Hello guys, this is my first post and would love to get some help on my trip planning to Italy and Greece in Sept this year!! I only got 2 weeks because of work and here's what i came up so far:

Day 0 - departing canada
Day 1 - arriving Rome around noon and check in hotel etc, asuming most day is pretty much gone, dinner and rest up for the vacation
Day 2 - Rome city
Day 3 - Vatican city
Day 4 - Pompeii (1 or 2 days??)
Day 5 - if 1 day in Pompeii, then fly from Rome to Santorini today
Day 6,7&8 - Santorini
Day 9&10 - another Greek island or Athens?
Day 11 - fly to Florence
Day 12 - Florence
Day 13 - Florence, and come back to Rome in the afternoon
Day 14 - Rome
Day 15 - coming back to Canada

Feel free to criticise and yell "impossible" or "wasting time" at me. Thanks a lot!!!

I think I would take the train to Florence on arrival day since that day is pretty much a loss anyway. Might as well spend it transporting. Visit Florence a few days, fly to Santorini, fly back to Rome, visit Rome and Pompeii (daytrip or overnight?), fly home.

I'd suggest flying to your furthest point, then working your way back. So fly to Athens then onto Santorini directly, visit another island or Athens, fly to Florence, and train to Rome. You'll be jet-lagged and sleepy your first day, so might as well use that time fruitfully. And this way you'll spend less time in transit.

If you go to another island, you need to figure how you'll get there and then how you'll get back to Athens. And how much of your time will be spent in transit. I'd stick to Athens for your second stop in Greece. Lots to see there and you will be close to the airport for your flight to Florence.

Definitely buy an open jaw ticket into Rome and out of Athens or vice versa. You only need one day in Pompeii.

my original plan was flying into Rome and out of Athens but the tickets are a few hundreds more for 2 people, so that's why I switched to in and out from Rome (right now i see a $900 return pp). But I will explore this option further. Or check the other way around like what Mimar said. hmmm...

we will probably go to Athens instead of another island.

This will be our first time to Europe so I'm not too familiar with how far the airports are or if trains are more convenient (and budget/time saving).

kybourbon, your suggestion is very good if i end up with in and out from rome, thanks.

I'm planning on leaving Sept 20 and come back Oct 5 so hopefully prices will drop a bit by then.

The couple hundred that you save in $$ you will likely spend getting back to Rome for your 'cheaper' flight, not to mention the wasted vacation time. Definitely fly open jaw to make the most of your time!

I was intrigued by your plan to fly from Athens to Florence. According to http://www.aia.gr/flight_schedule/european_en.htm the only destinations in Italy are Milan, Venice, Rome, and Naples.