2+ weeks in Crete in May

Looks great. One suggestion, however. You should carefully check out the Imbros Gorge hike. It looked too strenuous to us.

It sounds like a wonderful holiday.
Your Heraklion time is about right. The Venetian harbour and central old area is a good thing to add to the plan. You can easily spend a day in the central town.
Also its a great choice to head out to the airport to rent the car. A couple of years ago we rented a car for three weeks. We had no problems with driving but the 30 minutes we spent driving in the chaos of traffic in central Heraklion was terrifying.
Heraklion https://www.flickr.com/photos/stanbr54/sets/72157655935354556

South and central Crete is full of wonderful ancient sites. Phastos is an unrestored Knossos. Be sure to visit the summer palace at Agia Triada its just 3 or 4 kilometers from Phastos. For me the real treasure is Gortyz or Gortyn amd a few other spelling thrown in. It has a gated site that is interesting and quite compact. However after you leave that site the real adventure begins. The surrounding area is full of olive groves. Walk down the road and you will begin to see roman Columns lying in the olive groves. Wander into the groves and you will discover a half buried Roman city. There is a mostly buried amphitheater, a temple, the Governors Pratoreum the forum and even a statue still standing. It is an active archeological site and has a low wire fence but the views are unobstructed. On our last visit the gate was open and several of us were able to walk the whole site. Amazing.

Knossos, Phastos and Gortyz https://www.flickr.com/photos/stanbr54/sets/72157645085297380/
You might choose to stay at nearby Matala. There are Roman cave homes at this funky village.

While in the Amari valley do look for the private war museum. It is a very sobering experience.

Imbros gorge is a popular hike. Its fairly flat but I have been told that there are lots of round boulders and my knees won't survive that hike. However I do know there are two ways to do the hike. I will assume you want to start at the top. You can leave your car in the parking lot and hike down. At the bottom you will find a couple of tavernas. You can stop for a refreshment and ask them to call a taxi to take you up to the top to get your car. Beware the taxi might just be a local driver with a pick up truck. You could take the bus up to the top walk down and have a prearranged taxi pick up. The closest town is Chora Sfakion so that is a good jump off spot.
The ferry to Loutro departs from Chora Sfakion so park your car there.
You can also take the ferry to the bottom of the Samaria Gorge at Agia Roumeli. It arrives early enough for you to hike the flatter bottom section of the gorge. Its beautiful
Ferry trip Libyan Sea https://www.flickr.com/photos/stanbr54/sets/72157653434073393
Crete Libyan Sea villages https://www.flickr.com/photos/stanbr54/sets/72157645487373222/
Samaria Gorge hike the easy way. https://www.flickr.com/photos/stanbr54/albums/72157670610409530
You could spend the rest of the holiday in Chania. Keep the car and visit the beaches. Falasarna is about an hour away. There is also an ancient site there. If you have an I phone you can download an app that will recreate the building as they were in antiquity. You might also decide to stay at Falasarna but we do that as a day trip from Chania. Other recommended day trips are to Elafonissi and Balos Gramovosa. The latter requires a trip to Kissmos and a 7 hour boat excursion. Elafonissi can be reached by the KTEL bus as its a bit of a long drive.
Chania http://www.flickr.com/photos/stanbr54/sets/72157632117917828/
Theotokopoulou St area http://www.flickr.com/photos/stanbr54/sets/72157632118491316/
Gramovossa, Balos Elafonissi https://www.flickr.com/photos/stanbr54/albums/72157698932695812

Ancient Aptera, Melidoni Cave and village.

https://www.flickr.com/photos/stanbr54/albums/7215767211837963
Have fun.

stanbr:

I didn't realize the wealth of archeological sites in the south and central of the island. Most people know about Knossos but I've never heard of Phastos or Gortys. Both look amazing and haven't been altered and/or reconstructed like Knossos with the gaudy paintings done by the archeologist Arthur Evans.

Probably lots more not hyped like Knossos that may be just as important but not as well known.

The OPs trips sounds wonderful and I will have Crete on my to-go-back-to-list.

As usual, I agree heartily with expert Stanbr, so I shall just add some small tips to his scenario.

