Creating dream holidays in paradise!

If you have never sailed before and would like to learn, or if you would like to take a refresher course to brush up on your past skills, the Rob Swain Sailing School has courses available for all abilities. The courses are suitable for couples, families and singles.

Key features

Sailing School

  • From Beginner to Day Skipper in 7 Days
  • Accredited Training School
  • BVI is the Best Place to Learn to Sail
  • Coastal Passage Making Courses
  • Learn on Monohull or Catamaran


Speak to our specialists, they're ready to discuss and help create your dream experience!

Availability Request Enquiry Form 01279 871188
  • Monday: 14:00 – 17:30
  • Tuesday – Friday: 09:00 – 17:30
  • Weekends & Bank Holidays: Closed


The British Virgin Islands offers the most consistently ideal sailing conditions for learning to sail. Trade winds blow on the norm from ten to twenty knots throughout most of the year. More important than wind speed is the wind direction. The wind blows almost constantly from the east down in the British Virgin Islands. That makes for much easier learning – sailing out of Nanny Cay into the Sir Francis Drake Channel, the wind will be blowing on your left ear as you look ahead. Repetition is the key to learning sailing, and the wind helps here enormously. The Sir Francis Drake Channel is approximately 9 miles long and 4 miles wide. Blocking the Atlantic Ocean is the island of Tortola, and shielding us from the Caribbean Sea swells are eleven other islands. This geography makes for the perfect training ground – a lively 2-3 foot chop and constant trade winds. It is very sunny in the BVI (about 85 degrees), but the winds keep it comfortable.

The Rob Swain Sailing School

The Rob Swain Sailing School offers courses from beginner to advanced.  From people who have no sailing experience whatsoever to experienced sailors who wish to further and enhance their sailing skills.

Fast Track to Bareboating is designed for beginners and those who have had some sailing experience, but no formal training, who enjoy learning at a slightly more accelerated pace.

This 8 day / 7 night course combines the Basic Keelboat and Live Aboard Cruising courses offering the most comprehensive sailing course you will find anywhere. Upon completion of this course, students should have the skills, confidence and certification necessary to skipper their own boat.

The key to learning at a more accelerated pace is training on the correct boat.

Also important are the excellent instructors who know how to teach the fundamentals of sailing and have the years of experience not just sailing, but teaching sailing and can impart their knowledge to their students beyond what the standards require.

Fast Track to Bareboating is comprised of two parts. The Basic Keelboat curriculum is structured to challenge every level of person and rewards each with the objective and subjective know how to command a boat of this size.  You will start with classroom work, then start your practical learning on a specially adapted J24 keelboat. You will stay for 2 nights at Nanny Cay hotel (right on the dockside) while learning this part of the course.

The second component of the course is Live Aboard Cruising and the following five days will be living aboard a 40-46’ yacht learning and mastering the skills that will lead to the Day Skipper qualification. There are more advanced courses for those who wish to further their existing sailing skills.

This portion of the course is designed to instill complete confidence in captaining a bigger sailboat. Bareboating is not necessarily difficult to do.  If you want to do it with comfort and confidence, this is the correct and best course to help you to achieve your goal.

The level of competency that students will achieve in a week on this in-depth and comprehensive course is Day Skipper and the qualification is U.S.S.A. (U.S. Sailing Association) which is equivalent to R.Y.A. (Royal Yachting Association). It’s hard work but lots of fun as well!

This is a fun way to learn to sail in the BVI – an incredibly beautiful location that offers uncrowded anchorages, deserted beaches and amazing snorkelling.

Your experience with Swain Sailing School will be a great learning endeavour, and your trip to Tortola in the British Virgin Islands will be unforgettable!

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    What our clients say...

    Well a big thank you Joyce for organising our holiday in the BVI,it went like clockwork,you certainly know your stuff. Sebastian’s was lovely,food fantastic,entertainment excellent... read more

    Pete and Helen Palmer
    June 2023 Virgin Gorda

    Thanks for providing a very professional bespoke service to us in organising our two-week holiday to the British Virgin Islands. We both enjoy... read more

    Peter and Debbie Jewitt, Cheshire
    April 2023 - Tortola, Yacht Charter & Antigua

    We had a wonderful time. Thank you for all your planning for us. I'll definitely get back to you when we return to Anegada. We absolutely love... read more

    Signe and John Daly, Burlington, Vermont
    April 2023 - Anegada
    Read more Testimonials