Crete and Rhodes

In June we spent about 8 1/2 days of our two week trip to Greece in Crete and absolutely loved it. Thinking about that trip still makes me smile. We have some similar preferences: we don't lay on the beach and love historical sites. You might be interested in our trip report: https://community.ricksteves.com/travel-forum/trip-reports/two-week-trip-to-crete-and-greek-mainland If I had 5 days in Crete I might:
* spend one day in Heraklio seeing Knossos and the National Museum
* 1 1/2 days to either (a) to drive down to the Phaistos area to see museums and walk on Kommos beach and get into the countryside, or (b) northern Amari Valley with church frescoes, Moni Arkadiou, Eleftherna museum
* remaining time in the Chania area, with possible daytrips to Elafonisi or Balos Beach, Imbros Gorge or other closer sights depending on energy levels

Lonely Planet and Rough Guide really helped with trip planning, and all the great advice on this forum.

If you want to do both islands without wasting time in transit you are going to have to do some homework and research. From Crete to Rhodes here is only one ferry per week and it takes forever. IF you fly via Aegean Air , you have to fly back to Athens & change planes. Sky Express runs a direct flight from Heraklion to Rhodes or vice versa (I see some dates in September), but I am not sure if they run those flights in May as well... I do know their website says N/A for 2019 May. Also, do be aware that there are different prices for different weights of checked bags.

Your problem is that from Santorinit to Crete the only ferry goes to Heraklion. You don't want to miss Chania, so you'll have to bus or drive west. Then you'd have to backtrack to Heraklion airport to catch Sky Express to Rhodes.

A more efficient itinerary can be possible if you time it right ... 2 or 3 x per week, a modern BLUE STAR Ferry stops at Santorini just after midnight... I think abot 12:30 then goes express to Rhodes, docking about 8 AM. You could get a cabin & sail while you sleep! After 4 days in Rhodes (I'd allot less to rhodes than Crete), you could take Sky Express to Heraklion, then head west to Chania, and on your last day, fly from Chnia to ATH.

8 - 10 days between Rhodes & Crete, is, in my opinion not enough, as it's 3 -4 days without the travelling days.
Do you really want to go to Rhodes? As 10 days in Crete is just long enough to realise you are only just scratching the surface!

If it was my trip, I would go by ferry (1 of the big fast sea cats) from Santorini to Heraklion.
Spend a couple of days in Heraklion, visit Knossos & the wonderful Archaeological museum, then a couple of days perhaps on the South Coast/ Zaros area, as mentioned before, to see Phasitos & Gortys. I'd then head to Chania, one of the most beautiful towns in Greece. A couple of days for the city, to wander the tiny alleyways behind the Venetian harbour, a couple of days either in a small beach town in Apokoronas region (just East of Chania) - look at Kalyves or Almyrida, where you can eat next to sea, & drive inland to some pretty countryside, charming tiny traditional villages, mountains.... perhaps a couple of days on the stunning South-West coast, by ferry to Loutro maybe..... These really are just a few of the highlights.
Then fly from Chania to Athens for your onward journey.

Love your itinerary suggestions & your trip report, Lia.
I'm lucky enough to live near Chania but I still get a thrill when people enjoy this island!

& of course the Botanic Park should be on your list, Panarra. As should Ancent Aptera, maybe a winery (Manousakis at Vatolakkos is a wonderful experience), maybe Balos or Elafonisi beaches, still nice to wander along in May. Sunset at Falasarna.
& I resisted mentionning Elounda or Kato Zakros as they are even further away & definitely too much for 10 days!

Thank you so much for all your advice/suggestions, they have helped us make much better decisions. We have decided to skip Rhodes this trip and focus on Crete and add an extra two days. We prefer Airbnbs, B&Bs or agritourisms to hotels, unless the hotels are small and locally owned. We would love some suggestions on those, too, if anyone would like to share their ideas. Again, thank you for taking the time to share your expertise.

Good decision to just do Crete. There is so much to do there. I suspect you will be planning your return trip even before you depart the island.
I think jwugg has provided you with excellent suggestions. You have to arrive at Heraklion by ferry so spend a few days there. Visit the old town and harbour area. stay in the central area its all walkable. You can do Knossos by local bus. If you are really into ancient sites then consider renting a car and driving to Central Crete for Minoen Phastos and the amazing Roman ruined City at Gortyz.
Crete Archeological sites https://www.flickr.com/photos/stanbr54/sets/72157645085297380/

Bus transportation is very good and inexpensive so you don't really need a car to get to Rethymnon and Chania.

We stay in the old town area of Chania. This area is full of back alleys and has a Venetian era harbour.
We like the area around Theotokopoulou street which is full of small hotels in every price range. The street is just a 2 minute walk to the harbour so its a great location but its quiet at night for sleeping. Most of these hotels are small and family run. We stay with Natalie at Pension Nora. She has two 400 year old Cretan houses tucked away in an alley plus a studio house with two rooms. Right next door is Pension Jason. We are budget travelers but as I said this area is full of hotels in every class.
Theotokopoulou St area http://www.flickr.com/photos/stanbr54/sets/72157632118491316/

As mentioned you can do day trips to Falasarna, Balos and Gramovossa and Elafinisi by bus or organized tours. You might also want to do a day trip to Rethymnon to visit the Fortezza or perhaps a south coast village.
Western Crete http://www.flickr.com/photos/stanbr54/sets/72157632115757899/

Aptera images 38-62 Balos Gramovossa images 79-106
Chania http://www.flickr.com/photos/stanbr54/sets/72157632117917828/

Just putting a mention in for Loutro, on the southern coast. It will take time to journey to and from that area, but Loutro is amazing. Low-rise hotels, a few great little bars, a nice choice of little restaurants right on the emerald blue, crystal clear water. Water taxis leaving to other locales, or you can ride the ferries along the southern coast. We didn't have time to take hikes from Loutro but there appear to be some great little beaches and I think you can rent water toys like kayaks. You get to Loutro via a short ferry ride from Hora Sfakia - it's not possible to get there by road. Depending on how active you are, you might want to try Imbros Gorge, which is very close by Hora Sfakia. IMO if you start at the bottom of the gorge and hike for an hour or so you've seen the best part. BTW in Loutro we stayed at the Sifis http://www.sifishotel-loutro.com/ The rooms are basic and a bit retro, which fit Loutro's vibe perfectly.

In Crete, stay in Chania, one of Greece’s most beautiful towns/cities. We spent two weeks there and barely scratched the surface of western Crete. There is so much to see and do.
Rhodes is so far east and difficult to combine with the Cyclades and Crete.
However, it is an interesting place to visit too. You probably will have to dly there from Athens.