Wednesday, October 20, 2021

ABOUT US (340)775-2278

James "Jim" Jackson has spent a lifetime teaching. Seamanship, sailing, diving, skiing, music, and theater are just a few of his areas of expert instruction. Jim spent most of his professional career as a physicist and voice/data network architect for a worldwide company in the U.S. But it is safe to say that his interests are broad and his enthusiasm for sharing his knowledge is unequaled. Jim has been a PSIA Level III instructor and staff trainer at a ski school at a large resort. He has played rock and roll to delighted fans. Jim has led divers on journeys throughout the Caribbean. He has taught seamanship to mariners in the US Virgin Islands since his retirement from corporate life. Jim and wife Kathy Jackson (also a captain and scuba instructor) have lived in St. Thomas aboard their charter boat "Jamann" for the last decade. They run day trips and week long term charters while making time to teach classes each month at the Captain School. Jim is truly the busiest retired person you will ever meet! Kathy when not on charter, helps mariners with paperwork and heads up the Captain School administration. 

Captain Casey

Captain Casey as he is know to friends near and far, founded the Captain School in St. Thomas in the early 90's from his kitchen table at Sapphire Beach.  Casey is from Dallas Texas and has a personality that is even bigger than the Lone Star State!  His knowledge of seamanship combined with his easy manner and funny stories have helped thousands of mariners to meet their professional goals.  Taking a class with Casey is time well spent.  Casey spent many years in the Virgin Islands working with various local charter boat operators and even represented the VI for the 500 year Columbus Celebration by sailing his boat to the Med. Today Casey operates schools throughout the United States and remains a big part of the school here in the Virgin Islands.


Rob is a New Jersey native who hates the cold! He brings to the class room 40 plus years of experience on the water along with a sense of humor and many years of teaching experience.  Rob first sailed to the Virgin Islands in the early 90's . After working for 10 years in the charter boat industry, Rob got married to his long time first mate Heidi.  Heidi and her family have lived on St. Thomas since the early 70's.  Today Robert and Heidi enjoy boating and island hopping with their two young children.  "Living and working here in the VI is about as good as it gets!  I am very lucky to have the opportunity to work with local mariners and help them to obtain the professional qualification needed to work on the many boats that operate here in the VI.  I doubt there is a charterboat, fishing boat or ferry around that I haven't met the crew.  To me, getting to know so many great people is the best part of my job."

Captain John 

Born in St. Thomas US Virgin Islands in 1959, I am lucky that my parents decided to "go for it" many years ago. My father came here in the 50's on a submarine in the Navy and found cheap rum. He went back to Chicago to finish school and met and married my mother- telling her the big three "stories"- he had a job/ had round trip ticket's/ and money- they drove a Studebaker to New Jersey and then flew by DC3 to Miami and on to St. Thomas. The flight from Miami in those days was 8 hours with no AC! How my mother stuck with it I don't know.

I have great memories of our first pet- a donkey , and of many other "island life" stories. We started sailing at Sapphire Beach in 1963 and I remember racing around the buoys at 8 years old. Many years have passed and the sailing, boating and waters here are still unsurpassed- at least in my mind. I am still exploring areas of US and British Virgin Islands that I have not been to- or have not visited in a long time.

Now, with my own family, we are branching out as I want to "go for it " like my parents did and you never know where we will be next!

Feel free to contact me and we can share a sunset or a laugh.... or a race!

John "Humbug" Holmberg

Captain Jennifer 

Jennifer holds a 100 Ton Master License along with all of the endorsements.  She is an accomplished sailor who has cruised with husband Ryan and Sissy her dog from Texas to South America and all ports between.  Jen is originally from Oklahoma where she and her husband worked in the private aircraft leasing business.  Today Jennifer serves as the general manager at the Captain School.  If something need to be done, you can be sure that Jennifer will have a hand in it.  It is fair to say that we could not do what we do without her!  Jennifer is very well versed in dealing with Coast Guard paperwork and can help mariners navigate the in and outs.  She has also been instrumental in the implementation of our Drug and Alcohol Program and Consortium.

 Captain Joe 

Joe is originally from Massachusetts and has extensive sailing and racing experience off the coast of New England and Eastern Seaboard. He has been sailing in the Caribbean off and on since 1985 and in 2006 bought a condo “on island”. Recently retired from the Hi Tech world, Joe is now pursuing his “dream” – working with aspiring mariners on St. Thomas.

