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Couple weeks in Croatia, couple weeks in Italy

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I'm planning for another month in Europe vacation for us next summer, probably early June thru early July. The map so far looks like this. The red circled numbers represent number of nights at each location. The icons represent rail, boat, and rental auto travel.

http://techquarium.com/gallery2z/d/60904-2/DSC_9458.jpg

We've been to Italy before so we're pretty comfortable with that part of the trip. The Croatia part is a whole other thing. My first and biggest question is how do I get my rental car across the short stretch of Bosnia? Legally, with no hassles.

Also, with Croatia, we have a lot of flexibility in planning those 12 nights. Pula, Zadar, Split, and Dubrovnik were sort of equally spaced, but that whole segment of the map needs refinement. We mostly are looking for nice beaches, beautiful water, and perhaps a naturist area along the way.

We usually prefer to rent vacation apartments over hotels. I'd be interested to hear pros/cons from people. We did 5 AirBnb places in Europe last year and it went perfectly but the trade-off is committing to being in a place for a space of time. I'm thinking for the Croatia leg of this trip we might try to keep our options open as we travel.

Opinions, suggestions, and shared experiences are appreciated.

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