From kayaking and swimming to hiking and cycling, this 9-day itinerary of Dalmatia is perfectly crafted for your next travel adventure. You'll begin in southern Dalmatia in Dubrovnik where you'll kayak to nearby Elafiti Islands to swim and snorkel and ride a bike through the Konavle, and then venture through the dramatic Pelješac peninsula. You'll explore Korčula and Hvar covering the island terrain on a hiking and biking excursion and end your stay in the modern-ancient city of Split.


  • Paddle to and snorkel the hidden Green Cave on Šipan
  • Discover wine country and sample local brandies on a biking tour of the Konavle
  • Enjoy oysters & mussels and local Dingač wine on the Pelješac peninsula
  • Hike the historic Napoleon path on Korčula
  • Cycle through olive groves and vineyards and past coastal villages on Hvar

Brief Itinerary

Day Highlights Overnight
Day 1 Welcome to Dubrovnik! Dubrovnik
Day 2 Elafiti Islands by Speedboat: Kayaking, Swimming, & Villages Dubrovnik
Day 3 Cycle through Konavle Wine Country Dubrovnik
Day 4 Dubrovnik to Korčula via Pelješac Peninsula Korčula Town
Day 5 Hike through the Forests and Vineyards of Korčula Korčula Town
Day 6 Ferry from Korčula to Hvar Hvar Town
Day 7 Guided Cycling Tour around Hvar Island Hvar Town
Day 8 Ferry from Hvar to Split Split
Day 9 Depart Split  

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: Elafiti Islands by Private Speedboat: Kayaking, Swimming, & Villages

The rocky island of Šipan along the Adriatic Coast
The rocky island of Šipan along the Adriatic Coast

Today you'll set out on an exciting day trip to discover the vegetation-covered Elafiti Islands. Set between Dubrovnik and the Pelješac peninsula to the north, the small archipelago consists of 13 lush islands where only Koločep, Šipan, and Lopud are presently inhabited. Meet your skipper at Dubrovnik's Gruž harbor and board your private speedboat to cruise to the nearby island of Lopud.

You'll then switch into your sea-kayak after a brief introductory lesson and together with your snorkeling gear, paddle across the channel to the hidden Green Cave on Šipan. Tie up your kayak outside the mouth of the sandy-bottom cave to spend time snorkeling and exploring your surroundings. And if you're up for it, the spot is perfect for a little cliff jumping as well. After a full day of paddling, swimming, and visiting island villages, you'll return to Dubrovnik.

Day 3: 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

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Day 4: Dubrovnik to Korčula via Pelješac Peninsula

Mali Ston, Croatia
Mali Ston, Croatia

Today you'll leave Dubrovnik behind and drive an hour northwest to the Pelješac Peninsula as you make your way to Korčula. En route, stop in the medieval city of Ston to explore one of the longest defensive stone walls in Europe (originally built to keep predators away from the town's saltpans) and discover the importance this area held in the 14th century. Catch great views of the glittering saltpans, below, from a parapet walkway on Ston's 3,937-foot (1,200 m) wall.

For lunch, treat yourself to a light meal of Ston's famous fresh oysters or mussels accompanied by a glass of local Dingač red wine. Should you choose, you can take a tour of one of the area's family-run wineries for a further sampling of Dingač's famous reds. 

When you're ready, continue your journey to Orebić to catch the ferry to Korčula. Once on the island, the afternoon is yours to discover Korčula's numerous restaurants, taverns, shops, and bars as you roam the maze of gray stone houses, alleys, churches, and squares. Check into your hotel in Old Town before heading out to explore, either on foot or perhaps on a rented bicycle, traveling from the town center to one of the secluded beaches on the island.

Driving time (Ston to Orebić): 1 hour
Ferry time (Orebić to Korčula): 20 minutes

Day 5: Hike through the Forests and Vineyards of Korčula


Today, you'll explore Korčula by foot and hike through a nature park full of amazing karst rock formations, dense forest, and wildlife. The walk is peaceful and leisurely and will take you to the ancient Napoleon path along olive groves, small vineyards, and beautiful fields of sage, oregano, and other local herbs. End your hike in the village of Pupnat where a traditional local lunch has been prepared with ingredients from the fields you've just walked through.

