Dubrovnik, Southern Dalmatia, and Montenegro Itinerary
Dubrovnik has an international airport that is well-connected to all European hubs during the summer season. It is extremely popular in the summer, so be warned: you won't be sightseeing by yourself in August. Try to start your weeklong trip on a weekday (Monday to Monday, for example) instead of the weekend, so that your weekends are spent on a quiet island instead of in bustling Budva or Dubrovnik.
Days 1 and 2: Dubrovnik
If arriving by sea or air, you'll see one of the prettiest fortified cities in the world and you are very likely to immediately fall in love with it. From this view, you can tell why Dubrovnik (formerly Ragusa) was once master of all of Dalmatia. Choose a hotel slightly outside the city walls, as the crowds flock there daily in high season. Have lunch in one of the many fish restaurants near the fish market and enjoy some Dalmatian wine. Save the sightseeing for the late afternoon, when the cruise-ship day-trippers have departed. Stroll along the placa in the early evening with the locals, stopping along the way for some Italian-style ice cream.
Day 3: Pelješac and Korčula
Pelješac peninsula is home to Croatia’s best red wine growing region, Dingač. Do not miss the opportunity to travel down the windy roads via Mali Ston (renowned for its oysters) and stopping off at the family-owned wineries producing varietals like Plavac Mali or Pošip. At the town of Orebić catch a short ferry ride to Korčula, another jaw-droppingly gorgeous town fortified with bright limestone city walls. Check out the local dance Moreška and have fish overlooking hundreds of windsurfers taking advantage of the maestral wind in the Pelješki channel. Either spend a night at a local hotel or apartment or head back to Dubrovnik to your hotel.
Days 4, 5, and 6: Montenegro
Travel by bus or hire a car from Dubrovnik down the coast to the sparkling Bay of Kotor. See the Roman mosaics at Risan and the tiny islands of Perast, and stay at a boutique hotel in one of the charming fishing villages on the bay such as Perast or Dobrota. Continue to the UNESCO World Heritage Site town of Kotor and explore its churches, markets, and city walls, then have lunch in one of the marble piazzas. Take the road heading inland that emerges at the sea's edge not far from Budva and a stretch of coast where you can treat yourself to some excellent seafood and a day on the beach. Make sure to see the stunning yet exclusive Sveti Stefan hotel, the jewel of the Montenegrin coastline.
Day 7: Cavtat
Day 7 will most likely be a travel day, no matter if you travel by car, plane, or ferry. Have one last seafood lunch at the town Cavtat, taking the time to visit the mausoleum by Croatia’s prime sculptor Ivan Meštović, buy a bottle of Dalmatian wine to take home, and vow to come back next year.