Meet the BOSS Cruising Instructor Team

Barefoot Yacht Charters and BOSS are owned and run by sailors, one of whom is a former America’s Cup yachtsman whose family has lived here in St Vincent & The Grenadines for many generations.

Our team, some of whom have been with us for many years, are not only certified American Sailing Association  and/or Sail Canada Instructors and Instructor Evaluators,  but also people who know the islands intimately and are able to get along with folks of all ages and from all walks of life.  Several of our instructors have been recognized multiple times as ASA top 32 “outstanding instructors”.  Others are innovators and leaders in nautical education.

Rob McLean

Rob McLean

BOSS Lead Instructor / Coordinator (ASA and Sail Canada)

Rob McLean started sailing at the age of 4 and has 6 decades of sailing and boating experience. Since 1982 he has accumulated more than 20,000 miles of cruising experience on the Great Lakes, the Pacific and Atlantic coasts of North America, the Caribbean, and the Gulf of Mexico. He is certified as an Offshore Cruising and Celestial instructor and is a Sail Canada Senior Instructor Evaluator.

While his professional career continues, Rob enjoys spending a month or two each year transmitting his passion for sailing to others. He combines expertise in modern marine electronics with a love of classic rigs and traditional techniques. His approach to instruction puts a priority on safety and learning proper manoeuvres, combined with calm patience as students acquire new skills, while keeping the learning process light-hearted, since sailing is as much about having fun as mastery of nautical competencies. He subscribes to the Arabic proverb that a day spent sailing is not counted against one’s allotted lifespan! There is no better place to experience this than SVG.

Rob is certified as a monohull and catamaran Sail Canada and ASA Cruising and Coastal Navigation instructor, as a Sail Canada power boating instructor, and examines candidates for the Canadian Pleasure Craft Operator Card and Maritime radio certification. As a Sail Canada Instructor Evaluator he participates in training new instructors, and contributes to the ongoing development of the Sail Canada system as a member of various working groups and committees. In collaboration with Phil Morris of Wavelength Sailing of Kingston Ontario, Rob co-founded, which is Canada’s leading online platform for nautical education, offering online navigation, ashore knowledge, and maritime radio courses.

Full sailing resume is available at

Jimmy Slater

Jimmy Slater

ASA Instructor | TOP 32 ASA INSTRUCTOR, 2017 & 2018

I was born in Guyana and after working in the diamond and mineral mining industry there, came to live in St Vincent and the Grenadines 20 years ago – and in these beautiful cruising grounds, I’ve been able to spend time living my passion for sailing.

After many years skippering charter yachts of many sizes for different companies here, I decided to hook up with B.O.S.S. which is the most prominent sailing school in this region, and, after passing my ASA Instructor qualifications, I became a full-time Instructor with them.

Other than sailing, I love music and art – I paint, tattoo and create local artworks by hand.

Phillip Morris

Phillip Morris

ASA | Sail Canada Instructor

I learned to Sail in England and have been sailing on and off most of my life. When I came to Kingston over 25 years ago I began sailing regularly, originally in a DS 17 then an O’Day 25 and over the past 12 years in a CS 30 “Wavelength”. Although I considered myself an experienced sailor I took the CYA Basic Intermediate and Advanced cruising courses and through them gained a lot more experience and confidence in my sailing abilities. I corrected a few bad habits that I had acquired too!

I have always enjoyed teaching, so I decided to pass on my passion of sailing to others by becoming an Instructor in 2001. I am an NCCP Coach and a registered Sail Canada Instructor for PCOC, Basic, Intermediate and Advanced Cruising, Coastal Navigation and Maritime Radio Certificate.

I am also an IYT instructor certified to certify students to International Certificate of Competency (ICC) and International Bare boat Skipper. In 2017, following the partnership with Barefoot Offshore Sailing School in St. Vincent and the Grenadines, I certified as an American Sailing Association ASA Instructor for 101, 103, 104, 105 and 114 (Catamaran).

In 2010 I completed certification as a Sail Canada Senior Cruising Instructor Evaluator able to certify instructors to Advanced level and I regularly enjoy conducting instructor clinics.

I am also a member of the Canadian Power & Sail Squadron and have successfully completed a number of advanced courses including the Instructor course, Weather and Advanced Piloting Junior Navigation and Global Navigation (Offshore) courses. I volunteer as an Instructor for Power Squadron courses including Seamanship Sail. I have been on the executive for many years for Collins Bay Yacht Club.

