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The Best Sailing Vacations for Exploring Ancient Historical Sites

From the ancient temples of French Polynesia to Greek cliffside monasteries, drift back in time on these history-packed sailing holidays with Culture Trip.
Mark Nayler
18 Mar 2022
History buffs will find plenty to absorb their attention on these sailing trips. Along the way, you’ll have the chance to intersperse historical sightseeing with bucket-list activities such as swimming with sharks, hiking up volcanoes and sunbathing on treasure island beaches. Here’s our rundown of the best sailing holidays that combine antiquity and adventure, all bookable through TRIPS by Culture Trip.
1 . Visit thousand-year-old remains of sacred temples in remote French Polynesia
The star archaeological attractions on this catamaran tour of French Polynesia are the remains of Unesco-listed Marae Taputapuatea on Raiatea, once East Polynesia’s main temple. Dating from around 1000CE, this stone complex was believed to have been built by a descendant of ‘Oro, the God of life and death. You’ll also explore the archaeological sites of Huahine, one of the most sparsely populated Society Islands, home to the remains of important structures dating from 850CE to 1100CE.
From$1,117
Next available from28 May 2022
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2 . Discover ancient Turkey on this sailing expedition around the south coast
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.
From$5,540
Next available from13 Aug 2022
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3 . Explore medieval monasteries and Byzantine churches in Greece’s Cyclades islands
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.
From$1,895
Next available from27 May 2022
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4 . Sail to islands of myth and Roman ruins along the Dalmatian coast of Croatia
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.
From$1,705
Next available from28 May 2022
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5 . Visit the world’s oldest colonial church in the volcanic Cape Verde islands
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.
From$2,480
Next available from19 Nov 2022
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