Posted on October 11, 2025 by James Kell
10 Questions to Ask Any Sailing School
The Simple Questions That Reveal Everything
1. What happens if someone finishes the course but isn't ready for certification?
This cuts straight to whether they maintain real standards or just push everyone through. Good schools will say something like "we certify them to the level they are ready to succeed in." Schools focused on volume might dodge this or claim it never happens.
2. How do you build community among students during the week?
Listen for specific practices, not vague promises. Strong answers include structured activities like "highs and lows" sharing circles, team challenges, preparing shared meals, or vulnerability exercises. Weak answers are "we all go to dinner" or "the boat brings people together naturally."
3. Do students get opportunities to teach each other, or does all instruction come from the instructor?
This reveals their philosophy instantly. Progressive schools actively create peer teaching moments because they know teaching reinforces learning. Traditional schools will say "only certified instructors teach" or express concern about "bad habits."
4. Is there an alumni community? How do students stay connected after the course?
Great schools have names for their alumni (like "Ex-Virgins"), active WhatsApp groups, reunion sails, or structured pathways for continued learning. Weak schools have nothing beyond "follow us on Facebook."
5. Beyond sailing certifications, what training do your instructors receive in how to teach adults?
This separates professional educators from "good sailors who teach." Even sailing instruction qualifications on their own are insufficient. Listen for specific methodologies, communication training, or teaching frameworks. Many schools will stumble here because they only focus on sailing credentials.
6. Walk me through your first safety briefing - how long is it and what do you cover?
The best schools keep it short and focused (like the "Three Worst Things" in 3 minutes). Overwhelming schools deliver 20-minute lectures about every possible danger. This question reveals whether they empower or frighten students. And whether your course will be a boring book-based course or something that is practical and enlightening.
7. When students leave your course, what have they told you changed for them beyond just learning to sail?
Schools creating transformation will have specific stories about confidence breakthroughs, career changes, or life impacts. Transactional schools will struggle with this or only mention sailing skills. Have a look at reviews on TripAdvisor to get a better picture on this one.
8. After your course, could I confidently charter a boat with friends, or would I need an instructor?
This forces honesty about actual competence developed. Strong schools confidently say yes or no and explain why. Weak schools hedge with "depends on conditions" or "we recommend more courses first", or even worse, they may try to shoehorn several courses into an impossibly short period of time.
9. Do your instructors regularly participate in professional development or instructor clinics?
Simple yes/no question that reveals commitment to excellence. Follow up by asking when the last one was and what it covered. Many schools never invest in instructor development after initial certification.
10. Can you give me a specific example of how an instructor helped a struggling student last season?
This reveals both teaching philosophy and emotional intelligence. Listen for patience, breaking down skills, celebrating small wins, and maintaining student dignity. Red flags include blaming students, "some people just can't sail," or no specific examples.
How to Use These Questions
Ask them conversationally, not like an interrogation. You might only ask 3-4 that matter most to you.
Listen for specifics, not generalities. "We build community" means nothing. "We do vulnerability circles where everyone shares their high and low each day" means something.
Follow up when they're vague. If they say "we adapt to different learners," ask "can you give me an example from last week?"
Trust your gut. If they seem annoyed by questions about teaching philosophy or student experience, that tells you everything.
What You're Really Looking For
Schools that see you as a capable adult, not a student to be managed.
Specific practices, not philosophical platitudes.
Investment in instructor development, not just sailing credentials.
Community building, not just skill transfer.
Real competence, not just certification.
Transformation, not just transaction.
Red Flags
- Defensive about questions
- No specific examples
- "Everyone passes"
- "The instructor knows best"
- No alumni community
- No instructor development
- Safety through fear
- Certification focus over competence
Green Flags
- Specific practices described
- Named alumni community
- Regular instructor training
- Peer learning encouraged
- Standards maintained
- Brief, empowering safety approach
- Stories of transformation
- Confidence in student capabilities
The right school will welcome these questions. The wrong school will wonder why you're asking.