The Playbook For The Modern Man

10 Unforgettable Sailing Adventures Worth Leaving Home For

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1 of 10|New Zealand|Bay of Islands
2 of 10|France|Côte d'Azur
3 of 10|Tanzania|Zanzibar
4 of 10|Southern Caribbean|The Grenadines
5 of 10|Thailand|Andaman Sea
6 of 10|Croatia|Split
7 of 10|Ecuador|Galapagos Islands
8 of 10|French Polynesia|Tahiti
9 of 10|Vietnam|Ha Long Bay
10 of 10|Cape Horn|Chile

Boating isn’t just for polo-sporting prepsters in Sperrys.

There’s something special about the snap-crackle-pop of canvas, the sight of a mast as it stretches to the heavens, the gentle (or not-so) rock of a hull on the waves. Few things say freedom like an adventure under full sail.

Let your inner Jack Sparrow out at one of these top destinations for sailing. The rum is optional. The sailing brands we’ll also look after.


Bay of Islands | New Zealand

Thousands of miles of stunning coastline make New Zealand a maritime fantasy land. The nation has spawned some of the world’s best sailors, and has one of the highest per-capita rates of boat ownership on the planet. Visit the Bay of Islands in the ‘winterless north’ for clear waters and charming coves spread across nearly 150 islands. This one’s a must for big-game fisherman in particular.

Côte d’Azur | France

Sailing doesn’t get swankier than the French Riviera. From Nice, to Cannes, to Saint-Tropez, to Monaco, this celebrated stretch of land and sea is steeped in legend and celeb scandal. Dive headfirst into the glitz and glamour of the resorts, or enjoy the more natural beauty of unspoilt islands, rocky inlets and pristine beaches.

Zanzibar | Tanzania

Sail Zanzibar, an archipelago in the Indian Ocean off the coast of Tanzania, and you’ll feel like you’ve travelled to a previous century. An aura of ancient kingdoms and trading routes still lingers in historic Stone Town, the surrounding turquoise waters, and the traditional dhow vessels that still sail them. Be sure to catch at least one of the dramatic sunsets.

The Grenadines | Southern Caribbean

The Grenadines – also known as the Spice Islands – are a chain of 32 gorgeous isles sprinkled across the southern Caribbean. Sailing enthusiasts flock to these notoriously boat-friendly waters to enjoy abundant marine life and sparkling white sand beaches. Bequia, second largest island in the Grenadines, is especially known as a seafarer’s haven.

Andaman Sea | Thailand

The Andaman Sea, with Phuket as its bustling hub, is Thailand’s top maritime treasure. The area’s many islands are popular tourist destinations thanks to their breathtaking topography and the coral reefs that surround them. Enjoy rare seabirds and the famous limestone stalactites, then sail to the secluded depths of Phang Nga Bay for peaceful privacy, and end at Ko Phi Phi for a party.


Croatia has been named the new everything. Sailors who have grown weary of the French Riviera or touristy Greek Islands now cruise in the crystalline waters of the Adriatic Sea. As the in-crowd infiltrates, Croatia is becoming increasingly hyped, but with 1778 km of coastline and more than 1000 islands, you can easily escape the well-heeled yachties docking at Hvar.

Galapagos Islands | Ecuador

Follow in the footsteps of Charles Darwin, Captain Cook and Herman Melville with a journey to the Galapagos Islands. A melting pot of both marine and terrestrial species, this voyage is ideal for a nature lover, amateur scientist or history buff. The abundance of rare species is unparalleled, drawing international visitors despite the archipelago’s remote location.

French Polynesia

Gliding through these paradise islands is a sailor’s dream. French Polynesia is made up of five main groups of islands, including Tahiti, all so perfect you’d swear it must a movie set. Blue lagoons, lush vegetation, tumbling waterfalls and volcanic peaks abound, not to mention the captivating combo of traditional culture and exotic marine life. French Polynesia’s 118 islands are a tropical utopia.


Ha Long Bay | Vietnam

Vietnam’s Ha Long Bay is a devastatingly beautiful UNESCO World Heritage Site. Thousands of craggy limestone islands and outcrops jut magnificently from the bay’s serene waters, home to floating villages, caverns and deserted sandy beaches. Book a cruise on a junk ship for a traditional Vietnamese sailing experience. This is one you have to see to believe.

Cape Horn

Rounding the infamously dangerous Cape Horn is the aquatic equivalent of climbing Mount Everest. Large waves, strong currents, intense winds and icebergs are real risks, but despite the remote location and its many hazards, the route remains popular for recreational long-distance sails. Most choose to navigate the open waters of the Drake Passage, as it offers the most room to manoeuvre.

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