Enjoy a cycling tour of the Western Balkans, traversing parts of Croatia, Bosnia and Herzegovina, and Montenegro. You'll start in the medieval city of Dubrovnik and cycle through the Bay of Kotor, stopping in historic villages dotting the shore. Explore the towns of Kotor, Herceg Novi, and Cavtat, as well as the caves and wineries of Zavala and Ravno in Herzegovina. End the tour walking along walls and eating oysters in Ston on the Pelješac Peninsula, then bike through wineries, olive groves, and along beaches to return to Dubrovnik. 


  • Cycle through Croatia, Montenegro, and Bosnia & Herzegovina
  • Explore the medieval coastal towns of Kotor, Dubrovnik, and Cavtat
  • Taste regional wine and discover the caves of Herzegovina
  • Walk Europe's longest city walls and eat oysters in the town of Ston
  • Discover wineries, olive groves, and sandy beaches on Pelješac Peninsula

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Dubrovnik - Explore the city Dubrovnik
Day 2 Cycle through Bosnia and Herzegovina to Herceg Novi, Montenegro Herceg Novi
Day 3 Discover the coast of Montenegro and Bay of Kotor Kotor
Day 4 Enjoy the scenery in Konavle and explore the town of Cavtat Cavtat
Day 5 Discover the history, caves, and wine of Popovo Polje Valley Ravno
Day 6 Eat world-famous oysters and taste wine on the Pelješac Peninsula Ston
Day 7 Traverse the Pelješac Peninsula and transfer to Dubrovnik Dubrovnik
Day 8 Depart Dubrovnik  

Detailed Itinerary

Day 1: Arrive in Dubrovnik - Explore the city

Harbor and Beach of Dubrovnik
Harbor and Beach of Dubrovnik

Welcome to Croatia! Upon arriving at the airport in Dubrovnik, you'll transfer to your hotel. After settling into your room, you can enjoy the rest of the day to explore this historic walled city. Known as the "Pearl of the Adriatic", this region came into its own in the 12th and 13th centuries when it was under the rule of the Venetians. Throughout the Middle Ages, it was a fortress port encircled by stone walls and filled with an array of baroque, renaissance, and Gothic architecture.

After checking into your hotel, head out into the Old Town, walking along its walls and visiting the Lovrijenac and Bokar fortresses. There are almost too many sights to see, but you can't miss the Saint Ignatius Church, Rector's Palace, or the Dubrovnik Cathedral. Other interesting monuments include Sponza Palace, the Dominican Monastery, and the Dubrovnik Synagogue. Outside the walls, you can visit the Porat, the West Harbor, and Pile Gate.

As the sun starts to set, you can opt to ride the cable car up to Srđ Mountain to take in the views over the nearby Elafiti Islands. If you'd rather stay in the Old Town, you can grab an aperitif at Buza Bar on the waterfront. Afterward, return to your hotel for a welcome dinner with your hosts. During your meal, you'll discuss the details of the week to come and learn more about what your trip will entail.

Day 2: Cycle through Bosnia and Herzegovina to Herceg Novi, Montenegro

Views of Herceg Novi
Views of Herceg Novi

After breakfast, you'll transfer to today's starting point and get acquainted with your bicycle. After receiving all your gear, you'll start today's route, which will take you from Dubrovnik and across the border toward the town of Trebinje in Bosnia and Herzegovina. Here you can stop to enjoy lunch.

As you continue, you'll cycle through a hilly section of the route through three different countries. In addition to Croatia and Bosnia, you'll also cross into Montenegro. After about 40 miles (65 km), you'll arrive in the coastal town of Herceg Novi on the Bay of Kotor.

After settling into your accommodation, you can explore the Old Town of Herceg Novi. The town is filled with cobbled streets and stone staircases, leading you from its hillside fortification Kanli Kula Fortress to the coastal estate, the Sea Fortress. While exploring its streets, you can't miss the Clock Tower or the old walls. Enjoy visiting the many churches and plazas, as well as the seafront promenade and public beach.

In the evening, your hosts will give you plenty of recommendations for dinner. Enjoy your meal by the waterfront as the sun starts to set.

Day 3: Discover the coast of Montenegro and Bay of Kotor

Bay of Kotor, Montenegro
Bay of Kotor, Montenegro

In the morning, you'll enjoy breakfast at your hotel before starting today's route through the Bay of Kotor, also called Boka Bay. This fjord runs from the Adriatic coast to the city of Kotor, lined with tall, jagged cliffs and dotted with historic, medieval villages. 

Today's ride takes you through mainly flat terrain, weaving around the bay along its main road. You can stop at a few of the villages if you'd like, where you can enjoy lunch and swim. The town of Perast is particularly interesting and where you can explore the two small islands housing a church and a monastery.

The region of Boka Kotorska is protection under UNESCO, due to its very rich Croatian cultural heritage. In 1979, an earthquake destroyed and seriously damaged numerous cultural monuments. Some have been restored or removed, while others still lay in ruins. 

As you enter Kotor, you'll stop to enjoy a quick tour of the city, entering its historic old walls through medieval gates. If you're interested, you can hike the hill behind the city up to the ruins of Kotor Fortress, passing by the Church of Our Lady of Remedy. The views from the trail are worth the steep climb.

