My wife and I are planning a babymoon vacation in Greece in February (she'll be 5 months pregnant) and I wanted to get some itinerary suggestions for our trip (I've done some searches on Fodors/other sites, but wanted to give some notes about our preferences too to see if that changes anything).

We're planning on 10 days in Greece (11-days with travel). We're in our early 30's and like history/culture/sites. For some reference on preferences, when we traveled to Italy, we really enjoyed the ancient ruins of Ostia Antica/Pompeii, walking around the city centers of various cities of Italy eating gelato and exploring the city center, a day trip to the Leaning Tower and checking out some museums with lots of sculptures/historical stuff (not a huge fan of paintings though).

In general, we like staying in the city center and be in cities that are walkable and have interesting sites.

Also, should we plan on flying into and out of Athens?

For your interests, and considering the time of year, recommend sticking to the mainland and dividing time between Athens and Nafplio. February is the coldest month of the year, and the islands would not appeal to me in winter. It goes without saying that Athens has many ancient sites and museums, while Nafplio is a coastal town with several UNESCO ancient sites nearby:
http://www.visitnafplio.com

I agree with Heimdall's choices completely. Also, re flying into/out of Athens -- you don't say where you are from, but from your other posts I'm guessing USA. And from USA & canada you don't have any other choice of flight destination except Athens. in Winter, nonstop only from NYC and ?Montreal. If seeking a bargain ticket w. Europe connection. airlines w. OK Europe connections = Swissair, Lufthansa, BA, KLM, Alitalia. Avoid Air France thru Chas DeGaulle unless have at least 2 hr layover. Final tip: when choosing flight times, make sure homebound flight doesnt depart before 9 am or so; otherwise u'd have to be at airport by 6 AM... too early plus higher taxi €€.

Where to stay in Athens? Since someone 5 months pregnant tends to tire more easily (as I well recall), choose hotel NEAR to main sites in Athens. When exhaustion strikes, you want to be able to walk back easily. I really like this particular filter on booking.com (which I've reduced to a "tiny url") http://tinyurl.com/heq6edp -- it lists available hotels based on how close they are to the Acropolis. Clever, eh?? Enter your dates, and do not consider any hotels farther than .5 miles away ... this also automatically puts you in best areas -- Plaka, Makrogianni (next to Plaka), Monastiraki, Koukaki. My own fave is Makrog, just South of Acropolis, flanked by nice pedestrianized promenade. Several good moderate choices in this area, just a few hundred yards from Acrop. Museum & entrance to ancient sites = "sister hotels" Phillopos & Herodion.

In Nafplio, avoid hotels that are up the stairstep streets, despite their nice views. On sea level in Old town nice boutique places include Pension Omorfo Poli, Ipolliti. Hotel Agamemnon has BEST location in all of Old town -- On open square, several windows with balconies overlooking the sea. Small hotel (20? rooms), also has elevator, unusual outside of big chain hotels. http://tinyurl.com/heq6edp an excellent, NONcommercial guide to Nafplio, recommends Agamemnon.

For visiting Nafplio and nearby sites (Tiryns, Mycenae, Epidaurus etc) good idea to rent car; much more flexibility than local busses during offseason. If u don't want to drive thru Athens traffic, the Swift/Avanti rental agency will bring car to your hotel and DRIVE you to onramp of intercity highway, and then it's a piece of cake ... modern multi-lane road most of the way.

Have you checked the weather in February in Greece? The islands pretty much shut down, because it's windy, rainy and cold.

I can recommend two hotels in Athens. The Grand Bretagne is right near the Acropolis. The Westin Resort is more relaxing, on the water. We stayed at each one.

It's full name is The Westin Athens Astir Palace Beach Resort.
https://www.youtube.com/watch?v=JV_ik7i0pnA

We used CostcoTravel.com for our package. It includes a driver, who picks you up at the airport or ferry terminal (a luxurious treat!), and a local concierge if you need anything travel-related while you're there.

Tabernash2, those are two expensive hotels & not in everyone's budget, apart from that they are going in February so none of the beach resorts are advisable, not to mention the fact that the OP said they like staying in city centers We are all different & from your posts & choices it sounds as if yours are pretty much opposite to the OP's. For someone interested in history, sites & museums Athens needs lots of time, approx 30 visits & now living here for nearly 4 years I am still exploring & revisiting places!

