Late February 22 Trip Conundrums

You already have more than enough for 9-10 days, so I'd look at just refining your list. First, decide how much time you would like to have in Athens, then work backwards. I lean toward grouping Athens and the Peloponnese OR Athens and the north, though you could do a loop of both if you are not interested in spending a lot of time in Athens. (I didn't, but it is because I know I'll be back, and I will almost always have to transit through Athens, so I'll spend more time there later.) However, in winter, I would probably lean toward cities just because I am a winter weather wuss.
I have not been to Greece in winter, so hopefully some others can chime in, but I would not bother with any island--Nafplio is on the water and it's beautiful. There are also many sites you can visit from Nafplio, making it a great base.
With that late arrival and late departure, you can start in Athens and end somewhere near Athens. So, Athens a few days (3), then pick up car and head north to Delphi (1) and Meteora (2), then back south to Olympia (1), then across to Nafplio (3), which is close enough to Athens that you can return to the airport on departure day (unless you get bad weather that is, then it could get tricky). You can see from my parentheses that you might want to scale back a bit. But you have many options--you could skip the Peloponnese and visit Thessaloniki instead, or you could skip the north and add more time in the Peloponnese, where it is easy to fill the days.

Have a look at this thread. It might answer some of your questions about traveling to Greek islands in winter.

Are any islands worth trying to visit late February for a short,
possibly overnight stay, instead of one of the sites we mentioned
above?

The islands are always worth visiting, but not for just a night. You would have to find one that is really close to the mainland to make that feasible, and I wouldn't think it's worth the trouble if you have practically no time to spend there. Also, in that season you will have to leave room for unexpected weather events and planes or ferries being canceled.

Are the roads rough (black ice/sleet) to drive during this time of
year?

The weather is unpredictable that time of year. Most of the time, you will be fine, but you may have to deal with pouring rains or possibly even some snow... and the thing is, this is a country that is best equipped for summer and hot weather. A tiny bit of snow can bring everything to a total stillstand.

Although really general without specific locations, how challenging is
it to find a place to stay last minute in smaller cities/towns at a
reasonable rate? Does winter affect this tremendously?

Absolutely, many hotels in the touristy regions will be closed for the winter, and many Greeks spend the winter in Athens. However, those that stay in their home towns will be all the more happy to have some off season income. You should be able find a place to stay everywhere, and possibly even at a ridiculously low rate.

Delphi and Meteora are in MOUNTAIN territory ... and in past winters there is skiing around there... and that may affect hotel bookings. Even more, it can affect driving; if you are from new England or Colorado, no problem, but if you are from flat states, take this into consideration. And Meteora would not be much fun in rain or gloom; you mght do well to keep plans flexible & consult weather forecasts carefully.

Athens & Nafplio will be busy & buzy throughout your stay, and the big highway linking them is modern & easy to navigate in all weather. I would not attempt Olympia -- too long a drive. En route to Nafplio, you can hop off the highway 5 miles & see the "Sacred Games runner-up" -- NEMEA. Wonderfully excavated, great stadium, a hidden gem http://nemeangames.org/

If there is a bright clear sunny day, not too windy, you could hop a Metro to Piraeus and take 1 hour ferry to island of Aegina, just for the ferry & island experience. Important: you would only want to take a Conventional Open-Deck Ferry, because part of the fun is siting out, enjoying the seascape, the many kinds of watercraft etc. The other ferries - hydrofoil - are indoor seating only, salt-glazed windows no view. In winter there would be 1 open-deck ferry in morning, and one returning about 6 pm... you could check the schedule at any ticket office by your hotel. Here's a lovely foto album of a day-trip to Aegina in June... http://www.flickr.com/photos/36264706@N03/sets/72157621604646139/detail/ of course its full of flowers and such, but useful to see the fun of the ferry trip. if u do this, I'd suggest a car rental to get around the island. And I would not suggest trying any other island -- this is near, and safe to try (many Aegina residents commute daily), and its port town is fascinating to explore away from the seafront, narrow lanes and alleys and houses that are very Greek, not touristic.

The other ferries - hydrofoil - are indoor seating only, salt-glazed
windows no view

Excellent point. Let me add another one: Indoor seating is pure horror in case it gets a bit choppy at sea. I for one only have to look at the greenish tinge in other passengers' faces, or smell the scent that's in the air, and you can see me grabbing the paper bag myself. Fresh air and a good view of the horizon is what I need most in those moments.

You are trying to do to much in the time you have.

Every time you move from Point A to Point B eats up time and time is valuable on holiday.

I would recommend time in Athens and pick one island.

