Starting to plan a Crete/Santorini trip mid May (after Easter ) for myself and daughters (me 70s/daughters 40s). Reason for Santorini is the Fira to Oia walk and just to see beauty there. Mostly focused on Crete. Focusing on Chania and Rethymno areas. Will rent a car. Want to see Elafonisi Beach and do Imbros Gorge. Not interested in archaeological sites. Here are my questions to get started:

1. Should we stay in one location…Chania?
2. Better to start in Santorini or Crete?
3. Best way to get between islands…ferry or fly?

This travel board has been a great help on previous trips so I appreciate your advice!

A lot depends on your preferences, but FWIW, I'd start in Santorini, which I found utterly disappointing. In contrast, I loved Crete.

For the places you mention in Crete, Chania should work.

Ferry would likely be a bit quicker, but you'd have to check the schedules. You can start with rome2rio.

You might find some information of use in my trip report:
With Gratitude for a Glorious Solo Month in Greece

Crete is truly wonderful. Enjoy!

AFAIK, there are no nonstop flights between Santorini and Crete, so you will have to fly back to Athens and change airplanes there. High speed ferries between the two islands take just over two hours, so time wise ferries beat flights. Usually the ferries stop at Heraklion, and you will have to add travel time to Chania or Rethymno to your 2+ time by ferry.

Flights from Athens go to both Heraklion and Chania. Sometimes there are seat sales for connecting flights, so check before you decide. Crete is a very large island, and basing yourself in one place (eg Chania) doesn’t make sense to me. If you flew from Athens to Chania, based yourself for part of the time there, but then moved on to Heraklion before taking a ferry to Santorini would make sense logistically.

We caught the overnight ferry from the port close to Chania, to Piraeus. Cabin with twin beds and bathroom. Then caught an onward ferry to another island. It worked well for us, perhaps another option to look at. We loved Chania, very hospitable people.

There will most probably be a daily seajets catamaran Heraklion dp 8.00 - Santorini ar 10.00.

For daytrips to Elafonissi, Falassarna or Imbros Gorge, I would stay at Chania.
Rethymnon can be visited during a stop over between Heraklion an Cania.

We spent 8 days on Crete this July, in Heraklion and Chania. As someone mentioned up thread, ferries to Santorini go from Heraklion. We had a friend with us who did a day trip there and back, but that’s not something I would recommend.

Either fly in Santorini, ferry to Heraklion and then take a bus/car to Chania and wherever else you want to go. Or do it in the reverse. There are direct flights from Athens into both Heraklion and Chania.

Imbros Gorge would be lovely, we weren’t able to fit it in as temperatures were 100+ in July and we decided against it. Sadly, as I am unlikely to go back again.

I flew directly from Heraklion to Santorini, but maybe flight options have changed.

I'd consider skipping Santorini. Look at the travel posters, instead, and spend your time on Crete.
Santorini is undoubtedly beautiful but talk about over tourism...... My most recent trip was back in 2005 and it was truly awful. Even the restaurants--completely oriented towards the foreign masses.
Gorgeous but lacking any kind of soul. Overpriced accommodations, too.
Plenty of great hikes on Crete.

A great time to go, and a wonderful trip if planned right. To help you best we need to know how many Days you have (not counting ttake-off day, arrival day & departure day).
If it's 2 weeks, no prob... IF only 12 days plus those 3 travel days, you must be very transit efficient. On Arrival, allow 2 hr layover, then FLY to Island #1 .... after stay Ferry to Island #2... then FLY back to ATH airport for optional 2 days in Athens (you did not say whether you want to spend any time there...and although it is one of the world's great historic places, we don't want to press, if archeology is a yawn for you).

The KEY THing for Santorini is ttiming -- to avoid the awful crruise-crowd crush (even in May) on week-days, 3 megacruisers = 10,000 psgrs, PLUS all the ferry & jetplane tour groups. Ugh. Best scheme - Weekend has fewest cruise ships, so arrive Friday noon .,. leave by Monday aft. THis can be done 2 ways depending on trip length

12 DAY STAY -- Book aTHURSDAY flight that's NONStop from US east Coast -- those all arrive between 9 - 11 AM Friday -- get a 1 pm Domestic flight (Aegean Air or Sky Express) to Santorini... you can be on your balcony by 3 pm. Enjoy Sat-Sun in Santorini.; I recommend Staying in FIroStephani, NOT Oia or Fir.. (hotel &Sightseeing tips later). On Monday, 5pm - ferry to Heraklion CRETE ,... and then a smooth 2-hr bus along scenic north coast to CHANIA. Stay 5-6 days, then fly to ATH. NOTE: you always need to be at least in Athens area night before yur homebound flight ... same-day connection too iffy (and costly! if there's a delay/cancellation)

2 WEEK STAY (lv on 3rd SundaY) -- IN this case also book an Nonstop overnight flight from US, but you can do it on Fri or Sat.. Same AM Arrival befdre Noon; take domestic flight direct to CHANIA. you can enjoy 5 days there ... plan to bus or car rental on Thursday afdternoon to HERAKLION in order to get Friday 9 am Morning Hi-speed Ferry tio Santorini, arrive noon. After a weekend there, you might have 4-5 days left in Greece. If you don't want to see Athens, you might take a 2 hour BLUE STAR large open-deck ferry to NAXOS... a gorgeous island... for 3 days, then fly back to ATH, stay at a beach hotel near airport the night before leaving. Aanother 3 day option is the Stunnning town of Nafplio, at the tip of a peninsula, only 2.5 hours away from Athens but like a world away.

