I just booked a LAST minute trip to Greece. It will be my first visit to the country. I am a male in my mid-thirties and will be travelling alone. I will be arriving in Athens at 10:20 a.m. on 9/3 and departing on 9/12. I am very much a city guy, so I'd like to spend a decent amount of time in Athens. I'm also not a huge beach-goer and generally prefer exploring cities on foot and doing a fair amount of sightseeing. I am also a big time foodie (although I generally despise that term). Although I would like to partake in the Greek nightlife, it doesn't need to be the focal point of my trip. For that reason, unless someone wants to convice me otherwise, I'm planning to forgo Mykanos. I have some very specific questions that I would love some input on:

1. My initial thoughts are to spend about 2-2.5 days in Santorini, 3 days in Naxos and 3 days in Athens. In an ideal world, I'd have more time to explore Greece, but I have to make do with what I have. How does this itinerary sound based on my interests?

2. As I'm arriving at 10:20 a.m. on 9/3, I would like to take a flight to Santorini. How many airlines fly to Santorini from Athens? 9/3 is a Friday. Are all flights sold out this late in the game? How do I go about checking availability and purchasing flights?

3. I would like to return to Athens from Naxos either the night of the 8th on the high speed ferry or the morning of the 9th by air. How do I find out if all flights are sold out?

4. I am not a budget traveller, but I'm not trying to break the bank with accomodations either. If you were a single male in your 30s, where would you stay in Athens, Santorini and Naxos?

I'm feeling really pressed for time here and would greatly appreciate any input you could offer.

Many, many thanks!

Based on your interests I think you should eliminate one island and spend more time in Athens. Santorini will provide you with all the nightlife you could ask for on an island.

Check the websites for Aegean Airlines, Olympic Air and Athens Airways.

Ferry schedules: http://www.gtp.gr

For accomodations please state your maximum daily room budget.

The Aegean flights for the 3rd of Sept are all booked. There is a flight on the 4th and 5th both at at 5:30 AM but the bonus is they are really cheap at 15 euros.
I think that Santorini and Naxos are lovely islands as they contrast so well. Santorini for the views and Naxos for its lovely old town and Venetian influence.
If the islands are not a priority then consider Nauplion and Athens, Lots to see and do in the Nauplion area and it is only a couple of hours by car from Athens.
Pictures of Nauplion
http://travel.webshots.com/album/551991579dJbWvh

From what you wrote, I think you should scratch Naxos and spend more time in Athens. There is much to see and do in Athens and it's surrounding area, and of course many fine restaurants, tavernas, and clubs. Naxos will be getting quiet in September, and isn't known for it's nightlife even in high season, so if you are 'not a huge beach-goer' you may find it limiting. Santorini will still be busy, has the scenery, nightlife, and sightseeing to keep you busy for a few days.

Olympic Air currently has four flights to Santorini with fully flex seats available on Fri Sep 3rd, including one at 12:00 and another at 14:25.

It sounds like you are trying to do too much in the short time you have. Don't forget to factor in travel time. We travel a lot in Europe and a 2 hour flight can end up taking all day, by the time you do all the waiting around at airports, checking in and out of hotels etc. I would do as Brotherleelove suggests.

You can book flights direct on the airline websites and ferry tickets you can also book yourself but for the ferries you need to exchange your printed voucher in Greece for the actual ticket. For the flights, just print your e-ticket.

We have had some great meals in Greece but you need to find a family run type cafe or restaurant with authentic cooking, rather than the touristy places with average food.

Kay

Wow! Thanks for all these prompt responses. They are incredibly helpful.

Heimdall, many thanks for pointing out the availaiblity on Olympic Air flight on 9/3. I booked the noon flight from Athens, which gets me to Santorini before 1 p.m. I assume that the flight to Santorini leaves from the same Athens airport I fly into from the U.S. Is that correct?

I think I may have given the wrong impression in my post. I would like to see what the Greek nightlife has to offer, but it's very far down my "to do" list in Greece. I'm much more interested in sightseeing and eating.

I had the impression that there wasn't much to do in Santorini. Is that right? I figured that if I get there at 1 p.m. on 9/3, I'll have about half a day on 9/3, a full day on 9/4 and a full day on 9/5. I could take the 12:30 ferry to Naxos on 9/6, which would get me to Naxos at around 2 p.m. I could spend half a day on 9/6, a full day on 9/7 and a full day on 9/8 and take the dinner ferry to Athens. Then I'd spend 3 full days in Athens, 9/9, 9/10 and 9/11. Alternatively, I could take 4:20 p.m. ferry on 9/5 from Santorini to Naxos, which would give me about 2 full days in Santorini and 3 full days in Naxos. What do you think of those alternatives?

If I limited the trip to Santorini and Athens, how would you divide up the 9 days?

Are there day trips I can take to other islands from Santorini if I decide to base myself in Santorini?

I would like to pay under $200 USD/night. Can I find servicable accomodations in Santorini for that amount?

Also, in which general location would you recommend I stay in Santorini (Oia? Fira?) and Athens?

Thanks again for all your assistance! I owe you all a debt of gratitude.

I've just returned from my first trip to Santorini and spent 5 days there and did not manage to do everything we wanted.

