About us
U Sail Bermuda, a limited liability company (non-profit) has been founded by Charles & Maja Penruddocke. It is a sailing centre with the aim of making sailing, windsurfing, foiling, winging and stand up paddling available on Castle Harbour and Harrington Sound with a specific aim on the ages over 16. We are an accredited Royal Yachting Association training centre. We offer scheduled courses on weeks and weekends, rentals, on demand tasters and private tuition and instructor training. We have expanded with opening a second centre, U Sail Castle Harbour in partnership with Rosewood Tuckers Point Watercentre. You can find out more under the centres page.
Our Team
We pride ourselves as a family-run sailing centre to provide top-quality tuition and equipment to all our customers. We regularly conduct in-house staff training and personal instructor on water development time.
Charles Penruddocke
Owner, PR and Strategy
Charles Penruddocke
Owner, PR and Strategy
Charles Penruddocke started sailing at the age of 11 on a GP 14 in Wales. Since then he has always had a love of sailing boats of all sizes. It was therefore a no brainer, after retiring from the world of Reinsurance to set up and run a sailing, foiling and watersports centre, always readily accessible to anyone at a reasonable price. "How fortunate I am to have a great family of passionate sailors to make the dream a reality. Thank you, Maja, Thomas and Adriana."Qualifications:
Certificate of SCARS (Saving children and revealing secrets)RYA Powerboat Level 2RYA First Aid/CPR/AED training certificateRYA Powerboat Instructor 
Maja Penruddocke
Chief Finance Director/ Centre Welfare Officer
MAJA PENRUDDOCKE
Finance Director/Centre Welfare Officer
On May 29th, 2017 with the goal making sailing, windsurfing, foiling and stand up paddling available on demand, Maja, with her husband, Charles, started U Sail, as the Director of Finance and Welfare Officer. Maja gained her sailing experience on Lake Constance in Switzerland where she used to race in the “Drachen” keelboat and later sailing dinghies when her two kids started sailing. Maja brings a wealth of organizational and communication skills to the team.Qualifications:
Certificate of SCARS (Saving children and revealing secrets)RYA Safe and Fun - Safeguarding awarenessRYA First Aid/CPR/AED training certificateRYA Powerboat Level 2 RYA Welfare Officer course
Thomas Penruddocke
Operations Director & Chief Instructor
THOMAS PENRUDDOCKE
Operations Director & Chief Instructor
Thomas started to grow the business in March 2019 as activities director/office manager, having worked in the watersports industry for just over 5 years. He is working to drive the centre forward in all directions including a focus on marketing and sales. Working closely with the Director team and Chief Instructor, he is coordinating the on land administration inline with the on water policy creations. Thomas is very passionate about the watersports industry, previously working in RYA training clubs and centres overseas and in Bermuda. In 2018, he was involved in the pilot launch for the RYA Sail Foil Endorsement as one of the first 8 trained instructors.
Qualifications:RYA Senior Dinghy InstructorUK 3 Day Advanced First Aid at Work/CPR/AED training certificateRYA Safe and Fun - Safeguarding awarenessRYA Intermediate Non-planing Windsurf InstructorRYA Performance Flight Sail Foiling InstructorRYA Powerboat InstructorRYA First Aid InstructorRYA VHF Short Range Instructor / Assessor Race Coach
Adriana Penruddocke
Data Reporting, Analysis and Protection and Instructor
ADRIANA PNRUDDOCKE
Data Reporting, Analysis and Protection and Instructor
Adriana grew up sailing having competed in the Optimist at a young age. This included 1 Worlds and North American championships. As she progressed through her sailing career, she is now a current Laser Radial sailor with x2 Bermuda Laser National Champion and several World and European championships under her belt with plenty of racing experience to pass onto others. Adriana enjoys teaching others to learn to sail and bringing them to the world of sailing. She is currently spending most of her time campaigning for Paris 2024.
Qualifications:RYA Dinghy InstructorRYA First Aid/CPR/AED training certificateRYA Powerboat Level 2RYA VHF Short Range CertificationRYA Advanced Instructor EndorsementRYA Safe and Fun - Safeguarding awarenessRYA Start Windsurfing InstructorLaser Coach with experienced laser racing
Jade Smith
Multi Qualified Dinghy,Windsurf, Wing-Foil & Powerboating Instructor
Jade Smith
Dual Qualified Dinghy & Windsurf Instructor
Jade first joined U Sail Watersports as a Bermudian apprentice in September 2021 after completing his RYA Start Windsurf instructor course. Between his final year at school in Bermuda, he gained experience in the role of a windsurfing instructor at U Sail Castle Harbour centre under experienced instructors. In June 2022, he joined the team as a full-time instructor. He is also a keen sailor and across the last few months in leading up to graduating from high school had been trained up to upskill to his dinghy instructor in late June. Jade always puts his best effort forward when it comes to teaching on the water or recommending your choice of equipment. When its windy, you'll see Jade out on some windsurf kit, blasting across the water. Jade also participated in the Winging and Wing Foiling instructor course in May 2022 and is at the forefront of Bermuda's first qualified RYA Wing Foiling Instructor.
