Advanced & Offshore "Bluewater" Sailing

An offshore sailing program for individuals and couples alike to receive advanced "Blue Water" training while sailing vessels between exotic ports.  Certifications are available, and more importantly the quality of the training and experience you'll receive is second to none.

register now for sailing classes, courses and clinics

The Best 'Next Step' in Advanced and Offshore Sailing

Salt WashedSimply, this program is a sailor's dream. This may be the best way to step off the earth for a while, but notably it's not a trip for the faint-hearted! Students will be a major part of the crew, taking watches, trimming sails, navigating, planning and correcting headings all the while ensuring the safety and security of the team during your watch.

When students asked "what's next?" in training, we spoke with Capt. Mark Thompson. As a top RYA and NauticEd Instructor, catamaran expert and delivery captain of new vessels - Capt. Thompson's devised an offshore program that offers extraordinary value for training on new boats while having fun in exotic tropical ports-of-call.

This program is uniquely structured to sail new and top-of-the-line Catamarans and Keelboats offshore and between exotic ports of call. The training is second to none, including working with the top instructors, sailors and captains in the Yacht Delivery industry.

What is Blue Water Training?

Once students become Bareboat Charter Masters, then they're well prepared for coastal sailing while building experience and fine-tuning training.  The next step is heading over the horizon and truly out of site of land; or rather, venturing into the deep ocean "Blue Water" beyond the continental shelf. 

Sailing to (for example) the BVI's or Guadeloupe requires all the coastal skills and training in a bareboat.  Blue Water adds experience and training in passage planning, boat/crew management, watch systems, night sailing and navigation, weather routing and a more comprehensive level of safety equipment, and heavy weather procedures.  And, much more: you'll gain extraordinary confidence in your skills as you collect true sea miles.

+ read more about blue water sailing

Long-distance sailing is a great experience but isn't always for everyone, which is why we recommend students set aside certification/"sticker" concerns and consider the quality of the Captain, training, vessel and waters.  Often sailors consider volunteer crewing as an inexpensive option for gaining blue water experience, but that route isn't a substitute for pro-training (read  volunteer crew v. pro-training).

  • Students want a *highly* respected instructor who is experienced in blue water sailing as well as an expert in managing boats and crews.  The instructor needs to be mature and accomplished, training students how to plan sail long distances safely. As such, Captain Thompson is one of the World's best (bio below).
  • The vessel must be blue water capable, in excellent condition and equipped for voyages. These vessels are new, well equipped and vessel options ranging from a Beneteau 41.1 to Catamarans such as Isara 45 (for those wanting Catamaran experience).
  • And for the waters, we recommend going somewhere warm and having fun! But, it's not just seeking sun and fun - some sailing waters can be fairly miserable and rough (e.g., occasionally Northwest "Offshore" classes never make it offshore).  Good weather's never guaranteed, but ports such as the BVI's, Bermuda and Guadeloupe are safe bets for beautiful sailing conditions as well as unforgettable vacation.

docking cleat hitch


Advanced and offshore sailing requires Bareboat or equivalent experience, and preferably including Near Coastal sailing experience. Students share coordinated watches, requiring round-the-clock sailing - students needs to be physically and mentally prepared to sail for extended periods in a variety of conditions, including foul weather.  We review each application in detail, and we will make specific recommendations regarding any additional preparatory materials needed.

NauticEd Captains Rank License Certification


You'll receive expert training from one of the World's foremost offshore delivery captains.  For those wanting certification, NauticEd Captain certification as well as RYA certifications are available and upon Merit. Depending on your sailing background, the knowledge training may be an additional cost. Every sailor's background is unique - we'll review your background and make specific recommendations for certification as well as preparatory training.

What's Included?

Included are all on-board meals, snacks, soft drinks & water, linens, towels, and instructional materials.  Students should bring their own foul weather gear, canned alcoholic beverages, a healthy dose of realism and a library of stories and jokes!

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

offshore passage training and advanced catamaran trainingIf a Catamaran voyage (check the schedule, we sail both Cat and Keelboats), 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.

No Prior Catamaran Experience Needed. If a keelboat sailor, we'll train you on all of the details of sailing and managing an offshore passage with a Cat.

offshore sailing from bermuda to BVI's

Past Voyages

Whether more exotic ports such as Bermuda, the BVI's or Gaudeloupe - or famed US sailing ports like Annapolis or Charleston - these past voyages include examples of sailing some of the best passages available.

+ read Voyage Summaries


• Annapolis to BVI's + read more

annapolis to bermuda offshore sailingOn departure we'll head south on The Chesapeake Bay and you’ll pass historic towns and magnificent waterfront homes, anchoring nightly in secluded harbors and bays.

Our ocean passage commences at Virginia Beach but not before sailing by the incredible naval base and battleship row at Norfolk. Once clear of the headland, we’ll be setting south-east, plotting our course towards Bermuda, well beyond the horizon.

