Skip to main contentOFFSHORE SAILING SCHOOL SPECIALS & NEWS
Offshore Sailing School is dedicated to giving you the time of your life! British Virgin Islands Powerboat lessons and sailboat cruising instruction, Florida sailing lessons at all levels are exciting, safe, rewarding, and, most of all, fun!
Learn to Sail, Learn to Cruise, and Bareboat Charter courses on sailboats and powerboats.
Available at our Florida sailing schools and British Virgin Islands sailing school and power yacht school.
Sailing. Good for You. Good for the World!®
Kids & ‘Tweens Learn to Sail Free!
Summer is a ‘Coming.
Isn’t it Time to Give You and Your Kids Something Very Special, a Learning Vacation with You . . . Under Sail?
Our popular Kids & ‘Tweens Learn to Sail Sail Free adventure is now open for enrollment!
‘Tweens and Teens family sailing course vacations are a great way to get the kids started in sailing with you at a deep family discount.
Now Up to Three Kids, Ages 7-17, Can Learn to Sail FREE with Two Adults
- Course tuition is free for the kids
- Just two adults pay the regular tuition
Don’t wait! Take advantage of Offshore Sailing School’s signature 3-day Learn to Sail 101 course at our Ft. Myers Beach, FL sailing school.
Come for just the 3-day Learn to Sail 101 course, then add a couple extra days to enjoy the beaches and more wonderful activities that kids really love.
Want to Learn More and Start Family Cruising?
We’ve got you covered there too! Our family Fast Track to Cruising Course starts with two days of the Learn to Sail 101 course, then you and your family members board a spacious 40-47′ monohull or catamaran cruising yacht.
Call today for available dates for the courses below in the British Virgin Islands, Ft. Myers Beach, FL and St. Petersburg, FL.
Sailing. Good for You. Good for the World!®
Hey Guys! How About a Buddy Sailboat or Powerboat Cruising Course . . . Learning Together? 
Get your friends together – three of you – and pay just two tuitions! You each get a private cabin and share the learning experience with best friends. Or make it a 3-generation super adventure, or best buddies getaway. Whichever you choose, the opportunities to start cruising together in exotic ports all over the world are amazing!
New to Sailing or Powerboating or Want to Brush Up Your Skills?
Choose a Fast Track Course or go for just the Live Aboard Course:
- Fast Track to Catamaran Cruising 101/103/104/114
- Fast Track to Monohull Cruising 101/103/104
- Fast Track to Power Cruising 112
Our Sales Advisors Will tell you which of the locations below has availability:
Some facts to know:
- Courses listed available only on select dates for three-for-two buddy option
- Includes shared accommodations ashore, private cabin a cruising boat
- Full payment required at time you book
- Terms & Conditions you sign outline cancellation rules
- Space is limited!
So Many Wonderful Reasons Why a Fast Track Sail or Power Course Will Change Your Life with this Three-For-Two Offer
- Friends and family share a special bonding experience you never forget
- Your skills add up to earning a fabulous passport for seeing the world on a cruising yacht
Call Today! +1-800-221-4326 ♦ +1-239-454-1700 ♦ Sail@OffshoreSailing.com
Sailing. Good for You. Good for the World!®
ALREADY A SAILOR? RENEW YOUR SAILING SKILLS WITH A WEEKEND REFRESHER!
Available only at our Florida Locations
Call Today! +1-800-221-4326 ♦ +1-239-454-1700 ♦ Sail@OffshoreSailing.com
Sailing. Good for You. Good for the World!®
MONOHULL OR CATAMARAN DOCKING REFRESHER
A two-day weekend sailboat cruising course designed to provide ultimate confidence while docking a large sailboat cruising vessel with proficient ease in various wind conditions.
$2,995 per person. Live aboard while learning all day Saturday and up to 3 p.m. on Sunday. To learn more go to Monohull or Catamaran Docking Refresher course, or you can download a PDF: 2024 Weekend Warrior Sailing Class – DOCKING to learn more.
CATAMARAN ENDORSEMENT 114
A two-day weekend sailing lessons course for monohull sailors who wish to move into catamaran sailboat cruising, and for those who may have learned on or own a catamaran seeking more training in operating a catamaran while sailing, docking, anchoring, and picking up mooring balls.
$2,995 per person. Live aboard while learning all day Saturday and Sunday up to 3 p.m. Earn your Catamaran Endorsement 114 for catamaran live-aboard cruising on your own or a catamaran sailboat charter anywhere in the world! To learn more go to Catamaran Refresher & Endorsement course, or you can download the PDF 2024 Weekend Warrior Sailing Class – CAT ENDORSEMENT.
INTERNATIONAL PROFICIENCY CERTIFICATE (IPC) PREP, BAREBOAT CRUISING CERTIFICATION AND CAT
ENDORSEMENT
A three-day big sailboat sailing lessons course designed to help you obtain the IPC (International Proficiency Certificate) for chartering monohulls or catamarans anywhere in the world. $3,495 per person.
Sailing instruction is all day Friday, Saturday, and up to 3 p.m. on Sunday. Includes 3-night stay at partner resort where cruising sailboat is based.
P.S. Getting the IPC is easy when you earn Bareboat Cruising 103/104 certification. The International Proficiency Certificate is required to charter a yacht in many Mediterranean and Carribean sailing centers.
To learn more go to IPC Prep and Cruising Certification or call one of our friendly sailing advisors for more information today!
