Trebinje by car from Herceg Novi, with Tvrdoš and Hercegovačka Gračanica

Tvrdoš is a monastery dedicated to the Dormition of the Most Holy Mother of God, on the rocks beside the right bank of the Trebišnjica west of the city. The present church was built over earlier church foundations, and the glass section of the floor lets you see those remains beneath the space where services are held today.

The monastery's extensive restoration is associated with Metropolitan Visarion in 1509. The foundations, six stone columns, sections of wall and remnants of frescoes survive from the domed three-aisled church of that period. The church and monastery were destroyed in 1694 during the war between the Ottomans and Venetians. The church was rebuilt in 1928 with the support of Nikola Runjevac, a native of Trebinje who lived in America.

This history connects Tvrdoš directly with Herceg Novi. After the destruction, sacred objects and treasures were moved to Savina, while monastic life also continued in nearby Duži.

Saint Basil of Ostrog received his monastic tonsure and priestly ordination at Tvrdoš. The monastery is also associated with a long tradition of wine production in its cellars.

Trebinje's Old Town, known as Kastel, was built beside the right bank of the Trebišnjica. Its origins are tied to Ottoman efforts to fortify holdings in Herzegovina after Herceg Novi and Risan came under Venetian rule.

Osman Pasha Resulbegović began building the fortification in the early 18th century. Craftsmen came from Dubrovnik, while labourers came from surrounding places. Mosques and a clock tower took shape alongside the walls and towers, and a channel connected to the river surrounded the town. In front of today's entrance gate, a movable bridge once crossed that channel. The channel was later filled in.

Outside the walls, Jovana Dučića Street and Trg slobode form another part of the city walk. Beside this area is Platani, a garden known for the natural shade of its tall trees.

Arslanagića Bridge, also known as Perovića Bridge, is part of Trebinje's 16th-century Ottoman heritage. Its construction is associated with Mehmed Pasha Sokolović, and its later name with Arslan-aga, who was granted the right to charge for crossing the Trebišnjica. Arslan-aga arrived in Trebinje among families who left Herceg Novi after the withdrawal of Ottoman rule, so the bridge's history directly connects the two cities.

The bridge is not in its original location. It stood upstream near Mičevac until the construction of a hydroelectric system threatened that area. The bridge was dismantled and moved to its present site between Gradina and Police. Rather than remaining beneath the reservoir's water, its stone span was preserved as part of the city landscape.

The Church of the Annunciation, known as Hercegovačka Gračanica, was built on Crkvina hill above Trebinje. Jovan Dučić, the poet and diplomat, is buried there. The church was built to a design by Predrag Ristić, drawing on the architecture of Gračanica in Kosovo.

The church has five domes. Stone alternates with brick decoration on the exterior, while 16 columns support the interior. One of the columns has a circular base and rests on a stone brought from Gračanica in Kosovo. The tradition of carrying a stone from the hearth speaks of the bond between an old home and a new one.

Inside, the floor inspired by the Church of the Holy Archangels in Prizren, frescoes by Aleksandar Živadinović and an iconostasis made at Tvrdoš Monastery stand out. The floor is the work of Vladan Banković, and Sister Tekla of Dobrićevo painted the principal icons on the iconostasis.

The Crkvina complex includes a bell tower, an amphitheatre and buildings with gallery spaces. From the terrace, you can see how the Trebišnjica flows between the city's neighbourhoods.

The Museum of Herzegovina is in the Old Town, in a building that served as an Austro-Hungarian barracks and later as a school. Its archaeological collections include prehistoric, ancient and medieval material.

Add one full hour to the basic trip for the collection. An individual ticket costs 4 KM per person. Published opening hours are Monday to Saturday, 08:00-20:00, and Sunday, 14:00-20:00. The 14:00 opening on Sunday shifts lunch and the walk that follows. Choose this longer option when enough daylight remains after the museum for the bridge and the final view from Crkvina. The basic day trip does not depend on the museum being open.

With the museum, the plan takes about 13-14 hours. The visit is added during your time in the centre, while Gračanica remains the final attraction before the return.