I would like to spend 4-5 days each on Naxos and Santorini this August with my family but creating reasonable transportation logistics (flying from Boston) seems puzzling. i am looking at 2 main options: one would be to fly to and from Santorini, and then (because latest ferry to Naxos is at 3 pm) spend time in Santorini first; then ferry to Naxos, spend time there and in the morning when i am scheduled to fly out to the US take a ferry back to Santorini. Is it reasonable? i understand ferry might be cancelled due to winds and in that case i am delayed/plan does not work. Option 2 would be to fly to Athens first then take a ferry to Naxos (here the problem is that all ferries even in the summer will be at 6-7 am then ONE at 5:30 taking 6 hours to Naxos), spend time at Naxos, take ferry to Santorini and fly out of Santorini. Both options have issues. could someone read through and tell me your thoughts about the practicalities and reasonableness of each option? thank you so much.

No, it is NOT reasonable. It's NEVER a good idea to attempt to return to the mainland for your flight home on the same day you're leaving the country. It's safest to give yourselves at least a day in Athens to make sure you don't get stranded, especially in August when the winds are so strong. And there's no reason to backtrack to Santorini for a flight back to Athens. Naxos also has an airport. The only ferry ride necessary in your scenario is the one that takes you between islands. Which island you visit first will depend on your arrival time from Boston and the next flight out to an island. Santorini has more flight departure options than Naxos. If you take the Blue Star ferry you shouldn't have any problems due to high wind. It's very large and stable.

Aegean Airlines and Olympic Air are the same company now. They fly to Naxos and Santorini. Check their website for what's available for your travel dates.

I agree with brotherleelove2004. We did a similar trip last year. We flew from Athens to Santorini - a 45 minute flight, which was delayed for 2.5 hours. We took the ferry from Santorini to Naxos and were very pleasantly surprised. Left on time. Arrived on time and the seating (for only 20 euros) were first class. Air-conditioned lounge, leather armchairs, bar, cafe/restaurant - superb! Then we flew back to Athens from Naxos without a hitch. Mind you, don't expect a lavish airport in Naxos - it is very small and quite rustic, but all went well.

Your problem is thinking about flying direct to Santorini from Boston... there is no such flight. You need to clarify ... are you looking at a flight from Boston to an airport in Europe, where you would then change for a flight to Santorini?? That sounds like a way to get to Santorini without a stop in Athens airport --- but it traps you into having to RETURN to Santorini in order to get home. Toooo complicated, especially with the heavy tourist traffic in August.

As one of the weary and experienced N. American Greece-going "veterans" (May-June will be my 13th trip) here's our basic (and disillusioned) advice: Fly in/out of Athens --and go to your first island via Domestic flight -- UNLESS you can get an "open-jaw" ticket -- which would allow you to connect in Europe to a Santorini flight, then for the Return journey, allow to start from Athens. Here are some of your choices:

• NONSTOPS to/from USA -- There are a few longstanding nonstops from N. America (Delta from NYC, AA from PHL, Air Canada from ?Toronto), plus now off/on a UAE from EWK). They all arrive in the AM -- from 9:15 to about 10:30am. Arriving in AM, you would be able to get a domestic flight to Either Santorini OR Naxos. Which to choose?? Well, given the dire jampacked cruise-crowd mob scene on Santorini from Mon-Thurs, I would prefer to be on Naxos during week, and Santorini on the (marginally) less-crowded dates of F-S-S. it's up to you. If Naxos is your 2nd island, and you plan to go directly back to US at the end of your stay, without sightseeing in Athens, then you COULD take a ferry back to the mainland (fare is about €42 for reserved-economy seats) . It leaves at 6pm - arrives about 11:30 pm, you could taxi to a hotel near the airport. There's one about 25 minutes away, Hotel Avra, that provides free 24/7 shuttle IF you request in advance. That would assure you of being on mainland the night before US flight... none of use advocates doing the chancy thing of returning from Island on same day as homebound flight.

• EUROPE CONNECTION -- If you choose a flight that connects in Europe (usually because of saving money, or using frequent-flyer "miles") I would only suggest doing a direct flight from Europe to Santorini IF one could do an open-jaw as mentioned. If you land in ATH in Afternoon and propose going by FERRY to a cycladic island, realize that you'll be asking your family to do a 5-6 hour Ferry ride (or in case of Santorini, 8+ hours) on top of a looong flight.

