8-days in Greece, Rhodes or Crete?
 

Our first time in Greece and we have 8 days free before taking a chartered boat through the Cyclades in October. We've already planned 4 nights in Athens, coming and going, and would like to spend some quality time on a few other islands that we won't be seeing on the sailing trip. We don't like touristy attractions. Rhodes sounds fascinating, although it's so far away; we're thinking of staying in the old town and driving around the island - 3 or 4 days. Crete also sounds interesting, but it's a big island so where to stay and for how long. Are there other islands that may give us a better feel for the country? Another question is how do we get from place to place without losing whole days in travel. Thanks for any insights you can give us.

In October the tourist season is almost over so the smaller islands will likely we in slow down mode. Thus looking at Rhodes and Crete makes sense.

You will want to fly to Rhodes as it is a long way by ferry.
Rhodes town is a good place to base yourselves. You won't need a car there until you decide to make some day trips. You might even consider changing locations and renting a car and relocate to Lindos. There are lots of nice day drives and ruined Crusader castles in this area.
Lindos and Rhodes http://www.flickr.com/photos/stanbr5...7634754696058/

Having said all that Crete too is a great place. By October you may not be looking for a beach holiday and Crete offers you three Venetian era cities with old town areas and harbours that date back 7 0r 800 years. You can fly into Chania or Heraklion. I would do Chania first simply because its a nicer airport. You can rent a car but frankly the bus transportation is inexpensive frequent and professional.
Chania will take you two to 4 days with day trips possible.
Chania http://www.flickr.com/photos/stanbr5...7632117917828/
Chania May 2016 https://www.flickr.com/photos/stanbr...57671465596275

You can then move on to Rethymnon. Its harbour is much smaller than Chanias but it does have a nice old town area plus the Fortezza.
Rethymnon https://www.flickr.com/photos/stanbr...57654700502270

Finally you can move on to Heraklion where you can visit Knossos and the museum and see its old town central area.
Heraklion https://www.flickr.com/photos/stanbr...57655935354556

Crete Archeological sites https://www.flickr.com/photos/stanbr...7645085297380/

You might think of spending time on the mainland instead of yet another island. Nafplio, in the Peloponnese, is only 2-3 hours by road from Athens, and has some of the most important historic sites of Greece in the area:
http://www.visitnafplio.com

I didn't mention Nafplio and the Peloponnese because the OP specified Islands however that is a good suggestion Heimdall.
Peloponnese Battle Castles https://www.flickr.com/photos/stanbr...7645468134284/
Nafplio and Peloponnese http://www.flickr.com/photos/stanbr5...7632094108982/

Chartered boat?

What type of boat? Are you employing a captain/ crew?

Crete and Rhodes or similar islands in many respects but I love the crusader history of Rhodes Town.

Crete probably has the edge on the standard of accommodation, there are some high standard hotels in Elounda.

Stanbr, so many people seem to think of Greece as only Athens and the islands, so I like to point out alternatives. The OP wrote: <i>"...how do we get from place to place without losing whole days in travel."</i> A short drive from Athens to Nafplio would fit that criterion, and there are interesting things to see on the way.

Athens - Rhodes: Book a cabin in a Bluestar ferry, leave Piraeus (port of Athens) at either 18.00 or 19.00 (acording to the day of the week), have dinner and breakfast in the board restaurant and arrive at Rhodos between 8 and 10am.

Why take the boat and travel at night, when OP can fly directly from Athens to Rhodes. They won't see anything at night anyway.

If they take the plane, they waste a lot more time (during the day, when they could do something more intelligent):
metro to airport: 50 min
check in time: 2 hrs
flight time: 1 hr
baggage claim: 30 min
waitiing time for airport bus: ca 20 min
airport journey time: 40 min
Total about 5 1/2 hrs

For internal flights there is no need to be 2 hours before the flight at the airport..
For me spending the night on a ferry is much more time consuming and eventually even more expensive if you add the price of the cabin and the meals.
There is a flight departing at 19:25 hrs ( picked a random day in October), that would leave enough time for the OP to see Athens on the departure day

Thank you to all who replied. This site is such a wealth of information because of your generosity. Thanks for the o/n ferry suggestion, but since we arrive Athens in the evening, I think we will fly to Rhodes after spending the first night at/near the Athens airport. Maybe take two nights in old Rhodes, then two in Lindos? Back to Athens and then fly to Crete? I appreciate the suggestion to fly into Chania, however, it is considerably more expensive than Heraklion, so we will probably fly in and out of that airport, and drive to Chania.

Thank you for mentioning Nafplio - I'm thinking about a day trip there while we are in Athens. Is that possible?
And...Would anyone recommend that we skip Rhodes and spend our first 4 days on the mainland?

Re the charter sailboat, we are renting a catamaran through Kiricoulis. We've done this before in Croatia and Sardinia. We have our own crew of 8 experienced sailors. In 10 days, I'm not sure how much of the Cyclades we will be able to cover and we will definitely not be able to get to Crete or Rhodes.

I feel you would get a more rounded experience of Greece if you spend part of it on the mainland outside of Athens. I suggested Nafplio because some of the most important archaeological sites in Greece are located nearby, and you could stop at the Corinth Canal on the way from Athens. Have a close look at the Visit Nafplio link I provided in the earlier post.

Heimdal, thank you for your suggestion. We've decided to go directly to nafplio the day after we arrive and spend two nights in the area. Where do you suggest we stay? We will have a car.

I was in Rhodes - for the third time - about three years ago. The old town is certainly very touristy but still interesting to explore. If you can rent a car and drive along the perimeter of the island, stopping at some beach clubs or other quiet locations, it's quite beautiful and relaxing. So the island offers a mixture of sightseeing and resort time. I have flown to/from Rhodes from Athens and I have taken a ferry from Marmaris, Turkey.

You won't regret going to Nafplio! I'm not the best person to ask about hotels, but maybe stanbr or someone else can be of more help.

On our first visit to Nafplio we just parked the car and started walking around looking for a hotel. Shoulder season can give you some bargains on a walk up basis. The first time we drove on the main waterfront road. It gets smaller as you go and eventually turns left into the town. It looks like you are going nowhere but in fact it keeps going and starts to go up. At the top it ends at a parking lot. The whole area up there is full of little pensions. We found Elaini less than 100 meters from the parking lot. We have stayed there twice. Ask to see a room. If you like it ask for a price.

As I said its high up in the town so it is quiet and there are great views nearby. The problem for us now is walking up the stairs from the main waterfront area after dinner. Our knees are not up to it any more.
So on our next trip we looked for a hotel in the old town area near the waterfront.
We found hotel Agamemnon. It is right on the waterfront promenade with Bourtuzi fortress directly in front. The hotel was a bit tired but the price was right and location is unbeatable.
If you look at the Nafplio images I posted images from the hotel are there.

Three or four days is simply not enough for Rhodes or Crete.

Thank you again for the information on Nafplio, stanbr, and the great photos! And thank you komodo for the roadmap. I am close to finalizing the trip - I only wish I had checked in here before booking the flights. I would have allotted more time!

There are a number of great seaside villages in Laconia and Messenia, any of which could be mistaken for an island. Here are a few photos of the area around Kalamata, including Pylos, Methoni, and Koroni, also Ancient Messene and a nearby monastery: https://www.flickr.com/photos/heimda...57627739427148