Looking for ideas!!! We are trying to plan a trip for May this year. Hubby and I (in our 50s) will meet up with our sons 20 and 23 somewhere in Europe for a 7-10 trip. One will be in Tel Aviv other in Northern Italy.

We have been to Greece on cruises (but kids haven't - but they have been all over Europe).

Trying to decide if its better to book a cruise to all do together (like RCCL or Celebrity) or if its a better idea to go at this on our own- maybe even use hotel points. Not sure which islands to focus on - if I plan it without cruise. We all like to be active - dont want to lay on the beach for days on end, Im sure kids would like nightlife time as well.

May is still low season and I want to take advantage of less crowds and less heat.
Any advice?

The only advice I will give is this: if you like cruising, go on a cruise and you will spend most of your time aboard ship. If you want to see Greece, fly into Athens and spend some time there and maybe one or two islands. If you have time, a trip to Delphi would be amazing. You will see much more if you spend three nights on an island than the 8 or 10 hours the cruise ship will allow.

Highly recommend the Star Clippers Northern Cyclades cruise.
Nothing like a traditional cruise line & the ship itself is an adventure. Small, so better access to smaller ports.
Day in Ephesus was a highlight for me. Mykonos will appeal to your sons.

When you go on a cruise, you don't spend a lot of time at your destination. And because you have visited Greece on cruises, this time I highly recommend flying to Greece and visiting on your own so you can spend more time at each destination.

What are your interests? Do you like history, ruins, museums, beaches, beautiful scenery? Do you also want to visit the mainland?

A possible itinerary could be Santorini (3 nights), Naxos (4 nights), and Athens (3 nights). Or visit only one island and spend some time in Nafplio on the Peloponnese Peninsula where you can visit ancient ruins such as Mycenae, Epidaurus, and Mystras, amongst others.

I suggest Turkey instead: 3 full days in Cappadocia, the rest in Istanbul.

Reading and researching and I am over the big cruise idea (the cruise we did was a smaller ship.) I dont think its the right fit for our family,

Our ideal trip includes history, ruins, culture, food, biking, hiking, rock climbing (the kids), water sports, cooking, nature, maybe even diving (Hubby and boys certified - not me.). I also think the kids want nightlight for some of the trip.

How about Crete? It's got a bit of everything and may be more convenient flight-wise. I'd like the idea of not hopping around and dealing with ferries or extra flights but enjoying all that one island can offer. I've got a tentative plan for one day: flying into Heraklion (to see Minoan ruins), out of Chania (beautiful town for the final few days) with some nature in between.

Will research Crete!! Thanks!!

Crete is easy to get to from Athens, lots to see and do there, ruins, great beaches, hiking, interesting towns. I wouldn’t visit Santorini- you are really late planning and most hotels are already booked. You also might like Naxos or Paros.

I would think since our plan is May - availability on all the islands will still be good. I haven't started yet fully researching yet - but wondering when high season kicks in.

You shouldn’t have a problem with room availability in late May. By then all the hotels and rooms (domatia) will have opened for the season, but won’t be booked to full capacity until July or August. You might want to expand your search to apartments as well as rooms so you could all stay together. Another option is to look for a villa, but most are out of town, requiring a car, and have minimum stays of four days or more.

I am so glad you are not doing a cruise! Those big ships are awful and the small ships would be too boring for your sons. We actually did a small cruise and loved it, we were all day, every day in a port and slept through to the new location. We actually got off early in Santorini to spend more time there. But the nightlife was nonexistent and your sons would be out of place.

Our daughter and her husband honeymooned in Mykonos, Santorini and Athens and loved it. I would not recommend Santorini for the 4 of you.It is more of a romantic location. May is not peak season, but it is busy, I would start locking up accommodations. We went in May and so did our daughter. Mykonos was not crazy yet, but I don't if it would be active enough for your sons in May. Crete is a fantastic idea, especially if you get a car. Others here would be better advisors about nightlife locations, but of course Athens was great.

We are back (well for a few weeks now)
We did Athens - 2 nights
Flew to Santorini - 3 nights
Ferry to Naxos - 3 nights
Ferry to Mykonos - 3 nights - flight from Mykonos - Zurich - Miami (we didn't go back through Athens)

Everyone loved it all -
Santorini wasn't too romantic - the kids actually went out in Fira and there were lots of young 20 somethings out and partying. We did the 3 hour Fira - Oia hike which is just gorgeous.
We had a car in Naxos which was perfect and got to do the Mt Zas hike which took 5.5 hours round trip - it was HARD - and I loved it!!
We had a car for 24 hours in Mykonos which was cool - we went away from Old Town up into the interior and did a guided bike tour with Yummy Pedals - which we loved - then enjoyed farm to table lunch at their vineyard.

Try searching Terra Mare Resort in Lixouri, Greece (a 20-minute ferry ride across the harbour from the capital - Argostoli), on the island of Cephalonia in the Ionian archipelago. Renting a car will provide you with opportunity to visit the famous Myrtos Beach, Melissani Cave/Lake, Drogarati Cave, horseback riding at Bavarian Stables, various archeological sites, sea turtle hatchings....and did I mention the restaurants? Enjoy! If you need more detail...please reach out.

My husband and I are planning a similar trip for May '24 but without Mykonos. Would love to know where you stayed, ate, car rental, etc. Thanks!

I booked our trip really last minute so our lodging options were limited! In Santorini we stayed about a 5-10 minute walk to Fira at https://oramasantorini.com/ which was lovely and comfortable - but if I could choose I would have liked to be facing the Caldera in Fira, Imerovigli, or Oia.
In Naxos we stayed at https://naxiansecret.com/ which was very lovely - but too far to walk for Naxos town. Once we arrived we realized we needed the car and they arranged for it to be delivered to us at the hotel - SO EASY!! The rental company was Akrogiali. Our favorite meals in Naxos were at Doukato and To Elliniko.

Firstly, let me say I am sorry for your unfortunate circumstances, if you interacted with Hurricane Idalia, given your moniker MiamiBeachMomma. More to follow...

We stayed at the Royal Olympic Hotel in Athens initially and rented from Kosmos Rent-A-Car right (around the corner from the hotel). The hotel offers the most comprehensive breakfast buffet I've ever experienced from their rooftop venue and offers an incredible view of the Acropolis.

In Athens, I would heartily recommend Ydria Cafe Restaurant (for Moussaka, Souvlaki. Spaghetti, etc.) which is located in the Plaka.

We rented a Volkswagen Polo, and had the car for 14 days.