Claudina

We are going to Greece for the first time in mid-May for 9 days with our two daughters who are in their twenties, flying in and out of Athens. We want to spend a day or two in Athens and then explore the islands. Which islands would you visit? How many days in each island? Airbnbs to recommend? Must do activities? Thanks! I know this community has a wealth of knowledge and a passion for travel like we do!

KarenWoo

Which islands is subjective and depends, of course, on your interests. In May 2022 we visited Santorini and Naxos. Some people will suggest not visiting Santorini because of the crowds. Some people say they couldn't wait to leave Santorini. We didn't feel that way at all. Despite the crowds, IMO Santorini is worth visiting for its unique beauty and caldera views. We spent 3 nights and loved every minute of our visit. I recommend a minimum of 3 nights so that you can explore/hike on the caldera and the caldera villages, such as Firestefani, Fira, Oia and Imerovigli. Then rent a car for a day to explore Santorini. We did just that and it was one of the best days of our trip. We visited the Akrotiri Archaeological site, red sand beach, and black sand beach. There are also some villages and wineries you can visit. Santorini doesn't have to be expensive. We had a lovely room at Blue Dolphin Suites, with a patio overlooking the caldera for $230 per night.

Naxos is 2 hours from Santorini via the Blue Star Ferry. It's very different from Santorini. Less crowded. We spent 4 nights here. Rented a car for a day to explore Naxos, stopping at mountain villages and fishing villages with one of the best lunches on our trip.

I've heard that Paros and Antiparos are very nice as well.

If you can, I suggest flying directly to one of the islands first, such as Santorini. Then make your way back to Athens and spend the last couple nights of your trip in Athens. If you choose Naxos as your second island, you can then fly from Naxos to Athens Airport.

Some good guidebooks to help you plan are Lonely Planet, Michelin Green Guide, Rough Guides, and Fodors.

neckervd

2 days is the absolute minimum for Athens, even without museums and churches.
Islands: Mykonos and Santorini are well known for crowds of foreign tourists and high prices.
All other Islands are OK.
For stunning cycladic architecture, you may check Sifnos or Astypalea.
Rhodos has usually the warmest (less icy) seawater in May.

brotherleelove2004

Choose an island with an airport so you can fly there as soon as you reach Athens. Save Athens for the end so aren't scrambling at the last minute to return to the mainland in case of a strike, delay, mechanical breakdown or very bad weather.

TravellerSince1970

Everyone will send you to the Santorini's of this world, and Mykonos, et al, but I think you may want to consider Kefalonia (Cephalonia). It has great beaches (the 2nd most photographed in the world - Myrtos), it is not touristy, has Horseback riding (near Sami), has great food, has caves & grottos to discover, has resorts with Olympic-size swimming pools (i.e. - Terra Mare in Lixouri), you could volunteer time at a sea turtle sanctuary, they have an airport & car/bike rental, etc. Good luck!

TravellerSince1970

It sounds like a very hot time of the year that you've chosen (I would prefer either May or September), however I would respectfully suggest another, lesser known, island option.

Everyone will send you to the Santorini's of this world, and Mykonos, et al, but I think you may want to consider Kefalonia (Cephalonia).

It has great beaches (the 2nd most photographed in the world - Myrtos), it is not touristy, has Horseback riding (near Sami), has great food, has caves & grottos to discover, has resorts with Olympic-size swimming pools (i.e. - Terra Mare in Lixouri), you could volunteer time at a sea turtle sanctuary, they have an airport & car/bike rental, etc.

Good luck!