This 6-day itinerary provides an in-depth look at popular Dubrovnik and its surrounding scenic attractions. Spend time wandering the Pearl of the Adriatic's medieval streets and massive fortress walls and kayak out to nearby Lokrum Island for a unique perspective of the city. You'll sail to three of the vegetation-covered Elafiti Islands, visit an oyster farm in Mali Ston, and pedal through the charming countryside of the Konavle.


  • Paddle to Lokrum to swim in the island's saltwater lake, Croatia's own Dead Sea
  • Hoist anchor and sail amid the Elafiti Islands of Koločep, Šipan, and Lopud
  • Lunch on fresh-caught oysters and mussels and sample wine native to the Pelješac peninsula
  • Bike through the Konavle wine country and sample local brandies
  • Sip a cocktail from Dubrovnik's Buza Bar and enjoy the sunset over the Adriatic

Brief Itinerary

Day Highlights Overnight
Day 1 Welcome to Dubrovnik! Dubrovnik
Day 2 Walking Tour of Dubrovnik, Sea Kayaking around Lokrum Island Dubrovnik
Day 3 Pelješac Wine & Oyster Tour from Dubrovnik Dubrovnik
Day 4 Sail the Elafiti Islands: Koločep, Šipan, & Lopud Dubrovnik
Day 5 Cycle through Konavle Wine Country Dubrovnik
Day 6 Depart Dubrovnik  

Detailed Itinerary

Day 1: Welcome to Dubrovnik!

Old city walls and the Adriatic
Old city walls and the Adriatic

This is a treat because you'll be arriving in one of the most ancient fortress cities in Europe. Known as the "Adriatic Pearl," Dubrovnik is a piece of history. While there's evidence of settlements as far back as the Byzantine era, this area only 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 baroque churches and renaissance/gothic palaces that still stand today.

Upon arrival at the airport, you'll transfer to your hotel for check-in. Despite being tired from the journey, you'll likely want to get out and explore. Can't-miss activities include riding the cable car up to  Srđ Mountain to take in the sunset over the nearby Elafiti Islands, visiting Lovrijenac and Bokar fortresses, and walking along the smooth, limestone-paved streets of historic Old Town

After spending some time getting to know the city, duck into one of Dubrovnik's many wine bars to relax. It's a good plan, as there's no better manner in which to celebrate your first day in Croatia than by enjoying a glass of white or red wine as the sun goes down over Dubrovnik's Old Town. For dinner, there are a number of great restaurants you can choose from.

Day 2: Walking Tour of Dubrovnik, Sea Kayaking around Lokrum Island

St. Blaise Church on Stradun
St. Blaise Church on Stradun

Start your day early (around 8 am) to avoid the crowds and to embark on a tour of Dubrovnik where you'll meet your expert guide outside the entrance to the medieval city at the 16th-century Pile Gate. Entering Old Town, you'll uncover centuries of the city's rich history as you listen to stories of local life and legends and of the importance Dubrovnik once held in the era of the Republic. Highlights include Onofrio's  Fountain, the 15th century Rector's Palace, Luza Square, the Church of St. Blaise (St. Vlaho), and the café-lined streets of Brsalje Street

After touring the streets and alleys, you'll head for Lovrijenac Fortress as well as the city's impressive defensive walls, the second-largest set of city walls in the world. At certain places the wall rises 75 feet high, offering excellent vantage points for photos of the coastline. 

In the afternoon, head to the water for a guided kayaking adventure around the city and Lokrum Island—the closest island to Dubrovnik. Starting from Banje Beach, you will paddle to Lokrum Island where you can enjoy a swim in the saltwater lake named the Dead Sea, explore the 15th-century Benedictine monastery, and trek along the car-less trails through overgrown gardens. This is a great way to experience the cultural and historical sites of Dubrovnik from a unique perspective.

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Day 3: Pelješac Wine & Oyster Tour from Dubrovnik

View of Mali Ston and the Bay of Mali Ston
View of Mali Ston and the Bay of Mali Ston

Leave Dubrovnik behind for the day and head northeast to discover some of what the Pelješac peninsula is famous for: mussels and oysters, Dingač red wine, and stunning rugged landscapes. You'll set out beyond the village of Mali Ston, sister village to nearby Ston (and connected by an impressive stone wall) for an introduction to the peninsula's wine country, stopping to visit two popular wineries where you'll get to sample local varietals before returning to Mali Ston.

Next, switch gears and board a boat to cruise the Bay of Mali Ston as you find your way to the oyster beds. Learn about the region's oyster and mussel farming as well as learn what makes the European flat oysters or Ostrea edulis so distinctively unique than other varieties.  Enjoy a light lunch of the fresh-caught shellfish served with buzara (a traditional meal of mussels prepared in olive oil, garlic, and white wine) and a glass or two of local wine and grappa. When you're satiated and ready, you'll transfer back to Dubrovnik.

Driving time (Dubrovnik to Mali Ston): 1 hour

Day 4: Sail the Elafiti Islands: Koločep, Šipan, & Lopud

Koločep Island
Koločep Island

Today is reserved for a fun day of sailing to three of the Elafiti Islands: Koločep, Šipan, and Lopud. Set between Dubrovnik and the Pelješac peninsula to the north, the small archipelago consists of 13 lush islands where only these three are presently inhabited. 

Your first island stop is Koločep (referred to by locals as "Kalamota"). The southernmost inhabited island in Croatia is little over a square mile, and home to just over 150 year-round residents and there are no cars on the island adding to its relaxed, unspoiled atmosphere. From here you'll continue to make your way to Suđurađ on Šipan, the largest of the Elafiti, to discover the walled summer villa of a 16th-century shipowner.

Next, you'll set your course for Dubrovnik, stopping at Lopud on the return. Once functioning as a weekend retreat for Dubrovnik's nobility, Lopud was home to many of Dubrovnik's merchant fleet—ruins of the many shipowner homes still occupy the corners of Lopud's only village of the same name. Here you'll have the opportunity to explore the 15th-century Franciscan monastery that overlooks the village as well as take in the Croatian Adriatic beauty.

Day 5: Cycle through Konavle Wine Country

Waterfront town of Cavtat, Konavle
Waterfront town of Cavtat, Konavle

This morning you'll meet your driver to transfer to a starting point in Konavle, a famous wine region south of Dubrovnik. Here, you'll switch gears and hop on your bike to spend the day cycling through small villages and valleys. For lunch, your guide will lead you to a restaurant on the Ljuta river where you'll have the opportunity to participate in sampling local brandies. Afterward, continue biking past orchards, vineyards, and farms and get a real sense of Konavle country before returning to Dubrovnik in the late afternoon.

Driving time (Dubrovnik to Konavle): 30 minutes

Day 6: Depart Dubrovnik

Rector's Palace
Rector's Palace

Depending on when you depart, you may have time to visit one of Dubrovnik's museums, like the Franciscan Monastery and Museum. This large complex houses many treasures, including the world's third oldest pharmacy dating from 1317.

Alternatively, for a collection of 15,000 pieces of interesting works, visit the Rector's Palace and Cultural Historical Museum. Wander this well-preserved palace-turned-museum and explore its exhibits, some detailing life in the Republic of Ragusa during medieval times.

The drive to the airport from Dubrovnik takes around 45 minutes with normal traffic.