How to Gain Sailing Experience For Aspiring Cruisers

If your goal is to become a sailing cruiser, it’s important to ask how to gain sailing experience, the right sailing experience! Sailing schools teach students to sail, which is necessary. However, it’s only part of a cruiser’s skillset toolbox. Let’s examine the pros and cons of three avenues for gaining sailing experience: traditional sailing schools, chartering a sailboat, and the Sailing Lifestyle Experiences we offer.

How To Gain Sailing Experience – Sailing School Pros

Systematized Learning: Sailing schools offer a structured curriculum, providing a step-by-step progression of skills. This can be especially beneficial for beginners and those seeking a traditional education. This approach is also good for those who like to earn certificates.

Professional Instructors: Sailing schools typically have certified and experienced instructors who can provide hands-on guidance and valuable insights. Most instructors, however, are not sailing cruisers. They know how to sail a boat, but their skillset does not extend to bluewater boat ownership, maintenance, and servicing.

Diverse Courses: Schools offer a range of courses, from basic keelboat instruction to advanced offshore cruising, allowing individuals to tailor their education to their specific needs.

Safety Emphasis: Schools prioritize safety, ensuring that students learn essential safety procedures and practices.

Sailing School Cons

Cost: Sailing schools can be relatively expensive, especially considering multiple courses and people (your partner and family). The cost includes instruction, using the school’s boats, and sometimes accommodation.

Time: Schools have a variety of courses, each taking a substantial amount of time. Taking all the courses could take many months and even years.

Limited Real-World Experience: While you gain valuable theoretical knowledge, some argue that the controlled environment of a sailing school may not fully prepare you for the unpredictable nature of real-world cruising.

Sailing-Only: Sailing schools focus only on sailing. They don’t teach servicing, maintenance, provisioning, cleaning, budgeting, or other boat ownership skills. They also don’t focus heavily on the core required sailing cruiser skills. Those skills include maneuvering in tight spaces, anchoring, mooring balls, and docking.

Also, many sailing schools teach antiquated skills, such as plotting passages using dividers and charts. Nowadays, sailing cruisers use modern technology that seamlessly marries weather, navigation, and passage planning. Neither commercial nor recreational boats carry charts anymore. Another example of limited experience is that most sailing schools are in lakes or protected harbors, providing an environment different from real-life cruising.

Bareboat Sailing Charter Pros – How To Gain Sailing Experience

Real-World Experience: Chartering allows you to apply your sailing skills in a real-world setting. It’s learning by doing, and you experience the challenges and joys of sailing firsthand.

Flexibility: You can choose your destination, boat type, and duration of the charter. It’s a great way to test the waters before committing to a long-term cruising lifestyle. For example, if you have your heart set on sailing in Thailand, you can first charter a boat to ensure it truly ticks all boxes. Or, perhaps you want to buy a catamaran but have only ever sailed on monohulls. Charting a catamaran will give you a taste of the type of boat.

Cost-Effective for Short-Term Learning: Chartering can be a more cost-effective option for those looking for a shorter-term sailing experience than a full-fledged sailing school. There are, however, other ways to how to gain sailing experience.

Bareboat Sailing Charter Cons

Self-Guided Learning: While some charter companies offer briefings, you’re largely responsible for your learning. The quickest way to learn the sailing life is to make mistakes, but it’s not beneficial if you don’t have someone with you to demonstrate where you went wrong or how to do things correctly.

Boat Familiarity: Charter boats vary, and you may need to adapt to different models and equipment, which could be challenging for those still learning the basics.

Limited Instruction: Charter companies do not provide extensive instruction, and the level of support can vary. In some cases, you can hire a captain, however, charter captains are not teachers, nor do they have knowledge about the cruising lifestyle. This may leave you feeling less confident if issues arise.

Learn how to become a confident sailing cruiser! Full details on our experiences here: Sailing Lifestyle Experiences

Our Sailing Lifestyle Experiences Pros

Personalized Coaching: Our Experiences offers a personalized approach, focusing on coaching and mentoring. This can be highly beneficial for families or couples seeking tailored guidance.

Free-Flowing Learning: Rather than teach skills that are no longer used or cover elements that are too basic or too advanced, our Sailing Lifestyle Experience focuses on what you and your partner/family want to learn and then provides a safe and effective learning plan.

Sailing-Lifestyle Immersion: Our Experiences are about the LIFESTYLE and not just sailing. Not only will you learn or improve your sailing skills, but you’ll also learn how to operate, service, and maintain a bluewater sailboat. You’ll also see, smell, taste, touch, hear, and feel what it’s like to be a sailing cruiser. It’s definitely a way on how to gain sailing experience

Family-Friendly: Our Experiences were designed with families in mind, providing a supportive environment for learning and cruising together. And it’s not all about learning. The cruising life is about exploring, swimming/snorkeling, making new friends, seeing new sights, and making memories!

Extended Learning: Unlike schools and charters, our Experience allows for bespoke customization. Many families want to learn how to perform Man Overboard drills or experience sailing at night. Some couples want to practice anchoring and mooring balls until they nail it. Other couples are interested in learning to sail by day and then exploring fun bars and tasty local cuisine by night.

Our Sailing Lifestyle Experiences Cons

Limited Locations: Our Experiences are limited to the beautiful tropical environment of the Caribbean. We chose this location because most sailing cruisers sail in the tropics. When learning to sail in and around islands like St Martin or Grenada, you will experience open ocean sailing, a huge confidence builder. You’ll also meet a huge sailing cruising community!

Availability: Our Experiences have limited availability, and guests need to book well in advance to secure a spot.

Choosing between a sailing school, chartering, or our Sailing Lifestyle Experience depends on individual preferences, goals, and the desired learning experience.

How to gain sailing experience – Sailing schools are great for structured education, charters provide real-world experience, and our Sailing Lifestyle Experience offers a unique blend of coaching and family-friendly immersion. Ultimately, the best choice is the one that aligns with your learning style, budget, and long-term cruising aspirations.

Kim Brown:
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