suec1

A cruise that goes to Italy and Greece might be a good idea for maximizing sightseeing. If you are going soon you might be able to find some nice last minute deals - you can arrange flights thru the cruise line as well. I like Celebrity - upscale, not premium, but a nice product. I don't think you get as much of the flavor of a country from a cruise ship but you can see many of the A list sights and only have to unpack once (or maybe twice if you can add a few days at the beginning).

IMO Italy would be easier to do on your own as a land trip. But for maximum use of your time you will have to PLAN and pre-book as much as possible. You might want to consider a tour - again sightseeing time could be more efficient and transportation easier.

When I started my travels, I could not get enough of Italy - now I that I am nearing the end, I wish I had spent more time in Greece and it is on my bucket list for a return. So you've suggested two delightful countries - hopefully you can get some good advice and encouragement from our Fodor community.

suze

Do not miss Venice. And don't just rush thru in 1 day.

(that is my best suggestion in Italy for your bucket list trip)

ToujoursVoyager

One year, my sister wanted to go to Italy (her first time) and I wanted to go to Greece (our first time). So we did just that: 1 week in Italy and 1 week in Greece. We both had a wonderful time. She was in charge of Italy, and I, Greece.

Our final itinerary looked like this: Venice-Florence- Crete-Santorini-Folegandros-Athens. We were young, full of energy and no need for sleep.

After multiple trips to Europe, I am still discovering amazing breathtaking beautiful places. So here are my recommendation for your bucket list: (limiting myself to only Greece and Italy)
1) Amalfi Coast 2) Venice 3) Tuscany -Val d'Orcia- 4) yes, the famous Santorini 5) Koufounissia, a small cyclade of Naxos

Edward2005

How about Albania? It borders on the Adriatic and its chief exports are mud and debris. That's a joke. I've never been there but I'm sure it's wonderful.

eastenderusvi

fluffs: What is it that makes you pick Italy and Greece? What do you dream of? You talk about difficult days ahead...I'm sorry if this is morbid, but what is it YOU want to see before you die? Do you dream of seeing the Colosseum in Rome? Michaelangelo's David in Florence? Going down the Grand Canal in a gondola? Standing on the Acropolis? Drinking ouzo on an island? You picked these two countries for a reason. In two weeks, you could see some wonderful things, but you can't see it all. You have to ponder what is important to you and your traveling companion. If your companion doesn't give you any help (and I have been there before!) just consider what you know of them- city person, architecture fan, snooty food lover?- and throw them a few bones along the way. You don't have to plan for months.If you could share a few of your dreams, people here are willing to help!

PegS

I do feel sorry for the OP. Come back! We don't bite (much) we promise.

But do think about what moves you: beautiful scenery? Natural landscapes? World-class museums? Ancient history? Food? Friendly people? Famous monuments? Hidden gems?

Do you like cities? Or seascapes? Do you want to have a bustling, packed vacation? Or do you want to chill or people-watch?
If you can give us some answers we can help you narrow things down.