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Help- Travelling Within Italy to Croatia

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Hi there- My husband and I are planning a month long trip, from May 26-June 28. We are spending one week in France before heading to Italy for 10-12 days. The places we want to visit are:
- Cinqre Terre (Staying in Levanto)- travelling from Monaco by Train
- Venice: Train from Levanto to Venice
- Rome: High Speed Rail from Venice to Rome

(Somewhere between Venice and Rome we want to rent a car and travel throughout Tuscany/Wine- again, any suggestions would be greatly appreciated). We are thinking that a day would be enough?

From Rome, we were thinking of flying to Sicily.

Now, as Sicily is our last stop on our beautiful Italian vacation, we have to end up in Zagreb, Croatia. From there, we are renting a car, driving straight to Dubrovnik and driving up the coast ending, again, in Zagreb before flying home.

This is where I need your help.
- Does the above methods of travel make sense?
- What is the best way to go from Sicily to Zagreb, OR should we change the order of our
destinations OR is there another location we can 'swap out/add' that might make it more
do-able'?

My husband and I are mostly interested in enjoying some wine, relaxing on the beaches in Sicily, enjoying the countryside, trying to stay away from major Tourist destinations (with the exemption of Venice and Rome) and exploring some very unique experiences that Italy has to offer.

Might I add, we will be travelling with our 8 months year old son (Fingers crossed it all goes well)

I know this post is very complex but, as the trip is soon approaching, I am looking to you for a little guidance.

Thank you,

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