1Old City Wander (Stradun & Onofrio's Fountain) Walk
Start on the limestone-polished Stradun, Dubrovnik's main street, still cool in the shade of the town houses at this hour.
Four days is the sweet spot for Dubrovnik: one to ease down the Stradun's polished marble, one for the full city-walls loop with a swim under Fort Lovrijenac to recover, and two on the water, first car-free Lokrum and its saltwater Dead Sea, then Lopud's sandy Šunj beach in the Elaphiti Islands. Everything runs on foot and ferries, dinners stay in konoba territory rather than tourist-menu land, and September keeps the sea warm while the biggest crowds thin.
Start on the limestone-polished Stradun, Dubrovnik's main street, still cool in the shade of the town houses at this hour.
Walk out to Ploče Gate as the walls catch the late sun, the classic first postcard view before you've even climbed them.
Harbourside terrace right on the Old Port, famous for simple grilled fish and black risotto, arrive by 7 to get a rail-side table.
Walk the full 1,940m loop starting at Pile Gate before 8:30, before the cruise-ship crowds and heat arrive. Minčeta Tower gives the best panorama.
The 'Gibraltar of Dubrovnik' perched on a sea cliff outside the walls, climb it for the postcard shot back over the Old City rooftops.
The city's classic pebble beach right below the walls, swim with the Old City and Lokrum island framing the view.
Small, buzzy counter spot near the Old Port doing excellent tuna burgers and octopus sandwiches, order at the bar, no reservations needed.
Short 15-minute crossing from the Old Port; boats run frequently in season, no need to book ahead, just buy at the kiosk.
Wander the shaded 19th-century botanical garden planted by Habsburg archdukes, then climb to Fort Royal for the widest island view.
A calm, landlocked saltwater lake on Lokrum's far side, much stiller than the open sea, a favourite quiet swimming cove.
Catch one of the regular return sailings from Lokrum's small harbour back to the Old Port.
Just outside the walls near Pile, a relaxed taverna doing peka-style lamb and fresh grilled fish, less touristy than the harbour spots.
Passenger ferry from the Old Port to Lopud, about 50 minutes, check the timetable the day before, sailings thin out by afternoon.
A wide, shallow sandy beach on the island's far side, a 20-minute walk across the island, and the calmest swim of the whole trip.
Return sailing to the Old Port; grab a window seat for the last look back at the Elaphiti islands.
Drift the back lanes above the Stradun as the light turns gold and the day-trip crowds thin out, a quieter last look at the walls.
Cosy Bosnian-Dalmatian spot near Gundulić Square, known for ćevapi and sač, a warm, unfussy note to end the trip on.
Cuttlefish-ink risotto, the Dalmatian harbour classic; eat it within sight of the boats it came off.
Small plates of fried squid and marinated anchovies eaten standing or perched on a step; Dubrovnik's fast food, done right.
Ćevapi in warm somun bread and burek off the grill; the old town's best-value dinner and a nod to the neighbourhood's other culinary parent.
An hour up the coast, Mali Ston's beds have fed oyster lovers since Roman times. Not on this plan's four days, so ask Robin to build the Ston detour and it will.
No. Days 1 and 2 never leave the walls' shadow, and days 3 and 4 run on the Lokrum and Lopud ferries from the old harbour. A car in Dubrovnik is a parking problem with wheels.
Nothing is hard-capped, but September dinner tables at the harbour konobas fill by early evening, so book Lokanda Peskarija and Barba a day out. Buy the walls ticket at opening or online the night before to skip the queue.
They peak in the old town late morning to mid-afternoon. This plan already routes around them: walls and forts before the surge, islands during it, and the Stradun at dusk when the ships have gone.
Čilipi airport is about 30 minutes down the coast; the shuttle bus meets most flights and stops above the Old City at Pile, and taxis run a fixed-ish rate. The coast road views are a preview of the trip.
For the city and its islands, yes. What it leaves on the table is the Pelješac side, Ston's walls and oyster beds, and the Bay of Kotor over the border; those are the extra-day plays below.
The longest fortification walls in Europe climb the hill behind Ston, and the reward for walking them is an oyster-farm lunch in Mali Ston; the day-trip pairing this coast does best.
Cross into Montenegro for the fjord-like bay, Kotor's old town and the serpentine viewpoint road; leave early, borders queue in summer.
With more days in hand, the Srđ cable car stops being a choice and becomes the day-1 sunset ritual; the walls you will walk tomorrow look best drawn out below you.
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