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Sailing Events and Opportunities by Wavysail
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Category TypeSkippered/Crewed Charter Vacation,
Sailing Training AdventureBy the CabinStart Location, SplitContactsAndrew Cowen,Price
Ph: +44 07570 702256,
email: info@wavysail.comUSD 5.600 per cabinJoin us for a rare and powerful adventure, a 7-day liveaboard expedition in Croatia combining world-class sailing with elite-level freediving. Guided by Wavysail’s expert skippers and legendary freediver William Winram, this experience is designed for all levels ready to explore depth, resilience, and personal transformation. -You will be sailing through Croatia’s most stunning islands whilst anchoring in remote bays for breathwork, deep water sessions, and skills development. More than a freediving course or a sailing adventure, this is a full-body, full-mind immersion. -You will be part of a small crew, learning by doing, listening to a few stories from William and your skipper, and taking home skills that will serve you well in adventure and in life. Your home for the week is a beautifully maintained Oceanis 46, built in 2019 which gives us a perfect platform to explore above and below the waves. Plenty of space on board with great facilities, she features a stern platform allowing easy access to the water and wide, spacious decks, perfect for sailing, watching the world go by, or practicing breath work with William. You will have your own cabin. All safety gear is included in the experience and the trip is inclusive of food and drink consumed on board. See our website for full details Link to more information about this Opportunity. -
Category TypeSkippered/Crewed Charter Vacation,
Sailing Training Adventure,
Mile/Resume Building AdventureStart Location, SplitContactsAndrew Cowen,Price
Ph: +44 07570 702256,
email: info@wavysail.comUSD$3260 per personOur trip starts and ends at the bustling and beautiful city of Split. This is a hands-on sailing experience under expert supervision . It promises to be a real sailing adventure hosted by a skipper with hundreds of thousands of sailing miles behind them. You will be fully immersed in all aspects of sailing including passage planning and victualling as well as actually sailing this beautiful yacht. It will also be a relaxed schedule with time to stop at some of the wonderful ports along the coast and explore at leisure and, with a maximum of six crew, we will adapt the itinerary to suit individual wishes. The trip suits singles and couples (we have double and single cabins available) and there is no previous sailing experience required. Given the skipper's experience it will also suit people who want to get some practice sailing miles or hone their existing sailing skills. We can take a sextant with us and practice celestial navigation in a relaxed and sociable atmosphere if desired. Link to more information about this Opportunity. -
Category TypeSkippered/Crewed Charter Vacation,
Sailing Training Adventure,
Mile/Resume Building AdventureStart LocationSouth Africa, Cape Town, Western CapeContactsAndrew Cowen,Price
Ph: +44 07570 702256,
email: info@wavysail.comUS$10.500 per person return or USD 8,400 for 1 legEmbark on a truly extraordinary sailing expedition across the South Atlantic - designed not just to challenge and inspire, but to teach you exactly what it takes to plan and complete a major ocean crossing. Led by a highly experienced skipper and first mate, this is far more than a sailing trip - it’s an immersive ocean adventure. Split into two distinct legs, you can join either one or experience the full return journey, including time ashore on the legendary island of St Helena. Each leg includes around five days exploring the island, with self catering accommodation included in the voyage cost. Leg 1: Cape Town to St Helena (Approx. 3 Weeks) Your journey begins in Cape Town with “Boat Prep” at the Royal Cape Yacht Club, where you'll gain hands-on training in route planning, weather systems, provisioning, and offshore safety - everything needed for a successful ocean voyage. We then set sail along the rugged African coast, stopping in Lüderitz, Namibia. Here, you can log qualifying 60nm passages for your sailing certifications and explore the haunting desert ghost town of Kolmanskop. The voyage then crosses the open South Atlantic to the remote island of St Helena - a sub-tropical gem steeped in history. You’ll enjoy five full days ashore before choosing to fly back to Johannesburg or continue on to Leg 2. Leg 2: St Helena to Cape Town (Approx. 3 Weeks) Leg 2 begins with five immersive days on St Helena Island as the new crew settles in, prepares Aurora for the return, and connects with those finishing Leg 1. From there, we head west into deep ocean before turning south toward the remote volcanic archipelago of Tristan da Cunha - one of the world’s most isolated destinations. Expect dynamic weather, powerful seas, and incredible learning opportunities, including celestial navigation and deep-ocean routing. This leg includes over 1,500 nautical miles and qualifies as an RYA mileage trip for aspiring ocean sailors. Full Expedition: 4,500nm | 40 Days Those joining both legs will complete nearly 4,500 nautical miles over 40 days - earning skills, sea time, and unforgettable memories. Whether you’re seeking to develop as an offshore sailor or simply craving a once-in-a-lifetime sailing adventure, this South Atlantic crossing offers the real deal. Wavysail won "Adventure Sailing Operator of 2025" and is rated 4.9 / 5.0 by our crews. Link to more information about this Opportunity. -
