Self-Launched Croatian Islands Sail: Split to Dubrovnik

Arrive in Split and spend the morning exploring Diocletian's Palace — one of the world's most remarkable Roman ruins, free to wander. Grab a coffee in the peristyle square and duck into the Cathedral of Saint Domnius. Then take the short local bus (line 37, ~£2) or a cheap taxi (~£10) to nearby Trogir, a UNESCO-listed old town on a small island. Spend a couple of hours exploring its medieval streets and Kamerlengo Fortress (entry ~£3). Return to Split ferry terminal and take the Jadrolinija ferry to Supetar on Brač (~£5, 50 min). Check in to your guesthouse, rent a paddleboard (~£12/hr) at one of the local beach operators near Supetar, and enjoy a sunset dinner at a local konoba (tavern).

🚌Local bus Split→Trogir (~£2) or shared taxi (~£10). Jadrolinija car ferry Split→Supetar, Brač (~£5, departs roughly hourly in summer).

🛏Hostel or guesthouse in Supetar or Bol, Brač — e.g. Hostel Supetar or private rooms via Booking.com (~£25-35/night)

• →Explore Diocletian's Palace, Split (free)
• →Visit Old Town Trogir on foot (free, Kamerlengo Fortress ~£3)
• →Jadrolinija ferry Split → Supetar, Brač (~£5)
• →Paddleboarding near Supetar (~£12/hr rental)
• →Swimming in the Adriatic
• →Sunset dinner at a local konoba (~£18-22)

Take the morning catamaran from Supetar or the ferry from Split to Stari Grad on Hvar (~£8, ~1hr from Split via Jadrolinija). Drop your bag at your hostel in Hvar Town and head out to explore the Pakleni Islands — rent a small boat or kayak (~£30-45/day) or hop on the local water taxi (~£5-8) from Hvar Town harbour to reach the islands and swim at Laganini Bay. Back in Hvar Town, climb up to the Hvar Fortress (Španjola) for sweeping views over the islands (entry ~£4). In the evening, the famous Hvar nightlife is all around you — head to Hula Hula beach bar for sunset cocktails, then Kiva Bar for the late-night scene.

🚌Jadrolinija ferry or Krilo/TP Line catamaran Split→Stari Grad or direct to Hvar Town (~£8-12). Local water taxis to Pakleni Islands ~£5-8.

🛏Hostel in Hvar Town — e.g. Hostel Marinero or similar (~£28-38/night). Book well ahead in peak summer.

• →Ferry or catamaran to Hvar (~£8)
• →Water taxi to Pakleni Islands (~£5-8 each way)
• →Swimming and snorkelling at Laganini Bay (free)
• →Kayak or small boat hire (~£30-45/day)
• →Visit Hvar Fortress (~£4)
• →Sunset drinks at Hula Hula (free entry)
• →Nightlife at Kiva Bar

Take a morning catamaran from Hvar Town to Korčula or to Orebić on the Pelješac Peninsula (~£10-15). Pelješac is Croatia's premier wine-growing region — visit a local winery for a tasting (~£10-15) of the famous Plavac Mali red wine. Explore the quiet village of Orebić and swim in the crystal-clear lagoon. Pelješac is also famous for its oysters from Ston — take a short bus to Ston (~£3) and eat a platter of fresh oysters and mussels at one of the harbour-side restaurants (~£12-18). Self-cater a simple dinner from the local market or eat at a family-run konoba.

🚌Krilo catamaran Hvar→Korčula/Orebić (~£10-15). Local bus Orebić→Ston (~£3 each way).

🛏Guesthouse or private room in Orebić — e.g. Apartments Orebić via Booking.com (~£30-40/night)

• →Ferry or catamaran to Orebić/Pelješac (~£10-15)
• →Wine tasting at a local Pelješac vineyard (~£10-15)
• →Swimming in Pelješac lagoon (free)
• →Day trip to Ston for fresh oysters (~£3 bus, ~£12-18 for oyster platter)
• →Explore Ston's medieval salt pans and walls (free)

Take the short ferry from Orebić to Korčula Town (~£2, 15 min — one of Europe's best-value crossings). Korčula's old town is often called 'Little Dubrovnik' — explore its herringbone-patterned medieval streets, visit the Cathedral of Saint Mark (free), and seek out the house claimed to be Marco Polo's birthplace. Hire a scooter (~£15-20/day) to explore the island's vineyards and the charming fishing village of Lumbarda. In the afternoon, swim at Lumbarda's sandy beach (rare in Croatia — free). Don't miss sunset cocktails at Massimo's rooftop bar inside one of the town's towers — a genuinely unmissable experience.

🚌Jadrolinija ferry Orebić→Korčula (~£2, 15 min, runs frequently). Scooter hire from local rental shops in Korčula Town (~£15-20/day).

