Itinerary guidance requested

Everything looks fine.
However, I would rather take the 3pm ferry FB Ekaterini from Naxos to Rafina ar 9pm (just in time for dinner), enjoy the sun at the open deck during the whole journey and sleep at Rafina. The 2 hotels there are only a few steps from the boat pier. You can then easily reach Athens by local bus the next morning
With FB Bluestar 2, you will do half the trip in the darkness, leave the boat towards midnight, queue for a taxi and reach Athens long after midnight.

Thank you meckerdv. I have a follow up question. How much time should we allocate between the time we land to taking the flight to Santorini? Keeping in mind that we've to also go through immigration.

That's the question nobody can answer. Athens isn't a big airport, but
your plane may arrive late,
there may arrive another plane from outside the EU a few minutes before yours and then immigration may take more time,
if there will be many departures at the time your Santorini flight leaves, there may be queues at the security check.

May is still off-season, and you arrive on a Wednesday, not Friday or Saturday which has heavier arrival traffic. However, your late-day arrival tells me you made a connection in Europe mid-day, and those connections are the ones that may experience some delay (the morning nonstops from US are always on time). And the passport line for non-EU is always slower than the EU line. However, doesn't matter much if you have checked baggage, because you'd have to wait at the carousel anyway to pick bags up. YOu are supposed to be at the check-in line for domestic flights no later than 45 minutes before departure. And then there's the (slight)time required to get some Euros from an ATM, unless you're coming from a Euro country. (If you feel time is short, You can split duties - one person goes to baggage claim, one goes to ATM). That being said, the airport building isn't huge, and international is on one side, domestic on the other. Two hours is usually ample from disembarking to the next take-off.

Thank you, both meckerdv and travelerjan. A few comments and follow up questions.

1. We just reserved our flights yesterday and will now arrive around 11 am on Fri (may 26) in Athens. Keeping the above guidance in mind we'll book our flight to Santorini after 1 pm. However, Aegean Air does not seem to have any flights until 3:50 pm. Would you recommend Sky Express? Also, I've heard they have strict luggage limitations.

2. We are traveling from Canada (non-EU). Do you recommend using the ATM's at the airport?

3. Do you have hotel/location recommendations for Santorini, Naxos and Athens?

Ashen

FLIGHT - I would not do Sky express unless I were traveling with only a shoulder bag, and I assume you are using a rollaboard 20 or 21-inch bag. If you want to find out about Sky express' limitation, there's an easy way to find out. Don't ask us, go to the website. Take the 3.50 flight, and go across the street for a nice lunch.

ATMs - Of course use ATMs at Airport but use the Big Bank ATMS, like Alpha Bank. If an ATM machine asks if y ou want "dynamic conversion" Just Say NO. (that means it tells you in Looneys how much u are withdrawing, BUT it also means they charge a DOUBLE fee). Ask for withdrawal in Euros - you can do the math y ourself. When on an island, use the ATMs in a bank or right beside a bank. Others may be non-bank ATMs and charge big fees (just like the ATMs you often find in convenience stores or bars, in US or Canada.

LODGINGS & LOCATIONS -- In Santorini, I always recommend FIROSTEPHANI. It is at the North fringe of FIRA (the main town), but is walkable in 15 minutes to all the Fira attractions, yet has NO cruise-ship crowds or bus-groups, AND it has the lovely Caldera views of OIA (but again, not plagued by the ship-throngs that cram the Oia streets from 10am - 4 pm). In May for Naxos, I recommend staying at the Beach directly adjacent to Naxos Town ... again, because you can walk to the town attractions (cafes museums, shops, landmark sites), yet you are on a beach.
In ATHENS - I like the location just SOUTH of Acropolis, near the Acropolis Museum. It's walkable to almost all landmarks yet is quieter, on a wonderful long promenade along the south edge of Acropolis area. I am not going to recommend specific hotels in each of these because -- since you are very LATE in booking for May -- many of my recommends will be full. Instead, you advise that you go to Booking.com and put in your specific dates for each segment of your stay and search "Santorini FIrostephani" and Naxos St. George. For Athens, on booking. com there is a sorting process that will show you hotels that are close to a Landmark (in this case, Acropolis); I advise you to look only at hotels that are 1.2Km or closer -- this will assure that you don't get into faraway or "grungy" areas. Here's a "tiny url" for this: http://tinyurl.com/heq6edp

FINALLY (on hotels) -- when the list pops up, for any of the 3 destinations, just choose the top hotel and click on it -- that will bring up the Google Map for Santorini/Firostephani. Enlarge it, and you will see ALL the hotels that booking.com list in that area -- like little balloons. The RED balloons are fully booked ... the blue still have rooms. USE THIS MAP!!! it will keep you from jumping at a bargain, only to find that the hotel is actually way back from the beach, or the caldera, or the athens sights.

Good luck! And next time, start earlier.

This was super helpful. Many thanks.

Unfortunately, you are right, most of the hotels are reserved already.

Travelerjan,

We really appreciate your guidance. It's been invaluable at our end.

1. With regards to booking ferries between Santorini and Naxos & Naxos and Athens, do you recommend we reserve them ahead of time or stay flexible?

2. Is there a recommended time we should plan towards the ferry for Santorini to Naxos? For the ferry from Naxos to Athens, meckerdv recommended the 3pm ferry, which we are planning towards.

Ash

SANTORINI - NAXOS -- If you take the BLUE STAR at 3:15? it STARTS at Santorini, holds up to 1800 passengers, you buy Economy seat (deck), so no, you need not buy ticket until day before/day of. If you decide to take the 10:30 AM Champion Jet (car-carrying large Catamaran), it holds 500 passengers, buy ticket when u arrive on island. -- it also has back deck whre you can enjoy caldera view at departure. I like this one because you have left yourself such a short time on Naxos, at least it buys you an extra half-day to explore the fascinating port town. Remember -- Naxos is the largest island of all the cyclades, and Santorini is 12 miles long.

NAXOS - RAFINA -- This is a smaller ferry, so I'd say, buy the ticket at an airport travel agency when you arrive, because you have that extra time; opinions may differ.