I have just started planning a trip to Greece for May. A first for my husband and I. I'll be coming from Texas. This is my idea so far:
fly to Athens
Athens - 4 nights
Delphi - 1 night
Meteora - 2-3 nights
An island that you will suggest to me in the comment - 5-7 nights
Santorini - 3 nights
fly back home from Santorini

I haven't bought flights yet, so the number of nights in each place is not set in stone. Here are my questions:
1. Is going to Delphi/Meteora from Athens by bus too much of a hassle? Do I need to rent a car? If so, that means I have to plan some time to drive back to Athens to return the car.

2. I would like to spend 5-7 nights on an island with beautiful views where I could relax, enjoy life and soak up the culture. I'd like to wander through quaint towns with lively plazas, spend a few afternoons at the beach, maybe rent bikes or kayaks or go on a boat ride, listen to live music and eat delicious food. If there's some historic site and scenic hikes, that would be a plus.
I'd like to avoid renting a car, if possible, so an island with easy public transportation would be nice.
I'd like to fly there from Meteora and then ferry from there to Santorini. Alternatively, if the island doesn't have an airport, I could fly to an nearby larger island and ferry there. In that case, I could split my time between both islands.
I have a feeling that several Greek islands could probably fit this description, but please share which islands you have visited that is closer to the vibe I'm searching for.

3. I'd like to be in Santorini on May 16th-17th for 2 reasons. Based on what I found online, those are the days with the least cruise ships (only 1 each day) and also, the 16th happens to be my wedding anniversary. That means that beach time would be the 2nd week of May. Will it be warm enough for the beach?
Alternatively, I could go to Santorini before the other island, but I'm not sure if it's possible to fly back home from anywhere else so that I can avoid going back to Athens.

Thanks for your help!

I thoroughly enjoyed Naxos and think it would meet your needs well.
It's not an island, but another option, with some island-like features, would be Naflplio.

You might find some useful information in my trip report. The section on Naxos begins with post # 109; the section on Nafplio begins with post # 137. With Gratitude for a Glorious Solo Month in Greece

When you ask if it'll be warm enough the answer is it depends on you.

The running joke is northern Europeans go swimming when the polar bears think it's too cold. Different people have different cold tolerances.

For me I'd expect the beach to be more than warm enough. Will the water have warmed up? Likely not.

I doubt you're flying home direct from Santorini. You will likely need to head back to Athens. That means you might be better off putting Athens last.

For which island? The various groups are all over the place. Pick something easy to get to . Something not far from your main target Santorini.

No, there's no direct flight, but there are still flights from Santorini with a layover, so it shouldn't be necessary to go back to Athens. Visiting Athens last is a good idea, but I really want to put the more touristy stuff at the beginning of the trip since that can be tiring so that I can then rest and not go home exhausted.

Paros or Naxos should be decent bets: large enough for a week, accessible by plane from Athens (in case you do not want to take the ferry), yet at the same time not too run over by tourists (since the airports are too small for charter flights and have less cruise ships compared to other islands), direct and reliable ferry-link to Santorini (and please take one of the regular car-ferries, not a catamaran: the experience of entering the Santorini caldera standing on an open deck cannot be matched imo).

swimming? I have enjoyed swimming in the Aegean in late April, it was fresh but ok (65°F and up is it for me).

good point re: return flights - there can always be strong winds that keep small planes from landing/taking off. I once witnessed desperate tourists on Crete watching their connection in Athens slip away, and since it was different operators, suddenly were facing to buy new tickets on the spot ('just' to Germany, though). if Santorini has to be at the end, make sure to leave enough time or have a plan B (e.g. fast ferry)

FWIW, Santorini was the most touristy (and most unpleasantly touristy) of the places I visited in Greece. That said, it is a place that can lend itself to relaxing more than Athens.

When we flew to Santorini, we did not go through Athens. We flew from Boston to Santorini with a layover in Zurich. (All on the same ticket.) So I assume you can do something similar on the way home. And if your flights home are on the same ticket, the airline is responsible for putting you on the next available flight if for some reason you miss your connecting flight.

I suggest visiting Naxos for your other island. It's lovely and very different from Santorini so you get two different but equally interesting experiences. And you can take the Blue Star Ferry from Naxos to Santorini, a 2-hour ride. Rent a car in Naxos so that you can visit fishing villages and mountain villages. We stayed at Hotel Palatia in Naxos. On the edge of Old Town and St. Georges Beach. The owner is very friendly and helpful. We loved our stay at Hotel Palatia and Naxos!

You can avoid the crowds of Santorini by doing several things. Check to see when cruises are in port, and if possible, plan your Santorini stay when there aren't any cruise ships in port, or only 1 or 2. There was only one in port when we were there in May 2022. Additionally, we stayed in Firostefani which is quieter than Oia and Fira. I also recommend renting a car for a day in Santorini to drive around the island and see other places, which will be much less crowded. For example, we visited the Akrotiri Archaeological site, the red sand beaches, and the black sand beaches where we have a lovely lunch.

We did do a little bit of swimming while in Nafplio. The water temps were comfortable; there were other people in the water. And air temps were probably in the 80's. It was in the 90's by the time we arrived in Athens, our last stop.

I just noticed that you already looked into the cruise ship schedule. Smart thinking! If you don't want to rent a car, I know there is bus service on both Naxos and Santorini. And Naxos does have an airport.

