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What month? by squid

As starburns noted, July and August are peak with August being peak-of-the-peak. Hotels fill up and rates increase. If you are booking way ahead with flights, then it's less of an issue perhaps. We were last-minute and faced resulting constraints.

That said, we went to Croatia (and Montenegro and Bosnia) in August 2019 due to schedule constraints, and my wife and I kept saying we were glad we didn't let reports of crowds deter us. We just spent half a day in Split touring Diocletian's palace and were underwhelmed there yes with the crowds and also the sights themselves because we have been fortunate to see far better ruins (including Jerash in Jordan which just had a terrorist stabbing attack). Split was a big disappointment.

But other than waiting 30 minutes one time and 1.5 hours another time to cross the border we were fine. They are expanding the border facilities into Montenegro, you can look up the timeline of that.

Hvar was busy but not overly crowded. Outside of Hvar town, the island is desolate. Dubrovnik was not crowded the first day, but the second day there must have been more cruise ships in town because the crowds were overwhelming. We toured Dubrovnik the first day and just skipped through town the second day (one day is enough). You can view the cruise ship docking schedule online but it's a bit hard to fine.

Our tour guide in Dubrovnik said the city is pretty much empty outside of the peak months. In January you'll have it to yourself.

I would go over Labor Day or later if I could choose a date.

Montenegro could be worth a couple of days. Kotor's worth a stop. I wish we had had time to explore the interior and hike but that wasn't worth it with young kids. We stayed at a fancy hotel at Porto Montenegro but I would not recommend it unless you are somehow interested in looking at Russian and Arab super yachts.

One thing about Croatia is that sandy beaches are rare. You can swim of course and we did but it's off of platforms or rocks.