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Live Aboard Cruising Courses — OSS 103/104/114

Learn on a Monohull Cruising Yacht or Catamaran

Monohull or Catamaran

If you do not have any sailing experience on large cruising yachts,  we recommend you gain your Bareboat Cruising Certification on one of our classy and fast 43′-47′ Jeanneau monohulls.  In the OSS 103/104 Monohull Live Aboard Course at our Florida campuses you quickly learn how to control and capture the wind on all points of sail, feeling the excitement of steering a large cruising yacht on all points of sail, far better than on a catamaran.

The Ultimate Learn to Cruise Experience

Catamarans are the choice of many new cruising sailors because they have more room, and will not heel (lean over).  If you opt for the Catamaran Live Aboard Cruising experience, OSS 114 is added to your certifications for handling a twin-hulled cruising boat with two engines under sail and power.  Learn more about some of the yachts in the Offshore Sailing School fleet.  The choice is yours, of course. We teach a maximum of four students per week, so don’t wait to sign up to reserve a spot on one of our cruising sailboats!

Live Aboard Cruising Courses

How the Live Aboard Course Works

During the six-day live aboard sailing lessons program, you gain incredible confidence, knowledge and skills that qualify you for chartering and sailing big cruising boats without a hired captain or mate. You learn the mechanics of running a big yacht under sail and power; how to maneuver, dock, anchor and pick up moorings in crowded marinas and harbors. You learn how to act quickly in heavy weather and reduce sail area for comfortable sailing in big seas.  Among the many drills and techniques you experience, is the fun of cooking and dining aboard – preparing meals and cleaning up with your crewmates, just like you would if you were bareboat chartering (skippering the boat without hired crew). Offshore provisions your yacht with breakfast and lunch items, as well as food for most dinners aboard. You and your crewmates do the meal preps as learning to cook aboard is part of the Live Aboard Cruising course experience.

Live Aboard Cruising Courses
Live Aboard Cruising Courses

Bring the Family or a Friend and Stay a Day or Two Longer

All Live Aboard Cruising Courses are based at great vacation and sailing destinations. If you would like to relax ashore a day or two before the course starts or after it ends, we can happily make those arrangements for you. We also offer packages for live aboard family sailing! Get in touch to learn more about our monohull yacht and catamaran sailing lessons.

“The Live Aboard Cruising Course gave us exactly what we needed – big boat training and experience. We are pumped and plan to get into cruising within a year. The instruction was outstanding!”

O. Thomas Mueller – St. Petersburg, FL
Read more testimonials here

This has been one of the most rewarding experiences in my Backwards cap student posing at the boat's steering wheelLIFE! My dream to sail only started about 6 months ago and as a goal orientated person (US Air Force for 26 years) I knew there would be no better way to move forward than to take a sailing course. Sure it was challenging, it was tough, but it was a lot of fun. I highly recommend this course to anyone who wants to sail, or to anyone wanting to check off a bucket list item. Both of our instructors were excellent. They had incredible knowledge, patience and solid teaching techniques. Both boats were in impeccable condition. I had a lot riding on this course as if my wife didn’t like it, my dream to live aboard someday would have been crushed. Thank you, thank you!

Aaron Maynard – Myrtle Beach, SC
Fast Track to Cruising Course – July 2018
Read more testimonials here

A Cruising Course for Sailors Who Want to Own or Charter Cruising Yachts

The Live Aboard Cruising course assumes you already have US Sailing Basic Keelboat Certification and are ready to learn the techniques and skills for handling larger sailboats and bareboat cruising (chartering without a hired skipper). If you do not have US Sailing Basic Keelboat Certification but do have equivalent experience on sailboats of at least 26 feet with skippering and crewing experience. you must take the US Sailing Basic Keelboat test (additional fee to added to your package when you sign up) prior to taking the US Sailing Basic Cruising and Bareboat Cruising tests during the course.

Man steering a catamaranI have taken all US Sailing courses with Offshore Sailing School. Just finished the Catamaran Live Aboard Cruising Course (that’s me in the yellow shirt on the right).  It’s been an awesome adventure and experience. Instructors are awesome!! Lots of knowledge and experience where you can’t find anywhere in books. Our instructor had so much knowledge  I thought I was a brand new student, talking to Jedi Master YODA!!

Sam Hahn – New York, NY

Maximum Four Cabins Available Per Week

Because of the popularity of our live aboard sailing courses, and because we teach a maximum of four per week per cruising boat availability, please have several dates in mind when you contact us to book this cruising course. If you are interested in “Buy the Boat” live aboard family sailing packages, you can add up to 2 more family members. See the Course Schedules tab below for more details.

“My husband and I have traveled the world and this was by far one of our best adventures. An amazing vacation that ended with an acquired skill that will last us our lifetime. I am a teacher. My husband and I run our own Test Prep School and thought I knew everything. My teacher at Offshore taught me the importance of patience and independence. He guided but never coddled. The outcome: I learned more than I could ever have imagined. I am a new person!”