Yes, I'm aware that Santorini is very touristy, but I didn't mean touristy as in "lots of tourists", I meant as "many touristic places to visit in a few days". On the islands, I'll probably visit stuff too, but that's not my main goal.

for checking Greek ferry schedules, imo https://gtp.gr is still a reliable source. you cannot check for next May now, as the timetables are published at odd intervals, sometimes only weeks before they get into effect. however if you search for times this October, it will give you a guideline of what to expect. look out for 'ship type': cc/cm = catamaran, which personally I'd avoid. cf = car ferry with open decks - most scenic way to get around the islands

Sounds like a wonderful trip!
Even though in the middle of May, the water will be a little chilly to swim in at the beach, to sit and sun and enjoy the view and just walk in it ankle deep, would be perfect! The weather in the summer in Greece, gets to be unbearably hot in the summer, so for touring Athens and with any hiking, that weather is what you want. When we went, we left Athens for home on June 1, and that was about as hot as we could stand.

In Santorini, we stayed in Oia and enjoyed the views and the walkability to restaurants and shops. It is smart to plan around the cruise ships, We also had minimal cruisers descending and it wasn't overwhelming because of that. We stayed at Fanari Villas which we loved. We had a kitchenette with a caldera view. A wonderful breakfast was included. The restaurant there, I highly recommend, it would be perfect for your anniversary, with the delicious food, and caldera and sunset views. Ask for the corner table for 2. For my daughter's honeymoon, they stayed in Astra Villas in Imerovigli, and loved it! It was very peaceful, but she did comment there was not much to do around there.

Leaving from Athens at the end of the trip is easier, but it is a puzzle to put together, between flights, ferries and where you are coming from.
I highly recommend you look at KarenWoo"s Greece trip report. It is fantastic and very informative.
Enjoy!

Yes you can take the bus Athens to Delphi then another to Kalambaka (or vice versa). Services for the lattter are infrequent and has multiple (easy) changes. Then bus or bus/train back to Athens. There are no flights from Meteora as far as I know. Personally I would take a ferry to your island rather than fly. Naxos would be a good choice but there’s heaps of others (you need one with ferry connection to Santorini).

Thank you, coral22, for recommending my Greece trip report! I appreciate your compliments.

Incrou7, in case you are interested, here it is. There are photos, too, that might help you decide.
Trip Report Our Amazing Grecian Odyssey - Fodor's Travel Talk Forums (fodors.com)

Rent a car from Kosmos (downtown in Athens), after spending the night at the Royal Olympic Hotel (with best roof top breakfast), just around the corner, and drive 3 1/2 hours to Kyllini, where you will take the ferry to Kefalonia. There's horseback-riding to enjoy, green sea turtles to admire, several grottos to explore, lots of fine cuisine, great unpopulated beaches to dip your feet in, and almost no tourists. Use Terra Mare (125 bed resort, with Olympic. size pool, set in an orchard in Lixouri - 15-minute ferry ride from the capital, Argostoli) as your base of operations. Just sayin'....

You are correct that there are no flight from Meteora. I had googled it and got some results, but then realized they were from the Athens airport. So seems like renting a car is the best option since I'll have to go back to Athens anyway.

I had a look at it and Kefalonia looks lovely, but it's not very practical in terms of location. Would require me to rethink the whole trip.

I have seen things that made me want to go to Amorgos. Has anyone been there? Since I had a few suggestions for Naxos, I could easily do Naxos-Amorgos-Santorini.

I feel like I should stop looking for ideas cause that's just makes me upset that I can't go to all these beautiful places.

Amorgos IS beautiful and the fact that it is a slight hassle to get there makes it less overrun. there isn't a lot to do except relaxing and some hiking (and visiting Chozoviotissa monastery...). the few villages are pretty, however less impressive than the choras and villages of other islands imo.

getting there from Naxos with the small Express Scopelitis is fun (at least I think it is still running). onwards, you could even take a convenient catamaran to Santorini, alas thus missing out on the spectacular view when entering the Caldera.

I initially missed the detail that you would prefer bus to rental car on the islands - be aware that there are busses, but schedules are limited and geared towards locals, some places won't be served at all.

if you don't want to backtrack from Meteora, there are regional airports, too, e.g. Kozani - you will need to connect at Athens anyway. one-way car rentals are often free or incur only a small fee, so check what is more convenient to you.

personally, it would be ferry for me whenever possible, yet I understand it may not be an option for everyone.

I flew to Santorini from New York all on one ticket. The bus was easy to use to get around, from Fira to Akrotiri on one end and Oia on the other.
Then took the ferry to Naxos, great for beach time. Also, although I'm not big on bus tours, I took one that went all around the island with numerous stops so I didn't have to drive, and it was great.
Then flew to Athens from Naxos and ended the trip there.

Taking the bus from Athens to Delphi and Meteora can be done, but renting a car gives you a lot more freedom and comfort for this part of the journey. The drive is scenic and lets you stop at your own pace, and yes, you’ll need time to return the car to Athens unless you find a one-way rental. Plus, the flexibility will come in handy when exploring the majestic Meteora monasteries!
For that perfect island vibe, I’d suggest Naxos. It checks all your boxes: gorgeous beaches, picturesque old towns with lively plazas, plenty of restaurants with authentic Greek flavors, and excellent public transport.

Go to the Trip Advisor website. Find the forum advice page for each island you're considering. At the top of that page select "Things to do" to determine if that's an island you want to visit.

Turkish Airlines have actually the cheapest and almost fastest flights from Dallas or Housaon to Athens.
The sea water temperature at Rhodes (Eastern Coast) and Kasellorizo/Kas is about 19 degrees centigrade in early May and about 22 degrees in late May.
Cycladic Islands are more windy and seawater temperatues there are about 2 dgrees centigrade lower.
There aare direct buses from Athens to both, Delphi and Meteora (Kalambaka).
KTEL Trikkala has a daily bus from Delphi to Trikkala, where you can change to a Meteora bound bus.