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Bareboat Sailing Certification Courses — OSS 103/104/114

Earn Your Bareboat Certification While Staying at a Destination Resort

During this five-day Bareboat Charter Certification Course you gain the same incredible knowledge and skills covered in the Live Aboard Cruising Course, with the added benefit of a lot more docking practice since you return to base after each on-water bareboat cruising session. Learn more about our Caribbean and Florida bareboat charters below!

The course was fantastic. So much information in a very man and woman smiling behind wheel of a sailboatshort period of time. It’s a great course to get your feet “wet.” Rick is a fantastic instructor. Didn’t want it to end. Rick has the patience of JOB, the wisdom and knowledge of SOLOMON, and the attitude which encourages students in a positive, and clear way. Plus, he makes learning fun.

Michael and Mari Piscitelli – Lumberton, NJ

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Why Live Ashore During the Bareboat Sailing School Course

  • The format allows you to bring non-sailing family and friends to vacation with you and share non-sailing time together
  • You enjoy the privacy of your own air-conditioned hotel room each night
  • The schedule provides free time to explore surrounding areas and enjoy other resort activities
  • Best program for families with teens and tweens moving on to cruising certification
  • More time to practice docking and maneuvers, since no pressure to reach next port

“My overall experience was excellent. This was the perfect balance of classroom and on the water instruction.”

Dawn Bedlivy – Catonsville, MD

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Qualify for Sailboat Charters and Big Boat Cruising

When you enroll in our bareboat sailing school, you may choose to take the Bareboat Charter Cruising Course (learning while staying at the resort throughout) on a monohull or catamaran in the British Virgin Islands or on a monohull only bareboat charter in Florida. Please call early and have several dates in mind, as this charter sailing course fills up fast. The 246-page Fast Track to Cruising companion book is sent to you in advance to study. Feel free to also check out other books available for our courses in the Offshore Sailing School Bookstore! Close, personalized instruction for your bareboat sailing certification is provided by an expert Offshore Sailing School instructor, with Coast Guard license and US Sailing Instructor Certification at the Bareboat Cruising level or higher. Please see the tabs below for more details on our Florida bareboat charters and Caribbean bareboat charters.

“Excellent experience. Colgate is truly the best of the best sailing school. Everything is first class. Colgate delivers a value proposition – an excellent value for the price paid and instruction (and instructional environment) received. The books, the instructor, the hotel classroom, the location in St. Petersburg, FL and the CatalinaMorgan 44’ sailboat were all first class! And well worth the money and time spent.”

Thomas Bisanz – Frisco, TX

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Learn with Family, Friends or Come Alone

If you plan to learn with family members or friends, ask about “Buying the Boat” for a private experience, or our popular sailing lessons for kids where tweens and teens learn for free if everyone in your family is an Offshore Sailing School Learn to Sail Certification Course graduate. Though we normally teach no more than four students aboard a boat, we can take up to five in Private Bareboat Charter Cruising Courses if everyone has strong basic sailing experience, and the fifth person is FREE. Private Bareboat Charter Cruising Courses for Two are also available. We pair singles traveling alone, and couples, with others who want the same BVI or Florida bareboat charter course.

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 details, click here, or visit and search IPC.

A Bareboat Charter Certification Course – whether on a monohull or catamaran – prepares you to sail your own big boat and charter cruising boats 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 Course), the following knowledge and skills are learned and practiced. Here is more information about what you learn in OSS 103/104 Florida bareboat charter courses.

  • Planning a cruise
  • Familiarization with boat layout and sail plan
  • Operation of engine, stove and head
  • 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 and anchoring techniques
  • Proper and safe handling of halyards and lines
  • Proper and safe use of winches
  • Apparent wind and sail selection
  • Sail shape and trim
  • Inter-crew communication when trimming sails, docking and 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

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

  • Multiple scenarios related to wind direction and current while docking 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
  • All covered in Catamaran Endorsement OSS 114

Pre-requisite for Bareboat Charter Cruising Courses: US Sailing Basic Keelboat  (OSS 101) or equivalent experience is required to take this course. US Sailing Basic Cruising (OSS 103) and Bareboat Cruising Certification(OSS 104) and OSS 114 if learning on a catamaran, are included in your course package (normally a $150 extra charge). Unless you would prefer not to take the tests for certification, the US Sailing Basic Cruising and Bareboating textbooks are sent in advance in addition to Colgate’s Fast Track to

