27 days in Greece in April itinerary and weather

It's a very ambitious, if not overly ambitious and crammed, itinerary. To the point where I don't know what to say...

A few remarks though:

Is this layering weather/cashmere and Patagonia puffy's or any
shorts/dresses at all?

It will depend on the weather and especially the location. You want to go to islands and also to the mountainous regions of the Peloponnese. The weather is not the same at all.

Shorts/dresses are prohibited at Meteora Monasteries

We can sleep in a tent…but now prefer boutique, small, authentic
semi-luxury to an occasional splurge where location justifies it

The Grande Bretagne hotel is one of the most luxurious hotels in Athens. There are dozens of other hotels just as good and better located for visiting the city.

On 4/9 in Athens you won't have enough time to do everything you plan, you need at least one more day.

To visit Meteora and its monasteries from Athens you will need to stay there 2 nights.

From Meteora to Delphi it's about a 4 hour drive. You will need to stay there at least one night.

4/12: How will you, leaving Delphi, get to Hydra in the evening? Where will you return the car?
And why go to Hydra and Spetses when you are going to see lots of other islands later?

4/16-18 Peloponnese: It's impossible to see all these places in such a short time. Also if you pick up a car in Porto Heli where do you drop it off? in Athens? Good luck finding a rental company that allows it!

4/19-26: Sail/Catamaran/Yacht charter for a week in the Cyclades OR
spend more time on islands? weather a factor?

In April it is unlikely that you will be able to do that. The weather is not good enough to go sailing on a catamaran. The risk of cancellation at the last moment is very high. Also, have you taken a look at the prices?

4/26-29: Mykonos: 3 nights

is not compatible with your sentence:

"not loud party spots or touristy ports"

Paros, Anti Paros, Milos, Naxos, Folegandros, Kea, Syros, Sifnos – Or
Villa for a week on one of the islands with day trips?

You list names of islands without knowing how to get there. That's not how it works on the Greek islands.

You cannot take daytrips to other islands while staying on a base island. Going from one island to another takes most of the day.
Moreover, it is not because the islands seem close that you can go from one to the other whenever you want.
This is often impossible (especially in April)

The only consistent thing I detect is that you saw that May 1st is a strike day (no ferries on that day)

Many thanks! We've already ruled out the boat charter, removed the Peloponnese Peninsula and down to 2 nights in Mykonos to give ourselves a bit more breathing room and longer stays on other islands.
Where would you recommend staying in Athens then? Both 2-3 nights at the beginning and final last day for a different hotel?
Hotel recommendations if any in Istanbul? Wow--this is such a tremendous service and very much appreciated!!

Thank you!
Joan

I am a bit overwhelmed with your planned trip, way too much stuff in not enough time.
Good comments from Jo Lui.

Here are some of my thoughts. After many trips from the west coast to Greece I can tell you the first couple of days in Athens are really a blur. Its very busy and not the best choice for getting over jet lag.
Many experienced travellers to Greece recommend you get out to your first island on the day you arrive. Getting over jet lag on an island is way better than doing it in Athens.
Both Santorini and Mykonos have several flights a day from Athens so even if your transatlantic flight arrives later in the day you will have sufficient time to catch a flight to one of those islands. You should probably plan about 3 days to get into the swing of how Greece works. Both are in the same island chain so whichever one you choose gives you an opportunity to ferry to an island between Santorini and Mykonos. ( I would recommend Naxos, you can spend a week there and not see it all) then ferry to the
next island destination.
Now you will be ready to return to Athens to start your mainland tours. In my opinion Delphi and Meteora are two very different but important sites. You really will need 3 or 4 days to do these sites, 4 is probably better because they are about 5 hour drives apart and there are many interesting sites along the way between them.
While early May generally is a strike day, this year Easter also occurs in early May. Easter is a huge celebration in Greece and it would be a shame to miss it for a couple of days in Istanbul. Chances are you may run into travel difficulties getting out of Athens or getting back before your return flight home.
Use this time to explore Athens.

Some images to tempt you.
Santorini https://www.flickr.com/photos/stanbr54/albums/72157632154800782
Athens https://www.flickr.com/photos/stanbr54/albums/72157632121475515
Delphi and Meteora https://www.flickr.com/photos/stanbr54/albums/72157698930270992
Naxos 2022. https://www.flickr.com/photos/stanbr54/albums/72177720299940917/
Naxos town 2022 https://www.flickr.com/photos/stanbr54/albums/72177720299959098

Stanbr's suggestion to start by going to an island as soon as you arrive in Athens would be much more reasonable.