Qualifications:RYA Intermediate Planing Windsurf InstructorRYA First Aid/CPR/AED training certificateRYA Powerboat Level 2RYA Dinghy InstructorRYA Wing-surf & Wing- foiling InstructorRYA Safe and Fun - Safeguarding awareness
RYA Windfoil Endorsement
Josiah Wilson
Sales and Marketing Coordinator | Lead Senior Instructor, Multi Qualified Dinghy & Windsurf & Winging Instructor
Josiah Wilson
Sales and Marketing Coordinator | Senior Multi Qualified Dinghy & Windsurf & Winging Instructor
Josiah first joined the U Sail Watersports team at U Sail Castle Harbour in 2022 for the peak summer season after completing his A-Levels. He returned for multiple seasons, and in 2024, he took on the role of Lead Senior Instructor, running the center for the season.
Now in 2025, Josiah has transitioned to Sales & Marketing Coordinator, focusing on brand promotion, marketing, and liaising with schools to organize watersports trips. Alongside his management experience, he remains a highly qualified instructor, certified in dinghy sailing, multihull, sail foiling, intermediate planing windsurfing, windsurf foiling, and wing foiling instruction. While he’s shifted roles, you’ll still find him on the water whenever possible, continuing to share his passion for the sport.
Qualifications:
RYA Dinghy Instructor
RYA Senior Instructor
RYA First Aid/CPR/AED training certificateRYA Powerboat Level 2RYA Safe and Fun Safeguarding awarenessRYA Sail Foil Endorsement
RYA Multihull Endorsement
RYA Wing-Surf & Wing-Foil Instructor
RYA Intermediate Planing Windsurfing Instructor
RYA Wind Foil Endorsement
Eva Miller
Dual qualified Dinghy & Intermediate Non-Planing Windsurf Instructor
Eva Miller
Dual Qualified Dinghy & Windsurf Instructor
Eva Miller joined the U Sail Watersports 2023 summer season team in June and is here until September. She is currently studying a Chichester University where she has just completed second year in sports science and psychology. She is an excellent instructor in both dinghy sailing and has recently completed her start windsurf instructor before coming to join us on the sunny shores of Bermuda. She definitely loves to progress students into the Laser (ILCA) and is a keen sailor herself in the Laser class and enjoys to race as well. When it is windy in 20 knots +, you’ll find her out planning on some windsurfing kit.
Qualifications:RYA Dinghy Instructor
RYA Start Windsurf Instructor
RYA First Aid/CPR/AED training certificateRYA Powerboat Level 2RYA Safe and Fun Safeguarding awareness
Intermediate Non-Planing Windsurf Instructor
Charlotte Rudd
Senior Dual Qualified Instructor
Charlotte Rudd
Dinghy Instructor
Charlotte joins us on the U Sail Watersports team in June until September for the 2024 season. She is currently studying at Cambridge University. She has a few seasons of teaching in a variety of boats and different locations before joining us here on the shores of Bermuda. Before joining us, alongside 2 other U Sail instructors, she completed her RYA Senior Instructor, Start Windsurf and Powerboat Instructor course to upskill and be able to promote safe power boating. Charlotte is taking her sail foiling to the next level in the Waszp with some sustaining flights across the wind. If conditions are too much for Waszp foiling, then you can find Charlotte on an intermediate 151 Go board sending it across the wind to get planning and work towards that front foot strap.
Qualifications:
RYA Senior Instructor
RYA Dinghy Instructor
RYA Powerboat Instructor
RYA Start Windsurf Instructor
RYA First Aid/CPR/AED training certificateRYA Powerboat Level 2RYA Safe and Fun Safeguarding awareness
Matthew Hulst
Windsurf Instructor
Matthew Hulst
Qualified Start Windsurf Instructor
Matthew joins us for the summer 2023 as his first summer as a start windsurf instructor. Matthew started to windsurf with us back in August 2020 and has since been a regular windsurfer to the centre ever since. He successfully completed his RYA Start windsurf instructor last December 2023 and now he has been inspiring the next generation of future windsurfers to take windsurfing to hopefully where he is one day. When it’s windy in 20 knots +, you will find Matthew out on a Fox 105 board enjoying the water. Let’s not forgot those home made delicious cookies!
Qualifications:RYA Start Windsurf Instructor
RYA First Aid/CPR/AED training certificateRYA Powerboat Level 2RYA Safe and Fun Safeguarding awareness
Ruth Mello-Cann
Dinghy Instructor
Ruth Mello-Cann
Dinghy Instructor
Ruth first joined the U Sail team in March 2022 after becoming a newly qualified RYA Dinghy Instructor. She is an optimistic instructor who makes sure all of her students leave with a memorable experience. She loves working with youth and adults alike, enjoying the challenge of teaching different age groups. After working a full summer season in 2022, she went off to university to study Environmental Science and Sustainability and now works back at U Sail during school breaks and summer holidays. While working at U Sail as a Dinghy Instructor, she is working towards getting her RYA Wing-surf Instructor Qualification. Ruth also participated in the Winging and Wing Foiling instructor course in May 2022 and is at the forefront of RYA Winging in Bermuda.
Qualifications:RYA Dinghy InstructorRYA First Aid/CPR/AED training certificateRYA Powerboat Level 2RYA Safe and Fun - Safeguarding awareness
How to find us
Travelling from the east of the island, you go along Harrington Sound road until you get to the junction of paynters road where you take a left turn. Follow Paynters road until you get to two limestone pillars indicating Tuckers Point. If you are travelling from west (south shore road), take the left turn on to Paynters road and make a right turn by the limestone pillars. After this, keep travelling straight until you get a sign on your right for 'additional parking'.
All parents must park here as no cars are allowed except staff cars are allowed to drive down the hill to the watersports centre. Continue by foot to the Rosewood Watersports centre and find a U Sail Castle harbour team member.
