Adventure Sailing Vacations

Training and sun & fun: a sailing program for individuals and couples alike to receive advanced charter and near coastal training with some vacation time in exotic ports.  Certifications are available, and more importantly the quality of the training and experience you'll receive is second to none.



San Juan Cruise & Learn · Bareboat Charter Master Certification

learn sailing while cruising in the san juan islands
Explore a world-class sailing destination while sailing and training with local and veteran instructors.
Earn your Bareboat, Skipper or Crew certification.
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International Sailing License & Credentials (SLC)

Approved SLC school. The international sailing license and credentials.
*New* International Licensing.
Earn your SLC, the recreational sailing license valid for yacht charter companies worldwide including Europe.
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International Certificate of Competence (ICC)

The International Certificate of Competence is approved by the UN resolution 40
Earn your ICC! Assessments ongoing through 2019. The ICC is the only sailing license recognized by the United Nations.
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About the Voyages....

advanced near coastal sail training. Advanced Near Coastal Sailing

We sail outside the charter boundaries, often running long stretches between ports. While under the care of some of the World's Best instructors, you'll receive advanced training whether you're skippering or crewing. It's the perfect opportunity to gain advanced big boat experience, near coastal training and well beyond what's typically "allowed" by charter companies.

Adventure Vacation

The adventure includes discovering different ports and anchorages - exploring, snorkeling (some go diving), lazing on the beach, or often joining fellow crew for a few celebratory rounds after a rigorous sail.  These are Adventure Vacations - planned by professional sailors for active people who enjoy the challenge of the journey as well as the rich rewards of each destination in route.

Attention to Detail. We arrange all the details for the sailing adventure vacations.Attention to Detail

The adventure begins with the planning. We work closely with each participant in all details of the trip - from training to travel to what-to-bring.  Included in this is extensive research on each location - details, details, details....  Simply, we have the details covered.

Catamaran Training. Learn how to sail catamarans from the world's best sailing instrubors.

Optional Catamaran Training

Learn Catamaran sailing from one of the best. Capt. Mark Thompson is a professional catamaran sailor, known for managing many of the largest cats in the world. It's a rare opportunity to train with an instructor of his caliber and experience!

Advanced & Near Coastal Training

Personalized Training

The voyages include experience and training that qualifies for Crew, Bareboat, and RYA Day Skipper certifications.  Each is available for sailors wanting to enhance their sailing resume, and notably these certifications will require pre-trip preparatory knowledge training and prerequisite experience.  While everyone aboard participates in the sailing and training, not everyone wants to be certified. For those sailors who want certification, we'll review your sailing goals and resume and offer specific recommendations for available certifications as well as preparatory requirements.

International Certificate of CompetenceOptional ICC Licensing

These sails include practical training that qualifies students for the ICC (International Certificate of Competence), the pinnacle of international certification and the only license recognized by the United Nations. The ICC assessment may require additional knowledge training, and we give preparatory recommendations for each candidate. For more information on the ICC click HERE.

sailing adventure vacation teamThe Team - Authentic Collaboration

Behind the scenes is an affiliated team of many of the most experienced instructors and operators in sailing. We collaborate to provide sailing and adventure vacation opportunities well beyond the resources of any one sailing company - in preparation, educational resources, coordination and most importantly on-the-water.

Capt. Mark Thompson, Chief RYA and NauticEd Instuctor, Catamaran expert and principle of Yachting Education. Grant Headifen, Global Education Director for NauticEd. Chris Black, Director of Land's End Sailing. And, De Henderson, General Manager of Island Sailing.

Meet RYA Instructor Capt. Mark Thompson

Mark Thompson, ICC Training, RYA Instructor, Catamaran ExpertMark Thompson
RYA & NauticEd Instructor, ICC Assessor, Catamaran Expert

Mark Thompson with Yachting Education is the Assessor. He is an RYA Sailing Instructor with over 20 years of instruction experience. Mark's one of the best, is very patient and puts student at ease. While the ICC Assessment is pass-fail, Mark creates a positive and low-stress environment for candidates.

