Sailing Events and Opportunities by Josh Rundle Sailing Education

  • 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.

  • Turkish Riviera Instructional Charter

    2026, Sat Sep 05 5:00pm - Sat Sep 12
    image of Turkish Riviera Instructional Charter
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    , Marmaris to Fethiye
    Contacts
    Josh Rundle,
    Ph: 717-649-5322,
    email: josh@jrsailinged.com
    Price
    $5,000 per cabin plus provisions.
    Have you ever dreamed of cruising the Mediterranean? Wonder what it takes to do it yourself? Intimidated by med-mooring? Come join us as we cruise the Turkish Riviera, also known as the Turquoise Coast. Over the course of the week, you, your guest, and other sailing students will run the boat under the guidance and instruction of Capt. Josh Rundle as we explore the islands and coves from Marmaris to Fethiye. 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, Med-mooring, anchoring, maneuvering in tight marinas, navigating narrow channels, and much more. What’s the fun of flying to the literal crossroads of civilization if you don’t spend some time exploring the area, both on land and below the water. Throughout the week we will be sure to highlight options to take in the best sights, sounds, restaurants, and historical landmarks. All levels of sailors are welcome to join! Instructional Charters are perfect for those just starting out and taking a first step towards bareboat, bareboat qualified students uncomfortable with their “first charter”, experienced sailors wanting to have fun while brushing up on skills, and really anyone wanting to learn and actively participate while on a sailing vacation. Your guests and friends are also welcome! This is ‘experiential’ training that blends private instruction with a real-world charter and sailing vacation. Simply, this is vacation + instruction + having fun. This is not an intensive certification or licensing course! We’re going to work instruction into much of what we do, but our goal is to have fun doing it! Your guest (partner, friend, etc…) can participate or just enjoy the ride. We prefer that your guest is an active participant; that’s part of the fun! Certification, SLC Licensing, and endorsements may be available. It really depends on your prior experience, coursework, and training – contact Josh to discuss further. Pricing is by the cabin, whether single or dual occupancy (each cabin is big enough for 2 people). $5,000 per cabin. $500 for provisions (based on dual occupancy). Provisions include all the food and water on board. Each cabin includes its own head and shower. 8 guests, one captain, one first mate. Two people per cabin. Meals include continental breakfast and light lunches. Dinners ashore are the responsibility of the individual, not included in berth or provisions cost. All transportation to-from Turkey and ashore is the responsibility of the individual. Individual extracurricular activities may incur additional costs. Note – that’s something that we can discuss and plan ahead for! Link to more information about this Opportunity.