Instructional Charters in High Demand as Boaters Seek Practical On-Water Training

Instructional charters — weeklong trips that combine cruising with hands-on training — are experiencing a notable surge in popularity. Both novice and experienced boaters are signing up in large numbers, creating strong demand for instructors and training-equipped vessels across Florida, the Bahamas and the Virgin Islands.

“We have more boats than we have instructors,” says Beth Oliver, director of marketing for Offshore Sailing School, the official sailing school of The Moorings. “We would hire five more tomorrow if we could find them.”

Interest in learning and improving boating skills grew during the pandemic and has continued since. For many people, instructional charters are the ideal way to gain confidence on different boats, brush up on seamanship, or take advanced navigation and passagemaking classes — all while enjoying a warm-weather cruise.

Who’s Booking Instructional Charters

Bookings come from a broad mix: first-time boat buyers who want to learn basic handling, owners of small cruisers seeking experience on larger trawlers or catamarans, and seasoned sailors aiming for advanced certifications such as celestial navigation or offshore passagemaking. Some customers are owner-operators who want a trial run in a new cruising area before bringing their own boat south.

“The big thing now is that everyone and their brother wants to buy a boat and do the Loop,” says Barb Hansen, co-owner of Southwest Florida Yachts. Whether customers know all the details of a trip like that or not, many are eager to gain the skills needed for extended cruising.

Southwest Florida Yachts sees steady bookings for weeklong charters that combine warm-weather vacationing with directed instruction. Frequently, a client will request a captain for the first day or two to get comfortable with a new or larger vessel — then spend the remainder of the week on a bareboat basis. That short-term professional guidance helps with unfamiliar systems, larger beams, or different handling characteristics.

Customizable Training and Focus Areas

Instructional charters can be tailored to match the student’s experience and learning goals. Providers ask about the types of boats customers already operate and the cruising they have done so they can design a curriculum that fills gaps. For example, some boaters who routinely move from dock to dock may never have anchored overnight; instructional charters provide practical lessons in anchoring, setting scopes, and handling snubbers and rode under real conditions.

Offshore Sailing School follows US Sailing curriculum standards but adapts the focus as needed. Couples or families who charter an entire boat can receive instruction at different levels as long as each participant demonstrates proficiency in required skills. Advanced courses are also available for those with prerequisites.

Unique Program Styles and Flotillas

Cruise Abaco in the Bahamas operates a program that combines daytime captain-led training with bareboat evenings: the captain disembarks each night so guests can navigate to the next island on their own. “It’s captain by day and bareboat by night,” says co-owner Mark Gonsalves. This approach blends solid instruction with a genuine boating vacation and hands-on experience.

Offshore organizes advanced offerings like performance racing, coastal and offshore passagemaking, and celestial navigation. They also run flotillas that follow a lead boat, allowing participants to learn a cruising area in a supported group setting. Flotillas can create lasting social connections; many participants return year after year to cruise together.

Fleet Growth and Instructor Recruitment

High demand has prompted fleet expansions and new hires. Cruise Abaco expanded from a smaller operation to a larger fleet and recently added captains to meet interest. Similarly, providers like Offshore report strong bookings across locations such as Scrub Island in the British Virgin Islands, and have added vessels to offer more weekly options.

Some powerboat owners are even choosing sailing cats for comfort and space. They may motor much of the time but still benefit from the training and additional room aboard larger cruising catamarans.

Why Boaters Choose Instructional Charters

Instructional charters offer a low-stress, immersive way to learn: real-world practice, immediate feedback from professionals, and the chance to gain competence on a variety of boats. For many, the experience becomes part of a lifestyle — a way to travel, build skills, and connect with a community of fellow cruisers.

Offshore notes reciprocal discounts with The Moorings for graduates, reinforcing the connection between instruction and longer-term cruising plans. Whether someone sailed a small dinghy decades ago or captains a private boat now, instructional charters provide structured learning and memorable voyages.

This article was originally published in the December 2021 issue.