Undecided on WHEN to go - 2022

I would not go before middle of May if you are concerned about water temperatures. In 2018 we were in Santorini and Naxos the last week of May and Nafplio and Athens first week of June. The weather the last week of May on the islands was lovely. Santorini was crowded at times but according to people we spoke with was nothing like later in season. The water was a bit brisk but swimmable and we are from Florida.
I will return to Greece in late May again.

I looove very late May into early June. You get more vacation for your buck, because sun doesn't go down until 9 pm. I find that swims are wonderful any time past May 20 or so.... and many beaches are sloping, so you wade in for a few yards before you are waist-deep... sun can penetrate water, warm it up... I can stay in for ages, until my fingers wrinkle... and i'm waaay older than you1

In late may, rains are over but islands are still green, island like Naxos are lush still .. yet because it's Greece, the fruits are ripe -- apricots right off the tree, strawberries, cherries. If you are smart enough to go to Naxos ALL your foods will be local - the hill farms are bountiful, local restaurants serve their own meats & veg, make their own yogurt etc... not to mention their wine & olive oil. And Naxos has miles and miles and miles of uncrowded golden sand beaches, snorkeling galore. Plus Mountains

FIrst 2 weeks of June certainly off peak (except Santorini, always ON peak but we can help u strategize to dodge tour crowds). If you start looking early, give specific dates, we can steer u to favorite (family-run) lodgings w. balconies & sea views, for €⁄40-60 per night. These lovely places offer comfort AND authenticit, not glam, spas, fancy lobbies.

LOoking at 2022 Calendar, Let's say take-off FRiday June 3, Arrival AM June 4, FLy home Sunday June 19. That gives you 14 1/2 Days IN Greece (cant count dpearture days) You could manage a lot of your Wish List with adept scheduling to minimize transit time, maximize enjoyment time at destinations. Example: Arrive mid-morning - 2 hrs later, domestic flight (45 mins) to CHania Crete. 4 1/2 days Crete (rent car), ferry to Santorini for 48 hrs, 2 nights (just for the Famous Caldera View; beaches Meh), ferry to Naxos for 5 days/nights (there's a Naxos excursion boat that gives daytrip to Mykonos). Then fly to Ath for 2-3 days/nights. (it's really fab in June, and its famous Landmarks will crown your visit) Done!

BethFl

Brisk huh ? I am assuming to snorkel you suck it up and get in and then you get used to it I hope ! Comparing to Florida is good for me. We are from Texas so used to heat.

Janet, what a wonderful, thoughtful, thorough response !! I am now following as your descriptions of Naxos in May are so alluring !!

July, August, September. My favorite months in Greece. I love to swim although I rarely hang around for hours at the beach. The Mediterranean in Greece is crystal clear and there are lovely beach around every turn in the road. But really it doesn’t warm up until July. June is brisk. May is “I wish I was here in the summer”.

We are in Greece right now. The water was pretty cold until mid June and only warmed up because Greece had a heat wave of 90 degree weather. Daily activities: leisurely breakfast, walk or explore archeological sites, about 11am have a swim, big mid day meal, nap, afternoon swim, museums or archeological sites, evening walk and light meal. Greeks tend to come out between 7:30-8:30pm to walk, play with kids, eat and drink.

There is no high season this year because of the pandemic. I don’t think it will be back to normal next year either. Come anytime.

In my suggestion, there was some thought about OP's original wish -- to celebrate an anniversary -- and also didn't want to postpone that celebration unduly.... but I also have enjoyed visiting in September. I'd suggest the first 2 weeks or middle 2 weeks... and yes, the water would be warm if that's a mandate. Do be aware that after 4 + virtually rainless months, even the lush islands will have a somewhat brownish landscape (although the lovingly-grown flowers everywhere are a help!) . And the days are shorter by 2 hours. Also, in the smaller islands at least, one can get a feeling of a season-ending, as Greeks get their kids in school, take trips to Athens for dentist appts, and prepare to move on with their lives .. however, I emphasize that their hospitality is unwavering, all year long!

In my experience, people with family in Greece always favor July-August, altho these are the hottest, most crowded, most expensive months, because August is the month that most Greeks have their annual vacations... the lucky ones get the whole month... and so its a treasured social time that can't be measured.

thanks everyone! appreciate the responses. still struggling. LOL. even having having a holiday in Late May vs Sept doesn't help as they each have one :-)

Does it help that you can't go wrong with either? Like Janet, I love traveling in late May and have visited the Mediterranean area in late May for over a decade. I agree after May 20 is safe for swimming. Push it into early June and that will be fine. I would also not hesitate to travel in September.
You are going to places that are going to be crowded--Santorini and Mykonos--but you can find some respite while on Crete. When I visited the Peloponnese pre-pandemic in late May, we most often had sites and hikes completely to ourselves, I was astounded!

