island hopping - is this too fast?

I haven't been to Corsica, Sardinia, Malta or Cyprus, so my comments aren't to be taken too seriously.

Sicily is special in many ways, from the Greek sites to the architecture to the food. I believe Sardinia is more about beaches and scenery. I don't think you'll find them at all similar. I'd not allow less than 14 nights in Sicily, and I think you'd easily fill more time than that even with judicious use of rental cars. Two weeks isn't really long enough if you depend solely on public transportation.

This itinerary would involve way too much flying for me, so I'd consider dropping one of the short Island stays that requires flights in and out--maybe Malta or Cyprus. Not that they're uninteresting, but you can get to them from a variety of European cities on a later trip if you want an island break.

Istanbul is fascinating but an intense experience. I know you commonly take long trips (as I do), but I'd be concerned about having only five nights in Istanbul at the end of a long, probably tiring trip like this. There is so much to see in the city, and getting from place to place can be quite a challenge between the ferries, subway, trams, buses and funiculars. I'd suggest allowing more time in Istanbul so the trip doesn't end on a hectic note, though I think hoping for a relaxing visit to Istanbul is probably unreasonable..

Thanks acraven. I must admit I'm hedging my bets on Sicily - I'm not a huge Italy fan in general (go on shoot me now!) , having had more abused and hassled on mainland Italy more than any other European country (and any country with the exception of Egypt). It was better last year so maybe I'm now old enough to be ignored by the men now. If I had to pick between Sicily and Malta I'd probably choose Malta because the history is so varied. We would start in Palermo and end in Catantia so we don't have to backtrack.

I really want to do Corsica and Sardinia because no one seems to go there as a non-European tourist, but if its mainly scenery might cut the time down.

Cyprus looks very remote to me on the map - I know lots of Brits fly there but we are rarely in the UK (though do now have relatives in Ireland) . If we don't go to Turkish Cyprus then the flights to Istanbul are $$$ - bloody politics.

Yes I hear you about Istanbul - I had the whole thing reversed - starting there flying out of Milan - but Corsica starts shutting down by 1 October so that doesn't really work for an Sept/Oct trip. Do have the advantage that I've been there before so I know what to prioritize. Plus its cheap so we will get a nice hotel there.

I'd prefer more ferries too - but the timings don't really seem to work - at least they are very short flights from small airports and mainly within Schengen so minimal paperwork and waiting around. The reality is that we're be at the airport anywhere because it's the only place I'd hire a car in Europe to avoid the city centre congestion.

Thanks for your thoughts

@LIssie, I have some issues with your proposed plan... 😎

For context, of the "islands" you are considering, I've been to Sicily, Sardinia, Malta and will be going to Corsica in September 2024 (so have done a lot of planning for Corsica already). Can't help you with Cyprus or Crete (yet).

I"ve been told he wants the trip under 2 months. But we don't want to
drop any islands LOL.

There's the problem (well, one of your problems): Six "islands" plus Istanbul and Milan. "Under two months". Not a wise set of criteria.

One suggestion: stop thinking of (most of) these places as "islands." Yes, they are surrounded by the sea, and technically they are. But some of them are pretty large (Sicily, for example, is roughly the size of Belgium) and most of them lack perfect road systems, so it can take a while getting around on narrow, twisty roads along coastlines or through mountains. They each seem to have fairly distinct cultures and complex histories, making them more like separate small-ish countries in some ways. They're also not "single places" - some of them are regions.

For the places on your list that I've been to, your proposed time there seems awfully short - all of those places are worth 2-3 times the number of days you're considering.

To address a few of your specific questions...

September/October is the ideal time for thee places; the weather should generally be nice, the sea still warm enough for swimming (though by the end of October not for very long!). I suspect November would not be as enjoyable.

Corsica (there are direct flights from Milan)...

Check flight options carefully. I've been looking very intently at flights to Corsica, most are highly seasonal, with many flights dwindling or ending completely late summer/early September. Be careful if building a plan around that. We're going for two weeks and it's painful trying to squeeze in what I want in just 14 days.

Sardinia 7 days (short ferry hop) probably hire cars on each island

You probably can't take a car from one island to the other (certainly not for a one-way car rental). We spent almost 3 weeks on Sardinia and wished we had had another two weeks there. It's large and surprisingly diverse.

The two islands do have some things in common (those are all good things!) but very different histories and distinct cultures. Ever since we went to Sardinia we have been longing to visit it's French neighbor.

Malta (maybe fly) 5 day Probably not hire a car...

We did two weeks on Malta & Gozo (and we could have spent more). If you like Italy, you'll love Malta; it's like Italy only even more Italian (in fact, it's a lot like Sicily, but goes "beyond Sicily"). Conversely, if you really dislike Italy, you might want to drop Malta. Malta is a strange mix of Italy/Sicily/North Africa and the Old British Empire. Malta's history is fascinating, but most visitors only go as cruise-ship day-trippers. Without a car, you'll be stuck in the capital city with them all, missing all the good stuff that's beyond day-tripper range. Gozo (the second island) is awesome (some people say Gozo is the best part of Malta, like "old Malta" before the advent of cruise ship crowds and mass-tourism). We loved both.

IMHO you just have way too many places and not nearly enough time in them (don't get me started on just 5 days in Istanbul...).

If you really dislike Italy, drop Malta, drop Sicily, and drop Sardinia. Then spread your days across the other places (in Turkey, go to Istanbul and beyond). But no matter what you do, slow down, the places on your list are worth a lot more time than you're giving them.

Hope that helps a bit. Good luck.

