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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
15 Sep 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 . 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.

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2 . 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.

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3 . 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.

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4 . 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.

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Since you are here, we would like to share our vision for the future of travel – and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Bespoke Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Bespoke Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm – and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.