The southern most islands would give you a better chance of decent weather. An island like Crete has everything one would want in a Greek Island, mountains, coastline, lovely villages, archeological/historic sites, and so much more.

Still with the time you have it would only give you a taste of Crete as it's the largest Greek island.

If you are OK with cold, rain, wind then just about any island would work.

Just because the tourist season is over doesn't mean Greece shuts down. They'll always be shops, markets and tavernas open for locals which in the end will give you a more "Greek" experience rather than a tourist season.

You can check out all the Greek Islands here to give you some idea of what they are all about:

https://www.greektravel.com/greekislands/

I just looked at a calendar ... you just have 9 1/2 days Forget Meteora & Olympia, one night + half a day in Delphi & 3 in Nafplio, plus 3-4 days for Athens, maybe a sunny-day Island trip, and that's it. Be realistic ... your days are half as long as they would be in May-July... it gets dark by 5 or so. Can't pour a quart into a pint bottle. Allow time for each place & you can relax more & enjoy things.

wawindsor, once you had time to digest this and mull things over, let us know your thoughts on the kind of pace you'd like and your priorities for the trip.

The road from Delphi to the Pelopponese is a mountainous twisty one lane each way. I would not want to negotiate it in the winter and I’m from New England and now live in a mountainous state. It will be slow going and scary in the winter if there is any ice or snow on the road. It was slow going even in late spring when we were there.

An added though to my first post.

It sounds like you are interested in the mainland, especially the Peloponnese.

Another option beside Athens and one island is Athens and Nafplio in the Peloponnese.

It's one of Greece's nicest towns and a great place to base yourself to explore the area including world class archeological/historic sites.

Here's the BEST website for Nafplio filled with great info and what to do and where to go nearby.

https://www.visitnafplio.com/

Thank you all so much! The advice and answers have really helped to clarify that we need to focus on quality and not quantity! We are "flat staters" and that will make the difference. As for an island, we will look for those clear sunnier days for the short ferry trip to Aegina and the return. Meteora and Olympia will have to wait for the next trip. Nafplio sounds like a good base and a little more time in or near Athens is sounding advantageous this time of year, with Delphi as a possibility.

One follow-up would be how would we reach out to those folks to find accommodations, such as locals willing to put us up in lieu of possible closed or full hotels or pensions? Where would be a good place to start?

Again, so many thanks.

NAFPLIO -- first of all, start by consulting THE best (and noncommercial) website http://www.visitnafplio.com/ -- its created/run by a Scandinavian expat who lives there, and (like all people who move to a place & love it greatly) she knows more about ALL things Nafplio AND the vicinity than even people born there... Please click on the "walks" to see the enchanting walks right around Old City. Also, her website has charmng little video of Nafplio in February ... perfect for you!

NAFPLIO HOTELS -- she recommends (and I totally agree) that Hotel Agamemmnon has BEST location in Old Town and remarkably, is also reasonably priced. I'd stayed all over Old Town in 5-6 previous visits, stayed here last time, and it was The Best. Has balcony rooms right on the sea front with super views... there are almost no hotels directly on seafront, and others' views are partially blocked by taverna canopies. Sinc u are off-seaon u have chance to book one of these rooms. TIP: do it thru an agency like booking.com, because if u book direct it means an advance 1-night deposit in bank, and from USA a $ transfer to European bank is a hassle! If by chance it's full, look at Omorfo Poli, another nearby place, boutique & quiet. https://www.omorfipoli-pension.com Great Reviews. Another choice, since it's off-season, might be the Hotel Athena right on Main Square. https://www.hotelathenanafplio.gr/?lang=en On summer weekends, the square late-evening activity can be too lively but in winter, it could just be nicely buzzy. NOTE: some people on this Forum are "rick-heads" who do his tours, and they recommend Pension Marianna where the tour stays. It's fine, but waaay up high. The tour people come & go by bus... you would have to drive up or else walk many many many steps up stairsteps streets after dinner.

ATHENS HOTELS -- it's not clear if you are already booked into Athens accommodations.... if not yet, I recocommend places just SOUTH of Acropolis, in the area that's more car-free, no skyscrapers, no big streets. Check places like Hotel Herodion, its sister hotel Philliopos, Hotel Hera etc. Also, booking.com now offers in addition to hotels, pvt apartments, and I see many at very good rates, right in Plaka, in this south of Acropolis area. They come with booking.co advantages like cancellation refunds, easy date changes, more rules about check-in times etc ... which AirBnB often doesnt have.

DELPHI -- Hotel PAN, specify rooms facing DOWN the mountainside. If full, its sister hotel ARTEMIS, across street, will have same.