After exploring Kotor, you'll continue up the road to your accommodation. The rest of the day is yours to relax along the shore of the bay, swim in the sea, hike in the hills, or stroll through Kotor's Old Town.

Plan your trip to Croatia
Chat with a local specialist who can help organize your trip.

Day 4: Enjoy the scenery in Konavle and explore the town of Cavtat

The Harbor of Cavtat, Croatia
The Harbor of Cavtat, Croatia

Today's route will follow the other side of Boka Bay back toward the border with Croatia. Enjoy views of the hills surrounding the bay as you pass through small villages along its shores. Once you cross the border, you'll continue through the rural region of Konavle, a picturesque area that lies between the mountains and the Adriatic Sea.

In the afternoon, you'll arrive in the historic, coastal town of Cavtat. After settling into your accommodation, set out to enjoy this little village. There are many restaurants, cafes, and shops along the waterfront promenade. You can also explore its Old Town, the Cavtat Cemetery, the Church of St Nicholas, and the Monastery of Our Lady of the Snow

If you're interested in museums, you can visit the Cavtat Museum or The House of Vlaho Bukovac, which is filled with art and furnishings. When you're ready for dinner, you'll find plenty of options in the Old Town or along the promenade.

Day 5: Discover the history, caves, and wine of Popovo Polje Valley

Vjetrenica Cave, Bosnia and Herzegovina
Vjetrenica Cave, Bosnia and Herzegovina

The recent history of Bosnia and Herzegovina is tumultuous, due to the conflicts in the 1990s. Today's route takes you through the rural countryside where battles took place. In the morning, a short shuttle will take you to the border where today's route begins.

As you enter Bosnia and Herzegovina, you'll ride past the town of Ivanica following an old railroad along Popovo Polje Valley and the Trebisnjica River. This stretch was a war zone in the 90s, and you're sure to notice the remnants of its conflict. With buildings filled with bullet holes and signs warning of landmines across fields, you'll learn about the war and its lingering effect on the area. But although the region's history is bleak, your ride is juxtaposed with the beauty of its landscapes and the coastal views.

In the afternoon, you'll arrive in the small villages Zavala and Ravno. You'll first stop in Zavala for lunch to enjoy a traditional Herzegovinan meal, then to explore its cliffside Zavala Monastery and the Vjetrenica Cave. Afterward, you'll continue to Ravno and settle into your accommodation. Here you can visit the old train station, Stanica Ravno, which now hosts a hotel, a restaurant, and a wine cellar where you can taste different varietals from the region. 

In the evening, enjoy a peaceful walk or bike ride through the Popovo Polje Valley for incredible views as the sun starts to set.

Day 6: Eat world-famous oysters and taste wine on the Pelješac Peninsula

Walls and Harbor of Ston, Croatia
Walls and Harbor of Ston, Croatia

Although it's not as famous as its northern neighbor Dubrovnik, today's destination is the historic and well-preserved medieval town of Ston. It was once a major fort for the Ragusan Republic, whose base was located in present-day Dubrovnik. 

Today's short cycle will take you through the valley and up several hills, passing rural areas of Herzegovina and into Croatia. After crossing the border, you'll enter the Pelješac Peninsula where you'll settle into your accommodation in Ston. Known for its incredible oysters and mussels, you can't miss a traditional seafood meal at one of Ston's restaurants. Some suggestions include Bacus and Kapetanova Kuća.

After lunch, explore the city by walking along its medieval walls, as Ston has the longest city walls in Europe. The town is also known for its exceptional red wine varietals. You can taste some at different wineries or cafes in the area. In the evening, enjoy cycling the easy trails along the peninsula's waterways, stopping at beaches for a swim or to simply relax.

Day 7: Traverse the Pelješac Peninsula and transfer to Dubrovnik

Town of Orebic on the Peljesac Peninsula
Town of Orebic on the Peljesac Peninsula

Your last day of cycling will take you along the Pelješac Peninsula, which may be the most scenic route of the trip. You'll follow coastal roads with views of the sea, as well as waterfront wineries and small, red-roofed villages. It's the second-largest peninsula of Croatia, brimming with natural bays and coves, dense forests of pine and olive trees, sprawling beaches, reefs, and even fjords.

Pelješac has an ancient history, inhabited by IllyriansGreeks, and Romans, as well as Croats since the 7th century.
The peninsula is well-connected by an asphalt road joining all the settlements. The road branches off toward Trpanj to the east and Orebic to the west. You'll take the second detour and make your way to Orebic in time for lunch.

After lunch, you'll return your bike and take a shuttle back to Dubrovnik. Settle into your hotel and enjoy your final night in Croatia meandering the historic streets of the Old Town. You can swim at the public beach, enjoy a kayak sunset experience, or simply relax at a cafe overlooking the water. 

Day 8: Depart Dubrovnik

Old Walls of Dubrovnik at Sunrise
Old Walls of Dubrovnik at Sunrise

It's time to say goodbye to the Balkans. Depending on the time of your flight, you can enjoy a leisurely final morning in Dubrovnik. If you have the time, opt to visit one of Dubrovnik's museums, such as the Franciscan Monastery and Museum. This large complex houses many treasures, including the world's third-oldest pharmacy dating from 1317.

When you're ready, you'll transfer to the airport in time to catch your flight.