Sailing Training Adventures

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  • Sober Sailing series

    2026, Wed Jul 29 4:00pm - Wed Oct 28
    Category Type
    Practical Training/Assessment Event,
    Local On-The-Water Sailing Meetup,
    Skippered/Crewed Charter Vacation,
    SLC/ICC Training and Licensing Assessments,
    Sailing Training Adventure
    Entire Boat
    Operated by Start Location
    , santa cruz
    Every weds an onboard AA meeting at 4pm and community sail at 5... Learn more
  • The Grenadines - Caribbean Christmas

    2026, Sun Dec 20 12:00am - Sat Jan 02
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Operated by Start Location
    , Prickly Bay
    Escape the winter on this hands-on sailing adventure through the Windward Islands, timed perfectly for Christmas and New Year. We set sail from Grenada into the warmth of the Caribbean trade winds, island-hopping through the Grenadines as the year turns. As... Learn more
  • Uphill to Brazil 2200 NM - Blue Water Ocean Passage

    2027, Wed Jan 06 8:00am - Sat Oct 24
    Category Type
    Practical Training/Assessment Event,
    Specialized Endorsement Training,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Operated by Start Location
    , Le Marin, Martinique
    This trip is a very tough passage from Caribbean to Brazil and is for experienced sailors that are ready to take the step to blue water passage making. We will be setting out from the Caribbean Sea towards Brazil on a demanding and relatively uncommo... Learn more
  • 2027 Sea of Cortez Flotilla

    2027, Sat Feb 06 12:00pm - Sat Feb 13
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    Sailing Training Adventure
    By the Cabin Entire Boat
    Operated by Start Location
    , La Paz
    SOLD OUT - You may have heard about or seen pictures of the dramatic Sea of Cortez, north of La Paz. It’s still my favorite place to sail and explore, and I’d like to share the experience with you. This is our 12th year running sailing trips in th... Learn more
  • Bay of All Saints - Cruising Brazil

    2027, Sun Feb 28 9:00am - Sat Mar 06
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Operated by Start Location
    , Salvador, Brazil
    On this sail training adventure we explore “Baia de Todos los Santos, which is Brazil’s largest bay and a great cruising area. On the Eastern shore is the city of Salvador, the capital of Bahia State, with its many restored colonial buildings an... Learn more
  • Bay of All Saints - Cruising Brazil

    2027, Sun Feb 28 9:00am - Sat Mar 06
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Sailing Training Adventure
    By the Cabin
    Operated by Start Location
    , Salvador, Brazil
    On this sail training adventure we explore “Baia de Todos los Santos, which is Brazil’s largest bay and a great cruising area. On the Eastern shore is the city of Salvador, the capital of Bahia State, with its many restored colonial buildings an... Learn more
  • South Atlantic Expedition: Cape Town to St Helena

    2027, Mon Mar 01 10:00am - Thu Apr 22
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    Operated by Start Location
    South Africa, Cape Town, Western Cape
    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 firs... Learn more
  • Zanzibar to Madagascar

    2027, Thu Apr 15 12:00am - Sat May 01
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Operated by Start Location
    , Stone Town
    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 nautica... Learn more
  • INDIAN OCEAN: Madagascar to Zanzibar

    2027, Mon May 03 1:00pm - Wed May 19
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Operated by Start Location
    Madagascar, Nosy Be, Antsiranana
    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 relaxe... Learn more