3 Best Sights in Southern Dalmatia, Croatia

Perched 492 feet up the hill above Orebić is this modest 15th-century Franciscan monastery. During the heyday of the Dubrovnik Republic, the Pelješac Peninsula was under Dubrovnik's control, while just across the channel Korčula was ruled by their archrival, Venice. From their privileged vantage point on the hill, the Franciscan monks could spy upon their island neighbors, under strict orders to send a message to Dubrovnik if trouble looked likely. The monastery is also home to the Our Lady of the Angels icon that was said to protect captains on their voyages; when they passed under the monastery on their way home they would sound their sirens in greeting and the monks would ring the church bells in return. Today it's a welcoming retreat, with a lovely cloister and a small museum displaying scale models of the ships that local sea captains sailed across the oceans. You can also walk around the cemetery, where gray marble tombstones shaded by cypress trees mark the final resting places of many a local seafarer. It's worth the strenuous 40-minute hike from the center of Orebić (or the easier 5-minute drive) for the spectacular views across the channel to Korčula.

On the main square, the splendid 15th-century Gothic-Renaissance cathedral, built by several generations of celebrated local stonemasons, is one of the most important buildings on the island. Enter through the beautifully carved Romanesque main portal, which is guarded by Adam and Eve standing underneath twin lions. Inside the cathedral, there are two paintings by Tintoretto. Be sure to climb the bell tower next door; it's steep and awkward, but worthwhile for the views.

As you round the bend onto Lopud by sea, the first thing you'll notice is the imposing Franciscan monastery on the tip of the island. Dating back to 1483, it was abandoned and remained empty for 200 years before being rescued by Francesca Thyssen-Bornemisza, creator of the Thyssen-Bornemisza Art Contemporary Foundation (TBA21). After a meticulous 20-year refurbishment, the property has been converted into a luxury villa and private art gallery. It manages to retain the contemplative atmosphere of the monastery, with an infusion of furniture and art—everything from the Old Masters to modern photography—from the Thyssen-Bornemisza family's private collection, which at one point was second only to the collection of the Queen of England. The entire property, which sleeps 10 people, can be rented; if €10,000 per night is a bit out of budget, tours of the monastery can be arranged when the villa is not otherwise occupied.