I have stayed in 20+ hotels in Athens & there is a wide choice, but location is key, so if you provide a budget per night in euros you will get the best advice.
Athens & Nafplio as already suggested is a wise choice for your interests & the time of year. No car needed (or advised) in Athens, but certainly the best option for Nafplion. Yes, the weather will be dodgy, cold &/or wet, but still the chance of some sunny days
Another option is splitting your time between Athens & Thessaloniki (fly, train or bus). Thessaloniki is another wonderful city with much to see & do, but being further north It will be colder. The advantage of both cities is they have a wealth of museums if you do get really unlucky with the weather.

yiassas, the OP did not mention budget concerns.

Please re-read and see that I recommended a hotel smack in the middle of the city, near the Acropolis, the Grand Bretagne.

About this, you know nothing, y: ". . .from your posts & choices it sounds as if yours are pretty much opposite to the OP's"

You have posted on another thread that you spent 5 nights on Santorini & could have stayed longer & one full day in Athens was enough, that's pretty much opposite to the OP saying they like history, sites, culture & city centers.
I know they did not mention a budget for accommodation, which is why I asked for an idea in euros, rather than assume they wanted expensive or otherwise.
It's about finding the best for their needs, not what the rest of us prefer.

Suggesting Grande Bretagne, one of the most expensive hotels in Athens, without first knowing the OP's budget is rather presumptuous. It's a fine hotel, but I stay at another only a short distance away at a fraction of the price. Let's find out how much cadd wants to spend, then we can come up with some good suggestions.

Sorry, I didn't realize you two were the hall monitors here, in charge of chasing off any ideas you do not agree with, or deem fit for the OP. Last time I checked, different viewpoints were welcomed.

Just another point to note, even though the Astir Palace is not the best choice for February, it's closed anyway. It shut its doors after President Obama's stay in November & is not expected to reopen until April 2018, so not an option at all in 2017.

Thanks for the notes so far!

To answer the question about budget, we're pretty budget conscious and we'll likely be looking at Airbnb for good deals that are in the city center. Ideally this entire trip costs us $4-5k including airfare.

I've heard of a few islands/locations/cities, any suggestions on time breakout? 3/days there, 4 days there, 3 days here?

We're planning for a February 20 to March 4th trip, I was looking at the weather and it looks like late Spring/Fall'ish type of weather?

If you guys read my Italy post, curious if you guys have budgeting suggestions too.

It is still winter at the end of Feb/beginning of March. You may get some sunny days, but also wind & rain & the evenings & nights will definitely still be cold.
I go with the suggestion of mainly Athens, a few days in Nafplio, loads of sites around to see & the town & castle too. Possibly a day trip or overnight on Aegina, it's only an hour or so on the ferry & there is one site (Kollona) just a few minutes north of the harbour/ferry terminal in Aegina town. Other sites around the island too if you hire a car.
Bear in mind that the sites & most museums will still be on winter hours with the majority closing at 3pm.
Accommodation in Athens should be no problem, plenty to choose from, the location is key, far more important than saving a few dollars. Research hotels & Airbnb in the areas of Syntagma, Akropoli, Monastiraki, Plaka, Makrigianni, but any that take your fancy post on here before booking, some places are a bit free with their location description Avoid Omonia, not the best area & not so walkable to the sites either for your wife.
Start researching the above (also Thessaloniki if you don't mind it being even colder!) & come back with what you find & we can try & help from there

Ttt

So I booked my flight to Greece from Chicago.

How does traveling to islands work? I assume you fly from Athens to Santorini, right? Are the airline rules similar where you need to arrive "X" hours before, etc?

You can fly to Santorini, or take a ferry (if ferries are operating when you are there).

The 'fast ferry' from Athens to Santorini takes 5 hours and is quite nice. The other ferry takes almost twice as long as that.

We took the ferry to Santorini from Athens, and we flew back. If you fly into Santorini, be prepared for a pretty yucky airport. It was dirty, crowded and inefficient. A bad intro. to that glorious island.

However, be sure you investigate ferry schedules available in February.

PS. It would be best to fly directly to Santorini from Chicago, if it's not too late to book it that way.

Tabernash, it would be best of course, but it is not possible. Not in any season. There is no direct flight to Santorini from N. America. None. In no season. If you fly to Another European Country, in the high season, there are some direct flights to Santorini from, say, Rome, or Paris, or other large European cities. But in February?

Yes, of course. The OP would probably need to fly to Athens to Santorini. By flying "direct", I did not mean nonstop. Sheesh.

5 hours on a Ferry in February sounds long! Would it be terrible to fly? Also, 5 hours basically kills a half-day.

So I've booked Athens for 4 nights and now I have 6 nights to go. I've heard a lot of good things about Santorini, so I was thinking 3 nights there, what do you all think?

Thessaloniki / Nafpoli / Mykonos / Rhodes - what do you guys think?