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Canadian Family of 3 Planning First Trip to Italy - Please Help

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I have been threatening to do it for too long! It's time to buckle down and go to Italy! And I need your help!

I have just entered into the early stages of planning to bring myself, my wife and our two year-old son to Italy in June 2013, where we intend to spend my 30th birthday. I am very fond of research and planning, and I think the sooner I book the tickets the better. That way it'll force us into going, as I have a tendency to let other things get in the way. Then I can figure out the details in the months to come.

I am planning for a three week vacation, 21 days. I have no intentions to try and "see it all." I am thinking of planning for one, maybe two places of stay to be divided equally into that time. I feel like it may be folly to try and drag our little one to all the sights, so I'd rather set up in a couple of beautiful places over the course of our stay, where we'll have the option to take in the culture, relax and occasionally venture to one of the more significant sights for a day here and there. Our accommodations budget is about $5,000 for the entire trip. Food, entertainment and travel are budgeted separately.

I have been drawn to the idea of a self-catered villa in the Tuscan country side, where we may be able to venture into Florence, or another surrounding city, for a day-trip. Is this a sound idea? Can you offer any suggestions or alternatives?

Additionally, however, I think it would be nice to end up somewhere coastal for a portion of the trip, as I am a sucker for the sea. I understand the Amalfi Coast isn't necessarily suitable for a toddler. Can anybody suggest a coastal destination that is? And perhaps any ideas for accommodations?

Thank you so much for your time and your thoughts!

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