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

Bareboat Charter Cruising Course (next 4 Days) or Live Aboard Cruising Course (next 5 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 3-day Learn to Sail or Performance Sailing course, or no course at all.

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.

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! If you learn aboard a catamaran, you will also receive US Sailing Catamaran Endorsement. 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 for you to read before the course. Please allow up to 4 weeks to receive your certification stickers to add to the logbook you are given at the end of your course.

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 night accommodations* ashore/5 or 6 days private or shared cabin aboard, OR
• Learn to Sail/Bareboat Charter Cruising – 7 or 8 night 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 (sent after the course ends)
• 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
• $300 savings on future Offshore Sailing School certification courses and Colgate Sailing Adventures® flotilla vacations
• *Accommodations are NOT included at the Key West, Florida location

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 https://www.ussailing.org 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. Please call 888-454-7015 to confirm open locations as some resort marinas are under repair from Hurricane Ian in September 2022.

• Tween  Waters Island Resort & Spa, Captiva Island, FL
• Pink Shell Beach Resort & Marina, Ft. Myers Beach, FL (marina not operational currently)
• The Westin Cape Coral Resort at Marina Village, Cape Coral, FL (marina not operational currently)
• Downtown Hampton Inn & Suites, St. Petersburg, FL
• Key West, FL
• Scrub Island Resort, Spa & Marina, Scrub Island, British Virgin Islands
• The Moorings, Road Town, British Virgin Islands (power catamaran course only available here)

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. You will receive your specific Course Schedule with your enrollment documents.

Arrival Day – Check into resort if your package includes lodging
No instruction

Days 1 & 2 Learn to Sail Course
9:00* a.m. – 5:00 p.m. – Learn to Sail classroom session (*Note, this course begins at 8:30 a.m. at Scrub Island Resort, BVI, only), followed by on-water Learn to Sail course instruction aboard Colgate 26, with lunch break on own

Days 3-6 Cruising Course
9:00* a.m. – 5:00 p.m. Meet instructor and board boat, stow gear and provisions. Instruction aboard cruising boat

Day 7 
9:00 a.m. – 12:00 p.m. – Breakfast followed by certification tests; debrief, final round of docking practice
12:00-sunset –  Lunch followed by Practice Sail

Day 8 End of Live Aboard Cruising Course
No later than 10:00 a.m. – Breakfast and return boat to marina, but prepare for up to two hours after to “put the boat to bed,” gather onboard materials, offload own luggage, receive Graduate Certificate of Achievement and logbook, etc. Actual departure from marina may be noon. 

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

Sample schedule may vary depending on weather and which location you choose. Course Schedules vary between Florida and BVI locations. You will receive a specific Course Schedule for your course with enrollment materials.

Arrival Day
No instruction

Days 1 & 2 Learn to Sail Course
9:00* a.m. – 5:00 p.m. – Learn to Sail classroom session (*Note, this course begins at 8:30 a.m. at Scrub Island Resort, BVI, only), followed by on-water Learn to Sail course instruction aboard Colgate 26, with lunch break on own

Days 3 – 5 – Bareboat Charter Cruising Course 
9:00 a.m. – 1:00 p.m. – Lecture followed by on-water instruction aboard cruising boat
1:00 p.m. – 2:00 p.m. – Lunch break (may pick up lunches in morning and be on water all day)
2:00 p.m. – 5:00 p.m. – On-water instruction aboard cruising boat

Day 6 of Bareboat Charter Cruising Course
9:00 a.m. – 12:30 p.m. – Lecture , exam, and review
12:30 p.m. – 1:30 p.m. – Lunch break on own
1:30 p.m. – 5:00 p.m. – Test Sail and graduation

Day 7 – Departure Day
11:00 a.m. – Check out of hotel

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 sail@OffshoreSailing.com.

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 – Miami, 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