1st Time to Greece Looking for Expert Help

Late September is a great time to visit Greece. It is still warm the sea is warm but you might run into a day or so of rain.

Book that $560 fare.

Experienced travelers to Greece generally will suggest you get out to your first island immediately on landing in Greece. You will need a two hour window for the connecting fight. It is way better getting over jet lag on an island rather than Athens. Also it is a really good idea to be in Athens at the end of your trip so you are on the mainland for your return flight. Stuff can happen especially when you are trying to get back from an island for a same day flight. We were on a fight that got delayed 4 hours. 5 couples missed their same day return flight. Why take that chance.

So I would fly to the furthest island which would be Santorini. There are two or three evening flights for you to catch. Personally I think 3 nights is probably a minimum on Santorini. 2 nights is really only a day and a half.
Now ferry to Naxos. Naxos is a great companion island with Santorini. It will provide you with an authentic Greek experience. It has great beaches, lovely main town topped by a Venetian era Kastro, mountain villages and all of this at about half the price of Santorini. Naxos needs 5 to 7 days to visit properly.

I am now going to diverge from your proposed plan. By visiting two Cyclades island Santorini and Naxos you will have had a great island trip. There is absolutely no reason to include Hydra. It is nice and is recommended by Rick but that is because his Greek tours do not include an island so Hydra is intended to give you a little taste of an island. No need to do that after Naxos. I am also going to suggests your skip Mykonos. It too is beautiful but it markets itself as a high end jet setter destination. That means Santorini prices for meals and hotels and shopping but all this without the Caldera views. Naxos has everything Mykonos has but at half the price.

Another reason to cut your destinations down is because every time you change locations you lose a minimum of half a day. So each of your 2 day locations is really a day and a half. By dropping Hydra and Mykonos you now have 5 nights in Naxos and 3 in Santorini.

Fly back to Athens. Pick up your rental car. We use ACR Athens car rental. They are highly recommended. Drive to Nafplio. On the way stop in Corinth and visit the Canal, Ancient Corinth and Acrocorinth then Ancient Nemia. It has sister games to Olympia and is a tidy easily accessible site. Now go to Nafplio. It is a lovely seaside town. I can recommend hotel Agamemnon.

Nafplio needs a couple of days and a couple more to visit the ancient sites nearby. There is almost no way you can do Olympia and Monemvassia in a 4 day Nafplio segment. Olympia is a 5 hour drive each way. Monemvassia is probably 2.5 to 3.5 hours each way. Substitute Nemia for Olympia. You indicated you could add some time to your trip. I would suggest you consider 5 to 7 days for the Peoponnese including a night in Monemvassia. Its amazing to sleep in a Medieval walled town. Don't miss Mystras on the way to Monemvassia. Its the last Byzantine city.

Finish with your time in Athens.

Here is what I am proposing
Santorini http://www.flickr.com/photos/stanbr54/sets/72157632154800782/

Naxos Town http://www.flickr.com/photos/stanbr54/sets/72157632094558042/

Trip around Naxos

http://www.flickr.com/photos/stanbr54/sets/72157634605629689/

Naxos trip 2019 https://www.flickr.com/photos/stanbr54/albums/72157711294807761
Corinth area. https://www.flickr.com/photos/stanbr54/albums/72157711755443483
Athens http://www.flickr.com/photos/stanbr54/sets/72157632121475515/

Like he said. Perfect. Have done very similar and it was perfect. "Stanbr" is the embodiment of "seasoned traveler to Greece" -- probably 16 trips since '97 or so. Follow his instructions and y ou'll be SO happy.

Wow!!! Super insightful. We will use this information to rearrange and fine tune the trip. Thanks so much!!!

Going to Italy 3 times, I'll bet your experience was enhanced by some advance reading, both on the internet AND in Guidebooks. I advise that approach also with Greece ... Go to the library and take out an armful, see which appeals. Some are too oriented to transportation, hotel choices & restaurants, with very scanty background & history. If the latter appeals, look at some books that may be outdated on restaurants/hotels (u get those tips online anyway) but great on history, atmosphere, "hidden gems," culture etc. The Cadogan Guides to Greek Islands and the Peloponnese, by Dana Facaro, writes like an Angel... the Blue Guides, or Michelin, if you want indepth on ancient stuff.. The Rough GUides lately have become too jampacked with transport-hotels-dining alas... but if you can find an older edition 2012 or before... these do more backgrounding.

A quick note, since you mention having a car. Many Greek drivers take the painted lines dividing the roads as “suggestions,” rather than definitely marking which side of the road is yours and which is theirs. It’s a bit disconcerting when, coming around a blind curve, there’s a car partially on your side of the road, coming at you. We never had a head-on collision, and the other drivers managed to steer back over to their side in time, but it wasn’t always clear they would be doing so. Driving defensibly is necessary on the Peloponnese.

One way in which islands seem to look the same is the vast number of loose cats outside. If you’re dining outside, you may have feline companions.

And, as you must’ve found in Switzerland, yogurt is a key part of the diet. Breakfast starts with a big bowl of yogurt, topped with fruit, honey, and nuts.

A PS to Cyn's driving alert -- fortunately, most smaller greek roads have a usable "shoulder strip," so if you find yourself in terrain that involves a lot of blind-corner curves, u can keep the RH wheels sorta on the shoulder as you approach these... avoids sudden adjustments. Also, in late september when on these rural roads you'll have much less traffic ... in the hill village areas of Naxos, you may have to slow down or stop, not because of vehicles but because a herd of goats or sheep have decided to take a walk.

Thanks for all the info. Note, we have driven in Ireland and Tuscany, so I am thinking we will be ok as long as we avoid inner cities!! We love cats and dogs so any encounters will be welcomed!!!

Revamped itinerary based on your input. I think it flows nicely with plenty of time to explore or day trip.
Fly straight to Santorini upon arrival
4 nights Santorini
4 nights Naxos
3 nights Napflio
3 nights Monemvasio
3 nights Athens

Oh dear. Its a shame to have cut out Hydra. Our favourite place in all of Greece. If it were me I'd choose between Napflio and Monemvasia (I'd prefer Monemvasia), extend your time at that one place, do the other as a day trip from the one, and put Hydra back on the list.

I'd also second the advice to go to an island immediately upon landing. Last year, we landed, took the train straight to Piraeus and were in Hydra within 3 hours of landing.

I think that your new plan will be an absolute delight. Have a great time.

Do not do Olympia and Momevasia as day trips from Napflion! Napflion is surrounded by Greece’s top antiquities sites so please visit them- Mycenae, Tyrins, , Epidavros and more. Spend more time and do visit them. Olympia gave us goosebumps! Add time to visit them each.
Greece is very mountainous and driving is not as easy a map makes it look.

The cats are lovely, mostly very friendly.

Maybe go to Naxos first, then Santorini. Naxos is much more laid back and not very crowded by late September (it was nearly empty when I was there in mid-October).That will be a much better place to get over jetlag.

Santorini in mid-October was chock-full of tourists. If you rent a car, you can explore the island. Otherwise, you only need 2 days to see Fira and Oia with all the other tourists including thousands of day trippers from the cruise ships tendered off Fira. If you cut a day here, add it to Athens - there's much to see there.

I assume you'll fly to Athens to rent a car and drive to the Peloponnese.