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Romantic Italian Road trip---HELP

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Ciao all!

Me and my boyfriend (mid twenties couple) will be traveling to Italy in the beginning of June (8th to 16th). We are going to fly into Venice on the 8th till 10th. Then we are renting a car and driving to Florence (one night) then to Pisa(half a day) and then to Rome (13th to 16th). So I have several questions and I am looking for answers and suggestion to all or some of them below:

1. what is the best route for a gondola ride at sunset?

2. Amazing (NON touristy), romantic restaurant in venice (its my birthday, i want something super special).

3. a. Is it worth taking a city tour in venice?
b. if so, which one?

4. I am looking for a winery along the road from florence to rome....any suggestion of a good one? We prefer white wine but red is good too. - Budget wise we are flexible but saving is always appreciated ;)

5. For anyone who has driven the route....please share any special places that you have seen and consider worth visiting.

6. ****** we are foodies (I am also training to become a chef), we love to eat and love to try anything new so any restaurant/eateries that you can recommend anywhere along the route would also be greatly appreciated.

7. anything else that you think will ADD to our little trip...feel free to mention

thank you and looking forward reading your answers :D

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