+1-888-454-7015 or +1-239-454-1700 | Sail@OffshoreSailing.com
PLAN NOW FOR 2026 – JOIN A COLGATE SAILING ADVENTURES® FLOTILLA CRUISE!
Special discounts are available if you earn your Bareboat Cruising Certification from Offshore Sailing School!
+1-888-454-7015 or 239-454-1700 | Sail@OffshoreSailing.com
Offshore Sailing School graduates enjoy wonderful destination sailing trips all over the world. In 2025, two hassle-free cruising adventures include the Amalfi Coast of Italy, and a new Croatia-Montenegro adventure. In 2026, four new cruises are set including the Antigua in the Caribbean, the Bahamas, the Ionian Islands of Greece, and back to fabulous Croatia!
For 2025-2026 flotilla cruising trips and dates, click here.
If you have Offshore Sailing School’s US Sailing Bareboat Cruising Certification and the US Sailing IPC (International Proficiency Certificate), you get the best savings and might even be asked to be the designated skipper of one of the yachts!
+1-888-454-7015 or 239-454-1700 | Sail@OffshoreSailing.com
For Mother’s Day or Father’s Day, How About this Gift!
If you have a sailor or boater in your life you’d like to share a fun adventure with, here’s a book they might not be able to put down. At least that’s what friends tell us when they get this book. There’s a lot of history, intrigue, and excitement in the 61 years Offshore Sailing School has existed. When Steve Colgate started writing his “vignettes,” Doris said, “We need to put these into a book!” And so they did, with the help of a very fine author by the way. It’s an amazing tale of how they built Offshore Sailing School into an iconic brand and turned their lives into a story of exciting adventures. Renowned NY Times and Cruising World magazine author Herb McCormick captured the Colgate story in this intriguing biography. Purchase OFFSHORE High on Amazon.com, or order a special autographed copy here.
+1-800-221-4326 ♦ +1-239-454-1700 ♦ Sail@OffshoreSailing.com
Sailing. Good for You. Good for the World!®
OFFSHORE SAILING SCHOOL IS CELEBRATING 61 YEARS!
Steve and Doris Colgate at the Annapolis Sailboat Show, Annapolis MD
Not too many companies surpass 60 years with their original leaders still at the helm. Living in southwest Florida, those leaders have become somewhat of a legend. As mentioned above, the biography of Steve and Doris Colgate and the history of Offshore Sailing School were published in October 2021.
They’re still leading the way today. Doris was featured in the October 2019 Gulfshore Life Magazine as one of five impressive “Game Changers” in Southwest Florida. Doris and Steve were both featured in a 7-page spread in Gulfshore Life Magazine’s June 2024 issue. Gulfshore Life is a monthly magazine featuring stories about those involved in sports activities, art and artists, philanthropy and philanthropists, theater and other entertainment, fine dining, and more.
Steve Colgate and Doris Colgate are both in the National Sailing Hall of Fame. You can read more about the evolution of Offshore Sailing School in About Us, Steve’s bio and Doris’ bio.
OFFSHORE SAILING SCHOOL GRADUATES ENJOY BENEFITS!
Offshore Sailing School graduates of a US Sailing Certification courses you can enjoy a lot of great benefits. As part of our 60th Anniversary Year celebration, all graduates receive 15% off their next Offshore Sailing School certification course. Read all about exclusive Offshore Sailing School Alumni Benefits here.
Graduate benefits are not extended to any online courses and may not be used for non-certification courses, Colgate Sailing Adventure flotilla vacations, special events, or other discounted programs.
Sailing. Good for You. Good for the World!®
RETIRED & ACTIVE MILITARY SERVICE DISCOUNTS
If you are active military or a retired veteran, we thank you for your service, and offer you a 10% discount on your certification course package with resort stay at one of our Florida locations. You may choose any 3-day or longer Learn to Sail, Fast Track to Cruising®, or Live Aboard Cruising Course. When you enroll please mention you are active or retired military, as retroactive credit is not available. You will also be asked to send us a copy of proof of your military status.
The 10% veterans / active duty discount may not be used with other discount promotions or on other courses and programs offered by Offshore Sailing School. The discount only applies to the specific military personnel’s portion of the course package, not others in your party. To learn more, please get in touch with us here, call us, or email us. Thank you again for your service!
+1-888-454-7015 or 239-454-1700 | Sail@OffshoreSailing.com
Sailing. Good for You. Good for the World!®
OFFSHORE SAILING SCHOOL GRADS SHARE SAILING AND POWER CRUISING STORIES
Offshore Sailing School grads send lots of comments and photos. Here’s just one of many that will inspire you to join the sailing lifestyle . . .
I took the Fast Track to Cruising course with my 19 year old son. We learned so much and feel so confident and excited to take our family out on a charter. It was probably the most memorable, exciting trip we have ever taken. It is a great investment into our family’s future vacationing and lifetime of learning to sail. All of the instructors we had were super knowledgeable, easy going and friendly and made the course very educational and enjoyable.
David Haber (on right in photo) – Armonk, NY
Sailing. Good for You. Good for the World!®
POST A GOOGLE REVIEW
SIGN UP FOR OUR NEWSLETTER
We invite our graduates to post a Google review here. Our weekly newsletter is filled with interesting stories, industry updates, and sailing course specials. Visit our Sailing Newsletter Sign-Up page.
