Croatia & West Balkans
5-Day Moderate

Distance: 63 kms (39 miles) / Elevation Gain: 896 m (2957 feet) / Saddle Time: 3-5 hours

Today’s ride takes you from Dubrovnik’s medieval walls into the rugged hinterland, with an early climb offering sweeping views back over the Adriatic before you cross into Bosnia and Herzegovina. A short detour at roughly the midway point brings you to Trebinje, a charming riverside town surrounded by vineyards and dominated by the stone arches of its Ottoman bridge. A perfect mid-ride pause, the shaded squares and laid-back rhythm here feel worlds away from the coast.

From Trebinje, a rolling ride and a long descent guide you back towards the sea, where Montenegro’s Herceg Novi greets you at the entrance to the Bay of Kotor. Known as the “City of a Thousand Steps,” this lively harbor town is framed by Venetian fortresses and palm-lined promenades — the perfect spot to stretch out tired legs and enjoy your first Montenegrin evening by the water.

Distance: 39 kms (24 miles) / Elevation Gain: 700 m (2310 feet) / Saddle Time: 2-3.5 hours

Leaving Herceg Novi, the day begins by cutting inland via Bakoci before reaching the edge of the Bay of Kotor, often described as Europe’s southernmost fjord. The road then hugs the water, with every bend revealing new vistas of towering limestone cliffs dropping into the deep blue bay. Small fishing villages and stone churches dot the shoreline, offering perfect spots to pause and soak in the view.

As you continue deeper into the bay, the route flattens and smooths out, making for a rewarding stretch of uninterrupted riding. On arrival in Perast, look for the tiny islets of Our Lady of the Rocks and St. George’s Island, floating just offshore like storybook scenes. The day’s finish is the fortified town of Kotor, a UNESCO World Heritage Site where medieval walls climb impossibly high up the surrounding mountains. The evening is yours to wander cobbled alleys, sip Montenegrin wine, and savor the day’s ride into one of the Adriatic’s most dramatic settings.

Distance: 70 kms (43 miles) / Elevation Gain: 745 m (2458 feet) / Saddle Time: 3-5 hours

Today’s ride begins with a farewell to Montenegro’s majestic Bay of Kotor. A picturesque morning cycle next to the water’s edge unveils fresh perspectives of the Bay of Kotor. A short ferry trip across the bay brings you to Kamenari, then onwards to Herceg Novi before a steady climb carries you inland toward the Croatian border. Quiet backroads unfold through rugged landscapes, where olive groves and small hamlets break up the mountain scenery. The border crossing marks your return to Croatia, and with it comes a thrilling descent back toward the Adriatic.

Your destination is Cavtat, a serene coastal town often described as Dubrovnik’s quieter cousin. Its pine-shaded promenades, pebbled coves, and laid-back charm offer the perfect contrast to the day’s challenging climbs. After a rewarding ride, unwind by the waterfront with a cool drink as fishing boats drift in and the sun sets across the bay.

This morning, we have arranged a transfer back to Dubrovnik, watching the Adriatic and its scattered islands slip by as you return to where your adventure began.

After days of coastal climbs, sweeping descents, and hidden valleys, take a moment to reflect on the journey. From the quiet vineyards of Herzegovina to the dramatic Bay of Kotor. You’ve cycled across borders, cultures, and landscapes, experiencing the very best of the Adriatic and the Balkans.