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OFFSHORE 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 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 Can Learn to Sail FREE with Two Adults
- For families with at least 2 adults onboard, and up to 3 kids ages 7-17
- Course tuition is free for the kids
- Just the 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 the whole family will 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.
- Minimum age for the Fast Track to Cruising course on a monohull or catamaran is usually 12
- Two adults required
- Family “buy the boat” pricing less 10% available for courses May through August
Call today for available dates for these Fast Track courses 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?
Get your best buddies together – three of you – and pay just two tuitions!
For newbie sailors: Choose a Fast Track to Cruising course on a Monohull or Fast Track to Cruising Course on a Catamaran. The first two days you learn on the basics of sailing on a Colgate 26 keelboat. Then you board a 40′-47′ monohull or catamaran and live aboard for the next 6 days, learning and having a ton of fun together!
For experienced sailors: With good experience sailing a 20′-30′ keelboat (or larger), sign up for the Live Aboard Course on a Monohull or Catamaran and skip the first 2 days of the Fast Track course.
For power boaters: Choose the Fast Track to Power Cruising Course on a power cat and delve into how to handle a 48′ power cat with confidence and finesse
Whichever you choose: The opportunities to immediately start cruising together in exotic ports all over the world are amazing!
How do the Buddies courses work?
- One person signs up all three of you in order to get the discount.
- Just two tuitions are charged in the Fast Track or Live Aboard portion of the total package.
- Three best buddies each get a private cabin.
- Make it a 3-generation super adventure, and each of you get a private cabin too.
- Full payment is required at the time you sign up.
- No discounts or refunds allowed should one of you cancel or not show up.
- Terms & Conditions you sign outline cancellation rules.
- Select dates for this offer, check with a sales advisor to find out more.
Our Sales Advisors will tell you which of the locations below has availability:
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 and lifetime adventures 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!
Weekend Refresher courses are for experienced sailors who want to renew skills before putting their boats back in the water, or setting out on a bareboat charter, or just go sailing with friends. Here is a list of what you’ll find on the Weekend Refresher Page. No special discounts on these, they are short courses, priced to give you what you expect from our expert and caring instructors. Here are your options:
- 2-day Monohull or catamaran docking refresher 111 – $2,995 per person
- 2-day Catamaran Endorsement 114, $2,995 per person
- 3-day International Proficiency Preparation (IPC) with Bareboat Cruising Certification 103/104 and Catamaran Endorsement 114, $3,495 per person
Available only at our Florida Locations
The Catamaran Endorsement Course (114) was great. Kelly put us through our paces, explained clearly what was required, demonstrated handling techniques brilliantly, and made sure that each of the three of us had equal time skippering, handling close quarters evolutions, raising and lowering the sails,, reefing, anchoring, and picking up moorings. Although I have extensive sailing experience, it has all been aboard monohulls. At the end of the course, I felt confident in my ability to handle a large catamaran. A terrific experience.
Luke van Praag – East Hampton, NY
Check out all the weekend refresher courses here.
Call Today! +1-800-221-4326 ♦ +1-239-454-1700 ♦ Sail@OffshoreSailing.com
Sailing. Good for You. Good for the World!®
PLAN NOW FOR 2026 – JOIN A COLGATE SAILING ADVENTURES® FLOTILLA CRUISE!
Tahiti Flotilla Crew with Ari and Paulina from Motu Grill, Bora Bora
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!®
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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.