As the Principal and Chief Instructor for Yachting Education, Mark Thompson has a significant sailing resume including multiple Atlantic Ocean crossings and experience in Caribbean, Mediterranean, Australian and US waters.More about Capt. Thompson

Mark's career has centered on charter catamarans including a 5 year captaincy aboard the luxury yacht S/Y Lone Star. At 85ft LOA she was at one point the largest charter catamaran in the Caribbean and after crossing the Atlantic, Mark and his crew hosted families on more than 100 weeks of charter.

Mark is a Chief Instructor accredited under NauticEd & RYA programs and has taught hundreds of students in the art of sailing and the nuances of running catamarans. One critical issue he shares is the ability to smoothly and silently communicate and operate theses large powerful vessels.

Mark grew up in Melbourne Australia and joined the maritime industry after a career converting inner city office buildings into trendy apartments. During a year spent traveling the world he discovered a sailing career while driving through Viareggio Italy and thought "you mean I get paid to sail?"

His love of sailing is infectious and his calm, patient demeanor has empowered hundreds of students to consider a bareboat charter and many to purchase their own boat. Whatever your level of expertise, the practical time spent with Mark will be enlightening and your certification will open up a world of sailing opportunities.

FAQ & Answers

What's expected?

Sailing can be rigorous, especially when venturing outside typical charter boundaries.  Everyone needs to participate as either skipper or crew - this isn't a vacation, but an adventure sailing vacation!  Expect to be mentally and physically challenged on these voyages, but also to have a lot of fun.  Simply, the rewards of these voyages are commensurate with the with motivation, inspiration and effort. 

Even as professional sailors, we're not entirely certain what's going to happen after we cast off.  We train, plan and prepare.  We learn to make no excuses.  And, that gives us the confidence to completely immerse ourselves and enjoy the challenges.  We reach our destinations, often exhausted, but that intuitive sense of discovery doesn't stop there.  Whether at land or sea, we play and explore.

What's expected?  That's a difficult question.  Truthfully, the answer is what you expect of yourself?  To a sailor, that's not a question to ponder but an answer to discover.

Who's eligible, what's required?

Anyone who's active, willing to participate in all aspects of the voyage, enjoys challenges and who seeks a trip outside the typical boundaries of most sailing programs.   We're professional sailors who captain boats and train people for a living and can easily sail these boats ourselves - but we enjoy working with people inspired and motivated with a sense of adventure and discovery.  We can teach you how to sail - you need to bring a willingness to learn, explore and participate!

What's included?

All required safety equipment, meals, snacks, soft drinks & water, linens, towels, etc....  On-the-water training is also included - part of adventure traveling is learning and experience.

What's not included?

You'll need to make your own travel arrangements and bring your own foul weather gear, canned alcoholic beverages and a requirement is a healthy dose of realism and library of stories and jokes.  That said, we'll work with everyone on the details - coordinated travel and bulk discounts, travel requirements, sun lotion, bug spray, traveling with inflatable PFDs, etc....

Favorite candy? K'argh-amel.  Favorite knot? The Dragon Bowline.  And, so on - if light on sailor jokes, we'll teach you a few and trust we have our share of tall tales.

Why is certification optional?

Simply, all sailors and participants are unique: different goals, experience and training backgrounds - including several participants who don't want certification and instead just want to have fun.  We review each and every application and offer specific recommendations to achieve your trip and sailing goals.  Our team includes several of the top trainers and sailing educational programs on the planet - simply, we'll work with you to achieve your sailing certification and resume goals.

Is certification an additional cost?

Possibly, probably - again it depends on the sailor, their experience, the goals and what training is needed.  The on-the-water training is personalized, and there may be additional cost for the pre-trip knowledge training. Simply and to us, it makes more sense to personalize the training, the needs and the expense rather than build in those costs into the trip for everyone. As sailors we abhor wasting people's time and money - as applied to certification, we focus on the training that's needed.

Can I bring my spouse or friend?

Absolutely!!  It's why we structured this program this way - everyone's invited at various levels of experience and commitment.  They'll be expected to assist as crew, but that may include heckling the sailors while lounging on the trapeze....


Simply, we tailor these voyages and charters to each sailor's goals and needs. If you're not sure or have questions, certainly contact us....


Need Help? Contact Island SailingAlternatively, contact Chris Black directly at with questions or for more information.