Originally Posted by
hdogan
Bear in mind that both Krk and Rab are *south* of Istria, so if you'll be staying somewhere in Istria, you'd have to backtrack. The drive from Istria to Sibenik will likely take you 4-5 hours along the highway (uninteresting), or about an hour, hour and a half longer if you take the coastal road, which is a really beautiful ride.
Stop by in Zadar on the way to Sibenik.
Split to Dubrovnik is about 3-hours drive, with a border crossing in and out of Bosnia. If you really plan to drive there after dinner, it will either be an early dinner or a very late arrival.
Two days in Dubrovnik is too much, IMO. Frankly, it's a very small medieval town, and once you've seen it, well... you've seen it. Rather make your trip to Dubrovnik a bit longer, spend a day, day and a half there, and drive back to Split to take the ferry.
Weather can be on and off in late October, you may have wonderful warm autumn, but you may get really cold wind as well... just bring clothes for both cases

This was extremely helpful, hdogan, and much appreciated. Based on the travel times that you alerted us to from Istria to Sibenik, and the fact that we know we want to spend time down in Dubrovnik, Montenegro and other small towns, we decided to leave off Istria altogether.
We are grateful for any feedback to the revised plan which is:
The first day will be spent driving from Veneto along the coast, visiting small coastal towns and eventually settling in one somewhere north of Split for the evening. It may be Sibenik, it may be Zadar, or it may be somewhere else. We still need to do more research to figure out what towns to stop in and stay in and are open to suggestions.
The second day, we would likely see Split and probably stay around there.
The third day, we would likely see Korcula and maybe stay in Korcula or near Split or another quaint town, also maybe do some sailing that day. How does it work to do sailing? I actually am a sailor (as in sail sailboats for fun and regattas) but I assume someone is not going to rent me their sailboat to take out and sail myself, and my traveling partner does not sail so would not be able to crew, so are we just hiring a sailboat and skipper who will take us around? Any recommendations as to how to do this/who to use? We would likely only want it for a few hours.
The fourth day, we would head down to Dubrovnik and see all that we can see there despite the fact that it will be All Saints' Day.
The fifth day, we would head down to Montenegro. I am not sure if we should stay in Montenegro or just go there for a day trip and stay in Dubrovnik again. Suggestions?
The sixth day would be the trek back up to Venezia.
We really went into this trip with a few things that we knew:
a) We want to see and relax on as much of the beautiful Dalmatian coast as possible and enjoy the beautiful water, though I understand actually swimming in it may not be advised that time of year,
b) We are really looking for a trip where we can get to see how the Croatians live, experience it more like locals instead of from a resort-feel, maybe stay at small locally-run, family-owned hotels, etc.
However, the more that we are seeing trip reports for the Le Meridien in Split and the Hilton Imperial Dubrovnik, the more we are wondering if we should stay these places instead. We were thinking of maybe renting an apartment in Dubrovnik, but after what we have heard about the location of the Hilton, we just wonder if maybe we should rethink this. So I am wondering if there is advice as to which way to go: apartment or hotel? Rick Steve's seems to say apartment, but how easy is it renting an apartment for only two nights and is it just easier to stay in a hotel? If not an apartment, are there recommendations for good family-owned hotels? Any recommendations as to whether to stay in Kotor Bay,Montenegro or just do a day trip and stay in Dubrovnik?
Has anyone seen the sword-dancing in Korcula and is that worth seeing?
Thanks again for the help!