June itinerary for Greek islands with so many family needs

It would be nice if you could drop Santorini or Mykonos( liked it more than Santorini) for a more a more authentic Greek island like Paros or Naxos. We went to Oia on our first trip to Greece. Very pretty but crowded and looked Greek, but didn’t feel Greek like Paros and Crete. Do not stay at Esperas in Oia. It would not be good for children or, perhaps, the grandparents. Lots of steps up and down, climbing all the time. No railings where we were. We love Greece and have friends there. But we did like the atmosphere of Santorini and wished we could have left a day earlier than planned.
Actually, be very careful when booking a hotel to check how steep it is between some parts of the hotel to others.
In Mykonos we stayed at Petasos Beach Resort which would be quite good for a family of varying ages.
In your “heading north” itinerary, is there a way to include beautiful Napflion too? Napflion and Chania, my favorites!
One night in Heraklion is enough. Just visit Knossos and Archeological museum if it has reopened. Then go go Chania!

I'm going to say don't DIY, pay for the knowledge and experience of a good travel agent

Apparently you want to spend 8 or 9 nights in 3 islands, including Crete, plus Athens, which is totally unrealistic.
I have the feeling that you are confusing Greece and its islands with a Disneyland park where you can go from one attraction to another in a few minutes.

You are not going to visit or travel. All you are going to do is move your family from one place to another, spending your time on ferries, port-to-hotel / hotel-to-port transfers, waiting hours at ports, rooms checkin / checkout formalities, packing, unpacking, etc.
It's already complicated enough alone or as a couple. At 6 or 8 with kids and grandparents, for your first time in Greece, it's a guaranteed mess.

Except to see Delos, why would you want to go to Mykonos? Partying all night with your whole family listening to rap music and drinking cocktails?
This is mainly why people go to Mykonos. (plus some naïves manipulated by tourist marketing who believe that's only where they'll see white and blue houses and windmills)

Remove Mykonos from your schedule, you will save time, money (a lot of money). Explain to MIL that you can visit Delos from Paros or Naxos. In addition, day trips to Delos from Paros or Naxos stop for a few hours in Mykonos, and so MIL will have seen Mykonos.

Do you know what time your flight arrives in Athens?
Ferries do not depart all day. The few ferries that depart in the afternoon usually depart from Piraeus around 5:00 p.m.

It will take you at least 90 minutes to pass immigration control, collect your luggage and leave the airport.
At least one more hour to reach the port of Piraeus (I'm not talking about the Port of Rafina since I eliminated Mykonos for you)
You'll have to be at least 30 minutes at the port before the departure of the ferry, longer if you have not collected your ferry tickets.

So, if your flight arrives after 1:30 p.m., you are unlikely to be able to catch a ferry on the same day.

Since MIL wants to see Santorini and I have already removed Mykonos from your planning (sorry) , let's go for Santorini.
Note that a Piraeus - Santorini highspeed ferry trip will cost you more than €700 for 8 passengers, as expensive as a flight (and sometimes more expensive).
It's about 2 times cheaper by traditional ferry but the trip takes more than 7 hours.

Crete is an island that requires at least a one week stay (to see 50% of it)
Staying there for 2 or 3 nights is really not reasonable and does not honor this island.
About 16 useful hours to see the Minoan culture. It's a joke, right?

I agree with a lot of what JoLui has said. You are trying to cram in way too much for 8 to 9 nights. You are trying to visit 4 destinations in 8 or 9 nights. I find it difficult to believe that the children and grandparents won't become exhausted and resentful doing all this traveling. If all of you are not early risers, and are not on the same page for sightseeing, when to wake up, etc. it will be very difficult to do a lot in one day. Moving around a lot of people is going to be difficult and time consuming, and will consume too much of your time and leave you with not enough time for sightseeing and enjoying Greece.

Both Mykonos and Santorini are expensive, touristy and crowded islands. We visited Santorini which we loved and I think it is worth seeing at least once in your lifetime. I can't comment on Mykonos because I haven't been there. But I would definitely eliminate one of those islands. I agree with JoLui's suggestion to visit Naxos or Paros, which are quieter and more laid back. You can take the Blue Star Ferry from Santorini to Naxos and/or Paros.

I have not been to Crete but I am not sure it is worth it to visit Crete for 2 or 3 nights. It is a very large island with lots to do and see. But if it is important to you to visit Crete, then take the 2 nights from Mykonos and add it to Crete for a total of 5 nights.

All of these replies have been so helpful. I was concerned about the initial plans and you've confirmed my approach is wrong. I need to slow it down so we can actually enjoy this vacation. I'm hopeful to add in one or two islands to our already packed trip but I know I need to readjust my thinking and keep it simple and relaxing. Thank you everyone!

Don't turn what is supposed to be a vacation and fun time into a constant rush and hours of stress.

With ferry trips (and even with domestic flights), 3 nights on an island means about twenty hours available without planning and organization concerns to take advantage of it. Most of those hours with temperatures likely over 85°F during late June/early July.

No crystal ball is required to predict the typical early morning (if everyone is awake) with parents who want to see some old stones, grandparents who want to rest, and kids who prefer to go to the beach.

