The Itinerary

Having booked our international tickets to arrive and depart in Athens, we would have to find a way to reach Santorini, and perhaps make a few more stops along the way?

Option 1
Arrive Athens, spend a day and half in Athens, board the 4-day cruise from Piraeus the next day, disembark in Santorini on the 3rd day, spend 2 more nights in Santorini, fly from Santorini to Athens to Singapore.

Pros: Get to visit 7 destinations (6 destinations from the cruise + Athens).
Cons: Not advisable to take a domestic flight connecting to an international flight on the same day (because of likelihood of strikes). The cruise costs USD 560 per pax, not inclusive gratuities, and additional shore excursions. We also "lose out" 1 night because we're disembarking at Santorini.

Option 2
Arrive Athens, board the overnight ferry (that looks more like a cruise with proper cabins) at Piraeus to Chania. Take a one-day car tour from Chania to Heraklion. Stay overnight at Heraklion to board the next day's morning ferry to Santorini. Stay 3 nights in Santorini, fly to Athens, stay 2 more days in Athens, then depart for Singapore.

Pros: Chania seems like a nice place to visit. Quite cool to experience the "high-class" cabin. Minimise risk since our domestic and international flight is not on the same day.
Cons: The 10-hour car tour is quite expensive (385 EUR), which made us question how much do we want to visit Chania.

Option 3
Arrive Athens, stay overnight at Piraeus, to take the morning ferry to Mykonos. Spend a day in Mykonos, take the next morning's ferry to Santorini. Stay 3 nights in Santorini, fly to Athens, stay 2 more days in Athens, then depart for Singapore.

Pros: Minimise risk since our domestic and international flight is not on the same day. The cheapest option of the 3.
Cons: Mykonos may not be the best island for us (but that doesn't mean we're not cool). We'll just treat it as a sight-seeing opportunity, since a lot of celebrities will be there.

The husband was quite keen on Option 1 while I preferred Option 3. He liked having the convenience of leaving our luggage on board the cruise while we visit the various towns. Being the nice gentleman he was, the husband "agreed" that spending significantly more to visit more ancient towns is not a necessity and "agreed" to go with Option 3.