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Sailing Events and Opportunities by Wavysail

  • South Atlantic Expedition: Cape Town to St Helena

    2026, Mon Mar 02 10:00am - Sun Apr 12
    image of South Atlantic Expedition: Cape Town to St Helena
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    South Africa, Cape Town, Western Cape
    Contacts
    Heather Deary,
    Ph: +44 7753454988,
    email: heather@wavysail.com
    Price
    US$9,610.43 per person
    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 bed and breakfast accommodation included in the voyage cost. Leg 1: Cape Town to St Helena (Approx. 4 Weeks) Your journey begins in Cape Town with “Prep Week” 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 via Tristan Da Cunha (Approx. 5 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 | 48 Days Those joining both legs will complete nearly 4,500 nautical miles over 48 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.

  • INDIAN OCEAN: Zanzibar to Seychelles

    2026, Sat Apr 04 1:00pm - Mon Apr 13
    image of INDIAN OCEAN: Zanzibar to Seychelles
    Category Type
    Skippered/Crewed Charter Vacation,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    Tanzania, Stone Town, Zanzibar and Pemba
    Contacts
    Heather Deary,
    Ph: +44 7753454988,
    email: heather@wavysail.com
    Price
    $4114.83
    Join us for an unforgettable Indian Ocean adventure, aboard Synergy, our comfortable and well-equipped 40ft Fontaine Pajot catamaran. This is a crewed trip, with a highly experienced Skipper and First Mate on board to ensure your safety, comfort, and enjoyment. You’ll share this voyage with a small group of like-minded adventurers—perfect for solo travellers, couples, or friends. The journey begins in Stone Town, Zanzibar, and ends in Victoria, Seychelles, covering over 900 nautical miles of ocean sailing. The first few days are relaxed, exploring local anchorages and islands (including the famous Prison Island tortoises), before we set off on a full open-ocean passage with night sailing, watch systems, and opportunities for hands-on sailing experience. No prior offshore experience is required, but you’re welcome to get involved and learn as much as you like—this is a great chance to build confidence and skills under guidance. All onboard provisioning is included: fresh, hearty meals prepared by the crew, snacks, drinks, and plenty of water. We cater for most dietary requirements with advance notice. You’ll just need to cover any meals or drinks ashore, plus optional extras like transfers, flights, visas, and insurance (as applicable). The boat is fitted with snorkelling kit, and a tender for exploring remote anchorages. Synergy has 3 spacious guest cabins (double or twin layout), each sharing a bathroom per hull. Bedding is provided and comfort is prioritised. This is a true passage-making adventure: warm water, starlit skies, and the rewarding rhythm of life at sea. Spaces are limited, so book your cabin early to secure your place. Wavysail won "Adventure Sailing Operator of 2025" and is rated 4.9 / 5.0 by our crews Link to more information about this Opportunity.

  • INDIAN OCEAN: Seychelles to Madagascar

    2026, Tue Apr 14 1:00pm - Thu Apr 23
    image of INDIAN OCEAN: Seychelles to Madagascar
    Category Type
    Skippered/Crewed Charter Vacation,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    Seychelles, Victoria, Victoria
    Contacts
    Heather Deary,
    Ph: +44 7753454988,
    email: heather@wavysail.com
    Price
    $4114.83
    Sail with us aboard Synergy, our fully crewed 40ft Fontaine Pajot Lavessi catamaran, as we journey from Victoria, Mahé Seychelles to Nosy Be, Madagascar—a stunning 600-nautical-mile passage through some of the Indian Ocean’s most remote and rewarding waters. This crewed expedition includes a professional Skipper and First Mate, offering a hands-on sailing experience for those keen to learn, while being fully supported for those with no prior experience. Expect mostly downwind conditions, with steady breezes and a calmer sea state—especially once we reach the sheltered waters along Madagascar’s northern coast. Where permissions allow, we’ll stop at unspoilt islands like Desroches and the Farquhar Atolls, rich with marine life and perfect for snorkelling. As we approach Madagascar, the landscape transforms into lush islands, tranquil anchorages, and shallow turquoise bays. We make landfall in Hell-Ville, Nosy Be, where vibrant Malagasy culture meets relaxed beachside living. Many guests choose to extend their stay here to explore more of this extraordinary island. You’ll stay in one of three spacious guest cabins (double or twin layout), with shared bathroom facilities per hull. All onboard meals, snacks, and soft drinks are included, and we cater to most dietary requirements with notice. You’ll just need to cover any meals ashore, as well as optional extras like flights, visas, and transfers. A sturdy tender provides easy access to shore and hidden anchorages. This leg combines true offshore sailing with unforgettable island charm—ideal for anyone looking to experience life at sea in comfort and in great company. Link to more information about this Opportunity.

  • INDIAN OCEAN: Madagascar to Zanzibar

    2026, Fri Apr 24 1:00pm - Sun May 03
    image of INDIAN OCEAN: Madagascar to Zanzibar
    Category Type
    Skippered/Crewed Charter Vacation,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    Madagascar, Nosy Be, Antsiranana
    Contacts
    Heather Deary,
    Ph: +44 7753454988,
    email: heather@wavysail.com
    Price
    $4114.83
    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 1,800-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.

  • Sailing Tour of Scotland

    2026, Sat Jun 20 12:00am - Fri Jul 24
    image of Sailing Tour of Scotland
    Category Type
    Skippered/Crewed Charter Vacation,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    , Oban
    Contacts
    Andrew Cowen,
    Ph: +44 07570 702256,
    email: info@wavysail.com
    Price
    8800
    Join our unique twist on Scotland's famous "Northcoast 500" as we sail it on Big Blue, 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.