I didn't get a chance to say thank you for helping us planning our itinerary. Fingers crossed that good health is maintained, tests are negative, flights are on time, entry rules don't change too much, and the weather is unseasonably warm (haha!). Our current itinerary is open but confined to almost solely Athens and the eastern Pelopennese. Thanks again and I'll report back once we are back state-side.

Wow, wawindsor, I'd forgotten all about that October discussion... now it seems like a better idea than ever, to scram outa N AMerica for a time in Greece. I Keep Athens weather on my phone (to imagine what my friends there will be doing), and its farthest forecast, Sat Feb 12, is sunny with high of 60°! Take your folding umbrella and a waterproof & you'll be just fine! We look forward to your report upon return.

Yassas!

We have returned (sadly) but already began our return visit before we even left! I can't say thank you enough.

Ultimately, we spent a few days in Athens on the front end and stayed at the wonderful Hotel Attalos. Just enough noise and buzz for our taste, and close enough for us to get a good feel for all of the neighborhoods and historical sites around. Saw a few pickpockets and had to repeat "Ipa oxi!" to the woman who unwittingly placed roses in my girlfriend's hands. The major sites and sights visited, and tavernas sat in, we made our way to Cape Sounion after picking up the rental. The rain let up just as we got their for sunset. Beautiful indeed.

Long trek to Delphi but well worth the view from the Hotel Pan as the sun came up in the morning - just amazing. Then on to the monastery at Oisos Loukas, followed by Nafplio for a night at a wonderful place outside of the Old Town.

We drove down the Mani where rain and winding roads were challenging, but who needs lane markers, shoulders, guard rails, solid asphalt, less tractors, sheep, cows, or goats, or even slow drivers, eh? One of my favorite memories was a stop at a taverna in a small town on the coast where the owner, who spoke little English but worked so hard to get us to eat there, kept trying to get us to order "wrist" as he pointed to his knuckles on his closed hand, which we finally determined was "fish".

After our first night in Monemvasia, she was bit by the fortress-vibe bug and we stayed a second night and almost made it a third! A swing through Mystras via Sparti (and the Museum of the Olive and Olive Oil!) and we went back to Nafplio for an evening. The last night we made it back to Athens to finish out the sights and arrange for the mandatory return testing. As an added bonus, we spent a rainy, cold evening walking the streets of London on the way back - rain that we were fortunate enough to only have on 2 of our days in Greece in February!

As you all have conveyed, it was magical and enchanting. I loved the wildlife, the nightlife, the bees, wildflowers, agriculture, the people, the food...I can't imagine what it is like there during summer or shoulder season(?) but we can't get back there soon enough.

I hope I'm able to give back enough to this forum for the information it lent to the success of our trip.

What a great update! It sounds like a wonderful trip-happy for you!!
We hope to be there soon!

wawindsor,
We will be in Greece this May. Where did you get tested for Covid in Athens?
Thanks!

wawindsor, SO glad you had a good time! I knew you'd become addicted. Next trip, ideal timing would be between May 15- June 15 ... rain is over, but greenery still abounds, especially on fertile Islands like Naxos ... bu even on the drier isles. The sea is " brisk" at first, but after a moment is divine... everything's open, nothing is crowded, Greeks are out watering flowers, painting the white lines on the flagstoned walks, happy for warm weather, plenty of time to chat (and Greeks love to talk!). The days go on foroever --- you get 1 1/2 days for every day when it doesn't get dark unti after 9 pm.

2nd best time is between Sept 1 - 15... most of the crowd are leaving, the sea is warm & mellow, days are warm but not burny. I love this time too ... only downside for me is that -- after 3 months of no rain -- things are a bit brown-y, despite Greeks' great attention to their window & dooryard flowers... and also, the Greek hoteliers & restaurants, alto just aw wondeefully hospitable, are a little burned-out after coping with the huge MOBS of Late July thru August ... and they're begiinning to think a bit bout their own lives ... getting the kids into school, going to athens for dental work, all the chores of Fall... and a few of the shops are having "Final sale of Season" signs. but ... it's a good time to go also.

janet...sound like just our time to go. Who knows...if our wallet allows us to pour money into the Greek economy like we want to, we may end up basking in the sun next to some of the folks on the forum, including yourself!

kwkwoo...We tested on an early Monday morning at a pharmacy in Ermou 18, easy-peasy. There was another testing site no more than 10 meters from the pharmacy we went to.

wawindsor, thank you!!!!

I also plan on asking our hotel where we can get tested. Obviously the closer to our hotel the better. But it's nice to have your information on hand, too.