There’s something primally enjoyable about the feeling of skirting across the water carried only by the power of wind, the boat beneath you responding to your touch on the helm and your tug on the jib sheet as you chase the horizon. Humans have done this for thousands of years, and it’s undeniably the most romantic way to see the world.
Offshore Sailing School—which is celebrating 60 years in business—has enabled more than 160,000 people to capture this feeling. The US Sailing-certified school offers a wide variety of courses that cater to an array of experience levels, from those who have never stepped foot on a boat before to those looking to hone their racing skills.
“The Annapolis Sailboat Show in October will be the kickoff for all kinds of events in honor of our 60th anniversary,” say Steve and Doris Colgate, Offshore Sailing School’s founder and CEO, respectively. “We can’t wait to celebrate this fantastic community of sailors who continue to learn and live their cruising dreams out on the water.”
The Colgates are two of the most well-known, well-respected names in sailing education. They are what sets Offshore Sailing School apart. “They’re literally at the helm of the company and have been since the beginning,” says Beth Oliver, vice president and director of sales and marketing. Both have authored numerous books on sailing, and Doris also founded the National Women’s Sailing Association. Their many contributions to the sport won the attention of National Sailing Hall of Fame. Steve was inducted in 2015, and Doris was inducted in 2022.
When not traveling and sailing, the Colgates are at their headquarters daily in Fort Myers, Florida, overseeing operations at their four locations (and always scouting other suitable destinations to offer courses). Currently, the school runs courses from two resorts on the Gulf coast of Florida and two in the British Virgin Islands.
In Florida, the locations include ’Tween Waters Island Resort & Spa on Captiva Island. It has a spa, two pools, water toys, bicycles and several new restaurants. The reimagined Old Captiva House features elegant fine dining (reservations are recommended). Next door is The Shipyard, with a more casual flair for meals or light bites. A third option, the Crow’s Nest Steakhouse offers excellent food, craft cocktails, and sunset views over the Gulf of Mexico.
In the British Virgin Islands, Offshore Sailing School operates at a private island oasis, Scrub Island Resort, Spa & Marina, and at The Moorings base on Tortola for power catamaran certification courses. Offshore Sailing School has been the Official Sailing School of The Moorings since 1973.
The quality and depth of instruction is another standout feature. Students learn and race on the Colgate 26, an unsinkable 26-foot keelboat designed by Steve Colgate that allows four students to sail the boat from the cockpit while the instructor has separate space aft.
“It’s our belief that in order to learn how to sail, you should start on a keelboat with a tiller where the boat is very responsive. You can feel the maneuvers that you’re doing, and the boat handles much more efficiently and quickly than a 40- to 50-foot monohull or sailing catamaran, where the maneuvers take longer to execute,” Steve Colgate says. As the rigging replicates that of a larger yacht, the transition to bigger boats is seamless.
While the school has programs that follow both cruising and performance racing tracks, its most popular course is its trademarked Fast Track to Cruising®. It combines the entry-level Learn to Sail with the Bareboat Charter or Live Aboard Cruising course, and graduates leave with three certifications from US Sailing: Basic Keelboat, Basic Cruising and Bareboat Cruising (with Catamaran Endorsement if applicable). “It’s all the certifications that you would need to safely skipper or crew aboard a large cruising yacht with your family and friends,” Oliver says. The Bareboat Cruising certification also enables one to apply to US Sailing for the International Proficiency Certificate, which charter companies require in Mediterranean and other destinations around the globe.
The weeklong course includes two days of learning the basics on the Colgate 26, then students check out of the resort after three nights and move on board a 40- to 50-foot monohull or catamaran for six days. The day before the course ends, students drop off the instructor and spend the last night aboard on their own. “That’s how confident we are that you will be competent at the end of that week,” Oliver says. More-qualified sailors can jump straight into the course’s live aboard portion with an approved sailing resume.
Every program can open a new world for the student. “The phrase ‘this course was life changing’ shows up on probably 50 percent of the evaluations we receive after a course is finished,” Doris says. “Bill Pinkney took a course with Steve years ago and then sailed around all five Capes solo!”
While Pinkney distinguished himself as the first African American to sail around the world solo, graduates of Offshore Sailing School don’t need to be quite so ambitious to enjoy using their new skills. The school offers opportunities to join fellow graduates and other experienced sailors on the company’s Colgate Sailing Adventures® flotilla trips from ports all over the world.
“The Colgates have personally hosted more than 100 of these, anywhere from Spain to Tonga to Greece, and throughout the U.S. and British Columbia. It’s a great way for our students to stay engaged and be with like-minded people on vacation where all the worry has been taken out of it,” Oliver says. The school does the work of chartering the boats, preparing the itineraries, and provisioning. Qualified participants arrive, join their boat, and set off for days of exotic sailing, peppered with sightseeing, sundowner cocktails and beach barbecues. Destinations for 2024 include Florida’s Gulf coast, Belize and Greece’s Ionian archipelago.
“For me, the beauty of these flotillas is they bring together people with all different experience levels, from those who just had this weeklong course to those who’ve been sailing their whole life, and everywhere in between. You’re matched up (based on experience) and put on a boat with no captain or crew — you’re it,” graduate Mike Mahan says. He did his first flotilla trip after his Fast Track course week. More than a dozen trips later, he’s added to his credentials with Offshore Sailing School’s Coastal Navigation and Passage Making course and Offshore Sailing School’s Performance Race Week, and usually serves as the skipper on one of the flotilla yachts.
For anyone looking to go down this path, Doris Colgate has some insight: “The first couple of days may be a bit tiring because you are learning the language of sailing and feeling the amazing experience of making a boat move with wind power alone. In short time, it all comes together; you are in command and have learned a new, rewarding skill that will last a lifetime and introduce you to like-minded, active people who love seeing the world under sail.”
Get started at offshoresailing.com.