Italy or Two Smaller Trips

Look around at some of the "travel hacking" websites for ideas on how to bring the price down. You can probably afford to do both Italy AND Napa if you put some time/effort into it. Travelling in shoulder season instead of in summer is tip #1. Sign up for some credit cards with frequent flyer bonus miles to get at least one ticket for free (free seats are much easier to get outside peak season). Consider home exchanges (as someone else has mentioned) or air b&B, etc.

Happy travels!
 
Kids and Europe are not mutually exclusive. We've done 2 Italy trips with kids.

Without school age kids you can save a lot by going g shoulder season (May and September). Renting weekly apartments is much cheaper than hotels and let's you get to know an area more in depth.

For excellent Italy travel advice check out the slow travel forum slow talk.com.... I saved so much $ based on advice e over there.
 
Haven't been to Napa, but did spend two weeks touring Italy. It is not to be missed. I have also been to Hawaii twice for two weeks each, once before and once after children. They were indeed two different experiences and I recommend visiting Italy before having children.

We have taken our girls to Hawaii, Italy, and England when they were between the ages of 4-10. We asked the girls where they want to go next and Africa was the vote. Time to get planning for 2014?

Omalley
 
Definitely Italy. No brainer and not even comparable according to me... If Italy was 10 times the cost of Napa, I would still choose Italy.
 
Rome is the one place overseas that I still want to visit (I've been to more countries outside the US than US states). I have been to Florence. I will say this: if you go to Italy, travel light, use only a carryon, and if you are staying longer than a carryon would allow, plan for the cost of hotel laundry instead of taking a bigger suitcase. I was in Florence for 4 nights, on a round the world trip that took me to 4 countries for business. My big round the world trip suitcase got stuck in Rome, and the airline kept forgetting to put it on the next flight to Florence. 20 or so flights later, on my 4th night, my bag arrived...just in time to get on the plane the next morning...

R
 
Definitely Italy. No brainer and not even comparable according to me... If Italy was 10 times the cost of Napa, I would still choose Italy.
Wow, a little overselling IMO, 10 times? We loved Napa, and we loved Italy too...but different trips with different purposes.
 
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