Self-Launched Dalmatian Islands Cycling Adventure: Split to Dubrovnik

Start in Split: lock your bags at the hostel or the bus station lockers, do a quick self-guided wander of Diocletian's Palace (free to walk the cellars cost ~£7 if you want the full circuit), then pick up a hired bike — either in Split or, more simply, hire on Brač itself from one of the shops in Bol or Supetar (city/hybrid ~£18-25/day, e-bike ~£40-50/day). Take the Jadrolinija car ferry Split–Supetar (~1hr, ~£4-5 on foot, bikes usually free or a couple of pounds) or the faster passenger catamaran to Bol in season. Ride a 45km loop across the island: climb (or e-bike) up to Vidova Gora, the highest point of the Adriatic islands, for the view over Zlatni Rat beach, then descend through pine forest and old stone villages like Sutivan. If you have energy left, Zlatni Rat is a 15-minute pedal from Bol. Optional extras the tour offers as add-ons: the Dragon's Cave monastery above Murvica (walk-up, free) and the Blaca desert monastery (a hot, exposed hike — go early).

🚌Jadrolinija ferry Split–Supetar ~£5 (bike small fee) or catamaran to Bol ~£7

🛏Hostel or guesthouse in Bol or Supetar (~£20-28 dorm/room per person)

• →Self-guided walk of Diocletian's Palace, Split
• →Split–Supetar ferry or catamaran to Bol
• →Hire a bike on Brač
• →Cycle Bol–Vidova Gora–Sutivan loop (~45km)
• →Zlatni Rat beach swim
• →Optional Dragon's Cave or Blaca monastery visit

Ride to the ferry port in the morning and cross to Hvar — the direct Sućuraj–Drvenik route plus onward hop, or the simplest public option: ferry back toward Split and take the catamaran to Hvar town / Stari Grad (Jadrolinija and Krilo both run these; budget ~£8-12 total, check timetables the night before as off-season sailings are sparse). Once on Hvar, hire a bike locally (or bring one on the ferry — bikes travel cheaply) and ride a 25km loop from Stari Grad or Jelsa through the UNESCO-listed Stari Grad Plain — 2,400-year-old Greek agricultural parcel land still farmed today — via the stone villages of Vrboska and Pitve. Independent alternative to the tour's olive-farm lunch: book a small-group olive oil tasting at a Stari Grad or Jelsa farm direct (many accept walk-ins, ~£15-25), or grab pršut, cheese and local wine from a konoba. Evening in Stari Grad's harbour, which is far quieter than Hvar Town.

🚌Public ferry/catamaran Brač–Hvar ~£10-12, bike hire ~£20

🛏Hostel or sobe (private room guesthouse) in Stari Grad or Jelsa (~£22-30)

• →Morning ferry/catamaran crossing to Hvar
• →Cycle the Stari Grad Plain and old villages (~25km)
• →Optional olive oil tasting at a local farm
• →Explore Vrboska's little canals and Stari Grad old town
• →Konoba dinner in Stari Grad

A 35km loop to the north of the island, taking in Vrboska, the terraced vineyards and lavender-country back lanes, with a climb up to one of the hilltop viewpoints (the Spanish Fortress above Hvar Town is the classic — entry ~£8, or free if you ride up rather than through the gate). Skip the tour's post-ride massage and instead budget an hour at a public beach or a cheap local spa if you fancy it. Afternoon: coast down into Hvar Town, wander the main square, the 17th-century theatre and the Benedictine monastery with its lace collection, then take the water taxi to the Pakleni Islands for a swim if the weather's good (~£6 return). Dinner: konoba away from the riva — grilled fish and a carafe of local wine for ~£15-20.

