Sailing Flotillas

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  • Florida Gulf Coast Flotilla - Key West 2025 - SOLD OUT

    2025, Sat Dec 06 12:00pm - Sat Dec 13
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    Mile/Resume Building Adventure
    By the Cabin
    Operated by Start Location
    USA, Punta Gorda, FL
    Sold out -This 7-day "Mile Builder" passage to the Florida Keys and back will be perfect for anyone looking to log sea miles and build on their resume. 2 Catamarans and 2 Monohulls, 2 Instructors will guide you through an overnight sailing adventure... Learn more
  • Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Operated by Start Location
    Grenada, Port Louis Marina, Saint George's
    SORRY THIS IS SOLD OUT. BUT STAND BY MORE COMING. Ready to elevate your sailing skills? Join our exclusive women-only instructional sailing program from January 16-23, 2026, exploring the stunning Windward Islands of Grenada and St. Vincent and the Grenadines... Learn more
  • Sea of Cortez Flotilla 2026 February 7-14 - Sold Out -

    2026, Sat Feb 07 5:00pm - Sat Feb 14
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla
    By the Cabin Entire Boat
    Operated by Start Location
    Mexico, La Paz, Baja California Sur
    Join us on the amazing Sea of Cortez for a week in the Espiritu Santo Archipelago. Departing from La Paz, Baja California Sur, MX, every day includes sailing, exploring ashore, snorkeling and kayaking. Experience the best coves in one of the most sough... Learn more
  • Grenadines Flotilla with Satori Sailing

    2026, Sat Feb 14 8:00am - Sat Feb 21
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    Catamaran Endorsement,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Operated by Start Location
    Grenada, Grenadines, Saint George's
    Join Satori Sailing for an unforgettable sailing vacations in the Grenadines, the hidden jewel of the Caribbean!. Sail aboard a 45 foot catamaran with one of Satori Sailing's experienced captain/ instructors. You will enjoy your own cabin to be take... Learn more
  • Josh Rundle Sailing Education BVI Flotilla

    2026, Sat Feb 28 5:00pm - Sat Mar 07
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin Entire Boat
    Operated by Start Location
    British Virgin Islands, Road Town, Tortola
    Discover Paradise: Join Our British Virgin Islands Flotilla Adventure! Set Sail in a Tropical Paradise Escape to the stunning turquoise waters of the British Virgin Islands (BVI) with our expertly guided flotilla! Whether you're an experienced sailo... Learn more
  • Josh Rundle Sailing Education - BVI Flotilla Week 2

    2026, Sat Mar 07 5:00pm - Sat Mar 14
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin Entire Boat
    Operated by Start Location
    British Virgin Islands, Road Town, Tortola
    Discover Paradise: Join Our British Virgin Islands Flotilla Adventure! Set Sail in a Tropical Paradise Escape to the stunning turquoise waters of the British Virgin Islands (BVI) with our expertly guided flotilla! Whether you're an experienced sailo... Learn more
  • Croatia Flotilla 2026

    2026, Sat Jun 06 5:00pm - Sat Jun 13
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla
    By the Cabin Entire Boat
    Operated by Start Location
    Croatia (Hrvatska), Split/Trogir, Split-Dalmacija
    Contacts
    Lauren Zykorie,
    Ph: +1 512 696-1070 ext 2,
    email: lauren@nauticed.org
    Price
    from €5600
    Join NauticEd for an unforgettable adventure sailing Croatia’s stunning Dalmatia Coast. Having sailed Croatia more than a handful of times, NauticEd can officially confirm why it is a top Mediterranean destination for good reason. Sailing Croatia is about adventure and freedom, history and modernity. Learn more
  • Greece Ionians Jun 2026

    2026, Sat Jun 13 5:00pm - Sat Jun 20
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla
    By the Cabin Entire Boat
    Operated by Start Location
    Greece, Lefkas, Ioannina
    Contacts
    Emily Leach,
    Ph: +1 512-696-1070,
    email: emily@nauticed.org
    Price
    from €5500
    The Ionian Islands of Greece are a dreamscape for sailors: steady winds, calm seas, and charming harbors tucked into lush green shores. Add in the warmth of Greek hospitality, and you’ve got a sailing vacation that feels less like a trip and more like a reset. Learn more
  • BVI Flotilla June 2026

    2026, Sun Jun 14 6:00pm - Sun Jun 21
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    Sailing Training Adventure
    By the Cabin Entire Boat
    Operated by Start Location
    British Virgin Islands, Road Town, Tortola
    Explore the stunning British Virgin Islands with us on a unique and adventurous flotilla journey! This flotilla offers an incredible opportunity to discover the BVI’s hidden gems and off-the-beaten-path destinations that most charters miss. We’l... Learn more
  • Sporades Islands Greece Sailing Flotilla - SOLD OUT

    2026, Sat Sep 12 5:00pm - Sat Sep 19
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Operated by Start Location
    Greece, Skiathos, Magnisia
    Contacts
    Lauren Zykorie,
    Ph: 512-696-1070 ext 2-1,
    email: lauren@nauticed.org
    Price
    Various see linked site
    Our NauticEd Sporades Flotilla—fondly nicknamed the “Mamma Mia Tour”—is led by NauticEd instructor and Greek local, Nick Koufidis, who knows these islands like the back of his hand. Over the course of a week, you’ll sail from lively Skiathos to picturesque Skopelos and unspoiled Alonissos, dropping anchor in secluded bays, dining in charming waterfront tavernas, and visiting iconic Mamma Mia film locations. It’s the perfect blend of authentic Greek island life, crystal-clear Aegean waters, and the easy camaraderie of a small-group sailing adventure. We have several by-the-cabin reservations available. The Private Charter boats are sold out. Learn more