Mykonos to Crete or Thessoliniki

You mean only four or five days for both? Crete itself needs a minimum of a week. And you have way too much time on packed tiny Santorini and even for Mykonos .

I agree with Suki--too much island time, especially if you go in October and it could be too cold to swim. And Crete could take a week easily because of its size.

Thes/niki offers archeological, religious, and historical sightseeing as well as museums, concerts, and fine dining. There are direct flights to Italy from the airport, but you did not say where in Italy you were planning on going.

Several others on this discussion forum always recommend going directly to your farthest point of travel first (Crete or Santorini) rather than starting in Athens. Then you work your way back to the mainland and finish in the city you take your flight out of. This makes the most efficient use of your time. Perhaps a better approach would be arrive Athens, fly to Santorini and stay 3-4 nights. Then fly to your next island--Myknonos and stay 3-4 nights. Then head to the mainland for the rest of your stay (both Athens and Thes/niki will have many flights to Italy).

Probably the biggest consideration is what do you hope to do/see in Crete, in which case, you might start there and stay 5-6 nights, then go to Santorini, again ending on the mainland, but in this case, you will need to shave off some days from the other stops.

Hi thank you for the great advice...always nice to have input from seasoned travelers.
We are 2 couples and renting villas with pools in both Santorini and Mykonos...so there are some relax days in there for sure.
Plan is to do some day trips to other islands Naxos and Paros, and then we also like to hike. We are retired so we have time to have an extra one or two days on these islands... we are not rushed fortunately.
I like the idea of spending more time on Crete and perhaps skip Thessolniki at this time as I get the feeling Thessoloniki is a big city.
We would like to fly to Sicily, Italy from Crete rather then go back to Athens -- although I think most flights touch down in Athens or even require an overnight in Athens for connections.
I think getting to Venice is probably more doable from Greece by air or even by ferry.

Has anyone taken the ferry from Greece to Italy... ?

Hi SUrley, .. lovely to have 20 days or so to be in Greece .... and fortunately you have ample time to fine-tune your trip, because you have make a beginner's mistake in itinerary presumptions. Easy to fix, it may involve changing the exact timing of the villa rentals ... with 15 months advance notice, there should be no problem; if the owners prove difficult, that's a warning signal.

The problem is in your plan to do Day trips from Santorini or Mykonos to islands like Paros & Naxos. The ferry schedules are not set up for this to work well. If you'll look at a map, Santorini is farthest south of all Cycladic islands, several hours by ferry... cannot do daytrips because you'd have such a short time on either of those islands. In order to do day t rips, you really need to have a local company that has dedicated excursion vessels; these leave early (8-8:30) and arrive back at "home island" late (7- 8pm). There's a company based in Naxos-Paros that does these to either Mykonos-Delos or to Santorini, from May thru mid-late Septermber. THere are no such day-excursion companies on Either Santorini or Mykonos.

This is why Greece is home of the expression "island-HOPPING". You stay on one island a while, then HOP onward; you don't commute. What you CAN do is -- fly to your farthest point, then "hop" your way back to mainland.

Your most efficient itinerary, time-wise, would be: Day of arrival fly immediately to CHANIA in Western Crete (allow 2-hr window from arrival in ATH airport); spend 4-5 days MINIMUM in Crete, ending in Heraklion the night before 9:45am ferry to Santorini. Spend your time in Santorini (tho frankly I think 5 days is excessive for an island only 12 miles long), then hop on, to either Naxos OR Paros for 4-5 days. Make your Mykonos rental the final one, because it's the likeliest island to have direct flights to Italy. And no, doing a ferry from Greece to Italy is a BAD idea... complicated, very time-consuming.

Hi thank you for the great advice...
This is what our itinerary looks like at the moment.
I like the idea of ferries versus flights (I hope that is a good choice) --
And for those who mentioned that in both Santorini and Mykonos we have too many days there. We discussed as couples and were quite happy with staying at our villa for one or two of the days on each of these islands, using the pool, having late breakfast, making dinners, drinking wine, listening to music and yakking. Our vacation pacing is relaxed, and we don't really want something to do/see everyday.

