I need some suggestions on a route to take. Basically, I hope to travel either in May or June next year, and hope to spend a maximum of 7 nights in Greece. I’m hoping to create a 5-night itinerary, but I think with my requirements below, it might be impossible to do so. This trip is meant to be a surprise for my partner, so I’m hoping to combine our interests (both of us love history and photography) as well as spend some romantic alone time together.

These are the ‘requirements’ so to speak:

1.I have to go over to Thessaloniki to visit some friends.
2. I wish to spend some time in Athens visiting archeological and ancient sites because I'm very much into history. Given a choice between beach and history, I would opt for a day on the beach and the rest sightseeing. Nightlife would be good, although I would probably just spend a day checking the scene out and spending the other nights quietly with my partner.
3. Also, places to view the sunset/rise would be awesome. And maybe dining on the beach (I know there are countless such places in Greece!) And those white-washed buildings perched on a cliff overlooking the sea would be great (Santorini would be good for this, yes?)
4. Most importantly, I cannot swim, so perhaps activities involving swimming will be out, although I am able to scuba dive and snorkel.
5. I also hope to visit an island on top of Athens and Thessaloniki, and the more rural the island the better!

This is what I came up with
Thessaloniki (2 nights)
Athens (2 nights)
Santorini (or another island(?) for 2 nights)
Another island? (1 night on cruise?)
Back to Athens, fly back

I do realise that Santorini is one of the more popular tourist destinations, so I'm more than happy to exclude it from the list, although I would love to visit the volcano there.

Questions:
#1 Will it be too rushed if I were to include another island after Santorini? I'm looking at Paros/Naxos as the alternative islands. This is assuming I'm sticking to the 7-night itinerary (meaning 7 full days, not including the flights in and out Greece)
#2 Does it make more sense to visit an island closer to Thessaloniki instead? (ie on the way to Athens?)
#3 I was also looking at the ferry which goes to Venice. If I were to choose that route, does it still make sense to 'detour' to Santorini?
#4 I've seen that most people recommend spending the last few nights in Athens - in my case, given that I've to come from Thessaloniki, should I first spend some time in Athens and then onto the islands or do the opposite?
#5 My partner is very much into sailing and yachting, so I hope that I'll be able to include it in our trip - I'm thinking probably Athens - Santorini or Athens - (to another island). Any comments on that?

Thanks, would appreciate some feedback on the itinerary cos I'm still kinda lost

Since you have a short time, I would focus on Thessaloniki and Athens. From Saloniki, you could visit Vergina (Philip II tombs) and Kavala as well. You could go to a nearby island. You will waste alot of time getting to Santorini by plane or ferry for only a couple of days and spend too much time traveling and not really see anything. For your interests, it sounds like visiting two cities would suit you. I just came back from Athens and the new Acropolis Museum is outstanding, but there are many museums to visit there: National Gallery, Benaki (there are three), Byzantine, Cycladic, etc.
The islands you mentioned are nice but for a short trip, I would plan another trip.

1-With only 7 days for travel and relaxation you don't have time for more than one island combined with Thessaloniki and Athens. And even then you'll be stretching it a bit thin.

2-There are no islands quickly reached by ferry from Thessaloniki but you can fly on either Olympic Air or Aegean Airlines to many islands in just a short time. This will, however, require a return to Athens for a connecting flight.

3-Which route are you thinking about? Where are you coming from? Where do you go after Venice? Do you realize that the trip from Athens to Venice by ferry takes at least 36 hours including a 3-hour bus ride from Athens to Patras? No, if you chooose Venice it doesn't make sense to go to Santorini. You dont' have enough time.

4-If you do end up choosing an island in the Aegean Sea it's advised to save Athens for the end of your trip so you have a little extra time to get back to the mainland for your flight onward, in case of a cancellation from high winds or mechanical breakdowns.

5-If you take the ferry back to Athens after Santorini you will consume most of one of your 7 days by the time you get to a hotel in Athens after your arrival. It's best to fly.

Hi you both, thanks for the quick replies!

brotherleelove2004, yes, the Patras-Venice route was the one I was looking at. I will look into flying between Thessaloniki and Athens then!

Just another broad question, generally, from which country will it be cheapest to fly in/out of Greece from? I realise this might depend on many factors, but I'm just wondering because Greece will be one leg of my 2 month holiday in Europe, and I haven't made any concrete plans yet, and am wondering where to fit Greece in the whole scheme of things. (perhaps I should post this as a separate topic)

Thanks!

If you sign up for the Aegean Airlines email newsletter you will be able to take advantage of their promotional airfare sales between many European airports and Athens. These sales are published about 2 months before the specified dates.

http://en.aegeanair.com/newslettersubscription.aspx

Easyjet offers cheap flights from London.

Why do you want to take a ferry from Patras to Venice? In a random check on prices for Aegean Airlines flights from Athens to Venice for next June, I found a Saver fare of €38 plus taxes (a total of €83.59 all inclusive). That's probably cheaper than the ferry, and will give you an exta day in Greece or Italy.

We flew in and out of London and connected to Athens on Olympic.Worked well and saved money.

Heimdall, I was thinking that the ferry would provide scenic views of the sea? I haven't seen much reviews on it, so I'm just wondering it'll be worth the extra hours. Given the comments so far, I'm leaning towards flights too

Sadly, the only scenic views from a ferry are when passing an island or nearing land - the rest of the time you are looking at waves. I enjoy taking ferries, and it's fun to watch from the stern when the ferry is docking at a port, but apart from that I read a book or try to get some sleep. I have had some interesting views through windows of airplanes, though, including the Parthenon, the Ionian islands, and Venice from 35,000 ft, where I could make out the Grand Canal and other features of the city. In June there are usually few clouds, so get a window seat if your flight is in daytime.

AS brotherleelove mentioned, the Patras-Venice ferry would take about 36 hours, as opposed to 2 hrs 15 min from Athens to Venice by air. An extra day in Greece would give you more time to see the islands. If you plan to visit Santorini, recommend flying there as well.