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Sailing Events and Opportunities by Wavysail

  • South Atlantic Expedition: Cape Town to St Helena

    2027, Mon Mar 01 10:00am - Thu Apr 22
    image of South Atlantic Expedition: Cape Town to St Helena
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    Start Location
    South Africa, Cape Town, Western Cape
    Contacts
    Andrew Cowen,
    Ph: +44 07570 702256,
    email: info@wavysail.com
    Price
    US$10.500 per person return or USD 8,400 for 1 leg
    Embark 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 | 45 Days Those joining both legs will complete nearly 4,500 nautical miles over 45 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.

  • Tanzania

    2027, Sat Apr 03 1:00pm - Mon Apr 12
    image of Tanzania
    Category Type
    Skippered/Crewed Charter Vacation,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    , Dar Es Salaam
    Contacts
    Andrew Cowen,
    Ph: +44 07570 702256,
    email: info@wavysail.com
    Price
    $4860 USD, per person, or $3820 USD per person for 2 people shar
    Who is Wavysail? Wavysail is an award-winning British adventure sailing company rated 4.9/5.0 by our crews and named Adventure Sailing Operator of 2025. We run small-group offshore expeditions led by world-class skippers, with a maximum of six guests per trip — and on this one, just four. We are not a sail training school, but our skippers are among the most experienced afloat, and many hold RYA Instructor or Examiner qualifications. The Trip Departing and returning to Stone Town, Zanzibar, the Tanzania Explorer is a 10-day sailing adventure through one of the Indian Ocean's least-visited cruising grounds — a 200-nautical-mile island chain that most sailors never find. Aboard Synergy, our 40ft Fontaine Pajot Lavessi catamaran, and with only four guest berths available, this is as close to a private charter as group sailing gets. The islands within reach each offer something distinct. Pemba Island to the north: clove plantations, Ngezi rainforest, and coral walls plunging 300 metres in the Pemba Channel, one of East Africa's most nutrient-rich stretches of water. Mafia Island to the south: a marine park with over 460 fish species, nesting hawksbill and green turtles, and seasonal whale sharks. Beyond that, the Songo Songo Archipelago — a mangrove world of dhow-building villages and near-empty anchorages. The exact route is shaped by wind, conditions, and what the group on board wants — more open-water miles or more time at anchor exploring reefs and fishing villages. What doesn't change: the Pemba Channel, anchorages where fishing is done from traditional ngalawa outriggers, and reefs that have seen almost no dive tourism. Crew and provisioning A professional skipper and first mate manage all navigation, safety, and provisioning. All food and drink consumed on board is included — Wavysail provisions thoroughly for every voyage. Meals ashore and any excursions are at your own cost. What to expect No prior sailing experience is required, but you will be expected to take an active part in the sailing — helming, trimming, and standing watches. This is a hands-on adventure, not a charter where you sit back and watch. For those building NauticEd or RYA logbook miles, our skippers understand certification requirements and will make sure your sea time counts. Link to more information about this Opportunity.

  • Zanzibar to Madagascar

    2027, Thu Apr 15 12:00am - Sat May 01
    image of Zanzibar to Madagascar
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    , Stone Town
    Contacts
    Andrew Cowen,
    Ph: +44 07570 702256,
    email: info@wavysail.com
    Price
    $5595 per person, $7,700 for 2 people sharing
    Leave 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.

  • INDIAN OCEAN: Madagascar to Zanzibar

    2027, Mon May 03 1:00pm - Wed May 19
    image of INDIAN OCEAN: Madagascar to Zanzibar
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    Madagascar, Nosy Be, Antsiranana
    Contacts
    Andrew Cowen,
    Ph: +44 07570 702256,
    email: info@wavysail.com
    Price
    $5595 per person, $7,700 for 2 people sharing
    Sail 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.

  • South Atlantic Expedition: Cape Town to St Helena Island

    2027, Mon May 10 12:00am - Fri Jun 25
    image of South Atlantic Expedition: Cape Town to St Helena Island
    Category Type
    Skippered/Crewed Charter Vacation,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    , Cape Town - Saint Helena Island
    Contacts
    Andrew Cowen,
    Ph: +44 07570 702256,
    email: info@wavysail.com
    Price
    US$10.500 per person full trip, single berth
    Wavysail is an award-winning British adventure sailing company rated 4.9/5.0 by our crews and named Adventure Sailing Operator of 2025. We specialise in small-group offshore expeditions — maximum six guests — led by world-class skippers, most of whom hold RYA Ocean Yachtmaster Examiner or Instructor qualifications. We are not a sail training school, but if you want to sail serious miles under genuinely expert guidance, there is no better environment. The Expedition This is one of the great ocean passages — Cape Town across the South Atlantic to the remote island of St Helena, Napoleon's final exile and one of the most isolated inhabited places on earth. You will cross open ocean, call at Lüderitz on the Namibian coast, and spend several days ashore on St Helena before either flying home or continuing on Leg 2 back to Cape Town via Tristan da Cunha. Leg 1: Cape Town → St Helena | ~3 weeks | ~1,800nm Leg 2: St Helena → Cape Town via Tristan da Cunha | ~3 weeks | ~1,500nm+ Full expedition: ~4,500nm | 45 days For NauticEd sailors working toward RYA Ocean or equivalent qualifications, this passage is ideal. Each leg logs qualifying offshore mileage. Our skippers understand certification requirements inside-out and will ensure you get the most from your sea time — watch-keeping, weather routing, celestial navigation, and passage planning are all part of the experience. What's included — and what isn't You book a berth on a fully equipped expedition yacht with a professional skipper and first mate. All food and drink consumed on board is included — we provision thoroughly for offshore passages. Accommodation ashore on St Helena (self-catering) is included in the voyage cost. Not included: flights, travel insurance, meals ashore, and any optional excursions on St Helena. By the berth. You are joining a small group of up to six guests — singles and couples both welcome. Expect a sociable, committed crew with a shared appetite for proper ocean sailing. Experience required? Some sailing experience is expected — you don't need offshore credentials, but this is not a beginners' trip. If you have completed NauticEd's Skipper or Bareboat Charter Master courses and want to put real miles under your keel in serious conditions, this is exactly where to do it. Link to more information about this Opportunity.

  • Sailing Tour of Scotland

    2027, Sat Jun 19 12:00am - Sat Jul 24
    image of Sailing Tour of Scotland
    Category Type
    Skippered/Crewed Charter Vacation,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    , Largs - Scotland
    Contacts
    Andrew Cowen,
    Ph: +44 07570 702256,
    email: info@wavysail.com
    Price
    $9,600 per person, full trip, (35 days), or $4,100 per leg (10 d
    Join our unique twist on Scotland's famous "Northcoast 500" as we sail it on our beautiful expedition yacht. The adventure starts in Largs, within easy reach of Glasgow. We will complete the tour of Scotland in three uniquely different legs and you can join any or all of them. Leg 1 : Largs to Stornoway Leg 2 : Stornoway to Wick Leg 3: Wick to Largs 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.

  • Croatia Sailing Adventure

    2027, Sat Aug 21 3:00pm - Sat Aug 28
    image of Croatia Sailing Adventure
    Category Type
    Skippered/Crewed Charter Vacation,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    , Split
    Contacts
    Andrew Cowen,
    Ph: +44 07570 702256,
    email: info@wavysail.com
    Price
    USD$3260 per person
    Our 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.