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My Big Idea: Biking & Sailing the Adriatic. Possible? Help!

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This is a shot in the dark.

I got this trip idea in my head and became really hung up on it, I really want to do it. But I'm not finding the resources to make it happen via google searches and I think someone here in this forum can give me a clue on how to do it if it's possible. My idea isn't whacky, I just need to find a boat charter by the day instead of by the week, this is where my roadblock is. We're looking to keep the trip within about 2 weeks time + travel, so say 16 days total or less.

We want to do a cycling trip that originates in Venice, with a 2-3 night stay there before 6 nights spread through Italy, Slovenia & Croatia, then ferry back to Venice. We would then fly to Split or Dubrovnik and charter a boat (with skipper) for 4(ish) days along the Dalmatian Coast. We might like to make it as far as Kotor either by sail or land/air while we're in the neighborhood IF it's feasible. (I'm pretty sure it is too far to make by sail in our time allotted and not sure how difficult it is to reach by land, have not dug that deep into this yet). We'd then fly home from wherever makes sense from our ending point.

Alternatively we could fly from Venice to Greece or Turkey and charter the boat there, it doesn't have to be the Dalmatian Coast. Another option yet is to do the biking trip in southern Italy or Sicily and work the charter in from there or striking distance from there. Sailing Greek islands is very appealing to me.

I'm dying to do a sailing trip but husband is not so sold on it. That's why I'm looking for a short trip to try it out before committing to a standard 7-14 day trip. I have not been able to find anything under 7 days online but I think the option must exist somewhere. Maybe more in terms of "go see my guy down a the far end of the marina with the blue boat, tell him bob sent you and he'll take care of you" than in the internet tourist commerce sphere. But what do I know.

We would need a small boat as it would just be us or *fingers crossed* us plus one other couple. This is why I'm trying to collect info now, so I can give my sales pitch to the other couple when we see them them in a few weeks. I'd like to do the trip next spring or late summer, though I'm open to mid summer. Early June is probably my sweet spot.

Is this possible? Dumb idea? Know a guy with a boat?

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