Let's Go Sailing!
Whether you've set your sights on learning to sail, baby's first bareboat charter, or casting off for bluewater adventures, a school close by can provide classroom and hands-on instruction that fits your goal and budget. From our May 2012 issue.

When I stepped aboard a sailboat for the very first time almost 15 years ago, I was amazed and overwhelmed by—well, everything. Putting a new vocabulary into practice, safely directing the boat to where you want to go, returning vessel and crew to the dock at the end of the day—these were only the early challenges. For sailors who are interested in heading offshore or on an extended cruise, the required skill set is large and varied: navigation, boat and engine maintenance, communications, weather prediction, route planning, provisioning—the list goes on.
In the days of yore, if a prospective cruiser wanted to gain skills in these areas, the choice was pretty much limited to the School of Hard Knocks. These days, fortunately, that’s not the only school available, and no matter where you’re starting from or what your goals are, you can find a sailing school that’s right for you.
Goal: Bareboat Charter
Many sailing schools offer a “learn-to-bareboat” type of class that can often take you from landlubber to sailor in a week. The classes are typically based on American Sailing Association or US Sailing plans of study and include basic sailing, coastal cruising, and bareboat-charter instruction. The coursework is usually quite intense because there’s plenty of ground to cover. Once a student has completed a course, testing for certification is an option.
Steve and Doris Colgate’s Offshore Sailing School has been perfecting this model for years, and their Fast Track to Cruising course is the school’s most popular. No experience is necessary to enroll in this course, and the first two days are spent learning to sail aboard a Colgate 26, the school’s training sailboat. Students then spend the next five days aboard a 43- to 50-foot monohull or cruising catamaran to cover the coursework in Basic Cruising and Bareboat Cruising. The real test, however, comes at the end of the week, when the students take the boat out for 24 hours without the instructor. “I really think the last day was my favorite part of the class,” says Offshore Sailing School student Tom Huntington. “The other two students and I took the boat out on our own, and we had to decide on an anchorage, make dinner aboard, reef the sails in bad weather, and understand the varying depths while navigating the Intracoastal Waterway. This really helped to solidify the previous four days of coursework.”
Photo: Courtesy of Offshore Sailing School
Florida Sailing & Cruising School, in North Fort Myers, Florida, offers something similar. “Since people are so short on time these days, our most popular course is the five-day class,” says owner Barb Hansen. “It’s an intensive course that takes students from the basic sailing course through the basic coastal-cruising level and finally ends with the bareboat-charter class. After they complete the course successfully, I also recommend that people start to charter or go out on boats with friends to get as much hands-on experience as possible.”
There’s plenty to consider when deciding which sailing school is right for you, including location, the boats used for instruction, and class size. “The top schools provide sufficient classroom time to understand sailing principles but maximize time on the water,” says Captain Dave Bello of Fair Wind Sailing School. “They also keep class size low to limit the student-to-instructor ratio.”
Photo: Fair Wind Sailing School
Be sure to keep your goals in mind when choosing a sailing school. If your immediate goal is to bareboat charter in the Virgin Islands, consider taking a course there on a boat similar to what you’d like to charter. If your goal is to go cruising on a catamaran or to improve your racing skills, there are courses for that, too.