🚌Bike hire ~£20, water taxi ~£6

🛏Hostel or guesthouse in Hvar Town or Stari Grad (~£25-35 in season)

• →Cycling loop of north Hvar (~35km)
• →Spanish Fortress viewpoint
• →Hvar Town theatre and Benedictine monastery
• →Optional Pakleni Islands water taxi and swim
• →Konoba dinner in Hvar Town

Take the morning catamaran Hvar–Korčula (Krilo/Jadrolinija seasonal service, ~1.5hr, ~£12-15; in shoulder season it may run only a few days a week, so confirm and be ready to route via Split if needed). On Korčula, hire a bike and ride a 40km circuit through the vineyards and stone villages around Lumbarda and Pupnat, with a stop at a family winery for a glass of Grk or Pošip (~£8-12 for a tasting). Swap the tour's guided olive oil degustation for a self-booked tasting at one of the island's olive farms (~£10-15). Lunch at a family konoba near the sea at Lumbarda with a swim off the rocks — the tour's version of this is easy to replicate. Late afternoon: explore Korčula Town's fishbone-shaped old town, the Gothic-Renaissance cathedral of St Mark and the claimed birthplace house of Marco Polo (small entry fee). Optional: a water taxi to Proizd island for sunset.

🚌Catamaran ~£14, bike hire ~£20

🛏Hostel or guesthouse in Korčula Town (~£22-30)

• →Catamaran Hvar–Korčula
• →Cycle the Korčula wine roads (~40km)
• →Self-booked winery and olive oil tasting
• →Swim and seafood lunch at Lumbarda
• →Korčula Town old town and cathedral
• →Optional Proizd island sunset trip

Cross the short Orebic–Domince ferry from Korčula (or the Korčula–Orebic passenger boat, ~15min, ~£4) to the Pelješac peninsula. Hire a bike in Orebic or bring one across, then ride the ~40km wine road east through Potomje and Dingač — Croatia's most famous red wine terraces — with a stop at a family cellar (Korta Katarina at Orebić is the tour's pick; independent tastings there or nearby start around £15-20, book direct or just turn up in season). Continue to Ston, where you can walk a section of the 14th-century Ston Walls (the world's second-longest fortress wall, entry ~£8-10) and see the centuries-old salt pans still worked today. From Ston, take the local bus to Dubrovnik (~1.5-2hr, ~£8-12) — or, if you'd rather skip the bus, ride the last stretch and board at any coastal stop. Evening: sunset on the Stradun, then cheap-ish seafood or a pizza in the old town lanes.

🚌Ferry ~£4, bike hire ~£20, local bus Ston–Dubrovnik ~£10

🛏Hostel in Dubrovnik old town or Lapad (~£25-35 dorm)

• →Korčula–Orebic ferry
• →Cycle the Pelješac wine road / Dingač terraces (~40km)
• →Family winery tasting
• →Walk the Ston Walls
• →Visit the Ston salt pans
• →Local bus to Dubrovnik
• →Evening stroll on the Stradun

Do the final walking day self-guided: walk the full 1.9km circuit of the Dubrovnik City Walls early (opens ~8am, entry ~£30 — this is the priciest single ticket of the trip, so go before the cruise crowds and heat), taking in the Minčeta tower, the fortresses of St John and Revelin and the sea views over the old port. Then drop down into the old town: the Rector's Palace, the cathedral treasury, the Franciscan monastery pharmacy and Onofrio's Fountain are each a few pounds or covered by a Dubrovnik Pass (about £30 and it includes the walls plus several museums — worth it if you want more than one). Coffee and a burek for breakfast, a last swim at Banje beach below the walls, then airport bus (Platanus/Gruž–airport, ~£7) or the ferry onward to Split if you're looping back.

🚌Airport bus ~£7 or Split ferry/catamaran ~£20 if returning

🛏Check out; no night included unless you extend

• →Walk the Dubrovnik City Walls circuit
• →Self-guided old town walk (Rector's Palace, cathedral, Stradun)
• →Dubrovnik Pass museums
• →Swim at Banje beach
• →Airport bus or onward ferry