Part 3 of the Grand Anniversary Journey: Rome to Venice

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Every leg sailed aboard the Windstar Wind Surf. Read our full review

Otranto was our first stop on the Italian east coast, and the first one officially in the Adriatic Sea. It’s a walled village with a beautiful sea wall and harbor sitting right at the gates of the old city. The water ranged from mint green to a deeper blue, depending on depth, and a small beach right outside the wall provided a wonderful swimming area.

Otranto has deep ancient roots, dating back to a Greek settlement called Hydrus and later to Rome’s Hydruntum. But the event that defines the town today happened much more recently, in 1480, and we’d learn all about it once we reached the cathedral.

Otranto is similar to Ostuni in that it features mostly white walls and granite-stone streets. But the feel of the two towns is different. Otranto felt much more village-like, with slightly wider streets and plazas, clearly residential areas that looked a bit more updated, and dozens of nicer restaurants lining not just the main walkways but also many side streets.

Narrow sunlit alley with pale blue wooden tables and benches along one side, white walls, hanging string lights, and greenery overhead; decorative hat and scarves drape from a wire across the passage. — Inviting Alley of Otranto

Otranto is also famous for its castle and its cathedral, home to a marvelous, intricate mosaic floor called the Tree of Life. We entered the walled city by climbing several flights of iron stairs, a modern addition built where the old Porta a Mare, the historic sea gate, once connected the harbor to the town by a long stairway of its own. Our goal was to visit the cathedral first, tucked toward the back wall of the village, then work our way back through town, browsing shops until we found a spot for a relaxing lunch.

⛪ The Cathedral of Santa Maria Annunziata

Our first impression walking in was how bare and simple the cathedral felt: just a wooden cross and whitewashed walls visible from the entryway. Then I glanced down, and there it was: the famous mosaic floor, covering the entire cavernous length of the church.

The Tree of Life is genuinely astonishing to see in person. A monk named Pantaleone completed it in 1165, roughly 600,000 individual limestone tiles, stretching the entire length of the nave from the door to the altar. A massive tree trunk runs down the center, branches spreading into an overwhelming tangle of images: Adam and Eve’s expulsion from Eden, Cain slaying Abel, Noah’s flood, the Tower of Babel, King Arthur improbably riding a goat, Alexander the Great mounted on two winged griffins. Old Testament stories tangled up with medieval legend and mythology, proof of just how many cultures passed through this stretch of coastline.

Interior of a historic cathedral with tall arched columns, ornate vaulted ceiling, and a mosaic floor depicting animal figures and geometric patterns; a red rope barrier in the foreground. — Tree of Life

Scholars still debate exactly what it means, but the consensus is it’s practically a stone book: the tree symbolizes Christ, with earthly struggle near the entrance giving way to something more ordered and hopeful as you walk toward the altar. Whatever the precise symbolism, you can’t help but be pulled in by the sheer scale and strangeness of it, a 12th-century artist working out the whole span of human history under your feet.

Intricate historic mosaic floor in a church, with circular medallions and stylized figures; visitors sit in pews in the background. — Tree of Life Symbolism

The other thing the cathedral is known for is far more sobering: roughly 800 human skulls, housed in glass cases in a chapel just off the main altar.

In August 1480, an Ottoman fleet landed at Otranto and laid siege to the town. When it fell, the surviving townspeople were given a choice: convert to Islam, or die. All of them refused. They were marched to a nearby hill and beheaded. Their remains were brought back to the cathedral, where they still rest today. They became known as the Martyrs of Otranto, and Pope Francis formally canonized them as saints in 2013.

800 skulls of the Martyrs of Otranto — Martyrs of Otranto

Standing in front of those cases was one of the most sobering and spine-chilling things I’ve done while traveling. The thought of an entire town’s people killed this way, for refusing to renounce their faith, is almost too horrific to hold in your head, especially standing just a few feet from the actual evidence of it. It is a shame that human history continues to repeat itself with these types of atrocities.

🏰 The Castle

Otranto’s other great landmark is the Castello Aragonese, standing guard over the harbor. There’s been a fortress here since at least the 11th century, but the version you see today was rebuilt from scratch just after the 1480 siege, so Otranto could never be taken so easily again. Five-sided plan, a wide moat, three round towers. It’s also a small literary footnote: the castle lent its name, sight unseen, to Horace Walpole’s 1764 novel The Castle of Otranto, generally considered the first Gothic novel.

🍝 Through the Town

After the cathedral, we made our way back through the old town, wandering its network of narrow lanes and picking up a few little souvenirs along the way. We checked out a few menus before landing on a nice seafood restaurant with plenty of shade and fans working overtime against the heat.

Sign reading 'Lora di Mezzo', a restaurant and lounge bar on a wooden backdrop.

Lunch was amazing. We shared a bruschetta and some lightly fried calamari, then relaxed a bit before heading back to the ship for a workout and some downtime before the night’s festivities got going.

Plate of fried calamari rings and small squid pieces with a lemon wedge, greens, and a creamy dipping sauce on the side.

Plate of four crispy crostini topped with tomato mixture, greens, and dollops of creamy cheese on a white plate.

Otranto turned out to be a place that holds two very different experiences at once: a charming, sunlit village of white walls and good food, and one of the most haunting historical sites we’ve stood in. Both are worth the visit.

Seeing Double

Large white sailboat and several motor yachts docked at a sunny marina with turquoise water and a clear blue sky behind. — Windstar Surf Sister ship (Club Med)

As we approached the port this morning, we all started to see double as an identical sailing vessel was docked at the pier. At first, I thought it was one of Windstar’s small sailing ships, but I noticed a slightly different logo on the smoke stack. After a little research, I found that it was indeed our sister ship, owned by Club Med. Apparently, Club Med had built both ships and sold the Surf to Windstar back in 1998. It was crazy that both ships were in the same port on the same day.

Author’s note: Many of these towns resembled each other and had similar stories; the distinction was in the details of their specific culture and history. Otranto has a similar look and feel to Ostuni, but their stories are very different. The Tree of Life and the story of the Martyrs of Otranto brought the town to life and helped shape its future. So you see, I’m including a little more history in these posts, because that’s what has given these places their character.

Read the rest of the Grand Anniversary Journey: castabouttravel.com/journeys/windstar-mediterranean-barcelona-venice