I’m confident that most people who have been to Kotor have climbed up to the fortress of St. John. Most likely, this same majority has also seen the trail that goes to the left of the fortress and leads further up somewhere. This trail is a hiking path from Kotor to Lovcen. It will indeed take you there after a couple of dozen kilometers. Finding it is easy; just leave the old town and go around from the left side. You’ll see a signpost. Also, all hiking routes in Montenegro are marked with red dots with a white dot in the center.
You could also use this hiking trail to enter Kotor fortress through a window for free. However, the window is high, so kind people used to place a ladder there in the past. They have removed and replaced this ladder many times. But there are no guarantees that it will be there, so don’t count on a 100% chance of getting inside.
Currently, the entrance fee to the fortress is 15 euros per person. For permanent residents of Montenegro (I assume for citizens and probably for mushroom pickers), the entrance is free. There is a turnstile at the entrance, and a ticket seller is present. You can still enter for free if you go before 8 in the morning or after 8 in the evening.
When you stand on the walls of the fortress itself, it may seem like there’s nowhere higher to go. However, after walking a few kilometers along this trail, you realize that you can continue to climb higher and higher.
Walking here is much easier than climbing the stairs to the fortress itself. You may encounter goats leaping along the sheer cliffs in search of tasty bunches of grass or even cows. On the right, you have a view of the Bay of Kotor and the fortress, while on the left, the mountain seems to stretch endlessly.
In the middle of the trail, there’s even a residential house with a farm where you can not only buy water but also get rakija, goat cheese, and pršut. At some point, we got tired and decided to head back.
If you look closely at the photos of the fortress, you will see two small paths leading to a window. This is how you can enter the fortress if there’s a ladder or if you can pull yourself up effectively.