Joe is a 100GT Master with Sail, Tow, and STCW endorsements and is a USCG approved instructor. He is also a PADI SCUBA, DAN (Diver Alert Network), and Emergency First Response instructor and has taught at a number of colleges through out his career. He has a number of "instructional" stories to tell - you'll need plenty of time if you ask him about lighthouses!

“Becoming a professional mariner may be one of the most rewarding careers that you will have. Not just for the experiences, but for the people that you will meet along the way.”

"I look forward to meeting you!"


Captain Mike 

Captain Mike is the newest addition to the Captain School family.  He is a very welcome addition and brings great skills and experience with him to share with our students.   Mike was born in Maine and lived in Florida as well.  Mike joined the Coast Guard after he finished school and has spent most of his adult life (23years) at sea serving our country.  His training in the USCG along with the wide variety of experience working aboard ships large and small allows Mike to share with mariners lessons and skills not often found by one instructor.  Captain Mike's gregarious nature has made him one of the most poplular guys I know.  A short stroll with Mike will be met with many people shouting "Hey Mike"


Diego Lima is one of those heroes that run toward a fire not away from it.  Serving as a proffesional fire fighter here on St. Thomas makes him a great asset for the Captain School.  Diego is always happy to help mariners master the skills needed to effictively fight fires on our vessels and to make sure that we are always prepared to do so.  A native of St Thomas, Diego and his wife have two young childeren.  Racing motor cycles and playing basketball with his kids are his ways of relaxing.

Upcoming Classes


August 2021

7-11 STCW Basic Training (5 Days) $1200

September 2021

13-26 OUPV Captains License  $950

14-16 Vessel Security Officer $1000

28-Oct 1 Upgrade To Master (Nights) $400

October 2021

2 Sail Endorsement($250) 830-12 AM

2 Tow Endorsement ($250) 1-5 PM

8-10 Medical Care Provider  $750

11-24 OUPV Captains License  $950

11-15 STCW Basic Training (5 Days) $1200

18-21 Adv Fire Fighting  $900

November 2021

5-10 STCW II/3 Assesments (5-6 Days) $2500

11-15 STCW Basic Training (5 Days) $1200

16-19 Upgrade To Master (Nights) $400

20 Sail Endorsement($250) 830-12 AM

20 Tow Endorsement ($250) 1-5 PM

29 Nov-Dec 13 OUPV Captains License  $950

29 Nov- Dec 3 STCW Basic Training (5 Days) $1200

December 2021

29 Nov-Dec 13 OUPV Captains License  $950

29 Nov- Dec 3 STCW Basic Training (5 Days) $1200

(More Courses & Dates Coming Soon)

Medical Care Provider (3 Days) $750

STCW Basic Training (5 Days) $1200

OUPV Captains License (Nights / Weekend) $950

Crowd Management (1 Day) $300

Crisis Management (1 Day) $300

Upgrade To Master (Nights) $400

Advanced Fire Fighting (4 Days) $900 

Sail / Tow Endorsements  $200 / $200

STCW II/3 Assesments (7-8 Days) $2500

Dates May Be Subject To Change

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Training Flow Chart

Certifications Required for Crew-

Working on 6 passenger boats in the USVI

-CPR & First Aid

-Random Drug Testing Program

-add TWIC (from TSA) if entering secure port areas in US & BVI

Working on 6-12 Passenger Boats in the BVI

-add: STCW Basic Training

Working On Vessels with more than 12 passengers in BVI

-add: STCW Crowd Managment

-add TWIC (from TSA)

Additional: Helpful but not required by Law

-STCW Crisis Management

This information is not intended to answer all questions regrading licensing- use it as a guide only- information subject to change. Call for a personal consultation 340-775-2278

Certifications Required for Captains-

Operating 6 passenger boats in the USVI

-USCG OUPV Near Coastal License

-CPR & First Aid

-Random Drug Testing Program

-FCC Marine Radio Operator Permit

-TWIC Card (

Operating 1-12 Passenger Boats in the BVI

-Add: Master Upgrade to 50 or 100 Gross Ton Master Near Coastal

-add: STCW Basic Training

-add: STCW Advanced Fire Fighting

-add: STCW Medical Care Provider

-add: STCW Proficency in Survival Craft (Limited)

-add: STCW II/3 Endorsement on License 

Operating Vessels with more than 12 passengers in BVI

Same as above and

-add: STCW Crowd Managment

-add: STCW Crisis Management

-add: Vessel Security Officer

This information is not intended to answer all questions regrading licensing- use it as a guide only- information subject to change. Call for a personal consultation 340-775-2278