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The 5 best islands to sail around

Anchoring in deserted coves and diving into clear seas, al fresco dinners and sunbathing on deck – these are just a few of the joys of the life aquatic. Whether you have the qualifications to charter your own boat or you decide to enlist the services of a skipper, a sailing holiday will allow you to encounter places that are often unreachable other than by the water.

From floating just off the white sandy shores of the Balearic archipelago to circumnavigating Zanzibar on a catamaran, these are the five best islands in the world to sail around.

Mallorca, Spain

Drop anchor at Cala Mondrago, a short stretch of bright, white sand backed by a nature reserve

Drop anchor at Cala Mondrago, a short stretch of bright, white sand backed by a nature reserve

Mallorca is the largest of the Balearic islands (an archipelago off eastern Spain) and is ideal for both a beginner’s and an advanced sailing holiday. It takes one week to circumnavigate at a fast pace and two weeks following a more relaxed itinerary; we’d recommend the latter, so that you have time to stop in several of the finest harbours and ‘calas’ (Spanish for ‘bays’). Charter a yacht in the capital, Palma, or rent a boat with a skipper – due to prevailing winds, it’s advisable to round the island in a counterclockwise direction. One of your first ports of call should be Cala Mondrago, a short stretch of bright, white sand backed by a nature reserve – drop anchor (there are no buoys here) just offshore, where the crystalline sea is sheltered by two rocky headlands. And disembark to hike through the scented pine and agave forest, or to use the low cliffs for diving into the glistening water. Other must-visits on the east coast include Cala Mitjana, the long, pine-shaded Playa de Formentor and the nearby town of Port de Pollença, while the clear waters around Cala Deià on the west coast are great for snorkelling. Spend the night before you sail in the centre of Palma at Ramón Llull House.

Pag, Croatia

Pag's lunar landscape is best admired while bobbing just off its sun-drenched shores

Pag's lunar landscape is best admired while bobbing just off its sun-drenched shores

With only 48 of its 1,000-plus islands being populated, Croatia still has an undiscovered feel and is an outstanding destination for sailing – being somewhat reminiscent of the French Riviera in the 1960s. While popular spots like Hvar are comparably busy to St Tropez, islands like Pag offer peaceful anchorages even in the height of summer. Pag can be found close to the coastal city of Zadar, and is an incredibly barren place with an almost lunar landscape that’s best admired while bobbing just off its sun-drenched shores. The island has garnered a little more international attention as the location for Hideout Festival, held in the first week of July, so try to avoid this – or at least Zrće beach – if you want its azure Adriatic waters to yourself. Drop anchor near the tiny port of Tovarnele and head to the bistrot of the same name for fresh seafood, some of the island’s signature Pag cheese and homemade olive oil sourced from local trees. Many of these olive trees are over a thousand years old, making them some of the oldest in the world – and the oil they produce has a distinct quality and aroma that is truly irresistible. Before you set off, spend the night on dry land at Pag’s Boutique Hotel Intermezzo.

Zanzibar, Tanzania

Charter a yacht or catamaran and discover Zanzibar's untouched beaches of oyster-white sand

Charter a yacht or catamaran and discover Zanzibar's untouched beaches of oyster-white sand

Technically an archipelago not an island, Zanzibar makes an exquisite setting for sailing. Just off the coast of Tanzania, the tropical scenery here is flawless; traditional, wooden ‘dhow’ boats rest on the surface of the cyan-blue water of the Indian Ocean, which in turn laps beaches of oyster-white sand. Constant trade winds and a hot climate mean great conditions for a holiday on the water but the best sailing seasons are from December through till March and June until October. The local ‘dhow’ vessels have been used since the 18th century and though they are still used for local transport and tourist tours, the best way to enjoy a full sailing holiday here is to charter a yacht or catamaran. While you can’t bareboat charter here (since maps aren’t accurate enough), you’ll easily find an experienced skipper who knows the area well and can take you to the most untouched places, like the small island of Mnemba. Spend days sunbathing on deck and diving into the sea, and evenings watching flaming crimson and gold sunsets. Or, if you’re feeling more adventurous, partake in the Kraken Cup; this race was started by a British company called The Adventurists, and entails teams navigating boats made from hollowed-out mango trees around the Zanzibar archipelago. Get a taste for island life staying on the beach at Mama Root.

Bermuda, USA

Sailing is synonymous with Bermuda, an island that was discovered by shipwrecked sailors

Sailing is synonymous with Bermuda, an island that was discovered by shipwrecked sailors

Sailing is synonymous with Bermuda, a sub-tropical island floating in the North Atlantic that was discovered by a crew of shipwrecked sailors. The weather here is suitable for taking to the high seas, and the water is mostly calm and clear for leisurely cruising from cove to cove – the coastline, dotted with historic forts and beaches, is particularly pretty when seen from the sea. Plus, the island is home to a large sailing community and hosts major sailing events, including the world’s oldest regularly scheduled ocean race (the Newport Bermuda Race) and the prestigious 35th America’s Cup in 2017. Book yourself a lesson or two at one of the many local sailing clubs and schools, or charter a yacht, catamaran, fishing or ski boat from various vendors along the coastline – Fantasea Diving & Watersports even offers a glass-bottomed boat for snorkelling around the island’s coral reef. Spend some time ashore staying at Watercolours B&B.

Antigua, Caribbean

The view over English Harbour is filled with masts during Antigua Sailing Week in late April

The view over English Harbour is filled with masts during Antigua Sailing Week in late April

The small, paradisiacal island of Antigua is known as the sailing capital of the Eastern Caribbean. The headlands and coves of its undulating coastline mean there are ample anchorages and harbours to stop in as you circle its verdant shores, where rainforest is broken up by colourful cottages – jump off your boat into balmy waters and swim ashore to dry off on silken sands. The island is also known for its annual Antigua Sailing Week in late April, based out of the town of English Harbour on the south coast; this event involves athletes and amateurs racing around the island (non-sailors can also experience the race up close on a catamaran that follows the action, known as ‘Chase the Race’) and a whole bevy of reggae and rum punch-fuelled parties. It’s also a prime boat-spotting opportunity, with splendid vessels moored in all of the island’s harbours. While in English Harbour, check into the classic Copper and Lumber Store Historic Inn.