Where to go on a sailing holiday

Sailing holidays involve spending a fair bit of time on your boat, either on deck relaxing, learning how to sail, spotting wildlife amongst the waves or all those things. Typically, they stick to one country, sailing around its islands, coastline and fishing towns during the day, before docking in a secluded bay, secret cove or bustling port by night. The boat will steer towards sights of interest en route, so you get lots of opportunities to hop off the boat and experience the local landscape, be that via Roman ruins in Turkey, or kayaking through mangroves in Myanmar.

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Caribbean

The warm trade winds, reliable and steady, secure the Caribbean’s place as a playground for sailors, and stories of buccaneers and heists on the high seas make any long passages at sea pass fast. Every year, sailors gather for regattas and races, but there’s plenty of leisure sailing about. Islands like Saint Lucia, Grenada, Saint Maarten and Barbados are popular hubs for Caribbean sailing holidays.

Croatia

The Dalmatian coast stretches from the island of Rab in the north to the border with Montenegro. Its southern stretch, between Split and Dubrovnik, is a sailing hotspot. Hvar, Korcula and Brac boast ancient towns and beautiful beaches, while Mjlet is almost wholly protected by national park status. Further north, the Zadar Archipelago consists of hundreds of islands, only 20 of which are inhabited – island hopping heaven.

Greece

The Cyclades archipelago is the destination for a quintessentially Greek island-hopping sailing holiday. Sail between deserted islands, stopping to snorkel or swim, then hop off at beautiful islands such as Santorini, Naxos and Mykonos, for a feast at a waterside tavern or a hike to a traditional village, then back to the boat before the nightclubs open.

Greenland

Swap roads for channels, sounds, and one of the largest fjord systems in the world: going by boat is the best way to experience Greenland, a country where much of the land is practically inaccessible unless you reach it by sea. Your reward? A wilderness seen from the water – if you’re under sail power, you won’t just see it all, but hear it all too: the crack of ice, the sounds of seabirds, the surfacing whales.

Italy

The Ligurian Sea is the stretch of Mediterranean that runs between northwest Italy, Tuscany and Corsica. Conservation sailing holidays run here, where you can help collect data on the area’s many whales and dolphins. For more relaxed sailing, consider the coast south of Naples. Sip limoncello in the Bay of Naples whilst gazing at Vesuvius, spend time ashore at Pompeii, explore Capri’s Blue Grotto in a rowing boat and enjoy a gelato – or several.

Norway

Spitsbergen, the largest island in the Svalbard Archipelago, is north of Norway, a wild kingdom of polar bears, walruses, ice and rock. Further south, yet still nudging the Arctic Circle, the Lofoten Islands are fantastic for sailors – your off-shore vantage point shows you the true height of the mountains dropping straight into the sea. Norway’s fjords are a wonderful setting for whale and bird-watching holidays, with the chance of seeing the Northern Lights, too.

Scotland

The coast and isles of western Scotland were made for exploration by boat. This is the perfect way to discover remote islands, bays and the narrow straits known as kyles, and to spot the area’s wildlife, from sea eagles to minke whales. Scottish sailing trips are mostly participatory, so you’ll learn techniques as well as meet new people – great for dragging teens from screens!

Turkish coast

One of the most iconic sights in Turkey’s sailing scene is the gulets – the traditional wooden fishing boats that are now used for tourism. Glossy with varnish, their decks padded with sunbeds, these are wider than many other sailing boats. Sail away from busy, touristy Bodrum and discover Turkey’s mountainous, pristine Aegean coast, peppered with tiny islands, small fishing villages and hidden coves where simple wooden jetties are your route to cheerful restaurants.
Written by Joanna Simmons
Photo credits: [Page banner: Markos Mant] [Caribbean: Hans Isaacson] [Greenland: Dylan Shaw] [Scotland: Nils Leonhardt]