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All aboard for the loveliest old-school sailing holidays
There's something undeniably romantic about the sound of the wind in the sails, gently creaking masts and the sloshing of waves against the hull. Whether you're after all-out formal luxury, the glamour of a yacht on the French Riviera or a hands-on expedition along Greenland's coast, here are some of the best adventures under sail.
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The five-masted Royal Clipper, the flagship of the Star Clippers fleet, is the world's largest square rigger in service and modelled on the tall ship Preussen, which was launched in 1902 but wrecked near Dover in 1910. The modern incarnation carries 227 passengers and comes with three small pools, a spa with underwater viewing windows and its own marina platform for watersports. Sail the Grenadines and beyond in swashbuckling style on a leisurely cruise from Barbados to Grenada, Tobago Cays, St Vincent, Bequia, Martinique and St Lucia, with plenty of time to lounge in the giant bowsprit nets and watch the crew raising the 42 Ten nights — one night pre-cruise and two post-cruise at the Barbados Hilton, seven full board on the ship — from £3,549pp, including flights and transfers, departing on January 2 (
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Explore the pale pink beaches and multicoloured coral reefs of Indonesia's Komodo National Park the slow way on the wooden pinisi sailing ship Katharina. As well as walking with a ranger to spot the famous dragons, there's a chance to snorkel alongside enormous whale sharks and manta rays, see sea turtles (more benign than the drooling dragons) and swim under a rainforest waterfall. Katharina is a gaff-rigged ketch (a type of two-masted boat), built in Kalimantan, carrying 12 guests in style, with paddleboards, kayaks and snorkel gear, with a crew of 12 hoisting the distinctive dark red sails and producing exquisite Indonesian and international dishes for communal Nine nights — one pre-cruise in Bali and eight full board on the ship — from £5,320pp, including internal flights, departing from Komodo on August 9 ( Fly to Bali
Cruise the shores of Italy, Croatia and Montenegro on the 342-passenger Wind Surf, a five-masted sailing yacht that's easily small enough to squeeze into the more exclusive ports, including the prestigious San Basilio dock in the heart of Venice. In Dubrovnik, the ship anchors off the old town, with splendid views of the medieval ramparts, while other ports of call include Kotor, at the end of a deep fjord, Giardini Naxos, overlooked by pretty Taormina, and Sorrento on the Amalfi coast. On board, there's a relaxed vibe, with no formal dressing. Pick a warm night to dine on deck at Candles, the romantic alfresco steak and seafood Eight nights' full board from £3,289pp, departing from Venice on May 13, 2026 ( Fly to Venice
Sea Cloud is a graceful, four-masted barque, built in 1931 as the private yacht for Marjorie Merriweather Post, for much of her life one of the richest women in the US. The antiques, marble fireplaces and golden swan taps she chose are still in place — and when the 29 sails, a total area of 32,000 square feet, are aloft, the 64-passenger ship is a magnificent sight. You'll have plenty of sailing time on this circumnavigation of Sicily, cruising from Malta to ports including Palermo, Lipari in the Aeolian Islands, Taormina and Syracuse. Expect a degree of formality on board; the Captain's dinner is a time for 'elegant cocktail' attire and a jacket for Nine nights' all-inclusive from £6,699pp, including flights and crew tips, departing from Valletta on October 16 (
Explore Norway's glassy fjords the slow way on a vintage sailing ketch. The venerable tall ship Bessie Ellen, built in 1904 to transport cargo and now beautifully restored, carries up to 12 passengers on slow-paced holidays in northern Europe. You don't need sailing experience, although you can help the crew raise the sails if you want to. Sail from Stavanger into the serene Lysefjord, past ribbon-like waterfalls and basking seals, with views of the vertiginous Pulpit Rock and daily opportunities to head ashore for walks. Food on board is locally sourced — the ship is part of the Slow Food movement — and there's an honesty bar for Seven nights' full board from £1,720pp, sailing round-trip from Stavanger and departing on August 20 ( Fly to Stavanger
The five-masted, 386-passenger Club Med 2 is the twin of Windstar's Wind Surf, although life on board has a distinctly French flavour. In traditional Club Med style, plenty of activities are included, from waterskiing and wakeboarding to yoga on the warm teak decks. There's an open bar and in the evenings, a convivial vibe, fitting as you'll be sailing along one of the world's most glamorous coastlines, from Nice to Portofino. There's a full day anchored off Portofino, where you can mooch around the chic little town or play on the ship's water toys; the vessel has its own watersports Two nights' all-inclusive from £577pp, departing from Nice on September 11 ( Fly to Nice
