center of Naoussa where most of the restaurants (and shops already mentioned) are located. And as a friend says, there are 3 important things: 1: Location 2: Location 3: Location.

Coming from 3 islands, don't waste a day visiting Hydra. Enjoy Athens.

Emporikon Athens Hotel is well located. Just about equal distance from the Acropolis, Syntagma Square and Monastiraki Square and also not far from the "Baba au Rum" bar. https://www.babaaurum.com/ They have a "Lost Lovers" cocktail

(sorry I go to bars more often than archaeological sites in Athens)