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Insider's guide: The world's best sailing destinations

7 September 2021• Written by Sophia Wilson

Where is the best place in the world to go sailing? From testing trade winds to cocktail conditions, superyacht owners, captains and industry experts reveal their favourite sailing destinations in the world to help you plan your next sailing yacht cruise...

The Society Islands, French Polynesia

Recommended by: Captain Angus Biffin of 56.1-metre Asahi

Bora Bora is one of 14 island groups that make up the Society Islands.
Credit: Dana Neibert via Getty Images. Top image credit: Studio Borlenghi/ALeA/Getty Images

Starting a charter in Tahiti and finishing in Bora Bora offers great downwind sailing conditions given the ever-present east and southeast trade winds. The sail from Mo’orea to Huahine is always fast and exhilarating, and the geology of the Society Islands, with their natural deep-water lagoons, means you are guaranteed a flat, calm anchorage every night.

Local flavours: On the north-western corner of Mo’orea there are some beautiful motus (small islands) where we have organised a traditional Hangi lunch with the locals for our guests. Whole pig, seafood, root vegetables such as tarrow and local spinach are cooked underground with volcanic rocks. The flavour is amazing, especially when washed down with a few ice-cold Hinano beers.

Perfect timing: The trade winds are most predictable May to September.

Asahi is available for charter with Edmiston.

The Society Islands are a favourite of Captain Angus Biffin of 56.1-metre Asahi.
Credit: Edmiston

Western Norway

Recommended by: Ocean Independence senior charter broker Barbara Müller

There are hundreds of islands to explore on the western coast of Norway, or you can head into the fjords, going up to 60 nautical miles inland. You’ll be sailing between mountains, which means unforgettable scenery and challenging conditions – there can be anything from a lot of wind to none whatsoever, and it changes after each turn.

Memory lane: I had an incredible experience on a 13-metre sailing yacht in the fjordland many years ago. You would find yourself tacking one leg of the fjord and then using the spinnaker the next. Highlights included sailing the famous Geiranger Fjord and seeing the Preikestolen [Pulpit Rock] in the Lysefjord from below.

Perfect timing: Sailing season is June to August. In June it almost never gets dark, but in August it’s a little warmer.

Western Norway is a favourite of Ocean Independence senior charter broker Barbara Müller.
Credit: grandriver via Getty Images

The Great Lakes, North America

Recommended by: Captain Damien Dempsey of 37-metre Norfolk Star

In the summer of 2014, I took a 34-metre sloop through the Great Lakes of North America. They may not be a traditional superyacht destination, but we had some spectacular sailing with flat water and optimum 15- to 20-knot winds.

Clear winner: A highlight of my time up there was sailing the crystal-clear waters of Georgian Bay, in the Northeast part of Lake Huron. The water was so clear we saw crabs crawling along the lakebed more than five metres below.

Located within the borders of Ontario, Georgian Bay has clear waters and steady winds.
Credit: Maurice Prokaziuk via Getty Images

Perfect timing: The summer season, especially in the northern parts of this vast inland water system, is relatively short, but it can extend from as early as May through to mid-September. If warmer weather is your goal, then July and August offer the best conditions.

Norfolk Star is available for charter with Burgess.

The Great Lakes are a cruising favourite of Captain Damien Dempsey of 37-metre Norfolk Star.
Credit: Burgess

St Vincent to Grenada

Recommended by: Henry Guest, charter broker, Burgess

The great thing about sailing from St Vincent to Grenada is that the Caribbean’s consistent trade winds, which blow from east to northeast, funnel through the gaps between the islands so you can have some invigorating sailing knowing that the lee of the next island isn’t far away.

On board action: The final leg will be the longest of the trip, about 25 nautical miles to reach Grenada from Mopion Island (a tiny strip of sand with just one thatched beach umbrella that’s perfect for a beach set-up). With most of it being open to the Atlantic this can be a very lively beam reach sail, but once in the welcome lee of Grenada, you can enjoy a calmer couple of hours’ cruise down the west coast to St Georges.

Perfect timing: The most popular time of year to be in the Caribbean is from mid-December through the first week or so of January, but I think the later part of January right through to early spring is best.

Grenada and St Vincent are favourite destinations of burgess broker Henry Guest.
Credit: Petronella Pieprz via Getty Images

Eastern Tuamotu Islands, French Polynesia

Recommended by: Captain Clive Walker of 47.2-metre Asolare

My best cruising has been in the Pacific, most notably the Eastern Tuamotu Islands. The area boasts hundreds of uninhabited atolls, most of which can be entered with draughts up to five metres and offer beautiful calm anchorages. Zig-zagging between the array of atolls under sail in 10 to 15 knots of fresh daily trade winds is a joy for any keen sailor. Navigation is easy in the deep, flat water, so the area is the perfect platform for relaxed “cocktail sailing”.

There a countless atolls and reefs to explore in the Eastern Tuamotu Islands.
Credit: Reinhard Dirscherl / Alamy Stock Photo

View to remember: Every morning and evening a multitude of sharks enter the atoll passes, which for the brave is an unforgettable sight.

Perfect timing: As the Tuamotus are just south of the equator they can be visited any time of year. I have been twice between June and October.

Asolare is available for charter with Ocean Independence.

