When we signed up for a week-long sailing trip through Guadeloupe to complete our ASA 103 and 104 certifications, we expected some sun, some sailing, and a bit of a challenge. What we got was an unforgettable expedition that pushed us beyond our comfort zones — making us stronger, smarter, and more capable sailors than we could have imagined.
Arrival in Guadeloupe: High Spirits and Tough Forecasts
Flying in from New York via Miami, I met up with fellow CIYC member Josh Jorgensen and our instructor Eduardo Sanchez. We had bareboat chartered a Dufour 390, the Miro, through DreamYacht Charters, ready to set sail from Marina Bas du Fort in Pointe-à-Pitre.
After clearing customs in the Caribbean heat, we made our way to the marina, eager to familiarize ourselves with the yacht and — if lucky — depart early. That plan quickly unraveled when we learned that the forecast called for sustained winds of 25–35 knots and wave heights reaching 10 feet — intense enough that DreamYachts was shutting down operations early. We wouldn’t get our yacht briefing until the next morning. Disappointed but undeterred, we unpacked, grabbed a Caribbean lunch, provisioned for the week, and spent the evening exploring the lively port. If we couldn’t sail yet, we’d soak up some local flavor before the real adventure began.
Setting Out Into Heavy Weather
Thursday morning, after a delayed briefing on our Dufour 390, the DreamYacht staff once again
cautioned us: the conditions were serious. Ferry services for larger vessels were suspended, and
even experienced captains were staying cautious.
But we'd come to sail — and more importantly, to earn our ASA certifications. Turning back wasn’t an option. We decided to leave port and make for the relatively protected bay near Les Saintes, a five-hour sail away.
Motoring out of Pointe-à-Pitre's harbor was deceptively calm. But once we lost the shelter of land, the sea turned wild. We reefed the sails, clipped into jacklines, and pushed through 8-10 foot rolling waves and stiff winds. Two of us battled seasickness whenever we weren’t at the helm. Yet through it all, we gained invaluable real-world experience — adjusting sail trim, correcting for drift, reading waves, and managing fatigue. It was a crash course in serious sailing you simply don't get on a calm bay.
After six and a half grueling hours, we arrived in Les Saintes’ bay, only to find we’d have to tie up to a buoy still exposed to north-westerly winds. It wasn’t much shelter — but it was good enough.
Island Life and Hard Lessons
After securing the boat, we took the dinghy to shore through rough water, wandered the colorful streets of Les Saintes, and found a cozy restaurant just in time for a tropical rain squall. Returning to the yacht was a wet, cold, and bouncy ride — but at that point, it just added to the adventure. Sleeping that night was another story. With the boat rocking 45 degrees side to side, even lying flat required strategic arm positioning to avoid being tossed from the berth. The next day, we practiced maneuvers in the relatively calmer waters between Îles des Saintes. We drilled tacking, reefing, anchoring, and man-overboard procedures before securing a more sheltered mooring near Illet à Cabrit. A wild dinghy ride and a hike to the beautiful plage du Pain-de-Sucre rounded out the day.
Adapting the Plan, Expanding Our Skills
The tough weather persisted all week, forcing us to stay flexible. From Les Saintes, we sailed a difficult upwind course to Marie-Galante, requiring constant adjustment to fight the headwinds. There, we enjoyed a change of pace — driving and hiking around the island, snorkeling, and stumbling into a local food-truck festival in Saint Louis.
Given the conditions, we made the call to skip Terre-de-Bas and La Désirade, focusing instead on developing critical sailing skills. At St. François, we practiced refueling and docking in a tight marina — real-world skills that would have been harder to learn in easier conditions. We finished anchored in the sheltered lee of Ilet de Gosier, enjoying a last stroll through charming Le Gosier and preparing for our final ASA tests.
Certification and Reflection
Eduardo made sure we earned every bit of our ASA 103 and 104 credentials. Over two long days, we drilled essential topics: coastal navigation, anchoring, docking, sail trim, man-overboard recovery, and heavy weather strategies.
By the time we sat for the 100-question exams, we weren’t just cramming — we were reliving situations we'd already tackled firsthand. We both passed easily, a fitting close to an exhausting, exhilarating week.
Finally, under mercifully calm winds, we motored back to Pointe-à-Pitre, returned our trusty Miro, and squeezed in a quick city tour before heading to the airport.
Why This ASA 103/104 Experience Was Unmatched
Looking back, the benefits of this trip were massive:
Immediate Application: Every skill was tested and refined daily in real-world conditions.
Confidence Under Pressure: We learned to manage the boat, our crew, and ourselves in heavy seas and unpredictable weather.
Deeper Knowledge: Beyond textbook learning, we gained an instinct for handling a yacht that no classroom could replicate.
Unforgettable Adventure: We didn’t just “earn a certification.” We lived it — and have the stories (and scars) to prove it.
If you're serious about becoming a confident, capable skipper, don't wait for the perfect conditions. Take your ASA 103 and 104 certifications in a setting that challenges you, pushes you, and forces you to adapt. You’ll come back a better sailor — and you’ll have an adventure you'll never forget. We can’t recommend it enough.
Upcoming ASA Certification Opportunities in 2025
Looking forward to another great adventure? Our Instructors Eduardo Sanchez and Herb d'Entremont have been working on organizing 2 amazing off-0site ASA certification trips—and here are the details of the next adventure. This will be a great opportunity to advance your sailing skills in a beautiful setting while earning ASA 103 and 104 certifications.
Croatia ASA Charter
Dates: August 30 – September 6, 2025
Location: Split, Croatia
Caribbean ASA Charter
Dates: November 15–22, 2025
Location: St. Lucia & Martinique:
St. Lucia & Martini