The Best Sailing Vacations for Exploring Ancient Historical Sites

Soak up the history of Turkey on this trip around its southern coast in a gulet (traditional sailing boat). Starting in Fethiye, it encompasses an array of Greek, Roman and Byzantine sites. Enjoy sunset drinks in the sea-facing amphitheatre at Kas; snorkel around the submerged ruins of Lycian settlement Kekova; and visit the remains of Myra, where ancient mausoleums are carved into the cliffs beneath a well-preserved Roman arena. You’ll also wander around the crumbling houses of Kayakoy, a village abandoned in the early 1920s.

You’ll see plenty of ancient sites on a 10-day sailing adventure around the Cyclades islands of Greece. First up is Amorgos, where you’ll visit the amazingly preserved remains of a Minoan settlement dating to 10BCE, as well as the Byzantine churches of Hora and the snow-white Hozoviotissa Monastery, built into a cliffside in the 11th century. On Naxos, the largest Cycladic island, check out one of the oldest temples in Greece, and hike up to Kastro, a medieval castle high above town.

This cruise down the Dalmatian coast starts in Split, home to the fourth-century Dicoletian’s Palace. Key historical sites on the southbound journey to Dubrovnik include Korcula, a city inhabited by ancient Greeks, Romans and Slavs; the 15th-century Venetian-style churches of Lastovo; and the island of Mljet, where the Greek hero Odysseus is said to have lived for seven years after surviving a shipwreck. Enjoy a self-guided finale in Dubrovnik, walking the ramparts of its 13th-century walls, which formed the backdrop for TV series Game of Thrones.

Head to Santiago on this voyage around Cape Verde, a 10-strong archipelago off the western tip of continental Africa. Here, visit Unesco World Heritage site Cidade Velha, the most historic town in the country. Founded in 1462, it was once a hub of the slave trade. Today, it’s home to the oldest colonial church in the world. Spot more European-style architecture in Sao Filipe, capital of the aptly named Fire Island, where you’ll also have the option of hiking to the top of the Pico de Fogo volcano.