AMARI VALLEY -- Have never gone thru it, always longed to; was on the edge of it in one of the small towns where Nazis massacred to punish Cretan resistance. This website https://www.lifo.gr/team/lola/34139 - text in greek only - has still photos of one such atrocity in that area... pix were by a Wehrmacht photographer who couldn't live w. himself afterward & released photos to the press. One look at this experience under occupation -- & u will understand some Cretan attitudes even today.

MATALA - Even if u are not "beach people" this is a great place for a dip... splendid beach with that famous high bluff with caves... you can walk up there unless u have acrophobia. The hotel/pensions right on the sand are kinda packed together & a bit tacky, but just about ?1000 yards back, on left as u approach beach, is arrow to DIMITRI VILLA ... a swell place, beautifully landscaped, views to the mountains, great family-run place, their own cafe too.

IMBROS GORGE - shorter than Samaria but great views and simllarly narrow at the end - I did it in my late 60s & was OK afterward & next day (unlike Samaria which often requires a "recovery day"). Stanbr's right, it is all rocks, many the size of volleyballs & softballs, when u encounter ones the size of baseballs, it's a treat ... the main challenge is balance, so your knees work hardest - the solution is sturdy walking shoes and (a BIG Plus), trekking sticks - 2 apiece is swell, 1 apiece is a big help; on Amazon u can get terrific ones (Earthtrek) abt $27 USD that have 4 segments w central bungee cord, fold like a W down to 12", easy to pack.

FALASSARNA - 3 of us spent a memorable 2 nights there ... we got there by driving west from CHania, going down the Topolian GOrge road (spectacular) then at about ELON, turning west on small twisty road to the coast, then North to Falassarna. (it's a lot faster to just drive west from Chania). We booked at a family-run place -- Hotel Petalida - on a bluff overlooking beach & sunset. They have a main building with restaurant (considered the best seafood place in entire area)... family has its own fishingboat & serves Catch of the Day. But we asked for rooms in 1-story building right next to it, with patios on the view. Unbelieveable sunsets!!! Unlike all oher shores in Greece, Falassarna has (some) surf, created by wind since it's the westernmost place in all Greece... the wind comes all the way from Spain. About 500 yards from this cute place is a Hellenic/Roman ruins site, unfenced open 24/7. Amusing touches such as adjoining bathtubs.

For Loutro - park in Hora Sfakion. There is a parking lot in the center of town, up the hill from the ticket booth for the ferry. Usually there is an attendant wandering around who will gove you a ticket. In our case there wasnt when we departed but he was there when we returned 3 days later. We simply told him how long we'd been there and paid.
We stayed 3 nights in Loutro but would have been content with two. We hiked Imbros gorge top to bottom (you can do either), by taking a cab to the top and hiking back to Loutro. The cab was caught in Hora Sfakion, so we had to ferry there first. You can look at a map online to see what the best location for you to be the night (5.) depending on where you want to start/end, but Hora Sfakion was cute.
Matala beach was my teens' favorite, and ours too actually (we did much the same itinerary as you but in reverse), but we are a younger family (although generally beach averse)
You may want to keep the car once in Chania. We went on several day trips from there. While parking can be a challenge, we managed to find spots on a road near old town the 3 days we were there (with departures and returns). There are archeological sites, a renowned monastery (name? - ack), and several sites/beaches that require a drive (which are likely served by bus too but I prefer the freedom of my own transport)

Hi, I also believe that the itinerary looks amazing. Here are a few tips (I live on the island :-) )
For question 1 (Heraklion), it's really easy to go to Knossos by bus from the center, but also by car if you plan to rent it on the first day instead (having the car pick up on point number 2 confused me, are you going back to the airport to pick a car on your second day or after visiting the museum, the palace and the rest of the area?)
Once in Heraklio, I also recommend a visit to Heraklion's wine region. When in doubt, your hotel helpdesk would be able to help you choose a winery or a wine tour
For your question 6: Be aware that once you are in Loutro, you're already in the west, southwest - the park can be easily left in Chora Sfakion, once you cross Imbros (by car), you just need to turn west to reach Chora Sfakion, there are a few parking spaces near the harbor - Once you are in Loutro, catch a local boat to also visit Glyka Nera, or Marmara, 3 days in Loutro is a bit too much, maybe. Here you can check other beaches to see in the southern area.
For your question on point 7: I believe that staying one or two nights in Falassarna might be a great solution if you are planning to see the pink sand of Elafonisi as well as Balos. Here there are ideas for Falassarna (places to stay, where to eat and things to see), here for Elafonisi Beach, and this might help you plan the trip (driving vs not driving) to Balos.
For your question on point 10: I would like to add that if you are planning to spend 4 to 5 days in the old town of Chania, it's a great idea to go for a historic hotel in the district of Splantzia or in the Venetian quarter. There are options for every budget, and you can get a good harbor view from the rooftop bars that some of these hotels have. The rooftop bar is often much better for a sunset drink than the busier waterfront.
Hope you enjoy Crete and write back if you need more answers!

