Explore Southern Herzegovina, Dubrovnik and Bay of Kotor using Trebinje as Your Base

Updated: Aug 30

4–5 Day Itinerary:

Check into your accommodation in the Old Town or along the Trebišnjica River.
Stroll the Old Town (Kastel) — cobbled streets, Ottoman gates, and the Osman-Paša Mosque.
Cross the Arslanagić Bridge for river views.
Late afternoon coffee in Platanus Square under the shade of century-old plane trees.
Dinner at a riverside restaurant — try grilled trout or lamb under the bell with a glass of Žilavka.

Morning drive (30 minutes) to Dubrovnik — explore the Old City walls, Stradun, and Fort Lovrijenac.
Have lunch at a local konoba inside the walls or near the harbor.
Afternoon: Option to take a boat trip to Lokrum Island or a cable car up to Mount Srđ for panoramic views.
Return to Trebinje in the evening for a quiet glass of local wine away from the crowds.

Start with a visit to Tvrdoš Monastery — tour the 15th-century cellars and taste their award-winning wines.
Continue to Vukoje Winery for a vineyard tour, rooftop terrace lunch, and more tastings.
Visit Anđelić Winery for a more intimate, family-run experience.
Evening walk along the river in Trebinje, stopping for dessert or a nightcap at a café.

Drive to Mostar (about 2.5 hours) to see the Stari Most bridge and Old Bazaar.
On the way back, stop at Blagaj Tekke (Dervish monastery at the source of the Buna River).
If time allows, visit Počitelj, a preserved Ottoman-era hillside town.
Return to Trebinje for a farewell dinner and sunset at Crkvina Hill by the Hercegovačka Gračanica Monastery.

Border crossings: Bring your passport for day trips to Dubrovnik and Montenegro — allow some buffer time for summer traffic.
Car rental is the easiest way to follow this itinerary, but local buses connect Trebinje with Dubrovnik and Mostar.
Best seasons: Spring and autumn offer warm weather, fewer crowds, and lush scenery.
Wine tasting: Arrange in advance, especially for smaller wineries.
Pace yourself — part of Trebinje’s charm is enjoying the slow rhythm.