If there's one place you want to be able to dive in straight off the ship, it's the Greek islands. Swim stops on the 49-passenger Galileo, which has just had a complete makeover, are one of the highlights of this Jewels of the Cyclades itinerary, which visits lesser-known islands including Poliegos, Folegandros, Antiparos, Syros and Kythnos as well as the big hitters Santorini and Mykonos. The cruise is half-board, so you can pick the most inviting looking tavernas ashore for dinner. The Cyclades is a notoriously windy spot, so the ship's six sails will be put to good Nine nights — two B&B in an Athens hotel, seven half-board on the ship — from £2,167pp, including flights and transfers, departing from Athens on July 9 (
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Exploring the Nile under sail — we're talking about an elegant dahabiya as opposed to a rustic felucca — is a completely different experience from travelling on a regular riverboat. These small, luxurious sailing boats were popular among the wealthy in the late 19th century, all polished wood, fine dining and lounging areas on deck piled with cushions. Now, Oberoi Hotels is launching two extremely high- end, contemporary dahabiyas, Melouk and Malekat, each with two sails, a spa and a plunge pool, each carrying just 14. As well as visits to Karnak Temple, the Valley of the Kings and other big hitters, there are more immersive experiences, from Nubian cooking classes to fishing in the Nile and visits to local villages and farms. With exclusive moorings, you'll never be hemmed in by another ship either. Details Four nights' full board from £3,370pp, including activities, sailing between Luxor and Aswan, with departure dates from October to be confirmed ( Fly to Luxor or Aswan
Most gulets — those traditional wooden boats you see all along the Turkish coast — are engine powered, with the sails more for show. But the fleet operated by the Anglo-Dutch company SCIC Sailing includes proper sailing gulets, propelled mainly by the wind and crewed by experienced sailors. A week on the 16-passenger Nemesis is true barefoot cruising; you can help hoist the sails or simply lounge on deck, jumping into the turquoise Aegean to cool off when the boat is at anchor, or paddling a kayak along the bottle-green shoreline. Nights are spent in secluded bays, feasting on Turkish meze and Mediterranean dishes, with a couple of evenings in port so you can head ashore for dinner. The cabins are air-conditioned but it's fun to sleep under the stars on deck Seven nights' half-board from £1,186pp, including all drinks and some extra meals, sailing between Ortakent and Marmaris, departing on September 27 ( Fly to Bodrum and from Dalaman
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Take in the vast landscapes and ice-strewn seas around Greenland's Disko Bay from the expedition sailing yacht Valiente, which carries just 12 passengers. You'll anchor in pristine bays, with opportunities for hiking, fishing, visiting tiny Inuit communities and wildlife watching. As well as polar bears, there's a good chance of spotting humpback whales and, if you're lucky, narwhal. Most of the sailing is inshore, although there are some night passages under the midnight sun, as well as stops for beach bonfires. Although you don't need any sailing experience, this is a hands-on adventure, with guests joining the crew on watch and, divided into pairs, doing the cooking; luckily for all, recipes and ingredients are Seven nights' full board from £3,855pp, including activities, departing from Ilulissat on August 12 ( Fly to Ilulissat via Reykjavik
With only 32 guests attended by 33 crew members, you can expect an air of exclusivity on the three-masted yacht Le Ponant, which had a complete renovation in 2021 and is the first sailing yacht to have an affiliation with Relais & Châteaux. This unusual voyage around the Cape Verde archipelago takes in colourful fishing villages, rolling dunes, sparkling beaches, plunging valleys and, of course volcanoes, which dominate the landscape. You'll visit six islands, propelled by the wind as you sail between each one. On board, there's a small spa and a watersports marina — and with so few passengers, a real sense of being on a private Seven nights' all-inclusive from £6,920pp, departing from Mindelo on November 29 ( Fly to Mindelo
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Have you been on a sailing ship holiday? Share your memories in the comments