What do you seasoned Greek travellers think of this itinerary. I have realized a vacation in Greece is like no other and requires a lot of research well ahead. What are the must sees in Paros and Naxos? for those of you who have visited these islands.

ATHENS -- 4 nights September 11, 12, 13, 14
Athens to Santorini Ferry 4.5 hours Piraeus
SANTORINI --5 nights September 15, 16, 17, 18, 19 (private villa)
Santorini to Mykonos Ferry 2.5 hours
MYKONOS --6 nights September 20, 21, 22, 23, 24, 25 (private villa)
Mykonos to Paros Ferry 45 min
PAROS – 2 nights September 26, 27
Paros to Naxos Ferry 50 min
NAXOS – 2 nights September 28, 29
Naxos to Crete Ferry 4 hours
CRETE – 5 nights September 30 – October 1, 2, 3, 4

CRETE to ? October 5 --flights HER or CHQ to ? Italy, Spain, or Portugal TBD ? approx 13 days

Either Paros OR Naxos ... don't be greedy. If you try for both, too much time taken by the transfer process... at least half the day, even when you can see the other island on the horizon!

As for "must-sees" I realize that most people today haven't the patience to look at a guidebook, but want quick-quick lists at a click of a mouse, so let's look at already-published info, rather than have us repeat recommendations. Alas, Steves forums are not searchable by regions or islands, so I must refer you to a forum that does --
NAXOS
• https://www.tripadvisor.com/ShowForum-g189431-i1324-Naxos_Cyclades_South_Aegean.html
On upper RH are "Top Questions about" ... And lists activities, beaches, hiking opportunities, excursions etc. And please note, these are not questions generated by a staff of promotion copywriters. I know this personally, as in the past I submitted recommendation for such a list. In addition, there is a list of all Naxos topic contributions below....

PAROS
• https://www.tripadvisor.com/ShowForum-g189432-i1523-Paros_Cyclades_South_Aegean.html
It does not have a "top questions" but does list a Destination Expert whose name can be clicked to bring up his posts

Hi thank you Janet ... that is good advice... do you have a preference for Naxos or Paros... I will look at the links you sent as well.
I do have a travel guide book--but it is also good to hear about the personal advice and experience.
I appreciate you taking the time to review and respond our trip... :)
Shirley

Given the time of year, I would suggest Naxos. It has a substantial year-round population, so Naxos Town is always vibrant ... and none of that "emptying-out" feeling that Totally-touricized islands like Santorini-Mykonos get in the fall (restaurants closing, all the Balkan hired-help vanishing). Naxos of course very fertile island, its harvests coming in, vineyards busy... some wine festivals. Worth it to hire a car for a day or 2, to drive up to hill villages, see the mountains of marble, some ruins in orchards, etc. Paros is nice, I've been to both many times, but of the 2, Naxos has the more interesting attractive port town.

Its far-out beaches are nice to visit, not to stay, in fall closed-down by night... a best place to stay is the beach directly adjacent to town -- Ag. Giorgios (St. George), serene by night but only 10-15 minute stroll to all the attractions of Naxos town ... In AG. G, if you want Upscale, there aren't many "fawncy" places (that's why I like it).... the Naxos REsort Beach hotel has a pool and good landscaping, just back 100 yards frm beach... also nonbeach boutique hotel Villa Naxia... hard to book, must contact direct.

I really appreciated the information that ferries from Greece to Italy are a bad idea...I had actually been trying to figure this out as I am just beginning to plan a "DIY cruise" of some Greek islands for May 2020. So far I'm thinking from Piraeus to Santorini or Mykonos (not sure of the order), Crete for sure and possibly then Kythira/Antikythira. However, Naxos is piquing my attention... we have up to 2 weeks to spend doing this before heading to Italy for May 31. I am looking at Crete as the "main attraction", spending 4 or 5 days there. Any thoughts?