All of the information posted here is really helping us create and firm up plans. We loved the Korcula suggestion and tried everything we could to make that work but with ferry times, it just took too much time out of our schedule. Still, we liked the idea of the peninsula so have incorporated that into our plans.
Our trip will be similar to what I posted with minor changes:
Day 1: VENICE TO ZADAR: Drive from Venice to Zadar (E61 and coastal route once we get to Opatija area), stopping at a couple of towns for stretching our legs and meals. We know this will be a long day but have resolved to not be in a rush about it and just enjoy the beautiful scenery. Stay in Zadar at a sobe or apartment. Right now, we are considering an apartment in Old Town Zadar.
Day 2: ZADAR, SIBENIK, SPLIT: See Zadar in the morning and make our way to Split, stopping in Sibenik and other small towns. Arrive in Split by dinner time. Stay at Le Meridien Split/Lav.
Day 3: SPLIT, MAKARSKA, PELJESAC PENINSULA: See Old Town Split in the morning and then make our way down toward Ston/Mali Ston on the Peljesac peninsula, stopping in Makarska and driving through Metkovic where we read there may be (in the summer) mandarins and local honey roadside which is exciting to us, but I wonder if driving through at 6 PM on the last day of October is going to bring us bad luck finding roadside local goodies. We realize we are going to get to Mali Ston late in the day (about 7 PM), so we figured we would have dinner there (since the region is so highly acclaimed for gastronomy), and just stay the night there. However, we are having trouble finding a whole lot of options for accommodations in the area as most rentals are a minimum of one week and the hotels are not that exciting us. Keep in mind that we are not expecting fancy places - we are all for small, local hotel that are more modest, but we just are not finding a lot. Does anyone have any recommendations as to places to stay for one night near Ston or Mali Ston? We also considered just driving in late that night to Dubrovnik since it is so close but we were hoping to take it more leisurely. We also found that there are apartments for rent for one night in Slano which is on the way to Dubrovnik. We don't know anything about it other than it is on the way to Dubrovnik.
Day 4: DUBROVNIK: We will head to Dubrovnik, making it in time for a 10 AM church service. We plan to walk the walls, take the cable car, visit the other major sights (and maybe Buza Bar for the evening), and out to dinner somewhere. We will be at the Hilton Dubrovnik that night.
Day 5 : KOTOR BAY: We will drive to Kotor Bay, spending the day down there. We were hoping to hire specifically a sailboat and skipper for half of a day, but have run into trouble in that we are going during the off-season (we will be there Nov. 2) and it seems most boats stop at the end of October. Specifically, we wanted a sailboat and as mentioned here, I need a certain license to sail so we would need to hire a skipper instead of going bareboat. Stop for dinner in Cavtat or the Konavle region or somewhere on the way back for a "local" dinner (we are very interested in agrotorismo) to Dubrovnik and stay at the Hilton again for the evening.
Day 6: TO ITALY. We love the idea of taking the ferry back as suggested here by hdogan, but the ferry does not run the days we are traveling. We will drive the "quick" way instead of scenic this day as it will be the longest day of driving.
A few questions:
a) How do you find a reputable sobe or apartment (Zadar and peninsula are)? I see many listed on booking.com and other websites but know nothing about many of them so don't know how to discern what would be good Some tour guides say sobes are regulated and listed on certain websites (though I don't know what those official websites are) and other tour guides say they are unregulated. Should we feel comfortable with something on booking.com or not necessarily? Also, Rick Steve's guides say to book directly with the sobe instead of through a site, but we have no idea how to do such a thing as most are only listed on third party sites.
b) Any recommendations for accommodations in Zadar? We prefer to stay in Old Town.
c) Any recommendations for accommodations near Ston or Mali Ston or even Slano or somewhere else in the area?
d) Any recommendations for restaurants in Mali Ston and also on the way back from Kotor Bay near Cavtat or Konavle area? We love the idea of local farmhouses and whatnot.
e) We were unsuccessful renting sailboat in Split or Makarska or Zadar because they tend to rent longer (minimum one day but usually minimum of a week) so found a charter company that does rent for half-days but don't have skippers available the day we are there. Is there a trick to hiring a local sailor outside of using a charter company?
f) Will we find roadside goodies for sale when we pass through Metkovic?
Many thanks, again, for your fantastic help and information.