In addition to helping develop, Canada’s leading platform for online nautical education, I teach around 11 live aboard courses annually and have taught over 180 courses and instructor clinics to more than 500 students in boats up to 50’on the waters of Lake Ontario, Lake Huron and in the Caribbean. I look forward to seeing you on the water and hope I can pass on my passion for sailing!

Sail Canada (CYA) Instructor #18564

Joel Taylor

Joel Taylor

ASA and Sail Canada Instructor | TOP 32 ASA INSTRUCTOR, 2019 & 2020

As a lifelong sailor, there’s nothing I love more than being out on the water. Teaching sailing is wonderful because I get to introduce so many people to not just a sport but a way of life. I’ve even been fortunate to work with people with disabilities and encourage many people who didn’t think they could sail to learn new skills and share my passion for sailing. Sailing is for everyone and I love to help those who think they can’t participate in the sport to discover the freedom of being on the water.

Starting as both a dinghy and cruising instructor with Sail Canada, I‘ve gone on to acquire teaching qualifications as well with the Royal Yachting Association and the American Sailing Association as a cruising instructor. I achieved my RYA Yachtmaster Offshore (Sail), STCW commercial endorsement, Master of Yachts (200gt) and Cruising Instructor qualifications in back to back courses in November 2015. It was a fantastic challenge. I’ve recently been able to add Catamaran Instructor to the list for both Sail Canada and the ASA. So far, I’ve sailed the Pacific Northwest, the Great Lakes and the Caribbean. Altogether I have almost 30 years of sailing experience on dinghies and yachts of up to 55’.

When it’s time to relax at the end of the day, you’ll find me playing a little music on my mandolin or harmonica. And in the winter I enjoy Nordic skiing, something I’ve also enjoyed teaching.

Fintan Hartnett

Fintan Hartnett

ASA / Sail Canada Instructor

Fintan ‘Fin’ Hartnett has been a professional sailor and sailing instructor for almost 20 years. He is qualified as an ASA Instructor (BBCI & CCMI), Sail Canada Intermediate Instructor and Royal Yachting Association (RYA) Yachtmaster Instructor. He also has qualifications to teach VHF, Radar and powerboat training. Fin has taught in South Africa, the Caribbean, Canada, the USA, the UK and Europe. Fin lives in Kingston, Ontario with his wife and 3 boys and does woodwork in his spare time.

Ian Joseph

Ian Joseph

ASA Instructor / ASA Instructor Evaluator

Ian Joseph has taught sailing for the last 20 years. Hestarted sailing in 1982. He is an ASA Instructor Evaluator and has taught classes and certified instructors up to and including ASA 114. Ian has sailed extensively throughout the Caribbean, both coasts of the USA, French Polynesia, the Mediterranean and off South Africa. Ian has been associated with BOSS for the last five years. His passion is sailing and he delights in enabling others to derive the same pleasures from the sport.

Chris May

Chris May

ASA Instructor | TOP 32 ASA INSTRUCTOR, 2017 & 2019

After sailing on Lasers and 420s, I really got hooked the first time I sailed on a keelboat, a 40’ Cheoy Lee that my Navy ROTC unit rescued from a Customs storage yard after seizure. No self-tailing winches, no electronics, kerosene stove, but my oh my was the sailing sweet. I did my first offshore trip on Majestic and went on to command the Sailing Company before getting my commission and moving on to much larger ships. After leaving active duty as navigator on USS Nassau (LHA 4), I took groups on bareboat charters in the Caribbean, some of whom are now my best friends.

After several short summers racing on Lake Michigan, I decided to move to the Caribbean where my time on the water wouldn’t be limited to a few months, and scuba diving doesn’t require a drysuit. Now I live on my sailboat Troubadour, where I have time to practice my guitar and ukulele when I’m not teaching sailing.

What our clients say about us:

Vincent was an amazing instructor. Very well prepared, mixed teaching methods, professional, extremely knowledgeable, great personality and very passionate about sailing and teaching

Chris was very knowledgeable, but also able to convey that knowledge to the students. He was also patient, Thanks so much!

Extremely pleased with the entire experience, we learned a great deal and had a terrific time in the process

Alessandro was awesome. The cruise track was great, the lessons were very useful and the fellow crew/students will be good friends going forward. The layout of the course was perfect – we learned all the skills necessary for our certification with the ever helpful Alessandro and there was enough downtime for us to see the beautiful Grenadine Islands. Cheers!