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Eastern Europe Itinerary Help PLEASE 14days

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Hi Folks,

We have 16 days in Europe. My friend will arrive 7am in Milan from Hong Kong, and i will be flying from UK to meet her there

Here is my rough itinerary so I can start booking accomadations

Day 1 - Friend arrive at Milan airport then take train to Venice where i will fly from UK to Venice to meet up with her
Stay a night at Venice

Day 2 - One day at Venice

Day 3 - Take train to Trieste (2 hrs train)
Sightseeing at Trieste and stay 1 night at Trieste
Day 4 - Whole day at Trieste
Stay 1 night at Trieste

Day 5 - Rent a car at Trieste and drive to Bled in Slovenia.
Stay a night at Lake Bled
Day 6 - Enjoy Bled for half a day and drive down to Ljubjana
Stay a night at Ljubjana

Day 7 - Whole day at Ljubjana
Stay night at Ljubjana

Day 8 - Drive to Zadar or Split
Stay a night at Zadar or Split
Day 9 - Drive and spend a whole day at Pittvice National park

Day 10- Drive to dubrovnik
Stay at Dubrovnik
Day 11 - whole day at Dubrovnik
Day 12 Somewhere in Croatia? or drive to Montenegro?
Day 13 Somewhere in Croatia? Montenegro?

Day 14 - Drive back to Milan
Day 15- Whole day at Milan
Stay a night at Milan

Day 16 - Fly back home

This is only a rough idea. I am open to options, but the main place I really want to visit is Croatia and if enough time I would like to drive from Croatia to Montenegro.

So i have a few questions.

1. Should I fly to Milan and meet up with my friend first? Or fly to Venice and meet her?
2. Should we go to Venice or go to Lake Como? or can we drive to Hallstatt?
3. Where should we stay in Croatia? Dubrovnik and somewhere else?
4. Should we rent the car in Italy or in Slovenia? Which option would be cheaper?
5. Will we have any troubles driving in all those places?

Thank you guys

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