Category TypeSkippered/Crewed Charter Vacation,
Sailing Training Adventure,
Mile/Resume Building AdventureBy the CabinStart Location, Stone TownContactsAndrew Cowen,Price
Ph: +44 07570 702256,
email: info@wavysail.com$5595 per person, $7,700 for 2 people sharingLeave the spice-scented lanes of Stone Town behind and point the bow south-west into one of the Indian Ocean's great blue-water passages. Aboard Synergy, our crewed 40ft Fontaine Pajot Lavessi catamaran, this 16-day voyage covers roughly 1,000 nautical miles from the Zanzibar Archipelago to the wild northern coast of Madagascar. It's downwind sailing, remote island anchorages, night passages under a canopy of stars, and some of the least-visited waters on earth. Departing Stone Town, we explore Zanzibar's less-visited northern coast before clearing into open ocean. Trade winds on the beam and a favourable 1–2 knot current make for fast, exhilarating passages. Possible stops along the way include: Pemba Island which is a UNESCO-recognised marine environment with world-class diving in the Pemba Channel, clove plantations, and very few tourists; remote sand-bar anchorages near Fanjove Island, known for nesting green and hawksbill turtles; the volcanic Comoro Islands, with their ancient Swahili medinas and ylang-ylang-covered hillsides; Nosy Iranja, Madagascar — twin islands linked by a white-sand causeway at low tide, with nesting sea turtles and gin-clear water; and Nosy Be, our arrival point, where whale sharks cruise offshore seasonally and fishermen trade fresh lobster from their pirogues. No prior offshore sailing experience is required, but with our experienced Skipper, Paul for guidance this a fantastic combination of hands-on sailing, helming, trimming, night watches and navigation combined with relaxing fishing, reading, and enjoying everthing the Indian Ocean has to share Wavysail is an award winning specialist in off-shore adventure sailing. Provisioning and all safety gear is included. Skipper is an experienced RYA instructor and, although this is not a training passage, it is suitable for mile-building and skills building. All food and drink consumed on board is included in the price. Insurance and any shore based expenses is at your cost. Link to more information about this Opportunity. -
Category TypeSkippered/Crewed Charter Vacation,
Mile/Resume Building AdventureBy the CabinStart LocationMadagascar, Nosy Be, AntsirananaContactsAndrew Cowen,Price
Ph: +44 07570 702256,
email: info@wavysail.com$5595 per person, $7,700 for 2 people sharingSail aboard Synergy, our crewed 40ft Fontaine Pajot Lavessi catamaran, on the final leg of our Indian Ocean adventure—from Nosy Be, Madagascar to Zanzibar. This 1,000-nautical-mile passage is a stunning combination of open-ocean sailing and relaxed coastal cruising. With downwind conditions and favourable east-to-west currents, we make excellent progress south from Nosy Be, pausing at Russian Bay and the breathtaking Nosy Iranja before setting off into the Indian Ocean. If weather and permissions allow, we may venture to the remote and extraordinary Aldabra Atoll, a UNESCO World Heritage Site rarely visited by sailors. We then arc northward, skirting Mayotte and the Comoros, before reaching the East African coast at Mtwara, Tanzania. There, we anchor in sheltered Mikindani, rich with Swahili history and charm. As we head north, we follow the coastline to Zanzibar, avoiding stronger currents and enjoying stunning island stopovers—including Mafia Island, known for its marine biodiversity and pristine reefs. Life onboard Synergy is both adventurous and comfortable. You’ll share the journey with a small group of like-minded travellers and a professional Skipper and First Mate, who manage all navigation, safety, and provisioning. You’ll stay in one of three guest cabins (double or twin layout), each sharing a bathroom per hull. All onboard meals and snacks are included, and we cater for dietary needs with advance notice. Guests cover only shore-based meals, transfers, flights, and any optional excursions. Expect warm conditions, consistent winds, and a variety of sailing—from steady offshore legs to calm, scenic coastal stretches. With ample time to explore hidden anchorages and vibrant islands, this is an epic finale to our Indian Ocean voyage—and a deeply memorable way to return to Zanzibar. Link to more information about this Opportunity. -
Category TypeSkippered/Crewed Charter Vacation,
Mile/Resume Building AdventureBy the CabinStart Location, ObanContactsAndrew Cowen,Price
Ph: +44 07570 702256,
email: info@wavysail.com$8,400 per person, full trip, (35 days), or $3,400 per leg (10 dJoin our unique twist on Scotland's famous "Northcoast 500" as we sail it on our beautiful expedition yacht. The adventure starts in Oban, home of the famous Whisky distillery. We will complete the tour of Scotland in three uniquely different legs and you can join any or all of them. Leg 1 : Oban to Stornoway Leg 2 : Stornoway to Wick Leg 3: Wick to Oban via the Caledonian Canal Each leg is 10 days with a couple of days between legs for crew change-over. For those doing the full tour, you will keep the same berth throughout, with the option of having a cabin to yourself. You'll stay on board for the full month with time in Wick and Stornoway to visit these beautiful Scottish towns. No experience required, but for more experienced sailors, our expert skippers will give you all the support and learning you want! Wavysail won "Adventure Sailing Operator of 2025" and is rated 4.9 / 5.0 by our crews Link to more information about this Opportunity.