Hello Helpful Fodorites,
I am in the (very) early stage of planing our second trip to Greece for April of next year..
In April of 08, we stayed in Crete for 4 nights, Santorini for 2 nights, and Athens for 3.
We loved the islands and had great help from Stanbr, Brotherleelove, and Travelerjan.
Friends who have never been before are joining us next time. We are tempted to go back to Crete for 3 nighs, Santorini for 2, and skip Athens altogether, except for getting back to Athens the night before our flight home.
I know everyone travels differently but do you think we could fit it a third island such as Naxos, (stanbr, your pictures make me want to go) for 2 or 3 nights?
If we did this, what order would make the most sense?
We would have a total of 9 nights.
Thank you all in advance for your help.

Crete>Santorini>Naxos and Naxos>Santorini>Crete are the two most efficient routes. Which route you choose would depend on the ferry or plane connections you can make when you first arrive so as to not waste too much time getting to your first island. What those will be for next April is anyone's guess at this time. You'll have to wait to see what they will be.

If you're planning to fly, only Olympic Airlines flies to Naxos. If it's in your budget flying to your first island and back to Athens from your last makes the most sense time-wise and would give you enough time to go to Naxos. Otherwise stick to 2 islands.

While I do love Naxos 9 nights does stretch you pretty thin particularly if you plan to use the ferry. The ferry eats up a whole lot of a day by the time you check out of your hotel, wait for the ferry, take the ferry, arrive and then find a new hotel. Three island hops means you will use at least a day and a half around the ferry.

As Brotherlee says if you can fly to or from Naxos either to start or to end your vacation then you would have time to do all three.

If not then do the two you are familiar with. We have found that on second visits to an island we find the familiar sights and sounds to be relaxing and there will always be a new discovery to take delight in.

Lastly Naxos is well known for its beaches and in April you are a bit ahead of the beach crowd and Naxos will not be fully open for business as it is further north than Crete and Santorini.

Thank you both for your advice.
We would plan to fly between islands (vis Athens) like we did the last time but if Naxos is not fully operating maybe we'll skip it. While in Crete last time, we pretty much stayed in Chania so maybel next time we'll explore more of the island.
Are there day trips, by ferry, from either Crete or Santorini we could do if we stayed longer in each place?
Stanbr, in one of your older posts, you mentioned a boat ride that you had taken out of Chania, I believe, to see a fortress area that sounded intersting. Do you have any details on that?

We had intended to take an excursion boat around the Gramvousa Pennensula to Balos Lagoon and Gramvousa Island which has a Venetian fortress. However just as we got to the excursion port at Kissamos a huge storm blew up and we decided a boat ride would not be a good idea. We never had time to get back.
More info
http://www.cretetravel.com/Boat_trip...ousa_Balos.htm
or
http://www.gramvousa.com/

If boats are not your thing you could try the beach at Falassarna at the Cape of Koutri. It is about 55km from Chania.

If you decide to make this a two island trip then you will have time to spend say two nights in Athens at the end of the trip. There is lots to see in Athens Plaka area and it will be a shame for your friends to have so little time in Athens.
here is a new album I recently put together.
http://travel.webshots.com/album/570719132pdjjHG

Oh by the way if you can afford to fly you may want to look into sky express. They fly inter island from Heraklion to Santorini. Saves you a flight all the way back to Athens.
However as they use small aircraft baggage allowance can be a problem.

I just had another thought. Since you love Chania you could consider a visit to Nauplio. Beleive it or not I think it is even nicer than Chania. These are my two favorite cities in Greece. It too has Venetian influence with its three fortresses and old town.
It is only about a two hour drive from Athens airport so it is perfect place to start or end a vacation.
You could do Chania for three or 4 days days Santorini for two and Nauplio for two with that last night in Athens.

Nauplio feels like an island although it is on the mainland.

Here are Nauplio pictures.

http://travel.webshots.com/album/551991579dJbWvh

Stanbr,
I love the idea of staying in Nauplio!
What hotel did you stay at? We stayed at Pension Nora in Chania on your recommendation and loved it!
we've never rented a car when in Europe. Would we have to do that to get to Nuplio?

We rented the car off of the internet. Just Googled car rental Athens and dozens came up. I was actually looking for a 12 day rental and there were only a few that would supply for that lenght of time. We booked Pop's rent a car but had to cancel so have no actual experience with them.

There are others out there like Pops who will bring the car to you at the airport and thus you do not pay the airport fees. You meet them at a designated area and drop it off to them and away you go. The whole transaction took about 10 minutes total. We also rented from Ace Rent a car twice. Insurance was included.

Others on these forums recommend EconomyCarRentals.com.
They had the best deal and their prices include a zero deductible CDW. They are brokers. Also try AutoEurope.com
Again, they are brokers and the rental was through Europcar. AutoEurope says they will match any price you find elsewhere that is lower so they're worth checking... you can also phone them as they are based in Maine.
budget.gr site.

Depending on how far you have flown and how jet lagged you are Nauplio is a perfect place to relax and get over jet lag if one of you can drive right after getting a flight. If not then it is probably best left towards the end of your vacation.

In Nauplio we stayed at Pension Eleni
http://www.clickhere.gr/hotels-greec...ionelenien.htm
Make sure you get an upper level room. The first floor rooms open directly onto the roadway.
Just a few meters from Eleni is Jan's favorite, Hotel Leto.
The nice thing about this location is there is a parking lot in the square where you can park for free and it is only about a 50 meter walk to the hotels.
Nauplio is built on a mountainside and many people are quite surprised when they find they can not park anywhere near their hotel.
I can provide directions to the parking lot if you decide to book one of the nearby hotels.

I also have pictures of day trips from Nauplio.

http://travel.webshots.com/album/570747214TsFWOw

Stanbr, Thank you so much for your help.
I will check out both places to stay.
I think we'll stick to two islands and Nauplio

I recently put together an itinerary for a couple with just a few days like you and it was exactly as you have decided, Chania, Santorini Nauplio and then to Athens.
I think you will have a great time.
If you need to know how to get to that parking lot let me know.

Thank you.
That would be great!