Sailing Events and Opportunities by Josh Rundle Sailing Education

  • BVI - Instructional Sailing Challenge - SOLD OUT

    2025, Sun Nov 30 12:00am - Sun Dec 07
    image of BVI - Instructional Sailing Challenge - SOLD OUT
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    SLC/ICC Training and Licensing Assessments,
    Catamaran Endorsement,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    British Virgin Islands, Road Town, Tortola
    Contacts
    Capt Josh Rundle,
    Ph: 717-649-5322,
    email: josh@jrsailinged.com
    Price
    SOLD OUT
    SOLD OUT! Come Join us in BVI March 1 to March 7 or March 7 to March 14! Curious about sailing vacations? Wonder what it takes to do it yourself? Come to the western hemisphere’s greatest cruising grounds, the British Virgin Islands! Over the course of the week, you, your guest and other sailing students will run the boat under the guidance and instruction of our instructional skipper. Each day we will sail to a new location and spend 3-4 hours under sail or maneuvering under power. We will get plenty of practice docking, mooring, anchoring, maneuvering in tight marinas, navigating narrow channels, and much more. What’s the fun of flying to the BVIs of you don’t spend some time exploring the area, both on land and below the water. Our crew are very experienced and knowledgeable about the offerings of each island and will be sure to guide you to the best of the best. Hikes, snorkeling, free diving, SCUBA, beach bars, and restaurants! Each cabin includes your own head and shower. 8 guests, one captain, one first mate. Just one cabin left!. Two persons per cabin. Meals include continental breakfast and light lunches on board. All food and dinners ashore is the responsibility of the individual. Ages 18 and up. Price: $4,500 per cabin, plus $500 (based on dual occupancy) for food and provisions. Provisions include all food on board. All meals ashore are on the individual sailor. All transportation ashore is the responsibility of the individual. Link to more information about this Opportunity.

  • Josh Rundle Sailing Education BVI Flotilla

    2026, Sat Feb 28 5:00pm - Sat Mar 07
    image of Josh Rundle Sailing Education BVI Flotilla
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin Entire Boat
    Start Location
    British Virgin Islands, Road Town, Tortola
    Contacts
    Jessica Green,
    Ph: +1(410) 280-2040,
    email: Jessica@jportinc.com
    Price
    $4,900 per monohull cabin; $5,500 per catamaran cabin
    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 sailor or new to the adventure, our BVI flotilla offers the perfect blend of freedom and support as you explore the Caribbean's most breathtaking islands. What is a Flotilla? A flotilla is a group of sailboats, each independently captained, but sailing together along a pre-planned route. In our case, that means two catamarans, both Fountain Pajot Saona 47, and one monohull, a Benneteau Oceanis 48. Price per monohull cabin: $4,900 + plus provisions share Price per catamaran cabin: $5,500 + plus provisions share When Choose between one of two available 7-day flotillas: 1 March, 2026 - 7 March, 2026 8 March, 2026 - 14 March, 2026 Why Sail the British Virgin Islands? Known for its consistent winds, sheltered harbors, and island-hopping opportunities, the BVI is a sailor's dream. Picture this: secluded beaches, crystal-clear waters, and endless horizons. Every day brings a new adventure, from snorkeling over vibrant coral reefs to hiking through lush island trails, or enjoying the local Caribbean cuisine at a beachside bar. Perfect for All Skill Levels and Interests Whether you're a seasoned sailor or just learning the ropes, our flotilla is tailored for all. For those interested increasing their knowledge and experience, we provide instructional support along the way, while experienced sailors or happy passengers can enjoy the freedom to explore (or relax) at their own pace. Our NauticEd Instructor/Skippers are available to help guide your experience as you learn to operate a large cruising monohull or catamaran while we sail the western hemisphere’s premier cruising destination. Link to more information about this Opportunity.

  • Josh Rundle Sailing Education - BVI Flotilla Week 2

    2026, Sat Mar 07 5:00pm - Sat Mar 14
    image of Josh Rundle Sailing Education - BVI Flotilla Week 2
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin Entire Boat
    Start Location
    British Virgin Islands, Road Town, Tortola
    Contacts
    Jessica Green,
    Ph: +1(410) 280-2040,
    email: Jessica@jportinc.com
    Price
    $4,900 per monohull cabin; $5,500 per catamaran cabin
    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 sailor or new to the adventure, our BVI flotilla offers the perfect blend of freedom and support as you explore the Caribbean's most breathtaking islands. What is a Flotilla? A flotilla is a group of sailboats, each independently captained, but sailing together along a pre-planned route. In our case, that means two catamarans, both Fountain Pajot Saona 47, and one monohull, a Benneteau Oceanis 48. Price per monohull cabin: $4,900 + plus provisions share Price per catamaran cabin: $5,500 + plus provisions share When Choose between one of two available 7-day flotillas: 1 March, 2026 - 7 March, 2026 8 March, 2026 - 14 March, 2026 Why Sail the British Virgin Islands? Known for its consistent winds, sheltered harbors, and island-hopping opportunities, the BVI is a sailor's dream. Picture this: secluded beaches, crystal-clear waters, and endless horizons. Every day brings a new adventure, from snorkeling over vibrant coral reefs to hiking through lush island trails, or enjoying the local Caribbean cuisine at a beachside bar. Perfect for All Skill Levels and Interests Whether you're a seasoned sailor or just learning the ropes, our flotilla is tailored for all. For those interested increasing their knowledge and experience, we provide instructional support along the way, while experienced sailors or happy passengers can enjoy the freedom to explore (or relax) at their own pace. Our NauticEd Instructor/Skippers are available to help guide your experience as you learn to operate a large cruising monohull or catamaran while we sail the western hemisphere’s premier cruising destination. Link to more information about this Opportunity.