The Ultimate Skipper’s Sailing Vacation – Sail, Learn & Explore in Barbados!
Gain Confidence While Enjoying a Caribbean Sailing Vacation & Milebuilding Experience
Dreaming of skippering your own charter but need more hands-on experience? Finished your ASA 101 and looking to build your miles before you continue to next ASA course?
Join our 6-day, 5-night Sailing Confidence Builder in Barbados! This immersive sailing vacation blends skill-building with relaxation, allowing you to explore stunning Caribbean waters while developing the confidence to take the helm. Perfect for ASA 101, ASA 103 or ASA 104 graduates or anyone preparing for their first bareboat charter.
What You’ll Gain from This Sailing Vacation & Milebuilding Course
✔ 100+ Nautical Miles Logged – Essential for milebuilding & advanced sailing certifications.
✔ Confidence to Charter Your Own Boat – Gain real-world experience before your next sailing trip.
✔ Hands-On Skippering & Leadership Skills – Navigate, plan, and make critical decisions.
✔ Caribbean Sailing Experience – Sail in stunning waters with expert guidance.
✔ Signed Mile Logbook for Future Certifications – Build your sailing credential
Why Choose This Sailing Vacation for Milebuilding?
✅ Hands-On Skipper Training – Navigate, dock, anchor & make real-time sailing decisions.
✅ 100+ Nautical Miles Logged – Gain essential milebuilding experience in the Caribbean.
✅ Night Sailing & Watchkeeping – Essential skills for longer passages & offshore sailing.
✅ Coastal Navigation & Passage Planning – Master charts, GPS, tides, and safe route planning.
✅ Stress-Free Learning – Improve your sailing skills while enjoying a Caribbean sailing getaway.
✅ Island Stops & Adventure – Explore Barbados' most scenic anchorages and beaches.
What to Expect:
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Liveaboard Experience: Spend 6 days/5 nights living aboard a well-equipped sailboat, experiencing the sailor’s life first-hand.
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Expert Instruction: Learn from certified ASA instructors with years of sailing experience.
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Hands-On Learning: Practice real sailing scenarios, ensuring you gain confidence and competence.
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Scenic Routes: Sail through picturesque waters, stopping at beautiful anchorages.
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All-Inclusive: The course fee includes instruction, accommodations on the sailboat, and meals (except for 2 dinners onshore and Gratuities to Instructor).
Duration: 6 days (liveaboard)
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Prerequisites: ASA 101, 103 or 104 certification. Your crew position will be assigned based on your certification level and where you need to build your sea miles.
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Vessel: Jeanneau Sun Oddysey 32i
Scheduled Group Classes
Cannot find your desired dates? Contact us to schedule Private Class!
Sample Itinerary
Experience the ultimate sailing adventure in Barbados with our structured Confidence booster course. This multi-day sailing vacation will immerse you in hands-on training while exploring the island’s stunning coastline.
Itinerary – 6 Days of Sailing, Training & Adventure
📅 Day 1 – Welcome Aboard & Skipper Prep
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Meet the team, safety briefing, provisioning tips.
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Hands-on charter prep & boat systems check.
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Navigation workshop: passage planning, weather routing,
and crew roles. Pick route options based on weather and
personal preferences.
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Shakedown sail & docking practice in Shallow Draught Marina.
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Daily hands-on anchoring & mooring practice.
✅ Key Skills: Passage planning, crew leadership, docking.
📅 Day 2 – Coastal Sailing & Anchoring
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Depart early for an approximately 30-40NM coastal passage.
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Coastal navigation exercise: pilotage, GPS waypoints, and
visual markers.
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Daily hands-on anchoring & mooring practice.
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Evening: Route debrief & relaxation.
✅ Key Skills: Coastal navigation, anchoring, boat handling.
📅 Day 3 – Night Sailing & Watchkeeping
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Longer 50+ NM coastal passage, rotating watch positions.
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Planning session for night sailing. in the morning.
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Watch system training – experience multi-hour shifts at sea.
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Night sailing: Steering by compass, reading lights.
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Arrival at anchorage in the night.
✅ Key Skills: Watchkeeping, night navigation, radar use.
📅 Day 4 – Relaxing, Sailing, Cruising
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Rest & morning debrief.
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Sailing, Cruising or Island visit.
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Daily hands-on anchoring & mooring practice.
✅ Key Skills: Cruising, advanced docking, relaxing.
📅 Day 5 – Final Skipper Challenge
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Each participant takes full responsibility as skipper.
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Real-world decision-making & navigation practice.
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Return to Carlisle Bay for final docking & mooring test.
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Daily hands-on anchoring & mooring practice.
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Farewell dinner & certification of completion.
✅ Key Skills: Independent skippering, final passage planning.
📅 Day 6 – Land Ho!
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Arrival to Shallow Draught Marina.
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Daily hands-on anchoring & mooring practice.
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Checkout (noon).
Ready to Set Sail?
This immersive course combines expert sailing instruction with a Caribbean sailing adventure. Whether you're aiming for becoming independent skipper on your own boat or chartered boat or just an unforgettable experience, our Learn-to-Sail Vacation is the perfect way to gain confidence at sea.
