Bareboat Sailboat and Live-Aboard Cruising Courses
Bareboat Cruising is a popular phrase coined by the first sailboat charter companies around 1970. Bareboating is self-hire cruising – like renting and driving your own car versus hiring a limousine with a chauffeur.
Bareboat Sailing is chartering a sailboat you can live on, without professional captain or crew to help you sail the boat. Everything you need for cruising comfort and safety including sheets, towels, galley and other gear, even food and beverages is part of the package.
Three Ways to Learn to Cruise
If you want to start sailing big boats on your own or charter, but aren’t ready for a larger yacht, all of our cruising courses offer the very best instruction you'll find. Three course choices and several schedules are available for this ultimate learning vacation. All of the choices below are offered as LIVE-ABOARD or LIVE-ASHORE experiences.
Where you can 
take these learning vacations
- Captiva Island, Florida – sailing on Pine Island Sound and the Gulf of Mexico
- St. Petersburg, Florida – sailing on Tampa Bay
- Ft. Myers Beach, Florida – sailing on the Gulf of Mexico
- St. Michaels, Maryland – sailing on the Miles River and Chesapeake Bay
- Tortola, British Virgin Islands – sailing in Sir Frances Drake Channel among the islands of the British Virgin Islands
Offshore Sailing School is the
Official Sailing School for The Moorings
A 37 Year Partnership
Fast Track to Cruising®
Fast Track to Cruising® takes you from no or little sailing experience to ready-to-cruise in one week. This is the course to take if you don’t have basic sailing skills and certification at the Basic Keelboat or Day Sailing level. You start with two days on a tiller-driven Colgate 26, then go straight to an awesome 43-50 foot cruising yacht for five days of truly comprehensive training.
Throughout this seven-day experience you build confidence and skills for your test mini-cruise without the instructor coaching and fabulous sail-charter vacations on a chartered or personally owned yacht. You’ll go home with three certifications and the skills to sail wherever the wind blows. If you already have Day Sailing or Basic Keelboat Certification (or equivalent experience), you can by-pass the Learn to Sail level and head straight to cruising.
Bar
eboat Cruising Preparation
If you take the five-day Bareboat Cruising Preparation course, you'll learn to cruise in five days on a 43-50 foot cruising sailboat while living ashore in a resort hotel or commuting from home.A five-day half-day schedule is available at our Chesapeake Bay campus, sailing by day on a brand new Hunter 50.
For some our standard half-days package is preferred, allowing for free time to study or share a multitude of other resort attractions with accompanying family and friend. With all our Bareboat Cruising Preparation course schedules, a test practice cruise without the instructor coaching aboard highlights this popular program.
This is a fun and relaxing way to get all the bareboat skills you need for cruising on your own or friends’ sailboats back home or chartering in exotic ports all over the world, while sleeping each evening in the privacy of your hotel room at night. You'll need Colgate Day Sailing or US SAILING Basic Keelboat Certification (or equivalent experience) for this course, and will achieve Basic Cruising and Bareboat Cruising Certification at course end. The Offshore Sailing School Bareboat Cruising Preparation Course — your passport to confident, safe big boat sailing
This course is available in two schedules over a five-day period:
- Half-days of instruction for those who want time to enjoy other resort amenities with friends or family
- Schedules start Monday (arrive Sunday evening) and end Friday afternoon (depart Friday late afternoon or the following day)
- See course locations for schedule options
Live Aboard Cruising
The ultimate dream for most sailors is to cruise exotic islands and see the world under sail. Go where the wind takes you. At a pace set by the rising moon and setting sun.
The Live Aboard Cruising course experience gives you a taste of all this (though of course you are on a schedule which includes all the components you need to learn for successful big boat cruising.
Live Aboard Cruising provides the joys of cruising while learning! This is real live-aboa
rd cruising and you can experience it with Offshore Sailing School, earning your Bareboat Cruising Certification in just five days on a beautiful 43' or 46' catamaran or 43'-50' monohull.
If you already know the basics of sailing (equivalent to our Learn to Sail course) and want to move up to bigger boats to get the true feeling of what it's like to live and learn aboard, this week-long course is for you.
Liveaboard Cruising is a truly remarkable experience for any sailor. Your classmates are others who want to learn the same skills, with accommodations in private cabins for singles and shared cabins for couples taking the course together. You need the same boat handling skills and experience as we require for the shore-based Bareboat Cruising Preparation course, and will receive the same certifications at course end.
Bareboat Refresher
Do you already have big boat experience and just need a refresher? Thinking of doing a bareboat cruise in the Caribbean but feeling a little rusty? Our Weekend Bareboat Refresher course brings you up to speed in ten hours of hands-on training on one of our 432' to 50' cruising boats or our Leopard 46 catamaran.
All you need is US SAILING or Offshore Sailing School Bareboat Cruising certification (which comes with the cruising courses listed above). You may also take this Refresher if you have equivalent experience to what you learn in our Live Aboard Cruising or Bareboat Cruising certification courses. This weekend program is designed to put you back on the helm after being away from sailing for awhile.