Ariana (and Khalid) Khashoggi – Highland Park, NJ
Read more testimonials here 

“I did this course withBrothers posing on a boat my 16 year old son. Now he has a gift he can use and enjoy for the rest of his life. And I have both a gift and a memory that will remain forever.”

Russ McCallian – Aurora, CO
Read more testimonials here 

Exclusive Sailing School for The Moorings

Offshore Sailing School has been the exclusive sailing school for The Moorings, the most prominent charter company in the world since 1988. Offshore Sailing School cruising course graduates are “Captains” in The Moorings preferred charter program and enjoy discounts up to 15% when booking a charter. If you take this course in the British Virgin Islands with family or friends, why not continue your cruising adventure with a bareboat charter vacation right after you graduate?

Photo of a man on a boat “Offshore made it easy to learn! From easing us through the many tactical details related to arrival and expectations with extensive email communications, to the excellent books to the truly remarkable instructor who made learning a joy – the result was one of the best weeks ever. Great memories, excellent skills development. What more could one ask for?”

Mark Waltz – Muskego, WI
Read more testimonials here

International Proficiency Certificate (IPC) for Chartering Overseas

If you plan to charter in Europe or other areas overseas, you may be required to show your certification credentials and an IPC, International Proficiency Certificate. US Sailing, the governing body of sailing in the United States, will issue this certificate for a nominal fee for U.S. citizens who have achieved US Sailing Basic Keelboat, Basic Cruising, and  Bareboat Cruising Certifications. For more information, click here.

A Note About Night Sailing

Most charter agencies do not allow night sailing and require that you are anchored, docked or on a mooring before sunset. Night sailing is not covered in this course, but is covered in Passage Making courses, the next step in your learning process.

A Live Aboard Cruising Course or Stay Ashore Bareboat Charter Cruising Course – whether on a monohull or catamaran – prepares you for charter cruising on your own, without professional captain and crew aboard (called Bareboat Cruising by charter companies). Depending on weather conditions and the learning pace of all in your class (maximum four per boat per instructor unless you opt for a Private Family Course), the following will be learned and practiced.

  • Planning a cruise
  • Familiarization with boat layout and sail plan
  • Operation of engine, generator if available, stove, toilets
  • Routine engine maintenance
  • Fueling techniques
  • Use and conservation of battery and charging systems
  • Water use and conservation
  • Use and location of thru-hull fittings
  • Maneuvering under power and sail with emphasis on windage considerations and close quarters
  • Big boat docking, mooring, and anchoring techniques
  • Proper and safe handling of halyards and lines
  • Proper and safe use of winches
  • Apparent wind, wind instruments, sail trim and set
  • Inter-crew communication when trimming sails, docking, mooring, anchoring
  • Genoa roller furling use
  • Overboard recovery procedures
  • Big boat heavy weather and reefing techniques
  • Heaving-to
  • Sailing wing and wing on bigger boats
  • Use of jennaker if available
  • Boom preventer use
  • More knots and their applications
  • Log procedures
  • Piloting techniques including set, drift and leeway calculations
  • GPS navigation
  • Rules of the Road
  • Danger bearings
  • Coast Guard requirements
  • VHF use
  • Courtesy using lights and sound signals
  • Use of safety harness
  • Emergency tiller use
  • Distress signals
  • Operating a dinghy

If you are learning on a catamaran, your training also includes:

  • Multiple scenarios related to wind direction and current while docking, mooring, and anchoring
  • Close quarters maneuvering on a catamaran versus a monohull
  • Windage considerations
  • Spring lines and other dock lines configurations for catamarans
  • Reefing by wind strength

Pre-requisite for Live Aboard Cruising Courses: US Sailing Basic Keelboat Certification

Certifications: US Sailing Basic Cruising and Bareboat Cruising certifications are tested for and included in the cost of this course. You receive a logbook from your instructor at the end of the course and US Sailing certification stickers for your logbook, are sent to you after verifying successful completing of the written tests.

Package rates vary by season and location, and include all the elements listed below. Not included are meals ashore, travel and other expenses you may incur. Please call 888-454-7015 for a quote.

At all locations, your Live Aboard Cruising Course includes:

  • Live Aboard Cruising Course tuition
  • US Sailing textbooks
  • Six days living aboard in a shared or private cabin
  • One or more nights accommodation ashore (including resort fee and taxes on both)*
  • All breakfasts, lunches, snacks and three dinners aboard
  • 24-hour practice test mini-cruise at course end, with or without instructor aboard
  • US Sailing Basic Cruising and Bareboat Cruising Certifications when tests are passed
  • Colgate Logbook (or page for logbook if you have our logbook from a previous course)
  • US Sailing Course Certification stickers for your logbook
  • Course diploma
  • Eligibility to participate in Colgate Sailing Adventures® Flotilla Cruises
  • Exclusive subscription benefit from Cruising World or Sailing World magazines
  • Discount charter benefits from The Moorings
  • *Accommodations are NOT included in Key West. Students must make their own arrangements

International Proficiency Certificate (IPC) for Chartering Overseas

If you plan to charter in Europe or other areas overseas, you may be required to show your certification certificates and an International Proficiency Certificate. US Sailing, the governing body of sailing in the United States, will issue this certificate for a nominal fee for U.S. citizens who have achieved US Sailing Bareboat Cruising Certification. For more details, view the IPC page on US Sailing’s website or go to and search IPC.

