Kayaking and Hiking Croatia’s Islands

Croatia’s Dalmatian Coast enchants with rugged islands, hidden coves, and a rich maritime history dating back to the Venetian Empires. From the walled city of Dubrovnik, the “pearl of the Adriatic,” set out by kayak and paddle along secluded inlets laced with limestone cliffs, all framed by turquoise water. On shore, hike through pine forests, fields of wildflowers, and vineyards to visit medieval monasteries and sun-drenched villages. Further north, venture into the lush hills of the Pelješac Peninsula and soak up the lively seafaring tradition of Orebić. The nearby island of Korčula offers more kayaking exploration and a beautifully preserved medieval town. Throughout our island-hopping adventure, discover Croatia’s unique history and charm.

Day 1 — Dubrovnik, Croatia

Arrive in Dubrovnik and transfer to our hotel, where we’ll gather for an orientation. Step back in time on a guided tour of Dubrovnik, which became a major maritime power after breaking with the Venetian Empire in the 14th century. Its marble streets, lined with baroque architecture from the 1600's, are surrounded by medieval walls. Walk along the upper ramparts for a sweeping view of the city and the azure waters surrounding it. (3 miles walking, 2 hours)
Hotel Dubrovnik Palace (D)

Day 2 — Lokrum Island

This morning, we’ll take to the sea on our first kayak excursion to the Elafiti Islands off Dubrovnik’s coast. Our destination, Lokrum Island, is a pristine nature reserve of dense forests and subtropical vegetation. Skim along craggy coves and green shores before embarking on a hike through pine, laurel, and cypress to the Hapsburg-era Botanical Garden, home to exotic plant species and peacocks. Explore the ruins of an 11th-century monastery and a French fort, then hike down to a rocky beach for swimming, snorkeling, and panoramic views of Dubrovnik. (2 miles paddling, 1-2 hours; 3 miles hiking, 2 hours)
Hotel Dubrovnik Palace (B,L,D)

Day 3 — Mljet Island

After breakfast, board a charter boat and head to Mljet Island, a rugged paradise that is said to have sheltered the Greek hero Odysseus. In Mljet National Park, our hiking trail skirts two saltwater lakes dotted with islands and inlets. Take a scenic boat ride to the Isle of St. Mary, where a 12th-century Benedictine monastery and church nudge the water. Continue hiking to the island’s highest point, Montokuc, to take in stunning views. (5 miles hiking, 3 hours)
Hotel Dubrovnik Palace (B,L)

Day 4 — Koločep Island/Ston/Orebić

After a final morning in Dubrovnik, set out by kayak to Koločep, the smallest of the inhabited Elafiti Islands, with only a couple settlements nestled among forests, vineyards, and pre-Romanesque churches. Paddle along limestone cliffs and wind-carved caves, and picnic beneath pomegranate trees before returning to the mainland.

This afternoon, we travel north to the Pelješac Peninsula, stopping in Ston to visit one of Europe’s longest fortified walls. Continue to the seaside town of Orebić, steeped in maritime tradition and our home for the next three nights. (2-3 miles paddling, 2-3 hours)
Hotel Indijan (B,L,D)

Day 5 — Pelješac Peninsula

Today’s hike through pine and cypress takes us high above the Pelješac Channel to a 15th-century Franciscan monastery and church, once a strategic lookout point against Venetian invasion. Wind down foot trails for a refreshing swim. In the evening, head inland to a konoba, or rustic restaurant. Along with Croatian delicacies, we’ll have a chance to sample the local dignač red wine. (4 miles hiking, 3 hours)
Hotel Indijan (B,L,D)

Day 6 — Korčula Island

Today, a short ferry ride brings us to Korčula Island, a former Greek colony of wooded hills and sandy beaches. Set out on kayak to explore around the island, with time for swimming and snorkeling followed by a picnic lunch. Later, explore the town of Korčula, a medieval walled city that is said to be the birthplace of Marco Polo. Savor the charm of this World Heritage site along with a glass of Pošip, a local white wine. (3 miles paddling, 2 hours)
Hotel Indijan (B,L,D)

Day 7 — Brač Island/Vidova Gora

Travel by ferry to Brač Island, famous for its white pebble beach and stone quarries used in building Diocletian’s Palace in Split and part of the White House. Keep an eye out for the hundred-plus bird species that thrive here while ascending Vidova Gora, which offers a panoramic view across the Adriatic to Italy. We’ll spend our last two nights in a beautifully restored Renaissance palace overlooking Pučišća Bay. (4 miles hiking, 3 hours)
Deskovic Palace (B,L,D)

Day 8 — Brač Island

Set out along a seaside trail and enjoy a swim in the island’s crystal-clear waters before hiking through pine and wildflowers to the 16th-century Blaca Hermitage. This isolated, cliff-side monastic complex once traded honey, wine, and olive oil with the Venetian Empire and was a renowned astronomical observatory. After exploring the monastery, return to Pučišća for a festive farewell dinner. (3 miles hiking, 2 hours)
Deskovic Palace (B,L,D)

Day 9 — Split/U.S.

Take a morning ferry to the bustling port city of Split. Discover the Roman-era Diocletian’s Palace, built by Emperor Diocletian for his later years. Enter its beguiling maze of marble streets, churches, and fortifications. Transfer to the airport this afternoon for your flight home.
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