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Travelling from Plovdiv, Bulgaria to Dubrovnik

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Taking a 3 week trip in June starting in Istanbul to Sofia/Plovdiv and then on to Dubrovnik. My husband thinks we can drive from Plovdiv to Dubrovnik in 1 day, I think it will be very difficult. Has anyone done this drive? No train service in Dubrovnik and flights are too pricy (there are 4 of us). We are also traveling up to Trieste and then from Venice to Rome. It's the Bulgaria to Dubrovnik part that seems the most daunting. Any help is appreciated!

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