We stayed in Oia at the Old Oia Houses which is EUR95 per night inc basic breakfast. We could not have been more pleased with the accommodation, the view of the caldera was spectacular, the accommodation was clean and comfortable and an oasis from the crowds who want to view the sunset. Location was perfect, as it was in the prettiest part of the town (in our opinion). It has to be one of the best value accommodations in Oia.

We felt we made the right decision to stay in Oia, but Fira must be seen as well.

Athens Airport is very small, and as long as your flight from the U.S. arrives on time you should have no problem making the 12:00 Santorini flight. When I checked the Olympic website only fully flex tickets were available, and if that's what you bought, then you are protected if you have to rearrange to a later flight. It's only about five minutes from Arrivals to the Olympic check-in counters, then maybe another 10 minutes to the domestic departure gates. Lines at the Olympic check-in counters are sometimes long, but shouldn't be too bad that late in the morning.

<i>I had the impression that there wasn't much to do in Santorini. Is that right?</i> On the contrary, there is lots to do on Santorini. I'm not the best qualified person to list the activities, but a trek up to Ancient Thera would be high on my list. There are vineyard tours, boat trips to the volcano, etc. You may prefer to stay in Fira rather than the quieter Oia.

Naxos is great for a beach lover like myself, but I wouldn't go there just for the sightseeing. There are a few ancient sites, and some quiet, picturesque mountain villages if you want to get off the beaten track.

My recommendation would be about three days on Santorini, then head straight back to Athens by flight or highspeed ferry. Spend the rest of your time in Athens and somewhere else on the mainland. Stanbr's recommendation of the Nafplion area is a good one - there is much more to see in that area than on Naxos.

In Athens, stay in or near the Plaka or Syntagma Square. I loved the Electra Palace, but it's not cheap. There are a lot of mid-range and budget options nearby.

In Santorini, I loved staying in quieter Oia, but considering that you are a male traveling solo in September, you would probably enjoy staying in Fira more, where there is a lot more going on and more nightlife.

If you go to Naxos, stay in Naxos town or in the St. George beach area, which is pretty much in town, just a short walk down the main drag. I imagine September will be very quiet there. I was there in May and it seemed extremely quiet, compared to Mykonos and Santorini anyway.

I wouldn't call Oia quiet - it was very busy, the main event of the evening after sunset would be eating or sitting in bars but not much else that I was aware of.

<i>I wouldn't call Oia quiet</i>

Neither would I. I wrote it was <i>quieter</i> (than Fira).

I've been to Greece just once so I'm really not an expert, but I found the island of Rhodes very interesting and charming. Maybe the other experts can opine if Rhodes meets your requirements rather than Naxos.

There's a lot of sightseeing to be done on mainland greece - by road from Athens. Santorini is a great choice. We loved it.

Indigo5

Thanks again for all of your terrific input. A few follow-up questions:

1. Can anyone recommend hotels/apartments in Santorini at or under $200 USD/day? A friend of a friend recommended Dana Villas in Firostefani. Is anyone familiar with this property? I'm inclined to stay in or near Fira. Any other suggestions for hotels in Fira at or under $200/night?

2. As noted above, I am arriving in Santorini midday on 9/3. Based on the comments above, I am now considering staying in Santorini until the morning of 9/6 and taking the Aegean Air flight at 6:55 a.m. or the Olympic Air flight at 10:30 a.m. back to Athens. From the Athens airport, I'd head straight to Nafplion. Can I rent a car at the Athens airport? My understanding is that the drive to Nafplion is about 2 hours, right? What are some of the best sites to see en route to Nafplion?

3. I would stay in Nafplion the nights of 9/6 and 9/7 and then head back to Athens at some point on 9/8. So I'd have about 2 days in the Nafplion area and 3.5 days in Athens. How does that allocation of time sound based on my interests?

4. Where should I stay in Nafplion?

5. Finally, I don't want this to be a whirlwind tour of Greece. Is the Santorini/Nafplion/Athens itinerary I outline above too ambitious for 9 days?

Thanks again for your feedback. It is greatly appreciated.

You have a good plan and are hitting highlight destinations. 9 days is not a lot of time but since you are flying you save a lot of time and can do the hops quickly. Yes you can rent a car at the airport and it is only a 2 hour drive to Nauplion. Just google car rental Athens and dozens of choices will come up. Many of these agencies meet you in front of the airport you give them a credit card imprint and away you go. Drop off is done the same way.

On the way stop at Corinth and take in the canal then find Ancient Corinth (the Roman era city) It can be done in an hour or two but is quite worth while. From there find Ancient Nemia. It is located about 5km from where the road turns south to Nauplion. Look for signs. Nemia was a sister city to Olympia and had its own games. The stadium is still there plus a partially restored temple and has a very good museum. Again an hour or so should do it.
On the way south you will pass Mycenae which can also be easily visited on a day excursion from Nauplion. You can see these sites at the end of my Nauplion album.
As you can see from my pictures Nauplion is charming and has those three Venetian Era fortresses. Nauplion will keep you busy for a couple of days.
Stay in the old city. A nice budget hotel is Hotel Leto with good ocean views. Right next door is Pension Irene where we normally stay. Both are high up in the city away from the noise of the waterfront but close enough to easily walk to all the action.
Enjoy you trip.

Yes, you have a good plan, and your allocation of time sounds about right for the days you have available.

Check brotherleelove's posts for suggestions on hotels in Santorini.