2 day dubrovnik to Montenegro trip - please advise

What would be must sees? How does this sound?
Dubrovnik - cross border - ?worth stopping in Risan (what to do?) - Herceg Novi (grab a coffee and breakfast, ?walk around) - Perast (grab a boat to Our Lady of the Rocks) - drive to Kotor - walk around Old Town - hike to top of Sveti Ivan’s Fortress (better to do old town first and the fortress or vice versa?) - head off to Lovcen/Njegos Mausoleum - ?worth a stop in Njegusi and then Cetinje - head to Budva - check out Sveti Stefan hilltop and sleep in Budva?

Didn't stop in Risan, cant help you there. Herceg Novi is well worth a stop for lunch... exactly what we did once.

Between Kotor and Perast I would sleep in Perast. One of our best experiences was at a little hotel with dining on the side of the bay. Beautiful evening, quaint town without too many tourists. After Dubrovnik, Kotor was a waste of time. The Ostrog Monastery is worth the time. Love Budva. Spent a few days and did so fishing off the coast. Great time. Stari Bar was also well worth a day. The best part of the trip however was when we went north into the mountains stayed in an amazing resort and spent 3 days fly fishing and zip lining over the Tara River Canyon. Loved Montenegro so much we have made 2 trip and a third is coming soon.

By the way, Dubrovnik was beautiful, but a real tourist Disneyland. Only a few hundred Croatians live inside the walls, it's all for tourists.

I liked Kotor quite a lot, but I hadn't been to Dubrovnik on the same trip, and I had some time there with no monster ship in port (which makes a huge difference). That wall looked like a serious workout (Google for pictures--it is not remotely level), and you would be most unhappy tackling it during the hot part of the day in August. I don't know whether it's a fee attraction with fixed hours, or whether you can just show up at any time. In any event, you certainly should drive around the Bay of Kotor.

Perast is much too small for me to want to spend the night there; YMMV. I preferred Kotor, Cetinje, Budva, Herceg-Novi and Ulcinj (that one's too far south for you). Since you have a car, you might opt to spend some time in Lovcen National Park rather than trying to visit a bunch of coastal cities. The historic districts of Budva and Kotor seemed rather similar to me; I don't think you need to visit both.

I don't believe you can actually enter Sveti Stefan unless you're staying at one of the hotels there.

I suggest visiting ViaMichelin.com and noting the estimated driving times (said to be generally optimistic) along the route you might take. I think it's going to take a lot longer than you think to get around, and I'm not sure how easy it will be to find a place to leave your car when you want to stop and explore. Perhaps I'm unduly pessimistic; I traveled by bus.

Coastal Montenegro, at least, will be very busy in August. Don't plan just to show up and snag a room in a place like Kotor or Budva. It might be easier in Herceg-Novi, Cetinje or Perast.

I'm nervous about your plan to spend the night before your flight in Montenegro. What if there's an accident on that glorious highway and you sit, stopped, for hours? If the flight you speak of is part of a transatlantic ticket, I wouldn't risk having to buy a replacement ticket at the walk-up price.

You asked "...worth a stop in Njegusi and then Cetinje..."

From Kotor there is a road that leads away from the bay inland to the towns of Njegusi and Cetinje. The views are spectacular. But, It goes up the side of a steep mountain and has 25 numbered 180 degree switchback turns and at least 75 other sharp turns. Rock wall on one side and nothing on the other. Can't remember the name or number of the road. Don't mean to rain on you parade, but don't want you to get into a hairy situation without any knowledge. If anyone in your party is prone to motion sickness or has a problem with heights you might want to avoid this road. You can go to bing.com, use the map feature, and see aerial views of the road from &*$$. You can also check it out on googlemaps.com. It is possible, however, to go to and from Kotor with using that particular road. On 12 Mar. 2017 there was a thread titled "Greece Montenegro Croatia". One person included a link to the map that shows the road. Another person had a link to a video made along parts of the road.

I think sleeping in Kotor is a good choice but get a place now. Between Dubrovnik and Kotor we stopped for a seafood lunch at this terrific place http://www.catovica-mlini.com/en/. Can’t miss the signs, it’s been discovered. The road TC describes is a great ride. Watch for speed traps in Montenegro. The police are very business like and will tell you what the fine will be and how much you need to bribe the judge! Have an International Drivers Permit. The border crossing between Croatia and Montenegro can be slow at times so beware.

I heard there are ferries that could help with travel times on the way back to dubrovnik. I think it leaves from Herceg Novi but I don’t see the destination. Do you know where it would drop us off and if worth taking?

I think you might be talking about the Kamenari-Lepetane ferry. If you figure the time from Kotor to Herceg Novi with the ferry vs the long way around, it comes out to about the same time. If i were pressed for time i would skip the ferry. Too many variables. For fun, given the time I would use it.

The horrible road out of Kotor over the mountain is highway P1. I've been on it. It is worth the time (takes longer than the "long way"). It really isn't that bad. Safe enough for tour buses at least. At the top is a small village with the prosciutto aging house / restaurant with outdoor seating and beer, cheese and of course some pretty excellent prosciutto. One of those places that makes traveling worth the effort. https://1drv.ms/f/s!Ai7Zk-szxfTJhewQY_yHi-ykYB3ONQ

Why stay in Perast? Well, other than the two islands there isn't much need to stay in Perast. Sometimes though, i just want an easy day and night. The Islands are worth the effort and we hired a fisherman in a small boat to take us out fishing. Provided a pretty good tour of that end of the bay at the same time. Great experience. The hotel was pretty amazing as was dinner by candle light on the edge of the bay as the sail boats went by. https://1drv.ms/f/s!Ai7Zk-szxfTJhewKZUTbvs8xIXAOxQ Kotor on the other hand was wall to wall tourists. For my style, we chose well.

FWIW—We have found Via Michelin driving times to be fairly accurate, but google maps overly optimistic, which is too bad as the latter is much more user friendly.