Resort Locations

At all locations where this course is offered, your course package includes:

  • Bareboat Charter Course tuition and US Sailing textbooks
  • Five or 6 night’s accommodations ashore at the resort
  • Daily resort fee, per person, allowing you to use all the amenities, WiFi, etc. at the resort
  • Taxes on accommodations and resort fee
  • Practice test mini-cruise at course end without instructor aboard, or onboard as silent observer
  • US Sailing Basic Cruising and Bareboat Cruising Certifications
  • Colgate Logbook (or course log page if you are a returning Offshore Sailing School graduate with a logbook)
  • Certification stickers
  • Course diploma
  • Eligibility to participate in Offshore Cruising Club Flotilla Cruises
  • Exclusive subscription benefit from Cruising World and Sailing World magazines
  • Discount charter benefits from The Moorings

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 information go to and search IPC. Contact us for more information on our bareboat catamaran charters and monohull charters.

Please visit Our Locations for Bareboat Charter Cruise Course packages. Rates vary by season, location, the boat you learn on, and include all the elements listed below. Not included are meals, travel and other expenses you may incur.

Sample schedules, may vary by location, sent to you upon enrollment.

Resort Locations

Sunday –  Arrival Day
No instruction

Monday and Wednesday – Days 1 & 3
9:00-10:00 – Classroom lecture
10:00-1:30  – On-water instruction
1.30-2:00 – Lunch break (or may pick up lunches in morning and lunch underway or at anchor)
2:00- 5:30 – On-water instruction

Tuesday and Thursday – Days 2 & 4
9:00-10:00 – Classroom lecture
10:00-1:00 – On-water instruction
1:00-3:00 – Lunch break and certification tests administered

Friday – Day 5
9:00-12:00 – Test sail without instructor aboard or as silent observer

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 Bareboat Charter 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 Bareboat Charter Cruising graduates have to say:

Fantastic experience!! From classroom to sea, gusts to gale conditions, I couldn’t have asked for a better “classroom” to get prepared for bareboat cruising. Captiva is an idyllic locale, the people friendly and the seafood superb.

Tom Brazelton – Verona, WI

Our instructor Brian was great. His patience level was fantastic and he made the experience a low stress environment. Would highly recommend this course to anybody looking to bareboat in the future.

Jim Richey – Winter Springs, FL

Wonderful experience. It was exciting to learn new things. Joelle was extremely knowledgeable and capable. She had excellent stories that brought to life the points she was making. She was upbeat and full of energy every day and also did a good job of repeating and summarizing information so that we could learn it.

Coral Jeffries – Asheville, NC

All our instructors were ‘sailors’ and ‘teachers.’ They made learning easy, sailing fun, and the experience great.

Terry Brabb – Louisville, KY

Garren was excellent at balancing instruction and patience. This gave me the extra confidence I needed to skipper a catamaran bareboat charter in the BVI with friends.

Chuck Lane – Northbrook, IL

The overall experience was superb. I would recommend the Offshore Sailing School to anyone at any level with an interest in improving their sailing skills and enjoyment.

Chad Montgomery – Knoxville, TN

Great way to spend a week with the family, actually learning a new skill that’s a lot of fun. It’s something we can all do together.

Stephen Nicolia – Collierville, TN

Our instructor gave us confidence without feeling as if we couldn’t make a mistake. My husband and I are going to book a bareboat charter next summer.

Judy Purinton – Blue Jay, CA

My overall experience was excellent. This was the perfect balance of classroom and on the water instruction. I learned a tremendous amount and was very prepared to take the tests. Brian was an excellent instructor – very knowledgeable, knew just when to give us instruction and how much, very patient.

Dawn Bedlivy – Catonsville, MD

Very enjoyable course. Excellent facilities, leaving with a volume of knowledge and experience. Coming back!

Nelson Corbin – Parkton, NC

Top 10 experience – it takes a lot to rattle my feathers, so I pick my words wisely. I needed to learn so much in a short time. It was a blast. The facility, the people, and most important my instructor, Garren.

Rodger Ames – Arvada, CO