🛏Hostel or guesthouse in Korčula Town — e.g. Old Town Hostel Korčula or guesthouses near the old walls (~£28-40/night)

• →Orebić→Korčula ferry (~£2, 15 min)
• →Explore Korčula Old Town (free)
• →Visit Cathedral of Saint Mark (free)
• →Marco Polo's Birthplace (~£3 entry)
• →Scooter hire to Lumbarda (~£15-20/day)
• →Swimming at Lumbarda beach (free)
• →Sunset cocktails at Massimo's rooftop bar

Take a morning catamaran from Korčula to Mljet (~£8-12, ~40 min). Mljet is one of Croatia's most beautiful islands, with over 70% covered in forest. Head straight to Mljet National Park — buy your entry ticket (~£9, includes a boat to St. Mary's Island Monastery in the saltwater lake) at the park gate. Rent a bicycle at the park (~£8-10/day) and cycle the trail around the lakes — it's one of the most scenic rides in the Adriatic. Swim and snorkel in the clear saltwater lakes, and take the small boat to visit the 12th-century Benedictine monastery on the island in the middle of the lake. Explore hidden sea caves along the coast on foot.

🚌Krilo or Jadrolinija catamaran Korčula→Pomena, Mljet (~£8-12). Bicycle hire inside the national park.

🛏Guesthouse in Pomena or Polače, Mljet — small family-run rooms (~£30-42/night). Book ahead as options are limited.

• →Catamaran Korčula→Mljet (~£8-12)
• →Mljet National Park entry including monastery boat (~£9)
• →Bicycle hire within the park (~£8-10/day)
• →Cycling the Great Lake trail (included with park entry)
• →Snorkelling and swimming in saltwater lakes (free with park entry)
• →Boat to St. Mary's Island Monastery (included with park entry)
• →Explore coastal caves on foot (free)

Šipan is the largest of the Elafiti Islands and one of Croatia's best-kept secrets — almost no cars, olive groves, and secluded bays. Take the ferry from Mljet (or via Dubrovnik) to Šipanska Luka, Šipan (~£10-15). Spend the day exactly as MedSailors does — exploring hidden coves, swimming in secluded bays, and paddleboarding (hire boards locally ~£12/hr). The island is tiny enough to explore on foot or by bicycle. For your final group dinner, the village of Šipanska Luka has a handful of excellent konobas — try Konoba kod Marka or similar for fresh seafood and local wine as a fitting farewell to island life.

🚌Jadrolinija ferry from Sobra (Mljet) or via Dubrovnik to Šipan (~£10-15). Alternatively, take a fast catamaran direct from Dubrovnik if looping back — check Jadrolinija timetables.

🛏Guesthouse or private room in Šipanska Luka — e.g. Rooms Batinica or similar (~£28-38/night). Very limited options — book ahead.

• →Ferry/catamaran to Šipan (~£10-15)
• →Explore Šipan on foot or bicycle (bike hire ~£10/day)
• →Swimming in secluded bays (free)
• →Paddleboard hire (~£12/hr)
• →Sunset drinks at the harbour (free to sit, drinks ~£4-6)
• →Farewell dinner at a local konoba (~£20-25)

Take the morning Jadrolinija ferry from Šipan to Dubrovnik's Gruž harbour (~£5-8, ~1hr). This is a stunning arrival by sea. Drop your bag at your hostel and head straight to the Old City Walls — walk the full 2km circuit (~£25) for the most iconic views of the terracotta rooftops and the Adriatic. Explore the Stradun (main street), the Franciscan Monastery's medieval pharmacy, and Fort Lovrijenac. Cool off with a swim at Buža Bar's rocky cliff-side platform — drinks with a sea view. In the evening, have a final waterfront drink in the old harbour. Fly home from Dubrovnik Airport (DBV), or take a bus back to Split (~£15-20, 4.5hrs) if needed.

🚌Jadrolinija ferry Šipan→Dubrovnik Gruž (~£5-8, ~1hr). Bus 1A/1B from Gruž to Old Town (~£1.50). Airport bus from Pile Gate (~£8) or taxi (~£20-25).

🛏Hostel in or near Dubrovnik Old Town — e.g. Hostel Angelina Old Town or Fresh Sheets Hostel (~£30-45/night). Note: Dubrovnik is the priciest stop — book early.

• →Ferry Šipan→Dubrovnik Gruž (~£5-8)
• →Walk Dubrovnik's Ancient City Walls (~£25)
• →Explore the Stradun and Old Town (free)
• →Visit Franciscan Monastery (~£5)
• →Swim at Buža Bar cliff platform (free, drinks ~£5-7)
• →Waterfront farewell drinks in Old Harbour