My wife and I (60s) are planning our first trip to Greece for May. We have seven nights total. I�ve read such great things about Naxos I have made that my focus. But I can�t go to Greece without seeing Santorini (can I?), despite all the warnings about the crowds, which sounds like a turn-off to me. Does it make sense to make a day trip to Santorini from Naxos, or would it be better to stay there - perhaps two nights in Santorini, three in Naxos, which would leave two for Athens? We wish we could stay longer, but we can�t. Our primary interests are food, wine, historical sites, old villages and scenic views. Not so much beaches or hiking. We also prefer not to change hotels more than necessary. We are used to packing a lot into every vacation day, as opposed to more leisurely or spontaneous travel. We would appreciate suggestions!

I think there's a good argument to be made for skipping Santorini, but if you feel compelled to go, note that visiting it as a day trip would mean being there when it is most crowded and least pleasant. Staying one night would at least let you have some time there without the hordes. Three nights is what I'd consider a minimum for Naxos; two nights (one day) is VERY little for Athens.

A day trip from Naxos to Santorini is just not possible:
The first catamaran from Naxos arrives at Santorini port at 1pm and th last ferry back leaves from there at 3.30 pm.
May be you will fly directly into Santorini when you ayrrive in Greece (there are much more flights to Santorini than to Naxos), spend 1 or 2 nights there and then proceed by SLOW FERRY (only in this way you will have the breathtakiing views from the Caldera (Sea) to the cliffs with the white villages on he top.

Based only on my own experience, I would skip Santorini on this trip.
I've never visited a place that felt so overwhelmed by tourism to the point that the crowds almost cancelled out the beautiful views.
That island was the most disappointing destination in many decades of travel.

On my only trip to the area a friend & I stayed about a week each on Santorini & Naxos. I loved Naxos & frankly wondered what all the fuss was regarding Santorini. Just one tourist’s preference, of course, but with so little time, even for fast travel, I recommend you get the most you can from one island, save the other for another time.

May is a great time to visit the islands. By all means, take the time to see Santorini. I recommend at least 2 nights, staying in the most beautiful village, Oia. You will not be disappointed, in spite of all the negativity. Arrange to fly back to Athens from Santorini for your flight home. This will save you time and the hassle of backtracking.

I think there are two options if the OP chooses to visit Santorini -- start there (as neckervd suggested), then Naxos, then Athens OR start in Athens, go to Naxos, end in Santorini. For flights, look for "open-jaw" (aka "mutli-city" -- into one city and out of another) options. Be sure to route all the way through on the same ticket; that way if a flight is cancelled / delayed, it will be up to the airline to get you where you want to go.

IMO, Santorini is beautiful and unique and well worth visiting. The caldera is awesome, is something you won't see in other places. We were there in May 2022, and honestly, I didn't think the crowds were that horrible. I realize of course that each person has their own level of tolerance but the crowds did not ruin our trip. Have you made your airline reservations yet? There is a site you can check to see how many cruise ships will be in port and you can plan your trip around those dates. There were only 1 or 2 cruise ships when we were there. We spent 3 nights on Santorini which also gave us the time to rent a car for a day and visit different places on Santorini, such as the Akrotiri archaeological site, red sand beach, and black sand beach. I wouldn't visit as a daytrip because you will be there when everyone else is there. The early mornings and evenings are quieter.

Can you extend your trip by one extra night? If so, spend 3 nights on Santorini. If not, spend 2 nights on Santorini. I also recommend staying in Firestefani which is less crowded than Oia and Fira.

I agree with kja about the open-jaw tickets.

I often agree with KarenWoo -- in this case, I do not. I'm glad I saw Akrotiri and the museums in Fira, but was otherwise not impressed with Santorini. The crowds were awful, people in the tourist profession were remarkably rude (unheard of elsewhere in Greece), and it It is not even close to one of most beautiful places I've been fortunate to see. I know I'm in a minority!