Yes the Corsica connections is what started me down the track of starting with Corscia - https://www.aircorsica.com/flights/ have flights to Figari until 12 Sept twice a week. ex Milan - Nice has many more flights and is year around.

Yes I realised the issue with taking a car across too - we'd drop a car at Figari airport - take bus/ferry/bus and then probably get a new car somewhere in Sardinia.

What did you do in Sardinia - a lot of hiking - I have the impression that there is a lot of outdoor activities and although the idea is nice the reality is that we're probably not fit enough for all day hikes even in Sept temperatures.

And no you're not helping at all LOL. From reading guide books it looks like buses go everywhere on Malta not just Valletta. Gozo is where I think a car may be useful. I will look up the cruise ship timetables and try to avoid being in town the same days as the large ones are.

Yeah we are absolutely not going to Turkey- we're going to Istanbul! In fact Sultanhament and the Bosphorous. Its a bit late in the year to being elsewhere in Turkey - I spent 5 weeks going down the coast to Syria (it was back in the 90s) and then back through the centre so I've seen a fair bit of it. We've done a trip to Ephesus previously - out of Rhodes.

But maybe we drop Cyprus and Istanbul and fly back out of Athens. Or I'll tell we're going for 3 months!

Thank you these are helpful comments

The air service is very spotty. While Air Corsica seems to have a lot of flights, the service to most Corsican airports (there are four) is extremely limited. Most flights go to Bastia, and most service is from Nice, Paris and a couple other airports in France (also connections from Germany, Italy and northern Europe - when we go, we're flying from Frankfurt, when we depart we fly to Strasbourg). So yes, there are other options but they thin out quickly - once you're into September, many dry up entirely. There's air service from a few other airlines, too, but do be careful about assumptions.

What did you do in Sardinia - a lot of hiking - I have the impression that there is a lot of outdoor activities and although the idea is nice the reality is that we're probably not fit enough for all day hikes even in Sept temperatures.

We only did one actual "hike" in Sardinia - and it was great - but it was a little more of an adventure than my spouse had expected. (We just did lots of easy, casual walks from the car to sights, nothing particularly demanding). On the one hike we did do I had to nearly drag MDW all the way back to the car park at the trailhead (she was just exhausted and cranky). I warned her (with ever-greater urgency as the sun was going down...) that it was either get moving back to the trailhead, or pay for the helicopter later that night. Turns out, the helicopter would not have come for us, since an incredibly powerful thunderstorm blew through a couple hours later (as we were driving out of there) with flash flooding and lots of lightning...it was a very difficult drive back through those mountains, if we had been stuck in the narrow canyon, I shudder the think how we would have done).

The outdoor landscape is spectacular, so there's plenty of outdoorsy appeal, but you don't need to engage in adventure sports, plenty of eye-candy scenery.

Yes, the bus system on Malta can get you a lot of places, but it's not always easy, efficient or on time. OTOH I found the driving there challenging (maybe less so for you if you're experienced driving left-side-of-the-road). A car for Gozo is a good idea, don't miss Gozo, it's great.

I will look up the cruise ship timetables and try to avoid being in
town the same days as the large ones are.

Good luck with tthat - I had the same idea (I looked up the expected port calls and made a fancy chart showing how many thousands of people to expect each day - here is my Cruise Ship Crowd Calendar) - it didn't do much good, since there will be multiple ships in port nearly every day. You need to be up early or out late in the day to avoid the crowds in Valletta - though the majority of cruisers stay within central Valletta, so you can dodge most of them by just going a few blocks off the main circuit and away from the most obvious tourist magnet places. You will see them in smaller groups on excursions even on Gozo and other places far from the cruise ship port.

And BTW I was wrong about Tuesday the 26th - two ships showed up that day; either they were unlisted or I just missed them. There were cruise ships every day (although on some days there were more/bigger ships than other days). It is what it is.

3 months sounds like a good plan. 👍

I don't care which side of the road the convention is to drive on solong as the car matches. My issue was that I'd forgotten how to drive a manual and it took a couple of days in Slovenia to remember LOL. Its more about parking I really, really dislike having to look for parking!

I think we're going to drop Cyprus and Istanbul and fly out of Athens home (we've been to Athens before so don't need to spend any time there except maybe and overnight at the airport

Milan 3N is fine. There's enough to see and I didn't feel like Milan was nearly as hectic as Rome.
Corsica has never been on my list, so no help there.
Sardinia - I've heard that it's where the Italians go to vacation. . . mostly relaxation. A friend visited with a rental car mostly to explore the archaeology (it's her hobby)
Sicily was my destination for 2 weeks and I loved it all, especially the 3 big sights for Greek temples, but there are many layers of history. The hardest part of planning was deciding what to omit and I could easily have spent another week seeing more and still having to skip a lot. I found Sicily more laid back than most of the mainland. After a few days in Palermo and Cefalu I rented a car. Driving was easy and the roads were good. My trip was April-May and I didn't have trouble with parking.
Malta was a jam-packed 5-day seminar tour in early June. It's amazing - layers of history and culture, picturesque seaside villages and some wonderful art (including 2 huge Caravaggios in a medieval church). On one's own, allow at least a week. I'm pretty sure there's snorkeling. I was there quite a few years ago, so things may have changed but guides with cars were plentiful and daily rates were very reasonable. Driving is awful. The group used only tourist buses and we often sat in long traffic jams which we were assured were typical.
Crete I loved Chania (5N) and not just because my name is Chani :-). You've been there so I need not say more.
Cyprus is a big tourist destination for us since it's so close. My one experience was completely atypical. People I know who've been there go for the relaxation and nature.