Except your flight from NYC (which I assume is the Emirates flight) arrives at 4:05pm on April 8th.

And taking into account a reasonable connection time of 2h/2h30 in Athens airport, there is only one possible destination island:

Santorini with only 3 flights. The first leaves at 8:20 p.m., the other two around 11:30 p.m.

Therefore you will:

1/ Wait between 4 hours and 6 hours at Athens airport before leaving for Santorini.

2/ You will be at your hotel in Santorini at 10:30 p.m. at the earliest.

Which in my opinion is a waste of time and money.

So, since you have 24 days, which is a lot, it is not essential to optimize your time by going directly to an island. In my opinion the best would be to stay at least one night in Athens upon your arrival, or for example 4 nights and visit the city before continuing your trip.

We did a trip to Greece a couple years ago using the 2 week itinerary in Rick’s book. We rented a car in a Athens, we skipped the Hydra beach excursions, drove to Delphi, etc, then at tail end after returning car in Athens, we took a quick flight to Mykonos for 2 nights, then ferry to Santorini for 3 nights. Too cold for Beach but plenty to see without beaches. From Santorini flew back to Athens for a night then flight back to states. Followed Rick’s suggestions to a tee. Nafplio is a gem of a stop

JoLui, Stan, Mshmeck,
All of your comments make perfect sense so thank you! We land too late in Athens to hop over to an island. We've traveled enough to know we will chill and nap and take our first day in Athens slow and then hit the ground running.
*Does anyone have any experience with Truetrips? They are Athens based and planned some trips for friends of mine including ferries, dining recs, lodging etc and were flawless. I've been finding Fantasy Travel a challenge and no feedback at all compared to this group!
Is there any one island we can park ourselves for a week and ferry/day trips to other closer in islands so we aren't jumping around as much?
* Going to really research where we should be to maximize the Easter celebrations first week of May before we leave.
Thanks to all!
Joan

JoLui,
What hotel and area do you recommend in Athens?

Joan,

Except when I only stay one night in Athens or Piraeus to take a flight or ferry the next day, I don't go to hotels, I rent apartments (and not necessarily in the best area for a first Athens visit). But I'm sure other forum members have plenty of hotels in Athens that they know and can recommend.

See this map of central Athens.
I put the preferred area where to find a hotel in blue and added the main places to see.

https://www.google.com/maps/d/edit?mid=1dDAGDsKkBs0iaJ63iGE-c0sCGcizd3E&usp=sharing

As for the Cyclades Islands, I know quite a few. I would never waste my time and money in Mykonos, even in April. Santorini is probably a must see once in a lifetime, stay there for 3 nights it will amaze you.

Among the islands that you mentioned in your first message you can remove Kea which is not accessible from Piraeus. Folegandros is pretty but very small (less than 800 inhabitants) and accommodation options in April will be limited.
Syros is the capital of the Cyclades but does not have the Cycladic style with its white washed houses, windmills and blue domes.

Personally I prefer Sifnos to Milos.
You can also add Paros and Naxos which are two large neighboring islands and where you will find quite a few accommodation options (Naxos is a favorite of many RS forum members).
I go more often to Paros which is perfect if you are looking for a villa to rent for several days.

As I already said, ferry daytrips from one island to another are very limited. The ferry connections and schedules connecting the islands are not planned for this kind of trip. The only easy daytrip option is to go to Antiparos from Paros. Or you have to contact a local travel agency. If you go on a daytrip to another island, you will not see much of this other island. To visit an island you have to stay there at least 3 days. A day trip that takes you there for a few hours is in my opinion a waste of time and money.

Except Santorini where the basics can easily be visited without a car, I highly recommend renting a car in the other islands. In April bus services are extremely limited

Perfect--Very much appreciate your information!

April 9 itinerary is impossible, all top sites packed into one day.
We loved staying at the Grand Bretagne two times. Enjoy it.
The first time we stayed at the Grand Bretagne was when we fled the Electra Palace after a disastrous experience there and the Grand Bretagne had a room available. And we felt so welcomed there.