About late May - one fun thing that occurs is .... Greek school trips! Greek schools are like every country's schools... in late Spring, most of your heavy classwork is done and kids are restless, so voila! field trips! You can encounter groups, often in school shirts, at ancient sites, with teachers explaining. I must say, the kids in general are MUCH better behaved than 13-year-old US groups! One of the most amsing was a group visiting the Ancient Theatre of Epidaurus. As u know, its accoustics inspire many visitors to stand center stage & sing national anthems, or recite from Shakespeare. This group's assignment was to stage a scene from Lysistrata, the famous ancient comedy about Greek women stopping a war, simply by withholding their "favors" until the men gave up weapons. You sould have seen the giggles & blushes!! Teens are the same everywhere.

Another treat that's not mentioned in any guidebook is -- The Last Day of School!! It's always in early June, and celebrated in the early evening with balloons, music, prizes, student recitals or dances, and (of course) applause & cheers from families seated in schoolyard. I first encountered it in Athens, in a school on a lane running down from the big "promenade" that runs along the South side of Acropolis. I heard cheers, music, & asked my waiter -- Oh, he said, it's the Last Day of School. I watched the fun, peeking thru the fence. In 2013, we were in Nafplio, and 2 in our party were walking in Old Town when they saw balloons, heard singing, and just brazenly walked into the schoolyard, saying "Ya-yah" (Greek word for grandmother). They sat in front row. clapped & cheered & had a super time! If u are in a town with a school, DO ask your hotel people... you may luck into a magical evening!

I was at several islands in early June. The weather was nice but the water was too cold for me to get in. I’m from warm California.

valadelphia - it does adn it doesn't :-)

good to know we will love either, but not helping me decide. I am one of those that always wants to make the right decision.

I do think either is good, I think the water is the main thing. interesting how many say too cold and how many say just fine.

I was trying to really see if there is only a few degrees difference betwee 1st week in June vs sept then it proably won't matter. if it is 10 degrees then it will matter.
example on https://www.climatestotravel.com/climate/greece

mykonos 70 degrees in June and 73 degrees in SEpt. *BUT 64 degrees in May)
(we would go May 27 or 28th arriveal in Crete...vs Sept 2nd arrival day

Crete - 72 degrees in June and 75 degrees in SEpt. *BUT 66 degrees in May)

janet - your writing is like painting a picture.

I would not worry about a big difference in crowds between late May and early June. I do think the sea temps will be much safer in September than May, but I'd be fine with the sea temp in early June. I am from the southeastern US and I like my swimming water to be like bath water. I have found the Mediterranean "bracing" in late May, but the air temps and blazing sun make it work. There is also a lot of regional variation--if the sea bed is shallow for example, you are going to find it much more pleasant than a deeper area.

Agree on the crowds..figure they will be about the same no matter which time we go.
May 27th arrive 28th, vs Sept 1st / 2nd
maybe I decide based on airline availability as I am planning ot use miles. :-)

I'm a writer, Stacey

Also, I've been to Greece THIRTEEN times ... earliest start date Spring was May 5 (water too brisk) -- September dates were between 5th & 10th. In septembers, I found the sea to be a little too much like a bath. I use the bathroom for that.

Most recent trips began May 26, 27, thru June 1. Water was perfect... slightly brisk for first 30 seconds, but very refreshing for entire rest of time. I am a swimmer, I stay in the water for 30-45 minutes a time, and on a beach afternoon I typically take 3 swims. I'm in my 80s and this is my kind of fun... I hope you can manage briskness for the first few seconds. The last 2-3 years (global warming??) Early June has been uncommonly hot — 3-day spurts of over-90° temp. Swims were life-enhancing.

THese are observations were not limited to 1-2 places but from swim off islands like (R- L across Aegean) Samos, Chios, Patmos, Rhodes, Crete, Santorini, Naxos, Paros, Anti-Paros, Amorgos, Folegandros, Milos, Sifnos, Serifos, Syros... some more but I forget, and a half-dozen sites on the Pelopponnese. In June you can see snorkeling everywhere. BTW, don't weigh yourself down bringing too much gear, in the Cyclades and Crete, at least, you can rent stuff almost anywhere.

These days alas, I just do laps in a large outdoor Sports Club pool 3 blocks from Independence Hall (I wave to the Liberty Bell en route). Getting in the pool is chillier than wading into Plaka Beach on naxos, & nowhere near as much fun..

Just love this Janet! Thanks so much :-)