Hello, All. My husband and I had a wonderful time on a well planned (1 year out) 3-week Switzerland trip in June/early July this year. As many of you understand, We came home with a travel bug and want to try and squeeze in a trip this mid/late Sept. or October. I've been studying Athens, Delphi, Meteora, The Peloponnese, Mykonos, Santorini, Naxos, Paros for this trip. This trip could wait until next May, if necessary, and we could do something simpler. Still, I thought I'd ask if such a mainland Greece plus 2-4 islands could happen on such short notice. Thanks for your feedback!
I don't see why not. If you're thinking about the difficulties of finding lodging this late, I would go online and start looking to see what you can find. Maybe even start booking, but make sure they're cancellable just in case.
Then start pricing flights using something like Google Flights to see what's out there. https://www.google.com/travel/flights?
You will need to work quickly but there's no reason you couldn't enjoy a wonderful vacation in Greece.
The issue may be more a question of your interests/desires versus your available time, rather than the ability to find and book things between now and then.
As someone who has flirted with a Greece trip many times, and has seen folks contemplating a trip to Greece here in this forum often, my observation has been that people consistently overestimate their ability to hop around Greece quickly and efficiently (especially its islands) and greatly underestimate the amount of time that simple logistics will eat up - just getting from point Λ to ϐ.
If your trip is short (I'd define that as two weeks or less) it seems quite difficult to make all your "must see" locations. Three weeks gives you a shot at that, but even then it can be tight. Those ferries eat days.
Booking late usually just means you pay more and/or enjoy your accommodations less, because all the juicy places were scooped up 11 months ago and you're stuck picking over what's left. You can either throw money at the problem or settle for less desirable places (often both). But Greece seems somewhat resistant to "squeezing in" trips unless you're willing to make hard choices. Geography and quirky ferry schedules pose challenges that may not be easily overcome. If you're willing to let go of some of your islands, that would probably help (but depends on your specific and priorities). If you really want everything you want, to make that work you might be looking at a longer trip later.
Why not? Have fun from someone who plans very far in advance and wonders why not just go have a good time on short notice! You'll probably find you'll be quite flexible!
You don't say exactly how much time you'll have for this trip in September/October, and I agree with David's point: traveling in Greece takes much longer than you imagine. I guarantee you'll realize this very quickly as soon as you try to figure out how to get from point A to point B.
You also need to think about why you chose the places you mention. What are you interested in?
So the biggest mistake you can make is to start by booking accommodations.
Having traveled to the Greek mainland and islands for over 30 years, I would never plan the trip you're planning if I didn't have at least a month. And it would take me several weeks to define doable and coherent itinerary with a good knowledge of the bus and ferry networks.
Remember that Greece is not comparable to Switzerland, it covers an area 8 times larger, in half of this area transport is only possible by boat which is, as you may have noticed, rarely the case in Switzerland.
My two cents is the logistics are easiest if you stick to the mainland and rent a car. I think you could do that for September/October and save the islands for another trip.
I agree totally with Beth ... can't do that whole list on ANY 2 week trip .. and mainland is best choice for fall (with car rental). However, realize that if you are that sight-greedy (Delphi-Meteora-AND-Pelops) you are in for lots of road-mlles ... and you can't travel via train while you recover from jet-lag... NO trains. Option: arrive ATH, get free shuttle to HOtel AVRA on beach for a dip & early night, return shuttle in AM to ATH for rental car, to Delphi (1 night), then to METEORA, then the looong haul to Pelopponnese ... stay in Nafplio at least 4 daays to cover scenic wonders nearby (plus wne festivals?)... then perhaps 1 night in Monemvasia, and a day at Mystra. That wold leave you ?4 days to enjoy the treasures of Athens at the end, when its' a bit cooler.
MAY is a perfect time to island-hop before the tour-mobs arrive ... our usual advice: start at Farthest isle to get over jet-lag without driving. Frankly we "vets" often recommend skipping Mykonos (overpriced, overcrowded, overhyped) and do Santorini only 2-days for the Famous Caldera View. One strategy = arriv ATH Th or FR, in AM allow 2-hr layover, tly to Santorini in afternoon (because fewest awful megacruise ships dock on weekend), spend 48 hours, then ferry onward. My faves, are Naxos and Antiparos... also look at Sifnos (as yet unspoiled by mass tourism), then ferry back to mainland & 3-4 daya in Athens.
Agree with @Mardee. If you want to go, do some quick research and start booking. Mid-late September would be a lovely time to be in Greece. Don’t know your timeframe, or whether you would have a car, but with two weeks ( +/-) you could do something like this:
Arrive Athens, drive directly to Delphi (1n)
Visit Delphi, drive to Meteora (3n)
Drive back to Athens (Piraeus), ferry to Sifnos (4n)
Ferry to Milos (3n)
Fly back to Athens (3n)
Depart from Athens
Or skip Milos, which is beautiful but touristy, and focus on Sifnos. Regardless, you will want to return and see more of Greece.
Happy planning! Happy travels!