After lunch, make your way back to medieval Korčula Town to explore the cobblestone streets, whitewashed buildings, and Gothic and Renaissance architectural masterpieces. Or spend the rest of the day enjoying the beach and water, paddleboarding, swimming, or relaxing on the sand.

Hiking distance: 7-14 miles (11-23 km)

Day 6: Ferry from Korčula to Hvar

Hvar and the Pakleni Islands in the distance
Hvar and the Pakleni Islands in the distance

Catch the ferry from Korčula to Hvar in the morning (1.5 hours) and check into your hotel. Another Croatian island in the Adriatic Sea, Hvar is a popular destination with tourists due to its natural setting, mild climate, and its historic town of the same name. You'll have the late morning to explore Hvar Town. Visit St. Stephen's Cathedral and climb the steps to the terrace outside of the historic Arsenal to enjoy views over the harbor and the surrounding area. 

Depending on interests, you may like to consider renting a scooter to drive through olive groves, lavender fields, and vineyards along the coastline. Bring a bottle of wine and watch the sunset from Španjola Fortress. The short walk up to this old 16th-century fortress is worth the hike for the stunning views of Hvar Town and the Pakleni islands. Alternatively, embark on a hike from Hvar town to Velo Grablje and Malo Grablje or go on an idyllic sunset kayaking tour of the nearby Pakleni archipelago.

Day 7: Guided Cycling Tour around Hvar Island

Croatia - Hvar - Cyclist explore plains around Stari Grad
Croatia - Hvar - Cyclist explore plains around Stari Grad

Start the morning with a self-guided walk along the Riva to Trg svetog Stjepana, the long, rectangular square that meets the sea. Here you can visit the Venetian arsenal and the town theater—one of the oldest Baroque playhouses in Europe. From the square, head into the Groda to explore the Hektorović Palace, Leporini Palace, and the Benedictine Convent.

In the afternoon, you'll be transferred from Old Town Hvar to Stari Grad to gear up and get ready for a cycling tour around the island—the best way to get to know all sides of Hvar. You'll bike through the center of well-preserved ancient Greek ruins on the Stari Grad Plain—an agricultural landscape set up by the ancient Greeks (and a UNESCO World Heritage Site)—and stop to explore small villages in the inner part of the island. 

Your guide will help you choose from a number of routes, ranging from 6 to 9 miles (10 -15 km). It'll be an easy ride on mostly flat roads through lavender fields, olive groves, and vineyards, palm trees and pine woods, and past coastal villages like Jelsa and Vrboska.

Day 8: Ferry from Hvar to Split


In the morning, you'll catch a one-hour ferry from Hvar to Split. Upon arriving in Split, check into your hotel and settle into your accommodation before taking the rest of the day to wander Split's historic center. 

Start at Pjaca Square for pretty views of white marble tiles, the Iron Gate (the western entrance to Diocletian's Palace), a Romanesque clock tower with the remains of a medieval sundial, and the 15th-century Town Hall. Stop for lunch at Trattoria Bajamont, just north of the Iron Gate. From there, visit the popular Voćnitrg or Fruit Square. Here you can enjoy renaissance architecture, influenced during Split's Venetian era. For a bit of shopping and a bite to eat head to Marmont Street, though you'll want to head to the waterfront to catch the sunset.

In the evening, take a stroll along Split's seafront Riva to admire the waterfront views before finding the off-beat Konoba Dioklecijan restaurant, just to the left of the Bronze Gate for a bite to eat, its outdoor terrace built into the walls of Diocletian's Palace.

Ferry duration (Hvar to Split): 1 hour

Day 9: Depart Split

Wander Split and discover its ancient buildings
Wander Split and discover its ancient buildings

If you have a free morning before departing, check out the Green Market (Pazar Market). A lively fruit and vegetable outdoor market just east of the Diocletian Palace, this is a great place to see how the locals shop and to pick up some fruit for your flight home. Farmers from the surrounding areas of Split come into town every day to sell their seasonal local produce from sunrise to 2 pm. 

Depending on traffic, it usually takes 45 minutes to travel from Old Town to the airport. Best to arrive at the airport at least two hours prior to your international departure (and with some extra time to drop off your rental car, if you have one).