I can provide TONS if info (and foto-albums) on hotels, sightseeing, hikes/strolls , adventures on all 3 places (I've done 13 trips to Greece, and on 9 of them, took along "newbie" friends). But first, tell us possible length of trip ... and which itinerary appeals more. BTW I agree that Mid-May (roughly 15th-30th is PERFECT ... best weather, everythings open, the biggest crowds haven't arrived, the sea is smooth as glass,and swimmable! No rain, but lots of greenery & flowers around.

I agree that IF you are flying though Athens, you should probably be there the night before ... but would note that you can probably fly from Crete to the U.S. with a connection elsewhere. And in any case, make sure the separate legs of your trip are on the same ticket.

1. For the location (since you will have a car), I understand why it seems tempting to just have one base. But in my experience, and since Crete is huge (and driving there might feel a bit exhausting) maybe it's better to split the island location in two and do day trips accordingly
2. As for the where to start, as ppl here have already mentioned I agree depends on where you are first landing in Greece.
3. I have personally never flew between islands, i have only taken the ferry. We have heavily relied on ferry hopper's app to organize our trips and have found it very useful. For example, for Crete Santorini I found the 2026 schedules here

Thank you so much for all tips and advice! I have been to Athens, Santorini and Naxos previously and only wanted to go back to Santorini so daughters could do the Oia/Fira walk. Now maybe thinking of not. Unfortunately only have 9 days (travel included in this) as they still work and have children at home.

I am looking at flights now (thanks for tip to stay in Athens for home departure).

I think maybe we will just stay in Crete so appreciate lodging, hikes and restaurants.

So thankful for all your help!

Glad to get the key facts... agree that -- with just 6 days -- best to stick to wonderful Crete. Luckily, by Mid-May, a wonderful SMALL-group (12 max in mini-bus) Tour outfit will be operating ... Called Wanderlust TOurs -- https://wanderlustchania.gr Run by a mother-daughter team, it has marvy tours, either half-day or full-day. Consider Balos & Falassarna beach tour .. or the short Falassarna Evening tour -- the SUNSET there is Magic. I suggest you use their website email to contact them in off-season and get full details. A fellow Chania-fan, top forums contributor "Stanbr" has been to Chania a dozen times, but now no longer drives. He & spouse LOVED these tours -- I can give lilnks to his photo albums of tours AND Chania. Wanderlust has a tour going down Imbros plus boatride to Loutro & back, but you want to Walk Imbros. I did and it's FAB. I advise rent car to Imbros entry... at end of walk (an easy 3-3.5 hour stint even if you stop for picnic-lunch hafway). At end u walk half a mile to a taverna where "taxis" (pick-up trucks) drive you back up the super-twisty rimside road (26 switchbacks!) for about €30. WARNING: whatever age, take a walking-stick!! IMbros path is all soft-ball-size ROCKS, so balancing is knee-stressful. A stick helps! Amazon has EARTHTREK foldables (collapses like a W, to size of a book!). Easy packable, regular & short-sizes, about $30.

BEST CHANIA location -- LEft Side of Old TOwn HArbor, up one street -- on Theotokopoulu St, wonderful car-free flagstoned lane... leads up right from harbor. Many small pensions, family-owned small hotels, studio, etc. many w kitchenettes if u want to do bkfst -- all have coffeemakers & fridges. On seaward end, great views from balconies or roof, look at HOtel Palazzo, funny quirky Casa Di Pietra, Hera Studios. ANemone Apts, Casa Veneta, Jason (Iason) Studios. Down the lane a bit, Studios Nora. TIP - do NOT get hung up on gettng a triple room much better availabilites if you choose single + double, and in May, in small places, prices V reasonable. & remember, you then get 2 bathrooms - in a triple, the 3rd bed is often a foldout & you want comfort for a 5-6 day stay. More later on dining, walks etc, if interested.

With your limited time, limiting yourselves to Crete -- and for that matter, western Crete -- makes sense to me. It is very easy to visit independently; no need for a tour unless that's your preference.

Restaurants in Chania: Glossitses and Tamam for dinner; Aroma for breakfasts.
Restaurant in Rethymno: Avli.

Kja, I believe some years ago Sky Express (a Crete based airline) had direct flights from Heraklion to Santorini, but as I wrote above, afaik there are none currently.

Thanks, Heimdall!

OP HBO,
For Crete, I might suggest going up into the highest and farthest mountain villages. They can feel a long way from the more trodden coastal towns.
I am done. the authentic

I am back from my original post and once again, thanks to all for replies and excellent advice. We are now a party of 6 people. Our AirBnB is booked and flights. We are traveling directly from Dulles-Athens-Chania. Two questions, I now need help with:

1. Should I book the rental car at the airport?
2. Anyone that has hiked the Samaria Gorge, I am 73, exercise and no knee issues, is it doable for me? I know the younger ones are interested in it.

That's it! Hope to hear and anything else you want to respond.

Coming from the U.S., you will not be safe to drive for at least 36 hours after arrival ... and that means not safe for you or for anyone else on the roads. So no, most definitely do NOT plan on picking your rental up at the airport.

I hiked the Imbros Gorge, not the Samaria Gorge, and so can't answer.

As above. A taxi ride from Chania airport into town is easy and affordable.

The Samaria Gorge hike is not short, but very easy. Good shoes would be a advantage nevertheless.