Driving trip from Dubrovnik to San Marino, Italy

Sounds like a great trip to me. I think you'll need to tell your car-rental firm where you plan to take the car, but I'm sure plenty of others have rented a car and taken it into Bosnia-Hercegovina and Slovenia. You'll probably need to drop the car in Croatia to avoid a painful extra fee, but doing that after visiting Slovenia shouldn't be all that difficult if you want to use the car to see (for example) the Julian Alps. If you search the Slovenia forum, you'll find some earlier threads about visiting parts of Slovenia beyond Ljubljana and Lake Bled.

Information has also been posted about getting from Slovenia to Italy by public transportation.

An area that not everyone thinks about visiting is the Istrian Peninsula. It's mostly Croatian, but a slice of the north belongs to Slovenia. There are many interesting coastal towns (Pula, Rovinj, Porec, and Piran among them), but the inland area is very pretty and rather difficult to visit without a car. It has some medieval towns that don't get very many tourists. A lot of coastal Croatia is beautiful but quite heavily touristed.

Spend the night near Plitvice so you can see the park minus the mobs of day-trippers, either late in the afternoon or early in the morning, or both.

When you get into Italy, consider a stop in Ravenna. It's on the way to San Marino and is a very pretty town aside from having some incredible sites with medieval mosaics. It's accessible by train but a bit off the main line, so it's not as touristy as it deserves to be.

One thing to keep in mind is that the tourist targets in much of this area are within pedestrianized historic districts, so your planning needs to include research into parking options at each stop.

This sounds like a minimum 4 week trip to cover so many countries. Three weeks will mean severe compromises.

You will have difficulty finding a car rental for Croatia to Italy and the cost will be prohibitive. If you hire a car in Croatia and return it there, ensure that you are covered to take it out of the EU into Bosnia etc.

An alternative to driving all the way would be to take the ferry from either Dubrovnik to Bari in Italy or from Split to Ancona then hire another vehicle upon landing. This would still leave plenty of time for driving.

You are travelling peak season, so try not to move accommodation too often - I would suggest 3-4 nights in each place. Dubrovnik is compact and can be covered in a day, but you could also take a day trip out to Mljet. Mostar deserves a full day, as does Sarajevo.

If you then drove back to the coast, you could drive to Drvenik and take the short ferry crossing to Sucuraj on Hvar and drive over to Stari Grad, Jelsa or one of the inland villages such as Dol for 3-4 nights. Avoid Hvar town at this time of year - parking is more difficult and it's peak party clubbing season.

Take the ferry to Split from Stari Grad and stay for 3 nights, also covering Trogir from here, then drive to Plitvice for a 1 night stay to enable you to get into the park as soon as it opens. It will still be very busy - you may want to consider the less busy Krka Park instead. Then drive to Rovinj as a base for Istria, which deserves a week to cover the pretty hill villages and the coast.

Other places that merit consideration include Primosten, a pretty coastal town, Pag island for its cheese, Korcula, Zadar and Zagreb.

Do you have any time left for Slovenia or Italy?

Other posters have given you some very sound advice, I would just like to add a few more notes. In terms of the time required for this sort of trip, I would like to have roughly two weeks in Croatia, a few days in Bosnia, around a week in Slovenia (depending on whether you would do any hiking there or not) and then as long as you wish in Italy, there really is a wealth of sights between the Slovenian border and San Marino. In short, a three-week time frame will be very, very rushed. Four weeks sounds much better, especially if you have already been to places such as Venice, which would otherwise eat up a lot of time.

If you plan on visiting mostly cities on the Italian leg of your trip, a rental car will not really be necessary, it may even be a burden. In Croatia and Slovenia, a rental car makes moving around a lot easier. I would try to get some quotes on a single rental for Croatia and Slovenia, picking up in Croatia and dropping off in Slovenia. See if the cost is acceptable, it will save you some time. Otherwise, the best option is probably to wind up the Croatian portion of your trip in the Istrian peninsula, for example in Rovinj, dropping off the car there, taking a bus across the border to Piran/Portoroz or Koper and then renting another car there for the Slovenian portion of your trip.

If you enjoy sailing, stop in Zadar and take a sailing tour of the Kornati Islands NP and other islands in that area. The region around Zadar is excellent for sailing, with lots of small scenic islands. For wine, Istria in Croatia and the Goriska Brda and Vipava Valley in Slovenia are the places to go. For hiking, the Julian Alps are by far the best option along your route bar taking a detour through the Italian Alps, for which you probably do not have time, though.

Thank you for being so helpful! You all have given me some great ideas as well as some thoughts on what should be our priorities. The Istria Peninsula sounds like a must-do, as do the Julian Alps. And thanks so much for the recommendations of different islands and sailing options.

So, here's a question: If we have already seen Venice, and are considering a ferry across to Italy, is the scenery more interesting if we ferry to Ancono or Bari than if we were to drive instead (forgoing the ferry) around the north end of the Adriatic?

The ferry itself involves no scenery at all as it crosses the sea and does not follow the coast. If you stick to one of the ferries, consider that there will be some significant backtracking involved in order to see most of Croatia. I wouldn't go as far as Istria and Slovenia if I had to return to Split or Dubrovnik to take the ferry across, as once you're that far north, it's much faster and easier to simply continue into Italy and onwards to San Marino using ground transportation.

If you opt for the ferry, then limit yourself to the area of Croatia between Split and Dubrovnik, as well as Bosnia and perhaps Montenegro and spend more time on the Adriatic Coast of Italy instead, between Ancona/Bari and San Marino. I'm afraid I cannot advise which option is better, I have not spent any significant amount of time in the Marche, Abruzzo and Apulia.

Thanks, Dejan! I worded my post poorly. I meant is the scenery better on the Adriatic coast if you ferry to Italy, which you answered at the end. Thanks a bunch. :)