Sample course schedules are sent upon enrollment with other confirmation materials and information.

Offshore Sailing School knows we cannot thrive without great employees and products. All graduates are asked to fill out an evaluation at the end of the course. The following testimonials come from those evaluations and individual correspondence with recent graduates of the Living Aboard Cruising Course. Many are happy to correspond by email or phone with you. If you would like us to put you in touch with anyone below, please call 888-454-7015 or email

Here’s what our Live Aboard Cruising graduates have to say:

This was my first experience with a catamaran and I am impressed with how much we all were able to learn on a compressed time schedule. I am very pleased to feel confident about handling a cruise in a 14 ton cat!

Laurent Mets – Chicago, IL

My experience was worth every penny. Jim was everything I would want from a sailing instructor and leader. I have done a fair amount of outdoor schooling and he ranks very high in my book. I would recommend the course without hesitation.

Christopher Moore – St. Petersburg, FL

Neil has been the most terrific instructor I have met in my sailing experience. (I was a sailing instructor for small boats as well and I can definitively judge this aspect.) The course was incredibly fun and well-structured. His level of knowledge is incredible and he was able to share his experiences and taught us the practical skills. Everything about my live aboard cruising course exceeded my expectations. Great sailing, the navigation and itinerary between islands were very well prepared, outstanding course content and sailing practice.

Vincent Schmitt – Hillsborough, NJ

My wife and I really enjoyed our Offshore Sailing experience. It did, indeed, exceed our expectations. The BVI is a beautiful place to learn. Our two fellow onboard students were pleasant to be with. Importantly, Amanda, our instructor, made learning fun. She was delightful, an excellent instructor, and we learned a lot from her.

Michael Leonhardt – Chicago, IL

Neil was amazing – knowledgeable, great teacher, we had a blast. Over all experience: Terrific course – I’m now ready to take a boat out on my own!

Brad Richards – Philadelphia, PA

We have taken Offshore courses and sailed the BVIs with 6 captains. Our entire family, kids included, said that Dutch (Neil) was the best captain, instructor and companion ever! We learned a lot and had a terrific experience.

James and Blanche Williams – New York, NY

The course exceeded my expectations. I have some experience as sailing crew and was nervous that I would slow the class down. I learned a lot and am now more confident. I would recommend this course enthusiastically.

Ann Hobbs – East Setauket, NY

We had an amazing six days on our live aboard! Would highly recommend this course! We learned so much and had fun at the same time. Simply amazing.

Lissa Uhlenhop – Las Vegas, NV

Amazing experience! Garren was excellent. He put my wife at ease as it was her first time on a live aboard. His technical knowledge and practical application of it is fantastic. A great week was had by all!

Eric Uhlenhop – Las Vegas, NV

Our family did the Live Aboard for our 13 year old son’s spring break. We wanted to learn how to sail the bigger boats so that we could cruise as a family. The live-aboard course allowed us to really learn and understand what it is like to bareboat. A 50 ft. sailboat is daunting but now we know we can handle it. We look forward to cruising in the BVI as a family.

Cathy, David and Will Madairy – Charlotte, NC

Jim was great. The weather was rough the first couple of days (20-25 knots gusting to 35) and he helped us make the best of it. If you can dock in that weather, you can do it in lots of situations. The rest of the week went very well. Hard work but worth it. My wife and I learned a lot. The feeling of satisfaction and accomplishment after taking the boat out and back on the last day was the perfect end to the week.

George Matook – Farmingham, MA

When I began I never handled a boat (sail or power) and by the end of the week I was sailing and maneuvering a 40’ boat out of a dock. Great learning experience! I could never imagine how much I would learn in such a short period of time.

Jennifer Eubanks – Marietta, CT

We were amazed at the end of the week by how much we had learned. Excellent experience. Looking forward to taking another class.

Dave Shanklin – Indianapolis, IN

Outstanding instruction, quality sailboat, and great winds in the BVI. We learned a great deal and had loads of fun!

Dan Riordan – McLean, VA

Our instructor was fantastic! Lots of knowledge, experience and patience! He definitely made the catamaran sailing course really fun and interesting. I highly recommend anyone interested in sailing to learn in the British Virgin Islands at Offshore Sailing School. Fantastic time!

Kent Killion – Prospect, NY

Just came back from the British Virgin Islands on our maiden voyage after taking the Fast Track to Catamaran Cruising course!! Took two of our 3 boys and one of the girlfriends. Very proud of our accomplishment. Thanks for all the great training!!

Dan Barzel – Cordova – TN

A terrific experience. I look forward to opportunities to continue sailing both through the Offshore Sailing Club and other activities, flotillas or future classes.

Kevin O’Neill – Hawthorne, NJ

Offshore is a great school to take you from no sailing experience to a competent live-aboard sailor in a week!

Markus Beissinger – Randolph, NJ