I can understand the desire to see it -- that's why I went! -- but the problem for the OP is that spending any time in Santorini would mean short-changing the time in Naxos and Athens -- and IMO, they definitely deserve the time!

cjs -- have you already booked a nonchangeable flight?? In your 60s (with presumably a long work-history) is it not possible for you to extend your stay for even 2 more days? Is your job that demanding? You do not tell us where you are from -- which IS important, because if you're from the West coast it's MUCH longer trip... and when you say "nights" it doesn't mean 7 DAYS... you can count Day 1 as a half-day only if you arrive before noon, and you cannot count departure day at all. So you may only have 5.5 to 6 days.

In that case I would advise you to be realistic: If you arrive by noon - if possible, get a 2pm domestic flight (40 mins) to NAxos. Stay for 4 nights. Early (9 am) gt FLy back to ATH, reach hotel by Noon... Book Hotel CLOSE to Acropolis area. Spend 2+ days seeing a few famous landmarks. FINAL TIP: for homebound leg, pick a departure no earlier than 10 am - that would mean you need to be in lilne by 8 am, it's an hour to airport, so must leave hotel by 7 am -- so must arise @6 to check out. Any earlier means short-changing a pleasant last-night dinner with a view of the Parthenon.

Again, book directly to your first destination -- do NOT stop in Athens en route unless that's the routing that works best! Put it all on one ticket so that if there's a problem, the airline is responsible for fixing it.

Kja -- I appreciate the idea of flying from a Europe port directly to an island, but it does not work from Naxos. Naxos ONLY has domestic flights because (thankfully) its airport and airstrips are too small to accoommodate jets (yay! less "package tourism") ... so one must take a turboprop from Athens. Right now that's only via Aegean/Olympic or Sky Express. These planes only accommodate about 45 passengers, and each lilne has about 3 flights per day... so advance planning is wise. I just hellped a friend with a May trip. Their return trip to ATH is from Naxos, and on the desired day, they got the last 2 seats on the 10j am flight... booking in December. Decision and action now is wise,

@ travelerjan: Thanks for clarifying that the routing would have to be through an airport in Greece, but I don't believe that means that the flights can't be on the same ticket. Aegean/Olympic and Sky Express each partner with some other airlines.

That's true, KJA -- and I just learned that Aegean now (yay!) has some flights from New York nonstop to Athens. I;m always concerned if inquirers are from West Coast, because that usually requires THREE planes to get to Naxos & I urge people to make the middle one a transatlantic nonstop to Athens, because that usually is not quite as long. But OP has not provided that info.

“A day trip from Naxos to Santorini is just not possible”
Unless my information is out of date, it is possible to do a day trip from Naxos with at least two different tour boats: Alexander and Naxos Star. Unless your trip is in late May, it might be too early in the season for the two to be operating. That said, the best idea is to start with Naxos, and then move on to Santorini with a flight from there back to Athens.

As I recall, it wasn’t until my ninth trip to Greece that I went to Santorini, and that was to meet a friend who spends a lot of time there. Travelerjan might remember that occasion, because when we got back to his hotel after a day of sightseeing, we were told a lady was looking for him while we were away.

Yes indeed Heimdall ... it was then I realized I was not fated ever to meet you 2 gents, my longtime forum companions ... altho I've been fortunate in linking up with quite a number of other "vets" over the years... and in fact have visited several outside of Greece - including a dellightful retired professor near Cambridge -- he & I met on a Crete thread, over our mutual suspicion about the Phaistos Disc, and now have a 20-year email and inperson friendship. The internet can be exasperating at times, but it has also brought together faraway people with shared enthusiasms. Hurray!

[email protected]
https://naxostours.net/en/cruises/
https://www.cycladicruises.gr/en/routes-santorini

You are right, Heimdall.I didn't know about these excursion boaats.

Of the 2 excursion boats (they run on alternating days I think), the Alexandros is preferable if one has a choice ... it is larger and a smoother ride --- important later in the season when the winds can make the seas rough.

To be clear, the excursion boat is Alexander, not Alexandros, easy to confuse the two names. Even more confusing is that Alexander is owned by Cycladic Cruises, an Antiparos company, and spends its winters tied up at a dock on Antiparos. In May the boat moves to Naxos and stays there for the summer.

There is a boat in the Cyclades called Alexandros, and it does round-island cruises from Antiparos, stopping to pick up passengers at Pounta on Paros.

THanks for the good catch, Heimdall -- so easy to get tripped up by Greek-ending variations.