6 of the most scenic places to learn how to sail
From the taverna-fringed Greek islands to the little-known bays of Thailand’s Andaman Sea, these are the best destinations for novice sailors.
Standing at the helm, skimming carefree through the surf and mooring whenever you please — sailing offers the freedom to go wherever the winds take you. And while the thought of hoisting sails may initially sound complex, there are plenty of places where beginners can learn the ropes and watch the experts at work. Here are some of the best.
1. The Mediterranean
Best for: complete novices
The Ionian is the ideal archipelago for first-time sailors, as it offers friendly winds, short distances between islands and plentiful moorings in harbours and bays. Start in Corfu and you’ll breeze downwind via seven islands in seven days, including little Paxos with its waterfront tavernas; Antipaxos with its turquoise anchorages; Lefkas, with its olive trees, cypresses and turquoise islets; and laidback Kefalonia to disembark. Board a stable catamaran with Fleewinter, and you’ll have a talented chef in the galley to take care of any leisurely lunches after impromptu swims. Charter with friends or book a single cabin, and the crew will be on hand to give you tutorials.
How to do it: Fleewinter has eight-day sailings, departing May to October.
2. Morocco
Best for: adventure
While most sailing holidays promise a relaxed time, Rubicon 3 offers adventure. Trips are as much about excitement as they are about learning how to sail a tough, 70ft former ocean-racing yacht — there are plenty of ropes to pull, and everyone aboard is expected to join in with the crew, including complete beginners. Morocco is a memorable destination for a first experience afloat; this trip sets a course south from Spain via Tangier, capital Rabat, the fortified city of El Jadida and Safi, famous for its pottery. In this region, almost unvisited by other yachts, the welcome is as warm as the breeze. Day-long passages here aren’t just an opportunity to perfect helming, they’re practise before the finale — a 24-hour ocean passage to the Canaries.
How to do it: Rubicon 3 has 12 days from Cadiz, departing in November.
3. Thailand
Best for: tropical isles
It’s the backpacker dream with a difference: an island-hopping circuit from Phuket through Thailand’s Andaman Sea, without the ferries or near-constant packing and unpacking. More than that, you can learn to sail while discovering the region’s extraordinary scenery, where longtail boats buzz over emerald seas, and islands rise like dragon’s teeth from the depths. This itinerary with G Adventures visits classics like Khao Phing Kan (aka James Bond Island for its appearance in The Man with the Golden Gun), but it’s the secret swimming spots only accessible by yacht off Ko Yao Yai and Koh Khai Nai that feel special. Throughout, sailing conditions are gentle — ideal for beginners. Your skipper will use wind power when possible and be around to offer tricks of the trade, and you’ll be welcome to help with navigation.
How to do it: G Adventures has seven days from Phuket, departing October and November.
4. British Virgin Islands
Best for: reliable warmth
Cobalt-blue anchorages, consistent warm trade winds, rum punches in piratical beach bars like Soggy Dollar, snorkelling adventures to The Baths National Park on Virgin Gorda: the British Virgin Islands have much to offer budding sailors. On this trip with Kraken Travel, the 62ft catamaran is luxurious and modern, with en suites adjoining each of the cabins and plenty of sunbathing space to accommodate guests who aren’t helping to tweak the sails on passages of up to four hours.
How to do it: Kraken Travel has seven nights from Tortola, departing December to January.
(The Great Loop is the epic U.S. adventure you’ve never heard of)
5. Cornwall
Best for: tradition
Manning a traditional boat is sailing at its most romantic: a wooden ship, hoisting sails by hand not hydraulics, the creak of ropes as you stand at the helm. A replica of a historic Falmouth working boat, the 90ft Pellew spends summers cruising from Falmouth skippered by the affable master mariner who built her, Luke Powell. He can teach you the ropes no matter your destination, whether it’s along the Cornish coast, across to the Scilly Isles or to the harbours of Brittany.
How to do it: VentureSail has trips from four to 10 days, departing August and September.
6. The Seychelles
Best for: expert advice
The Seychelles offers the castaway dream of discovering untouched tropical anchorages, where swaying coconut palms fringe warm seas. A skippered charter (on which you hire a boat with a liveaboard skipper) with Sunsail here offers the chance for one-to-one sailing tuition with a professional in an open-ocean cruising ground with vigorous winds, which is otherwise off-limits to novices. Your skipper will have a little black book of lunch-stop anchorages on islands like Mahé, Grand Anse and La Digue, and know the best locations to observe free-roaming giant tortoises and exotic birdlife in their natural habitats.
How to do it: Sunsail has five to 14 days from Mahé, departing year-round.