.

Have you considered a cruise? Norwegian has one leaving June 11:
Athens (Piraeus),Greece
Rhodes,Greece
Bodrum,Turkey
Mykonos,Greece
Paros,Greece
Heraklion,Crete
Santorini,Greece
Athens (Piraeus),Greece

Somebody (apparently you) is going to need to take charge, grasp the bull by the horns, and read the riot act to everyone (well, maybe no lectures...), but your initial approach suggests to me that too many people seem to have unrealistic and incompatible expectations. Traveling solo, you get to make all the choices. Once you start adding others, it may look like a democracy for a while, but soon you need someone to pick up the ball, lay down the law, and make sure that Decisions Will Be Made and everyone understands they're not all going to get everything they want. With every additional person that you add, things get more complicated and potentially more chaotic. Everybody's going to need to compromise, and someone is going to have to call balls and strikes. Embrace that role!

First task: Get clarity about who is, and who is not on the bus. Are there 4 of you, or 8? You can not begin to make a rational plan until you have that high-level question resolved.

Next task: Figure out exactly how long you really have - and get specific, pick real dates: they can be the actual dates you will depart from home and return, or proposed dates you might, but you need hard numbers for how many days you really have. Without that, you can't plan anything.

As you begin real-world planning, always remember this axiom:

A group only moves at the speed of it's slowest, crankiest, least energetic, least enthusiastic member.

The bigger the group, the slower you will move, and the less you will be able to pull off each day.

Doesn't mean you kick anyone off the bus, but it does mean that you (as the trip planner), and anyone else who wants to be on the bus, needs to have realistic expectations.

Good luck, and Carpe diem!

Before your northern swing, FOr steps 1 thru 5, if I count it right, you have at most 9 nights, which is 8.5 days at most (OR 8 nights which is 7.5 days at most. To try more than 2 island plus NO days in Athens is Insane. Ferries are mostly out of the question due to time required. Your family will hate staying in/around Heraklion.... its a big concrete city with no beach, heavy traffic. Santorini will be a costly Zoo of cruise crowds and nothing for kids to see/do (beaches are hot black cinders).

The unspoken factor (hinted at via "family village") is who's underwriting the trip, and does that affect whose must-list matters most? Are you willing to rent a large van, seating 6-8 people plus luggage (only possible if u can enforce 1 bag each, carry-on size) for your mainland "northern part" Possibly ditto, to enable 4 nights (3 days) in Crete? Or -- more sanely - book lodgings in a Crete place where u could use local transport?

The only halfway feasible thing I could suggest is: International flight(s) too ATH that arrive by MID-Morning (this requires nonstop from N America, NO Change in Europe) Then domestic flight to CHANIA Crete 4 nights (3 days) Next, 9:30 Ferry from HEraklion to Santorini. (3nights - 2 days). FLY All 6-8 back to ATH get van for your mainland expedition.

To make a CRETE holiday with this large 3-generation mix requires several Apartment units with kitchenettes, on or a short walk from beach, plus on-premises cafe & mini-mart & recreation PLUS local transport 15-20 mini busride to CHANIA Old town. The only place I've discovered, with good reviews from large groups like yours, is Golden Sands. This website - http://www.travel-to-crete.com/hotels/chrissiakti/goldensand/ gives best descript of facilities. (The hotel's own website disappeared during COVID Years) Another possibility is the "town beach" area just outside CHANIA Old Town - descript & apts/hotels - https://www.west-crete.com/chania-nea-chora.htm IF you email inquiring for either, you MUST give specific dates, and if you can find accoms to suit your group in 2-3 units you'll be VERY lucky. Places like these have local bus right by premises, give you flexibility.

All 6 - 8 of you would have to get to Heraklion early intheAM to catch a ferry to SANTORINII -- by 8:30 latest for either 9 am or 9:30 daily ferry. Are u able to wrassle everybody up & out by 6 am to get to dock by 8 or so? If not, you'll have to spend a night in HERaklion area. Eeek. In Santorini (2 nights?) I warn highly against staying in OIA, first for cost, and then for huge crowds filling the lanes between 10 am- 4 pm, and then again 6:30pm- 9:30l. SEe if u can find anything in FIROSTEPHAN (It also is on the cliff edge with the famous view, and walkable to FIra town, also has bus service) ... you would need at least 2 units sleeping 4 each -- I think you already are late to locate anything under $1,000 - $1,200 per night, and I'm not talking luxury either. At best a BR + a LR w 2 daybeds.

Following your 2 evenings enjoying The Famous View, you would need to b ook domestic Air back to ATH Airport (the best ferry is not the fast one, but BLUE STAR LArge ferries, which would take a full day). You can pick up Van at airport. I really think that you need to consider a greece-based Travel Agency for your challenge. THere are 3 rellable ones, Athens-based, that are well-reviewed on these forums for working online w N Americans. Dolphin-Hellas, Fantasy Travel, Aegean Thesaurus. IF my rough itinerary suggestions appeal, I suggest sending identical emails to each WITH details & budget range for lodgings. THen u can compare promptness & pricing. Good luck -- and please remember, you cannot please everyone. That way lies madness.