Hands-On Sailing Instruction aboard a Chartered Sailing Vacation
Learn by Living the Dream – Captained Instructional Charters and Sailing Vacations
Whether you’re looking to grow your skills, earn certifications, or simply gain confidence at the helm, Capt. Josh will guide you every step of the way — all aboard a fully-arranged charter yacht vacation. Capt. Josh will take care of the planning so you can focus on what matters most: sailing, learning, having fun, and making memories that last a lifetime.
Or if you’d like your own Bareboat Charter, then Capt. Josh can help you arrange your perfect sailing vacation.
Upcoming Instructional Charters
British Virgin Islands Nov 30 – Dec 07, 2025 | Cabins are Available!
Turn your sailing dream into an extraordinary learning experience. Join Capt. Josh in the British Virgin Islands for a private sailing charter where you’ll gain hands-on skills, real-world sailing experience, and unforgettable memories in one of the world’s best cruising grounds. Perfect for anyone who wants to learn and gain charter experience, build skills, and have a great time exploring the BVI.
Ionian Islands, Greece Sept 13 – 20, 2025 | Fully Booked
Join Capt. Josh for an unforgettable instructional sailing adventure through Greece’s Ionian Islands, September 13–20. Starting in Preveza aboard a spacious Lagoon 42 catamaran, you’ll gain hands-on sailing skills, explore charming coastal towns, and build real-world confidence chartering—all while enjoying the beauty and culture of the Greek islands.
– Fully Booked, No Availability –
Why do an Instructional Charter?
People choose a captained charter with instruction for a variety of reasons – everyone has different goals, and the advantage of a Capt. Josh’s private instruction aboard a charter means lessons can be tailored to your pace, goals, and experience level. Whether you’re training or just having fun, it’s all about you.
- Learning while on vacation: It’s the best of both worlds – a sailing vacation and a learning experience. Partners or families can enjoy the charter while one or more guests train.
- Build confidence with a real-world charter experience: Some sailors are just starting out and want to try chartering, while others are “rusty” with skills and/or not confident chartering in unfamiliar waters.
- Gain Bareboat certifications and International Licensing: As a top-rated NauticEd instructor, Capt. Josh can certify and license qualified candidates on a full range of certifications, depending on your goals – from crew to bareboat charter to international SLC licensing. Additionally, and depending on the nature of the charter, Capt. Josh can endorse students for Catamarans, near-coastal sailing, navigation, and more! *Note: speak with Capt. Josh about the different pathways to certification and licensing.
Contact Capt. Josh to discuss whether a Captained Charter is right for you.
Personalized Sailing Vacations
Book your Charter and Sailing Vacation through us
Capt. Josh has aligned with NauticEd Sailing Vacations agency to bring you the best when it comes to chartering and adventuring on the water anywhere on the globe. The NauticEd Sailing Vacations team has vast experience with all destinations and yacht charter companies. They know the good ones and the not so good. You don’t pay a fee for this service – yet you get great advice and a professional booking service.
Even if you’re not feeling “skipperish” yet, you can ask Capt. Josh to captain your charter or NauticEd can hire you a captain.
Join an organized Sailing Flotilla
Throughout the year, NauticEd runs organized skippered charters in tropical and exotic places such as the BVI or Greece. Come join the fun with us – either by the cabin on a skippered boat or skipper your own chartered boat as we explore and adventure as a Flotilla group. This is a great opportunity to explore sailing destinations within a group of like-minded sailors, friends, and family.
Contact us to get started
Contact Capt. Josh Rundle to schedule training, certification, and licensing, or charter and sailing vacations. Certainly feel welcome to contact Capt. Rundle with any questions on achieving your sailing goals.