Live Aboard Cruising Courses

Learn on a Catamaran or Monohull

During these six-day live aboard sailing lessons you gain incredible knowledge and skills that qualify you for chartering and handling big cruising boats and bareboat cruising on your own. From docking and anchoring, to picking up moorings and maneuvering in crowded harbors, to quick actions in heavy weather, this is the ultimate learning vacation. All Live Aboard Cruising Courses are based at great sailing destinations. If you would like to relax ashore a day or two before the course starts or after it ends, we are happy to make those arrangements for you. We also offer packages for live aboard family sailing!
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“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
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A Cruising Course for Intermediate Sailors

This live aboard cruising course assumes you have small to mid-sized sailboat experience, ready to learn the techniques and skills for handling larger sailboats and bareboat cruising. You may learn on a 43’-50’ monohull or catamarans up to 47’. In the British Virgin Islands, you sail on the newest addition to our fleet – a beautiful Moorings 50.5 – fifty feet of sheer cruising fun. Because of the popularity of our live aboard sailing courses call early and have several dates in mind, especially if you are interested in live aboard family sailing packages. The 246-page Fast Track to Cruising course companion book is sent to you in advance to study. Close, personalized instruction is provided by an expert live aboard sailing instructor with you throughout the first five days. 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
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Learn with Family and Friends or Come Alone

If you are planning a live aboard family sailing vacation, ask about “Buying the Boat” for a private experience in our live aboard sailing school. Though we normally teach no more than four aboard a boat, we can take up to six in Private Courses if everyone has good basic sailing experience. PrivateBareboat Cruising
Live Aboard Cruising Courses for Two are also available.Singles and couples are paired with others in the same course. Often lasting friendships are formed, with classmates cruising together after the course. Your home and classroom is a beautiful cruising monohull or catamaran with three or four cabins, a generous main salon and galley area, hot water showers, swim deck and shower, spacious cockpit, air conditioning (in Florida) and all the equipment you need for safe, successful big boat handling.

“I did this course with 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
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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 for over 35 years. We have an exceptional yacht in our fleet here – the Moorings 50.5, fifty feet of sheer cruising fun. Offshore Sailing School cruising course graduates are now “Captains” in The Moorings preferred charter program. If you take this course in the British Virgin Islands with family or friends, why not continue your cruising adventure with a charter vacation right after you graduate?

For a seamless getaway package, we can add that charter to your live aboard sailing lessons in your vacation package at your Offshore Sailing School discounted Moorings Captain’s charter fee. Just tell your sailing advisor when you sign up for the course that you want to extend your learning experience with a do-it-yourself bareboat charter cruise!

“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 Cruising

Most countries outside the Caribbean, Canada and the United States require an International Cruising Certificate to charter boats in their waters. The International Proficiency Certificate for U.S. citizens is issued by US Sailing – the governing body of Sailing in the United States. If you already have US Sailing Bareboat Cruising Certification you can apply directly to US Sailing for this certificate. Download the IPC Application Form to learn more.

A Live Aboard 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 knowledge and skills will be learned and practiced during your live aboard cruising lessons.

  • 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

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

Certifications: Colgate Coastal Cruising and Colgate Bareboat Cruising Certifications come with this course, when you pass those tests. US Sailing Basic Cruising and Bareboat Cruising certifications are available for a fee of $150 per person, paid at the time you sign up for course. If you opt for US Sailing certification, the US Sailing Basic Cruising and Bareboat Cruising textbooks are sent in advance in addition to the Fast Track to Cruising textbook. Certification testing will then be based on the US Sailing books.


Package rates start at $2530 per person double occupancy, $2710 single occupancy if learning on a monohull; $2740 per person double occupancy, $2905 single occupancy if learning on a catamaran. 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.
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At all locations, your Live Aboard Cruising Course includes:

  • Live Aboard Cruising Course tuition
  • Steve and Doris Colgate’s 246-page Fast Track to Cruising textbook, published by McGraw-Hill (also available in e-book format)
  • Six days living aboard in a shared or private cabin
  • One or more nights accommodation ashore (including resort fee and taxes on both)
  • Or evening start aboard the boat (depends on location)
  • All breakfasts, lunches, snacks and three dinners aboard
  • 24-hour practice test mini-cruise at course end
  • Colgate Coastal Cruising and Bareboat Cruising Certifications
  • US Sailing Basic Cruising and Bareboat Cruising Certifications available for an extra charge
  • Colgate Logbook (or page for logbook if you have our logbook from a previous course)
  • Certification stickers
  • Course diploma
  • Eligibility to participate in alumni-only Offshore Cruising Club Flotilla Cruises
  • Exclusive subscription benefit from Cruising World or Sailing World magazines
  • Discount charter benefits from The Moorings

International Proficiency Certificate (IPC) for Chartering Overseas

If you plan to charter with The Moorings, Sunsail or another reputable charter company in Europe or other areas overseas, you may be required to show your certification certificates or 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. Download the IPC Application Form to learn more.


Sample schedule, may vary by location, sent to you upon enrollment
Sunday –  Arrival Day
No instruction

Monday Day 1
9:00 –  Meet instructor and board boat, stow gear and provisions
Boat show safety briefing and chart briefing as soon as everyone has settled in
Instruction under sail starts right after chart briefing
5:00 –  Drop anchor, pick up mooring or dock’ debrief, relax or study, dinner, anchor checks

Tuesday – Thursday Days 2-4
Sunrise Breakfast and classroom session
9:00 –  Set sail – various drills, practice maneuvers, sail handling, overboard recovery
5:00 –  Drop anchor, pick up mooring or dock; debrief, relax, study, dinner and anchor checks

Friday Day 5
Sunrise Breakfast and classroom session
9:00-noon –  Colgate Coastal Cruising and Bareboat Cruising or US Sailing Basic Cruising and Bareboat Cruising certification tests; final round of docking practice
Noon -sunset –  Test mini-cruise (without instructor aboard, or aboard as silent observer)

Saturday Day 6
No later than noon Return boat to base – graduation party


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 sail@OffshoreSailing.com.

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!

Lauren 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

Rick Hinman was extremely knowledgeable, professional, patient, and all around great guy. He taught so thoroughly and eased my anxiety with his patience and humor. It was an amazing course!! My classroom was a cruising sailboat. We sailed among manatees, dolphins, egrets, falcons and herons. I am a new owner of a sailboat and am eager to try everything I learned at Offshore Sailing School this summer.

Jill Hoovler – Delaware, OH

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


Start Cruising Now!

Call 888-454-7015 or 239-454-1700
Email Sail@OffshoreSailing.com

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