The Eastern Tuamotu Islands are a favourite of Captain Clive Walker of 47.2-metre Asolare.
Credit: Ocean Independence

British Virgin Islands

Recommended by: Vanessa Morlot, Camper & Nicholsons charter broker

The BVIs are perfect for sailing because their configuration means you can do small hops between islands or longer crossings – like from Virgin Gorda to Anegada. The trade winds are super-consistent, and even when they get stronger during the Christmas winds there is always somewhere to shelter because of the way the islands are scattered.

Scenic stop-off: My favourite anchorage is Little Harbour on Peter Island – you can see the bottom of the ocean and turtles and rays swimming beneath you. When I visited with my family we returned for an extra night. My children just loved the nature and it created such amazing memories.

Perfect timing: The best time is between November and early March. There is very  little chance of rain and winds are around  15 to 20 knots.

The crystal-clear waters surrounding Peter Island in the BVIs mean you can spot rays and green turtles without stepping off your boat.
Credits: cdwheatley via Getty Images

Dodecanese Islands

Recommended by: Ilia Riga, owner of 49.8-metre Almyra II

The Dodecanese are less well known than some of the other Greek islands, but their location means they are protected from the east and northeast by the Turkish coastline, ensuring consistent but mild winds. Typically wind speeds do not exceed 25 knots and rarely drop below nine knots, allowing for easy sailing conditions.

Housed next to the famous windmill in Agia Marina, Leros, Mylos serves fresh fish prepared with local ingredients.
Credit: Metin Bul via Getty Images

Perfect timing: The meltemi tends to blow strongest in August, which can make the central Aegean Sea too windy, but the Dodecanese remain well protected with an average of 24 knots. At the end of the month the wind gradually fades but remains strong enough for sailing.

Island life: There are plenty of islands to explore, but three of my favourites are Arkoi, Levitha and Leros. The latter is a scuba-diving paradise, with numerous wrecks from the First World War, and there is a wonderful fish restaurant called Mylos in front of the iconic windmill, which in my opinion is the best fish restaurant in Greece.

Almyra II is available for charter with IYC.

Arkoi is one of more than 150 islands to make up the Dodecanese group.
Credit: nejdetduzen via Getty Images

St Barths

Recommended by: Nicola Breymaier, charter broker, Fraser

I always recommend St Barths for a top sailing experience, particularly the St Barths Bucket or Les Voiles de St Barth. The consistently strong winds provide top conditions for sailing and racing, especially in the spring, and you can’t beat the island as a scenic backdrop. Les Voiles is more competitive, whereas the Bucket is more focused on the fun and social side.

The 2022 St Barths Bucket Regatta takes place from 17 to 20 March.
Credit: cdwheatley via Getty Images

All-rounder: At these events it is often just as much fun to charter a yacht as a spectator as it is to be part of the race itself. I would recommend finding a yacht with diving and fishing gear and so there is plenty to do on board in any conditions.

Après sea: The beach clubs and bars in St Barths are all legendary. Some favourites include Shellona, on the aptly named Shell Beach, and Nikki Beach, which is on Plage de St Jean on the opposite side of the island.

Vava'u, Tonga

Recommended by: Anthony Brookes, captain of 62-metre Athos

The remote island of Vava’u offers the chance to spot migrating humpback whales.
Credit: Susanne Michaela Huss via Getty Images

It’s not the easiest place to get to, but the Vava’u group is northern Tonga is the most amazing sailing destination. There are more than 40 islands within a barrier reef, and they are reasonably distanced so you can spend a couple of hours sailing between each island. The flat waters are also a major plus. It’s great to have a few big waves now and then but no one (apart from maybe the odd rufty-tufty around-the-world sailor) wants to do that for hours on end.

Fine dining: I first went there in 1987 and have been nearly a dozen times since. There’s a restaurant called La Paella on Tapana Island which is definitely worth visiting if you are sailing in the atoll.

Perfect timing: The end of September until mid-November is the middle of the sailing season – and you also get the humpback whales migrating through.

Athos is available for charter with Y.CO.

Tonga is a favourite of Anthony Brookes, captain of 62-metre Athos.
Credit: Oliver Riley

Strait of Bonifacio

Recommended by: Gianluca Mazzetti, Yachting Partners International sales broker

Between Sardinia and Corsica is the Strait of Bonifacio, which is a special place for sailing. If you look at a map you can see that the mistral comes from the Gulf of Lion in Marseille down the west coast of Sardinia to that channel. The wind is just fantastic, regularly above 18 knots, and I have had many exciting days out on the water there.

The Strait of Bonifacio is a favourite sailing destination for YPI sales broker Gianluca Mazzetti.
Credit: Daniele Macis via Getty Images

Après sea: The area is great for sailing but there are also lots of beautiful islands to stop off at. Any yachts in the area should always visit Cavallo Island, which is home to the Hôtel & Spa des Pêcheurs. I know the owner well and visit a few times each year; the restaurant is excellent with very good service.

Perfect timing: Conditions are excellent from May to September, but try and avoid visiting in August as it gets crowded.

The island of Cavallo is three kilometres east of the Corsican mainland on the Strait of Bonifacio.
Credit: Guido Sannino / Alamy Stock Photo

This feature is taken from the September 2021 Life Under Sail issue of BOAT International. Get this magazine sent straight to your door, or subscribe and never miss an issue.

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