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8 of the Best Sailing Holiday Destinations in the World

A sailing holiday brings with it endless possibilities and the opportunity to truly get to know a landscape. From the sea, you can explore spectacular coasts and enticing towns and cities, venture off the beaten path or join the party, and experience the simple joy of sailing or motor cruising. 


The world is a big watery place, and yacht charters can be found in the most glorious destinations, from the Caribbean to the Mediterranean, the Indian Ocean, Pacific Islands and Australia. Faced with the dazzling array of crewed charters or bareboat sailing holidays can be overwhelming. How do you choose between one paradise and another?


Here we look at 8 of our favourite sailing vacation destinations in the world to offer some inspiration. 


1 - Greek Islands

With deep blue seas, golden sand beaches and hundreds of islands steeped in ancient traditions and whitewashed fishermen’s cottages, it doesn’t get more picturesque than the Greek Islands. And there are plenty to choose from – 6,000 in fact. The Cyclades beckon with exuberant islands such as Mykonos and the unmatched beauty of Santorini, while further north the Ionian Islands are a maze of rustic harbours, olive groves filled with bell-toting sheep and traditional tavernas. Explore the Kefalonia of Captain Corelli’s Mandolin, or venture in search of hidden gems well off the tourist trail. With 300 days of sunshine a year, hearty traditional cuisine, and a history dating back centuries, it is no wonder the Greek Islands are still one of the best-loved sailing destinations in the world. 


2 - The BVI’s, Caribbean

The British Virgin Islands are a sailor’s dream come true. With their warm winds, uncrowded sugar sand beaches and authentic Caribbean vibe, they offer a true tropical paradise for a sailing holiday. From Tortola, venture out to explore tiny islets and cays, where sheltered anchorages create the perfect natural swimming pool. With world-class snorkelling and scuba diving, these are some of the clearest and most abundant seas in the Caribbean teeming with sea turtles and tropical fish. 

Water-borne adventure awaits in the BVI’s, and it makes for the ideal family destination. Explore natural beauty of The Baths rock formations on Virgin Gorda, while away a lazy afternoon at the legendary Soggy Dollar Bar on the island of Jost Van Dyke, or go in search of shipwrecks steeped in pirate lore.


3 - Whitsunday Islands, Australia

The 74 islands that just peep their heads above the turquoise waters of the Great Barrier Reef’s Coral Sea are some of the most astounding on planet earth. A swirl of pastel yellow sand melts into azure seas, where turtles and thriving schools of iridescent fish await snorkelers and scuba divers. Enjoy a sailing holiday in the Whitsunday Islands and experience the jungle-clad islands, pond-calm bays and undisturbed, pristine natural beauty. In fact, Whitehaven Beach is often voted one of the best beaches in the world. As you cruise from island to island, keep an eye out for migrating whales, and you’ll almost be guaranteed to have dolphins follow you on your way.


4 - Galapagos Islands

When Charles Darwin sailed the HMS Beagle into Ecuador’s Galapagos Islands, it was to change the way we understood evolution. Today, the Galapagos are still home to some of the rarest and most astounding wildlife on the planet, and to cruise these waters is a once-in-a lifetime experience. The spectacular volcanic archipelago in the Pacific Ocean, some 1000 km off the South American coast, is home to barking sea lions, swimming iguanas, giant tortoises and blue-footed boobies. In the chilly waters great schools of hammerhead sharks can be spotted on scuba excursions. 

The region is highly protected to conserve the delicate natural balance and so sailing holidays in the Galapagos are guaranteed to offer pristine beaches, crowd-free islets and incomparable wildlife-spotting adventures. Just don’t forget your camera. 


5 – Croatia

Croatia’s stunning coast is fast becoming one of the best charter destinations in Europe. From the picturesque UNESCO walled town of Dubrovnik in the far south, all the way up the Dalmatian Coast and Adriatic Sea lies a wealth of islands and historic cities. Croatia has almost 1,200 islands to explore, where dazzling turquoise waters – these really are some of the clearest you’ll ever see - and gentle bays give way to quaint fishing villages and delightful little restaurants. Islands such as Hvar and Korcula manage to blend an upmarket nightlife with a traditional town vibe, while you can take your pick of charming islands where age-old traditions and a slow-paced way of life still prevail. With spectacular national parks to explore, ancient cities such as Split steeped in Roman history and warm afternoon winds to help you on your way, an island-hopping cruise through Croatia is simply magical.


6 – St Vincent and the Grenadines, Caribbean

When you imagine the powder sand beaches and topaz-coloured seas of the Caribbean, it is St Vincent and the Grenadines which fulfils the idyll. This small chain of islands in the south Caribbean Sea is utter paradise, and makes for one of the world’s most perfect sailing destinations. With fewer crowds than other parts of the Caribbean, and plenty of hidden beaches to discover, it is like cruising through your own little tropical world. With 32 islands to choose from – only 9 of which are inhabited – you can channel your inner pirate as you search for hidden treasures – Pirates of the Caribbean was perhaps unsurprisingly filmed here – and explore the healthy reefs of islands such as Tobago Cays Marine Park. From upmarket yacht-filled harbours such as Bequia to low-key Canouan Island, where you can climb the summit of Mount Royal for panoramic views, the adventures are endless.


7 - French Polynesia

One of the most remote destinations on the planet, French Polynesia sits in the heart of the South Pacific Ocean spanning a gargantuan 2000 square kilometres. The 118 islands – 67 of which are inhabited – make for one of the wildest and most astounding cruising destinations imaginable, where islands such as Tahiti, Bora Bora and Moorea need little introduction. If you’re in search of swaying palms, pond calm turquoise bays and sugar sand beaches, then you’ll find it all and more. There is a strong Polynesia heritage and culture on the islands, and a history which includes tales of Captain James Cook. 

Days are spent snorkelling the teeming reefs, climbing through jungle-clad islands in search of hidden waterfalls, and catching the trade winds as you island hop from one gem to another. In this wild, watery world nature reigns supreme, the bright blue skies melting into turquoise seas and studded by emerald isles, where blissful tranquillity and exploration await.


8 – Bay of Islands, New Zealand

While the tropical sunshine of other destinations on this list is usually our first thought when planning a sailing charter vacation, there is more to explore than sandy beaches and swaying palms. New Zealand’s Bay of Islands makes for one of the world’s most beautiful sailing destinations, the 150 islands completely undeveloped – and perfect for discovering by boat. And it’s not short on sandy beaches! You’ll discover endless anchorages, secluded bays, a rich Maori history and waters teeming with fish – renowned for its big game fishing. With bareboat charters and skippered charters available, you can head off to explore deserted isles, spot penguins, dolphins and whales, or explore the boutique towns of Opua, Paihia, Russell and Kerikeri.

Rightboat.com offers sailing charters all over the world. Whether it’s a luxury crewed charter, a bareboat charter or skippered charter we can help you plan the perfect sailing holiday for you and your family. Please don’t hesitate to get in touch and let us put you in touch with the very best yachts in the most astounding destinations. 


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6. Must Visit Croatian Destinations

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8. 10 Greek Islands to Explore

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Written By: Samantha Wilson

Samantha Wilson has spent her entire life on and around boats, from tiny sailing dinghies all the way up to superyachts. She writes for many boating and yachting publications, top charter agencies, and some of the largest travel businesses in the industry, combining her knowledge and passion of boating, travel and writing to create topical, useful and engaging content.

Get in touch:Linkedin

More from: Samantha Wilson

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