WHichever overseas flight you choose, face the fact that either getting TO an island or FROM an island will involve a domestic flight. This will be costly... but everything about visiting Greece in High Season is bound to be costly. I do wish you well in your plans, and hope everything works out well!

Hello everyone who responded. I am not a backtracker by no means))) I have spent a good number of hours on expedia mapping out different flights so i know all about flight options (there are one-stop flights from Santorini to Boston- the NON 5am ones are unfortunately not every day and it's frsutrating since I am dealing with tight family schedule trying to accomodate school vacation and college vacation time). to clarify: The most financially reasonable option: FLY TO ATHENS -FLY OUT OF SANTORINI. from Athens i could take a ferry to Naxos. there is one flight i am looking at that gets me to Athens at 2am so i could make a 7am ferry to Naxos. I guess i am trying to avoid a very small plane...

I agree with the above posts. Whichever route you take from Boston to Santorini will involve a change at an airport somewhere in Europe. Athens Airport is probably the best airport for this, as it is small by international standards, easy to get from Arrivals to Domestic Departures, and has the most flights to Santorini. Were you to fly via London, for example, you will most likely have to change airports, e.g. Heathrow to Gatwick, and lose a day on the way.

Whether you fly first to Naxos or Santorini from Athens makes little difference, but if you can get a timely flight to Naxos I would do that first. Naxos has a very short runway, and the small turboprops that fly there can take more passengers from Athens to Naxos than vice-versa. Flights back to Athens have takeoff weight restrictions, so hold fewer passengers.

Santorini has a long runway because the airport was built for dual military/civil use. Now it has flights to Athens with regional jets, including those from Aegean Airlines. These larger aircraft are less likely to be affected by weather, so a same day flight to Athens as your flight home is safer, but still having some risks.

@Heimdall and @travelerjan- i do want your approval)) but i am looking at flights from Boston via either Madrid or London to ATHENS (I could then get to a ferry for Naxos; spend time in Naxos; ferry to Santorini, time in Santorini and FLY OUT of Santorini at decent time (3pm) via London to Boston. no change of airports is required- all Heathrow. expedia gives you good multi-city (its called) options. does it sound reasonable to take BLUE (BIG) ferry to Naxos from Athens on same day as arrival to Athens? ((without visiting Athens or possibly a quick trip to Akropolis with private driver between airport and Port). thoughts? thank you

Hi weekend_celebrations, we cross-posted. You and I seem to have the same idea, and yes with a 2am arrival in Athens a ferry to Naxos is definitely an option. If you booked one of the 06:25 Olympic Air flights, on the other hand, you would be on Naxos around 7am, about the same time the ferry is departing Athens. Look for ferries from both Piraeus and Rafina. All other things being equal I would choose Rafina, because it is nearer the airport and the bus drops you off right at the port. That said, Piraeus has the best morning ferry to Naxos, Blue Star Delos.

@Heimdall thank you about Rafina tip! had no idea its the other Athens port!! what about pre-booking Blue Star vs Seajets (or another high speed)- could high-speeds get cancelled? (hate flying in general so anytime i can avoid would rather))

and a 17:30 Blue ferry from Piraeus to Naxos is long 6 hrs BUT gives me many flight options (and possibly time for quick Athens tour)

If both flights are via Heathrow, will they be from the same terminal? Terminals 4 & 5 are on the other side of the runway from Terminals 2 & 3, and you need to factor that into your layover time. If the UK leaves the EU (Brexit) without a deal at the end of March it probably won't affect inbound flights from the US, but most likely will affect flights from the remaining EU countries.

I am thinking if expedia offers it- connections are minimally acceptable...

It's Blue Star Ferries, not Blue Ferries, and you won't need to pre-book unless travelling on a weekend in August. Just buy your tickets when you get to Greece. If you are having a quick look around Athens before the 17:30 ferry there are Blue Star agents in central Athens. Otherwise, buy your tickets at the Blue Star booth next to the ferry. Get there around 16:30.

British airways has among the shortest flights up to Athens and back from Santorini.
it's up to you whether you want to wait some 2 hrs at Athens airport before going on either by plane (suggestion of Heimdall) or by taxi to Piraeus or Rafina (slow ferry from Piraeus at 6.45am, catamarans from Piraeus at 7.00 (Champion Jet2) and from Rafina at 7.15 (Superrunner)
or if you prefer to spend the first 2 nights at Athens (you will arrive there around 7pm EST).