By now the crew have formed a cohesive team and rotating shifts ensure everyone contributes to the safety and management of the vessel. Our expected landfall is 3-4 days off so there’s plenty of time to practice knot tying, navigation or sharing that great recipe you’ve memorized.

“Land-ahoy” will have a whole new meaning by the time we sight our destination and enjoy a cold beer ashore.

• Bermuda to British Virgin Islands + read more

offshore sailing from bermuda to BVI'sBermuda was discovered in 1505 by Spanish Captain Juan de Bermudez and first appeared on a Spanish chart in 1511. A summary of her colorful and often tragic history can be read HERE.

For the Blue Water Cruisers in all of us, this voyage will inspire the pursuit of a nautical global circumnavigation. Our course will traverse almost 1000 miles of the Atlantic Ocean before entering the British Virgin Islands. From the temperate latitudes to the north, we’ll head almost due south, making best use of the prevailing south easterly trade winds.

After many days at sea, the Virgin Islands will appear on the horizon just as they did for Columbus, Drake and every mariner since 1492.

Time prevailing we’ll take-in the beauty of the islands, anchoring in secluded tropical coves and snorkeling amongst some of the most diverse corals in the Caribbean. It isn’t called “Nature’s Little Secrets” for nothing.

• Boston to Bermuda  + read more

offshore sailing from Boston to Bermuda

Retracing the steps of many sailors over the past 300 odd years, this voyage incorporates nearly 700 miles of Blue-water sailing, crossing the Gulf Stream and the challenge of navigating successfully to a low-lying, reef enshrouded island.

Although this is not a trip for the feint-hearted the 41.1 Beneteau is wonderfully designed for any ocean crossing and this should be a great sail. From the bustling waterways of the northeast we’ll soon enter the Atlantic Ocean tracking south towards the Gulf Stream and sub-tropical Bermuda.

A great overview of the passage is available HERE.

Returning to USA or Europe is easy with hundreds of flights & destinations departing Bermuda, however for those who’d prefer a more leisurely return to civilization, Bermuda is destination central for Cruise ships from USA, UK & Europe. Or you could roll the dice and catch a lift to anywhere in the world.

• Guadeloupe to British Virgin Islands + read more

offshore sailing from guadeloupe to BVI'sA voyage through the Caribbean should be on every sailor’s agenda. When you mix in the diversity of cultures, languages and ethnicities, the Caribbean is a treasure trove of desirable destinations and sailing opportunities.

This passage begins on the island of Guadeloupe and heads north through a succession of former English, Dutch and French colonial islands.

Guadeloupe is the center of the Caribbean's Creole culture, boasting a spirited blend of French and African influences. As well known for its sugar and rum as for its beaches and resorts, the archipelago offers an interesting mix of modern cities, rural hamlets, rainforests and secluded beaches. (courtesy:

Heading north with a following sea and a beam reach, the sailing is absolutely magnificent. The air is always warm, the seas a beautiful turquoise-blue and the sun a radiant glow through light cumulous clouds. HERE"S a full description of the Eastern Caribbean Island chain.

Our passage will take us through the heart of British colonization at Antigua then St Kitts & Nevis before re-entering the sophistication of French St Barts. Along the way we’ll pass a succession of non-active volcanos and even some with a bit of attitude, pass islands smothered in cane fields cultivated by hand until recently, smell the deep Tropical forests where the islands touch the sky and sail overnight under the majesty of a star filled sky.

Our arrival to the British Virgin Islands heralds “Nature’s Little Secrets”, a catchy advertising phrase which is pretty close to the truth. Watch THIS and you’ll be hooked.

BTW, for sailors with some fishing skills, bring your gear. You never know what you’ll land when you’re offshore, but there’s nothing sweeter than sushi on the aft deck.

close past voyages

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.+ read 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.

Upcoming Offshore Passages

Registration & Questions

To register or if you have questions, please select the date, submit and we'll follow-up. Our process begins with answering questions and discussing training, goals and other details related to the voyage and travel. Simply, we tailor these voyages to each sailor's goals and needs.

Upcoming Offshore Voyages (date is first day)

  • Aug31Sat
    Basic Sailing - Portland
    10:00 amIsland Sailing, 515 NE Tomahawk Island Dr, Portland, OR 97217, United States
  • Sep09Mon
    RYA Day Skipper Course (Ft. Lauderdale, 5 Day)
  • Sep14Sat
    ICC Assessment - Ft. Lauderdale
    All day
  • Sep21Sat
    Basic Sailing - Portland
    10:00 amIsland Sailing, 515 NE Tomahawk Island Dr, Portland, OR 97217, United States
Show more



Need Help? Contact Island SailingAlternatively, you can contact Chris Black directly at with questions, for more information or to sign-up!

Please note: bookings are first-come/first-serve. The booking process includes some required paperwork and waivers before payment.

For payment, a twenty (20%) per cent deposit is required at time of booking. The balance is due sixty (60) days before departure, or within seven (7) days from the initial deposit when the departure date is within sixty (60) days.

Please see Booking Conditions, Policies & Release for details.