Wow! You all are awesome! Thank you so much for the useful and detailed information. I appreciate your taking the time to post. Gabi, we plan to spend 3 nights in Heraklion, 2 full days: day 1 the archeological museum, day 2 bus to Knossos, then on our exit day we will go to the airport to pick up a rental car and drive to the Phaestos/Agiofarango Gorge area. Thinking about staying 1 night in that area - suggestions? Rethinking the Imbros Gorge - it may be too challenging if it's really rocky. We're really getting excited about Crete!

Barbara I was 68 when I did the gorge, and did NOT have trekking sticks, just a crooked tree branch I grabbed at the last minute, and I'm not an athlete, just do Silver Sneakers exercise class at the gym. Y Ou can do it!

I was in Chania for 5N, then 2N in Heraklion. I loved Chania (not only because my name is Chani :-). It was a great place to just relax and explore slowly. I stayed at the Elia Palatina Hotel and recommend it. They have rooms with balconies with a harbor view. I had a city view room. The harbor view rooms seemed to be smaller than mine, but not at all tiny. In Heraklion, I spent about 2-3 hours at the museum (and I lingered) and about 1/2 day at the ruins (slowly). I had enough time to see the harbor and visit the Venetian Fortress and a couple other places in 1.5 days there. I stayed at a new hotel, the Dom Boutique, very modern, comfortable, superb breakfast. The rooms are a bit small and they were doing construction work while I was there, began around 9 am and was done by 7-8 pm, so no nighttime noise, but also no mid-afternoon naps.

Sorry for the delay in the reply, Barbara (is there a way to get a notification when you get an answer, I could have helped you earlier!) Anyways, yes I agree that doing the Heraklion part without the car is fine, As long as you cover the museums, the archaeological site of Knossos, the city center (there are a few things worth seeing), you'll be fine. If instead you'd like to include a visit to the wine region, or other more "inland" trips, either to the mountains or nearby villages, I would say that maybe picking the car earlier would be a money saver. Think it this way: you will spend less money hiring the car one day in advance than booking tours to take you to wineries, for instance. I don't know if you're aware, Heraklion is one of Greece's finest wine regions, and it's fairly easy to arrange a visit to a winery on your own (and cheaper than booking a winery visit through a tour company). In the region you can visit Lyrarakis, Gavalas, and a lot more wineries - the website wines of Crete has a list of all the wineries open to the public in Heraklion and in all regions of Crete.

About Agiofarago, It's doable of course, but not sure how time effective it would be. If I understood correctly you would be crossing the mountains to the south from Heraklion, spend the day there and then go back to the north to reach the west? Be aware that the only "good" road is the coastal highway on the north coast, there's no highway connecting all the southern villages so you find often in the position of zigzagging from north to south and back, and then to the south again when you want to visit several southern villages in a row (I hope this is clear?), Deep gorges and high mountain ranges won't allow the existence of a southern road connecting every southern village.

A good option could be to go down from Heraklion to Agio Farago, spend the time there and then try to go back passing through Matala, that way you will be seeing another beautiful southern village, and then start climbing back up to the northern coastal road. (Check the route Heraklion - Agiofarago - Matala on Google maps, I did and it looks good). If you are not sure about Matala, you can check here, where there are also plenty of other things to see in the area (Festos, Kommos, and stunning beaches). Let me know if you need more help. I'll try to check this conversation more often to see if you left a reply :-) Happy to be of help! (you will love Crete!)

Ah.. I forgot, where to stay near Agiofarago? The best places are Matala, Kalamaki, Kamilari or Pitsida when in the South... The closest place to stay near Agiofarago is Kali Limenes but it is a very small village. The distances are fairly short between all the villages and the beach itself, so if you have a car, none of the options I mentioned will be a problem. As soon as I get the link to a better resource on this (I'm looking for it), I'll post it here!