Get Started:

Call: (888) 454-7015

Fast Track to Cruising® Courses — OSS 101/103/104

An Offshore Sailing School Bareboat Cruising Certification Exclusive

Don’t be fooled by copy-cats trying to trade on the Offshore Sailing School brand and trademarks. There is only one program – the Fast Track to Cruising® Course developed by Offshore Sailing School in 2006 – that truly gives you the knowledge, skills and confidence to handle sailboats up to 50’ without hired captain or professional crew. After staying at resort Friday – Sunday nights while learning to sail aboard a Colgate 26, the cruising portion is available as a Live Aboard (for 5 nights) or Bareboat Cruising (stay-ashore for five nights).

Couch to Captain’s Chair in One Week!

  • Two days learning on an award winning Colgate 26
  • Six days learning on a 43′ to 50′ monohull or 40′ to 48′ catamaran (includes OSS 114 Endorsement if learning on a catamaran)
  • Three certifications including Bareboat Cruising Certification
  • All in one amazing week with the finest instructors you’ll find anywhere
  • You’ll also have the ability to apply to US Sailing to receive the IPC, International Proficiency Certificate, required by charter companies in certain European countries

888-454-7015 or 239-454-1700 •

Offshore Sailing School has been the Official Sailing School for The Moorings charter company for more than 40 years. Our standard monohull for Bareboat Cruising Certification in the BVI is a Moorings 51.4, fifty feet of sheer fun with four private ensuite cabins, that gives you the confidence to charter any size boat anywhere!

Florida sailing and cruising school

“My wife and I had an absolutely wonderful experience in the Fast Track to Cruising Course in the British Virgin Islands. The instructors were excellent – extremely knowledgeable and patient. I had some small boat experience and my wife was a complete novice, but we’re now comfortable and excited to take our first bareboat charter on our own.”

Wyatt Blasingame – Morrison, CO

Read more testimonials here 

No Experience Required

Whether you have no sailing experience, sail small boats, or are returning to sailing after a long hiatus, this is the perfect sailing training course. You can learn internationally or locally at the Florida sailing and cruising school as well as other US locations. You will be amazed at how much you learn, starting with the comprehensive Fast Track to Cruising textbook you receive in advance, then receive comprehensive training in the classroom and hands-on training on the water from professional, experienced instructors who receive accolades from their students on course evaluations.

Florida sailing and cruising school

“One of the most productive vacations I have ever been on. The instructors were amazing, I learned a lot and had so much fun. I can’t stop telling everyone I know how cool this experience was. I will be sending my parents this trip as a gift.”

Charles Zahalka, MD – Las Vegas, NV

Read more testimonials here

Programs for Women-Only are Available Too

The Fast Track to Cruising® course for women only is an exclusive and very rewarding opportunity for women to enjoy the camaraderie of other women while learning from expert US Sailing-certified instructors.

“My husband and I have been bareboat chartering for the past 10 years. It was our 17 year old daughters that wanted to get certified. They wanted to ensure that they could sail on their own one day. We took the live aboard as a family and took our knowledge and skills to the next level. We all now know “why” we make each sail adjustment, tack, jibe, etc. Sailing is now a bigger thrill than ever.”

Susan Burns (with her two daughters in the photo) – Nashville, TN

Read more testimonials 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 (OSS 106 and OSS 108), the next step in your learning process.

Our Fast Track® sailing courses prepare you for charter cruising, without professional captain and crew aboard (called Bareboat Cruising by charter companies). You start with the Learn to Sail course and continue with the Bareboat Charter Cruising Course format where you stay ashore at night, or the Live Aboard Cruising format (see both below). 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 are learned and practiced.

Learn to Sail Course – First Two Days

  • Nautical terminology
  • Rigging and sails
  • Getting underway
  • Proper winch techniques
  • Finding wind direction
  • Points of sailing
  • Tacking and jibing
  • Wind and sail interaction
  • Maneuvering in close quarters
  • Wind pressure and lift
  • Heeling and stability
  • Apparent wind
  • Wind shifts
  • Sailing wing and wing
  • Stopping and starting under sail, without an engine
  • Sailing backwards, no engine
  • Rudderless sailing
  • Sail trim and sail shape
  • Boat balance
  • Hull speed
  • Mooring and anchoring
  • Docking under sail
  • Most used knots
  • Right-of-way rules
  • Grounding remedies
  • Heavy weather techniques
  • Reefing sails (reducing sail area)
  • Steering with a compass
  • Sailing in current
  • Weather and lee helm

Bareboat Charter Cruising Course (next 5 Days) or Live Aboard Cruising Course (next 6 Days)

Bareboat Charter Cruising: Sleep at the resort or home while you sail and learn during the day. This schedule provides free time to enjoy the resort if you have accompanying family or friends taking a 5-day Learn to Sail or Performance Sailing course, or no course at all. Best schedule if you prefer the privacy and amenities of a hotel room at night.

