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The world’s best sailing trips

From basking in the turquoise seas of the Caribbean to a wildlife adventure in the Pacific Northwest, Simon Heptinstall’s selection of the best sailing holidays lets you explore a variety of coastal waters

Home life The world’s best sailing trips
The world’s best sailing trips

Whether it’s the Atlantic or Indian Ocean, Africa or the Arctic, sailing holidays allow you to be involved as much or as little as you like – because more and more operators are offering the chance to sail your own vessel, hire a boat with a skipper or join a small boat cruise. 

The world’s best sailing trips

Here are seven of this year’s best destinations for marine holidays afloat:

1. Croatia
The islands and inlets of Croatia offer more than 2,500 miles (4,058km) of beautiful Adriatic Riviera to explore. Little wonder that this land of terracotta roofs, stone villas and ancient harbours has become one of Europe’s most popular cruising and sailing destinations. 

Sailing on a small yacht is the best way to see some of the more remote and secluded natural islands on the Dalmatian coast, like the 130 isles of the Kornati archipelago between Sibenik and Zadar, or the pretty Brijuni Islands National Park to the north. Rental yachts are readily available from the coastal cities, with or without a skipper. Or let someone else do all the work on one of the high-quality small-ship cruises that allow you to enjoy the sun while sailing between the more popular islands, such as the party capital Hvar, and the famous, old walled city of Dubrovnik.

2. British Virgin Islands
This group of tranquil islands in the eastern Caribbean has become a top global sailing destination, attracting sailors ranging from billionaire yacht owners to luxury cruise-ship passengers. They travel here to take advantage of the steady winds, calm currents and gorgeous turquoise sea around more than 50 islands, only 15 of which are inhabited. Many form part of a strictly protected and unspoilt national park. 

Sail yourself, hire a crew or join a small cruise to experience the Virgin Islands’ exclusive charm. Highlights can include a snorkelling adventure at a coral reef, diving pristine sites or landing at deserted beaches. After discovering historic pirates’ haunts in a sparkling protected bay, it’s customary to end up at a quirky waterside bar, sharing your sailing tales with other visitors.

3. Greece
With all its islands and peninsulas, Greece has the longest coastline of any country in the Mediterranean, spanning almost 8,500 miles (13,676km). This means there are hundreds of different sailing-holiday opportunities, whether you take a skippered boat, join a guided flotilla or rent a ‘bare boat’ and hoist the sails yourself. 

Major islands such as Corfu, Rhodes, Santorini and Crete are also easy to visit aboard scores of cruise ships and ferries plying the Ionian and Aegean Seas. The Greek Islands are the original home of island-hopping in Europe and have become one of the top cruising grounds in the world.

The coast is often spectacularly mountainous and dotted with pretty harbour towns and villages. Wherever you sail, it’s easy to find anchorages and enjoy a local meal at a waterside table in the nearest port. 

4. New Zealand
Sailors in the know have discovered there’s a lot more to New Zealand than two sparsely-populated islands on the other side of the world. In fact, the mix of hundreds of islands, fjords and peninsulas makes this the ninth-longest coastline on the planet – boasting some hugely exciting ocean-sailing adventures.  

Taking a vacation to sail in New Zealand is a chance to discover some extraordinary and colourful sea-life in the crystal clear waters. Visiting sailors can cruise past some of the best coastal landscapes anywhere on the globe, ranging from alpine fjords to sub-tropical reefs. Hotspots include the maritime reserves of the Bay of Islands, Hauraki Gulf and Marlborough Sound. And Auckland has earned the nickname ‘The City of Sails’ for a good reason: it claims to have the world’s greatest number of boats per head of population.

5. Thailand
With two separate and very different coastlines, Thailand is a paradise for anyone choosing a sailing trip in south-east Asia. Beginners might start on the eastern Gulf coast with the busy but beautiful Samui archipelago. Further north, the Ko Chang islands offer less developed moorings at unspoilt beaches. The west coast has even more islands in the Andaman Sea, with unsurpassed diving and sensational seascapes.

It’s an exotic destination where it’s possible to sail lazily around hundreds of dreamy tropical islands amid emerald-green seas, discovering perfect places where the white sand beaches have a beautiful backdrop of lush rainforests.

6. Australia – East Coast
The island nation of Australia has such an enormous quantity and variety of coastlines that it’s hard to know where to begin a sailing adventure. There are more than 10,000 beaches, 758 estuaries and the largest area of ocean jurisdiction anywhere. 

Most visiting sailors opt for the East Coast, from Sydney’s famous Harbour up to the fabulous Queensland Peninsular. Highlights include the Great Barrier Reef and the Whitsunday Islands, a 74-strong chain off Queensland that is renowned as a sailing destination. The islands make a stunning base for exploring the world’s longest coral barrier and there are plenty of opportunities for chartering and joining small-boat cruises.

7. Canada – West Coast
The coast of British Columbia is the gateway to the summer sailing playground of the Pacific Northwest. It’s a vast region of islands, inlets, rivers and fjords with a backdrop of snow-topped mountains and huge forests. The scenery, wildlife and seclusion make this one of North America’s most highly-rated sailing areas. 

If you’re bare boating, the changeable conditions mean it’s best for more experienced sailors. Otherwise, let an expert local skipper take reassuring command or join one of the many small cruises through the region around Vancouver, Vancouver Island and the Inside Passage. It might rank among Canada’s most fabulous cruising destinations, but it’s also a favourite of wildlife spotters and fishing fans. Close to shore, sailors can watch for sea otters and seals, while further out they might spot orcas and other whales.

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