Island-hop around southern Croatia on this action-packed five-day tour. The itinerary starts and ends in Dubrovnik, the so-called "Pearl of the Adriatic," where you'll have plenty of time to walk around the city's charming OId Town. You'll spend two nights in the medieval city of Ston, the perfect jumping-off point for exploring the rugged Peljesac Peninsula. Then it's onward to Koločep Island and Lopud Island, where you'll hike on coastal trails overlooking the Adriatic Sea, dine on fresh oysters and mussels, and sample Dingac— the region's renowned red wine—at a local winery. Enjoy one last night on the town in bustling Dubrovnik before the trip ends.


  • Explore the natural beauty of the Peljesac Peninsula
  • Tour Dubrovnik's charming Old City
  • Dine on fresh oysters and mussels in medieval Ston
  • Ride a cable car up Srd Mountain for sweeping views
  • Sample Dingac red wine at a family-run winery
  • Go hiking on the quiet coastal trails of Lopud Island

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Dubrovnik, Transfer to Ston Ston
Day 2 Explore the Pelješac Peninsula Ston
Day 3 Hike on Koločep Island & Visit Dubrovnik Dubrovnik
Day 4 Boat Ride to Elafiti & Hiking Dubrovnik
Day 5 Depart Dubrovnik  

Detailed Itinerary

Day 1: Arrive in Dubrovnik, Transfer to Ston

A cable car heading up Srđ Mountain, overlooking Dubrovnik
Welcome to Croatia! Arrive in Dubrovnik and transfer to your hotel on the Pelješac Peninsula in Ston. Spend the afternoon and evening exploring the medieval city, home to one of the longest defensive stone walls in Europe, and learn about the importance this area held in the 14th century. Enjoy a light meal of fresh oysters or mussels after you climb the parapet walkway of Ston's wall for beautiful views over the town and its glittering saltworks. Then get some rest before the tour continues on day two. 

Day 2: Explore the Pelješac Peninsula

Explore Pelješac peninsula
Saltworks in Ston
Today you will explore the rugged Pelješac Peninsula. A mountainous finger of land reaching into the Adriatic Sea, the Pelješac region is home to Croatia's finest red wines, tastiest oysters, and some of the best sand and shingle beaches in the country. Set off on a hike along Ston's famous medieval walls, taking in breathtaking vistas as you climb, ending at Ston's tiny idyllic neighbor of Mali Ston. Visit a family-run winery to try the region's renowned Dingač red wine. For dinner, choose a local restaurant to sample the area's famous shellfish. You'll spend the night in Ston.
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Day 3: Hike on Koločep Island & Visit Dubrovnik

Rocky cliffs on Koločep Island

Begin the day by exploring Croatia's southernmost inhabited island, Koločep. One of the Elafiti islands, Koločep, is home to roughly 100 people. As there are no cars on the island, it's a great destination to get away from the crowds that flock to Dubrovnik. Choose from any of the scenic walks and hiking trails, kayak around the island, or, if you prefer, park yourself on the elusive sandy beach (most Croatian beaches are pebbly). Break up the day with lunch from a great family-run restaurant that serves the country's best-grilled calamari.

In the afternoon, continue to Dubrovnik. Often referred to as the "Pearl of the Adriatic," Dubrovnik is a world-renowned city of exceptional charm. Meet your guide at the Pile Gate, the historic entrance to the city's Old Town, for your walking tour of centuries-old attractions. Wander inside the 16th-century stone walls through side streets and narrow alleys to learn about the local stories and legends. Discover Onofrio's Fountain, Rector's Palace, and Orlando Column before walking through the city walls and enjoying views over the Adriatic. Another great option for stellar views is to hike or ride the cable car up to Srđ Mountain for views of the city and the nearby Elafiti Islands. Just before sunset is a great time to head to the top of the hill.

Day 4: Boat Ride to Elafiti & Hiking

A coastal trail on Lopud
A coastal trail on Lopud

Today starts with a boat ride to the Elafiti Island of Lopud. During Dubrovnik's historic prime, Lopud functioned as a weekend retreat for the city's nobility and was home to many of its merchant fleets. Ruins of many ship owners' homes still occupy the corners of Lopud's only village of the same name. Covering an area of nearly two square miles (4.6 square km), Lopud is the most economically developed of the Elafiti Islands and is home to the region's largest sandy beach, Šunj.

There are several hiking trails to choose between that lead you to Mediterranean and subtropical vegetation, though you might like to trek the 6 mile (10 km) loop around the larger part of the island. You will be rewarded with some of the island's best attractions, including a visit to Sutvrac Fortress, where you will have stunning panoramic views of nearby Šipan and the Pelješac Peninsula to the north. For lunch, you can hike to one of the island's farms to enjoy homemade cuisine prepared by a local family.

In the afternoon, make your way back to Dubrovnik. The remainder of the evening is at your leisure, allowing time for you to wander and explore the city. Walk down the limestone-paved Stradun, Dubrovnik's main street, to get your bearings and choose from some of Croatia's best restaurants and wine bars.

Day 5: Depart Dubrovnik

Sunset over Dubrovnik
Sunset over Dubrovnik

The trip comes to an end today. You'll head to the airport to catch a flight out. Safe travels!

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