Live Aboard Cruising: Board the boat and live aboard while moving from port to port. A unique learning experience that immerses you in the cruising lifestyle, with classroom aboard before setting sail each day, sleeping in a private or shared cabin, sharing common space and meal preparation with classmates. You do all the cooking and cleaning up, just like you would if you were bareboat chartering. There is no chef and the instructors do not cook your meals. Cooking aboard is part of the learning process.

  • 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
  • Meal preparation aboard (there is no chef)
  • 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
  • Proper docking techniques for catamaran including spring lines and other dock lines

Pre-requisite for the Fast Track to Cruising® Course: No prior sailing experience required

Three Certifications: US Sailing Basic Keelboat, Basic Cruising and Bareboat Cruising are included with all resort packages! Normally a $150 extra charge, Offshore includes this cost and you earn these certifications when you pass those tests, unless you’d rather not take the tests. US Sailing Basic Keelboat, Basic Cruising and Bareboat Cruising textbooks are sent in advance in addition to our Fast Track to Cruising® textbook.

Resort Locations

At all resort locations, your cruising course includes:

  • Learn to Sail and Bareboat Charter Cruising or Live Aboard Cruising Course tuitions and US Sailing textbooks
  • Learn to Sail/Live Aboard Cruising – 3 nights accommodations ashore/5 or 6 days private or shared cabin aboard, OR
  • Learn to Sail/Bareboat Charter Cruising – 7 or 8 nights resort accommodations depending on location, sleep ashore throughout
  • Daily per person or per room resort fee (depending on location) covering all amenities, services, WiFi at resort
  • Mandatory taxes on shore accommodations and resort fee
  • All breakfasts, lunches, snacks and three dinners from Monday lunch through Saturday breakfast during Live Aboard Cruising Course, except two dinners ashore during cruising course
  • Practice test cruise at course end
  • US Sailing Basic Keelboat, Basic Cruising and Bareboat Cruising Certifications (all three available for an extra fee), and US Sailing Catamaran Endorsement certificate if you learn aboard a catamaran
  • Offshore Sailing School Logbook with certification stickers
  • Course diploma
  • Eligibility to participate in future Colgate Sailing Adventures® hosted flotilla vacations
  • Exclusive subscription benefit from Cruising World or Sailing World magazines mailed to US address
  • Discount charter benefits for first charter with The Moorings
  • 10% savings on future Offshore Sailing School certification course if you book next course within six months of completing last 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 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.

Please see Our Locations for more information.  Packages include everything listed below. Rates vary by season, location, type of boat (monohull or catamaran), and whether you choose a shore-based or live-aboard course. Not included are meals unless otherwise noted, travel and other expenses you may incur.

  • Fast Track to Cruising – 8-days with Live Aboard Cruising Course at resort locations

    Sample schedule may vary depending on weather and which location you choose.

    Friday – Arrival Day
    No instruction

    Saturday & Sunday – Days 1 & 2 Learn to Sail Course
    9:00-10:00 – Learn to Sail classroom session
    10:00-1:00 – On-water Learn to Sail course instruction – Colgate 26
    1:00-2:00 – Lunch
    2:00-5:00 – On-water Learn to Sail course instruction – Colgate 26

    Monday – Day 3 – First Day of Live Aboard Cruising Course
    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 4-6 – Live Aboard Cruising Course
    Sunrise – Breakfast and classroom session
    Colgate Day Sailing or US Sailing Basic Keelboat certification test, Wednesday
    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 7 – Live Aboard Cruising Course
    Sunrise – Breakfast and classroom session
    9:00-12:00 – Course continues with certification tests; debrief. final round of docking practice
    12:00-sunset – Test mini-cruise (without instructor aboard, or with you as silent observer)

    Saturday – Day 8 – End of Live Aboard Cruising Course
    No later than noon – Return boat to base


    Fast Track to Cruising – 7-days with Bareboat Charter Course at resort locations

    Sample schedule may vary depending on weather and which location you choose.

