Once you’ve checked in, ease into the day with an hour or so wandering Kotor Old Town. Start at the Sea Gate and follow the lanes through the squares; it’s compact, so there’s no need to march to a checklist. The stone paving can be slippery, so wear shoes with decent grip. If you arrive late, keep this walk short and save the museum visit for another time.
If it’s open, visit the Kotor Maritime Museum in the Old Town for a concise introduction to the bay’s seafaring families and history; allow 45–60 minutes. Holiday-period hours can change, so check directly before setting out, especially on 26 December. If it’s closed, don’t rush around looking for an alternative—take more time to explore the Old Town, then head to Konoba Scala Santa for dinner. Expect about €20–35 per person; booking ahead is sensible, as some restaurants keep reduced winter hours.
After dinner, stroll along the Kotor waterfront for half an hour or so, with the harbor and dark mountain slopes as your backdrop. Sunset is early in late December, so go before dinner if you’d like to see the last light; otherwise, the evening lights make for a pleasant first look at the bay. Keep a warm layer handy, as it can feel chilly beside the water.
Start at Cathedral of Saint Tryphon, the Romanesque landmark on St Tryphon Square. Allow about 45 minutes for the interior and treasury; entry is usually around €3, but Sunday services and winter hours can affect access, so check the notice at the door and dress respectfully. From there, it’s only a few minutes’ walk to the Kotor Cats Museum. It’s a small, cheerful stop—30–45 minutes is plenty—and admission is usually about €1. Both are easy to visit on foot, though the stone lanes can be slick after rain.
Have lunch nearby, then tackle San Giovanni Fortress while there’s still good daylight. Budget 2–3 hours for the steep stair climb and return, and wear sturdy shoes; the stone steps can be slippery. Winter access and closing times may change, so check locally before setting off and don’t start late in the afternoon. The climb is strenuous, but the view across the bay is the payoff. If the route is closed or the weather turns, save the ascent for another visit rather than attempting it in fading light.
Walk down to BBQ Tanjga, near the southern edge of town, for a relaxed dinner of grilled meats and generous portions; expect roughly €10–20 per person. It’s casual and popular, so allow 45–60 minutes and be prepared for a short wait at peak dinner time. After the fortress climb, this is a satisfying, no-fuss finish to the day.
Take a taxi or pre-arranged car from Kotor to Perast—about 20–30 minutes along the bay road, depending on traffic. Buses also run this route, but winter and holiday timetables can be sparse, so check locally before relying on one. Give yourself an hour to wander Perast’s compact waterfront and stone lanes; it’s especially peaceful in winter. Keep an eye on the time, as daylight is short and some cafés and sights may have reduced seasonal hours.
From the waterfront, ask locally whether boats are running to Our Lady of the Rocks. The crossing takes only a few minutes, but winter services can be limited or weather-dependent; confirm the return boat before you leave shore. If the church and small museum are open, allow around 1–1.5 hours including the boat ride. Then settle in at Conte Restaurant on the waterfront for seafood or regional dishes, with bay views; budget roughly €25–45 per person and check holiday opening hours ahead.
Continue by taxi or car to Risan, around 15–20 minutes farther along the bay, for the Roman Mosaics. Allow about 45 minutes, but confirm holiday opening arrangements before setting out. On the return toward Kotor, take around 30 minutes for safe roadside pull-offs and winter light over the bay. Use designated lay-bys rather than stopping on the narrow road, and allow extra time if the surface is wet.
Take a morning departure and allow for the border crossing to stretch the journey; holiday schedules and delays can make arrival later than expected. From Dubrovnik Bus Station in Gruž, take a local bus toward Pile Gate (around 15–20 minutes; buy a ticket at a kiosk or from the driver) or a taxi. Leave your luggage at your accommodation if you can, then give yourself about 30 minutes to pass through Pile Gate and get your bearings.
From the gate, follow Stradun at an unhurried pace. Its polished limestone can be slick in winter rain, so wear shoes with good grip; allow 45–60 minutes for the main street and a few of the side lanes. Late December is quieter than summer, but some shops and attractions keep reduced hours, so treat this as a gentle orientation walk rather than a tightly timed sightseeing stop.
Continue downhill toward Lokanda Peskarija at the Old Port for seafood and harbor views. Budget roughly €20–35 per person and allow 1–1.5 hours; check directly before setting out, as holiday opening can vary and the restaurant may have seasonal hours. If it’s closed, ask locally about nearby places serving lunch rather than counting on every Old Town kitchen being open.
Start early with the Dubrovnik City Walls while there’s good daylight and before the winter closing time. Allow about two hours for the circuit; the walk is exposed to wind, and the stone can be slick after rain, so wear grippy shoes and bring a warm layer. Winter hours are shorter than summer hours—often around 9 a.m. to 3 p.m.—so check the official notice before setting out and arrive well before last entry. Budget roughly €40 for admission, though prices and seasonal arrangements can change.
After the walls, head into the Old Town for the Rector’s Palace and its history museum; allow 1–1½ hours. It’s a natural next stop after the circuit, but check the museum’s holiday-week hours at the entrance in case they differ from the usual winter schedule. Continue to Dubrovnik Cathedral for its Baroque interior and treasury, allowing about 45 minutes; be mindful of services and keep voices low if worship is underway. A modest treasury fee may apply.
Finish at Buza Bar, reached through a discreet opening in the Old Town sea wall. It’s a memorable spot for a drink above the water, but many cliffside bars close or operate limited hours in winter—check before making it your sunset plan, and take care on the steps. Then walk back through the lanes to Nishta for a relaxed vegetarian dinner; allow 1–1½ hours and around €15–30 per person. As 30 December falls in the holiday period, confirm the restaurant is open and reserve if possible.
With the bus taking much of the day, keep your Split plans compact: drop your bags and head into the historic center rather than trying to fit in a museum. Spend about 1–1.5 hours exploring Diocletian’s Palace—its lanes and courtyards are part of the living Old Town, so wandering the open-air complex is free, though some interior sights charge admission and may have reduced winter hours.
Within the palace, pause at the Peristyle for 20–30 minutes. This grand stone courtyard is especially atmospheric as the light fades; take care on the smooth paving if it’s wet. Then walk roughly 10 minutes west into Varoš for dinner at Konoba Varoš. Allow 1–1.5 hours and around €20–35 per person for Dalmatian specialties. It’s New Year’s Eve, so confirm the restaurant is serving and reserve ahead if possible; holiday hours and transport schedules may be limited.
Begin at Saint Domnius Cathedral and Bell Tower in the Old Town. Allow 1–1.5 hours for the cathedral and, if the tower is open, the climb for views over the harbor and rooftops. Entry to the cathedral is usually a few euros, with the tower sometimes ticketed separately; hours can be shorter on New Year’s Day, so check the posted notice before setting off. The tower’s steps are narrow and steep, so take your time.
From the cathedral, walk to Green Market (Pazar) on the eastern side of the Old Town for a 30–45-minute browse. It’s a lively spot on regular mornings, but many stalls may be closed or operating reduced hours on 1 January—treat this as a flexible stop rather than counting on a full market. Then stroll along the Riva for about 45 minutes, with a coffee break if you find a waterfront café open; expect holiday hours to vary.
Head west from the center toward Marjan Hill for a winter walk and lookout views. Allow 1.5–2 hours, but keep to a shorter route if the trails are wet, and aim to be back before dusk—the days are short in January. For your final evening, book Bokeria Kitchen & Wine Bar in the Old Town for Croatian-inspired dishes; budget around €25–45 per person and confirm it is open on New Year’s Day before relying on it.
No packing list attached yet.