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Go to Split and spend a couple of nights drinking in Diocletian's palace. One of the most powerful roman emperors decided that Split was way cooler than Rome, and that guy knew how to party.
Grab a boat in Split and set sail towards Hvar. Make port in Palmizana and ask what's the quickest route to "Laganini". That's a beach bar on the other side of the island and its your home base for the day.
When the sun goes down grab a water taxi to Hvar and continue your bacchanal in the ancient streets of one of the most important docking point of the ancient greeks and Romans, and check out Kiva, Carpe Diem, Pink Champagne. and Carpe Diem beach (located 5 minutes by boat from the coast of Hvar, but don’t bother before 4 am).
Winston Churchill said that the Balkans produce more history than they can handle.
The Croatian side of the Adriatic was the most important sea route for centuries for the Greeks, Romans, Venice, Napoleon the Habsburg monarchy and throughout WWI and WWII.
All along the coast, there are countless excavation sites dating from antiquity onwards.
In addition, the Adriatic is a melting pot of cultures, religions, and nationalities. The best way to find out more is to buy a couple of rounds of wine to some locals.
Croatia has a LOT of islands, and the great thing is that they are all relatively close, which means that you can spend more time picking the perfect cove for swimming, and then, later on, choose another for lunch, and another to spend the night.
There is a very small chance of getting a bad skipper. Even if you get someone who is a first-time skipper its more than likely that they grew up around boats and this is the first time they are getting paid (before they did the same thing for free with their friends, on a lot less nice ships)
Even if worst comes to worst, we have an amazing coast guard and search and rescue squads. So whatever happens you are in safe hands.
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