    Friday – Arrival Day
    No instruction

    Saturday & Sunday – Days 1 & 2 Learn to Sail Course
    9:00-10:00 – Learn to Sail classroom session
    10:00-1:00 – On-water Learn to Sail course instruction – Colgate 26
    1:00-2:00 – Lunch
    2:00-5:00 – On-water Learn to Sail course instruction – Colgate 26

    Monday and Wednesday – Days 3 and 5 – Bareboat Charter Cruising Course (Full Day Sailing)
    9:00-10:00 – Classroom lecture for all
    10:00-1:30 – On-water instruction on cruising boat
    1:30-2:00 – Lunch break (may pick up lunches in morning and be on water all day)
    2:00-5:30 – On-water instruction on cruising boat

    Tuesday and Thursday – Days 4 and 6 of Bareboat Charter Cruising Course (Half Day Sailing)
    9:00-10:00 – Classroom lecture for all
    10:00-1:30 – On-water instruction on cruising boat
    1:30-2:00 – Lunch break
    2:00- 3:00 – Certification tests taken

    Friday – Day 7 of Bareboat Charter Cruising Course (Half-Day Sailing)
    9:00-12:00 – Test sail without instructor aboard or as silent observer on cruising boat

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 Fast Track to Cruising® Courses. 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 some of our Fast Track to Cruising graduates have to say. There are many more with contact information in our Alumni Testimonials section.

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


I went from novice, wondering if sailing was for me, to a sailing enthusiast – comfortable with a large boat, in one short week. 

Mike Mahan – Live Oak, FL


The experience was outstanding. My wife was so worried she would not enjoy it; I thought she would bite her nails off and pull her hair out on the trip down to the class. About 2/3 of the way through the week she thanked me for making her come and still says it was one of the best weeks she has ever had. She is telling everyone she sees to do it. My thanks to the instructors for their patience and caring, not to mention their humor. 

Steve Allen – Albany, GA


This experience was life-changing and opened my eyes to a whole new world of opportunities. Before taking this course I had never sailed, yet alone been on a boat. I never imagined that after only one week I would be sailing with confidence. I entered the course excited and terrified, but the moment I arrived I felt a sense of ease. My instructors were extremely patient, never intimidating, and always encouraging. The difference between Offshore Sailing and other organizations is that both of my instructors had extensive experience and knowledge in sailing. 

Jennifer Card – Chicago, IL


My wife and I are planning on purchasing a boat in the next few years and I feel this course was a great decision in preparing us to own a boat. 

Joseph Boucher – Pasadena, MD


We had an amazing experience! Mike and I really only took this course because it was important to my brother-in-law who had a passion to learn and we wanted to spend time together. Neil took two beginners with only slight curiosity and made us extremely passionate to sail and continue the journey. He’s an amazing teacher with the patience of a saint!! We came away with way more knowledge and excitement to learn. We rented the 4600 catamaran right after our courses which will allow us to put all this great info to work. 

Heather Nichols – Solana Beach, CA


I just wanted to let you know what a great time I had in St. Petersburg. Everything was perfect from the accommodations, weather, boat, instructor and classmates. The boat was provisioned perfectly. I couldn’t be happier with the experience I had at Offshore Sailing School and want to congratulate you on a superbly run organization. Cory was a great instructor and a fun guy to share a week with. 

Brad Vaughan – Overland Park, KS


It is obvious that Offshore Sailing School puts a lot of effort in their selection of instructors. We thoroughly enjoyed the class and look forward to getting back out on the water with newly gained confidence in sailing. My wife and I have very different learning styles. Jim recognized that quickly and adjusted his teaching where we were both able to grasp the subjects covered and apply them in an actual sail experience. This was a family course for us and my two children (9 and 11) were a little apprehensive at times throughout the week. Despite that, on our sail Friday without an instructor, they all put what they learned to work and we had an excellent day at sea! 

Kyle Couture – Birmingham, AL


I now feel much better equipped to handle our boat and I can’t wait to get out on the water. Both instructors had infinite patience. Both instructors were excellent. They taught clearly, patiently and were very encouraging. I felt comfortable under way in a way I never have before. 

Mary Frith – Hamilton, Bermuda


Everything we encountered has made me more confident of my sailing skills. The food choices were excellent and the quantity good enough to have only a bit left over. The quality of literature is priceless and this well-developed program is truly a blessing. The Jeanneaus are in great shape. A pleasure. Thanks for the memories AND the much needed time at sea!! 

Lynn Mendelman – East Hampton, NY


Thank you for a great learning experience! Your very knowledgeable instructors, good balance between classroom and on water time and small class size provides a unique experience which leaves students with skills and knowledge that will last a lifetime. Truly an amazing week! Thank you Steve and Doris Colgate for your incredible sailing school! Congratulations on the 50 year anniversary of Offshore and wishing you 50 more years of continued success!! Thanks for letting me be part of it!!! 

Judith Azzarello – Willow Spring, IL


A true pleasure, excellent instructor. Experience was superb!! I am very excited to get out on the water in Canada. 

Cindy Sorockan – Edmonton, ALB