What my first 8-day Ibiza sailing trip taught me

Hi All,

Today, I want to share some reflections on sailing—what it meant to finally cross it off my bucket list, and the lessons it offered along the way. Depending on where you grew up, sailing might have been an easily accessible childhood family activity or something that felt very distant. I recently watched an interview with a lady who completed the Clipper Round the World Race over 330 days in 2024. Her story inspired me to put this post together. In 2024, I faced down a long-held fear of the ocean and stepped into a dream I’d carried for years. Sailing taught me more than how to read the wind and waves; it showed me how to move with resilience, rhythm, and trust—the way of water.

Below, you’ll find a Q&A-style reflection on the experience, along with practical tips for anyone curious about starting their own sailing journey.

What’s on your bucket list right now?

Q. How did you first become interested in sailing?

Growing up in South Korea and Canada, I loved canoeing and kayaking. Even though I was afraid of the water, paddling became my favorite summer sport—it felt spiritual, especially in its connection with Indigenous traditions in Canada. In high school, I joined a week-long whitewater canoe trip in Montreal, Quebec, while some of my friends continued for a full month, ending with a solo week in the wilderness. That tradition—silence, initiation, resilience—stayed with me.

Still, I had a trauma to overcome. I once nearly drowned in open water in Hawai’i when I was little, and for nearly 30 years afterward, I stayed close to shore, always near the mountains. Yet the dream remained. During our regular family trips to Hawai’i one day, in honor of my grandmother, I made myself a promise: one day, I would sail with my future kids and partner in Hawai’i.

Q. What finally pushed you to start sailing?

Sailing had been on my list for years, but for a long time it remained just that—a list. During the pandemic, while some friends were sailing across oceans or traveling by caravan through Europe and Australia, I spent nine months alone in my London flat. That contrast stayed with me.

By 2024, I was ready for something different. It became a year of reflection, of rediscovering joy outside of work after two decades of being defined by study and work as an expat. Sailing felt like both a challenge and a reward. Step by step, I built my relationship with the water again—first by relearning how to swim, then by saying yes when the opportunity to sail finally arrived.

As luck would have it—or perhaps by the power of manifestation and a little Universal magic—the moment I decided to go on a sailing trip, the right people started to appear in a month! We self-organized a trip: Simon, who has been sailing and racing for nearly 20 years, led the way, and six of us rented a boat in Valencia, Spain, to sail around Ibiza together. I learned everything on board. To prepare, I had already taken a keelboat course at Queen Mary Sailing Club, and more recently, I pushed myself further by completing the Level 1 Dinghy course (it’s more of a prerequisite for racing than for leisurely sailing)—you have to learn how to read the wind, the water, and the boat’s movement all at once. There were moments I wanted to give up, but I didn’t. I’m grateful to my instructor, Matt, whose patience helped me step out of my comfort zone.

Sailing isn’t just a skill I’m learning—it’s become a way to step outside my comfort zone, to honor resilience, and to find joy in places I once overlooked. Also, one day, it is for my future family.

Q. You also spent eight days sailing in Ibiza. What was that like?

Sailing is poetic.

Yes, there were the not-so-glamorous moments—seasickness (which I totally underestimated - kitchen was a no-go zone for me), throwing up, the endless rocking at night. But then came the gifts: lying on deck under the Milky Way, watching shooting stars, witnessing moonrise and moonset (did you know the moon looks like the sun when you’re out in the open sea?), and greeting both sunrise and sunset, all against the backdrop of crashing waves. Waking up in the middle of the ocean, wrapped in utter silence, felt like stepping into another world. Those moments felt eternal. Sailing strips you down, and then gives you everything—the sky, the sea, the silence, the rhythm.

Of course, some efficiency-oriented people might prefer a powerboat—especially if they’re very sensitive to seasickness. But for me, the entire trip felt like an initiation.

Q. What surprised you the most?

• Sea sickness. I completely underestimated it and thought I could just wing it. In reality, I was very vulnerable to seasickness—as were a couple of other crew members. I couldn’t go below deck while we were sailing because that’s where the movement felt the strongest. It was humbling to realize how much your body reacts at sea.
• Water and storage. On a boat, water and storage are precious. When you set sail, you bring the water tank with you—for showers, flushing, cooking, washing dishes, everything. You have to use it mindfully. At times, you even empty the toilet tank manually, which makes you very humble and intimately aware of your own body. :)
• Muscle power. Sailing requires a surprising amount of physical strength, especially to control the sails.
• Family traditions. Along the Ibiza coastline, I saw boats filled with extended families—grandparents, parents, and children—reading quietly or gathering for dinner together. That was a moment I deeply admired.
• Sleeping at sea. Sleeping on a boat feels completely different from sleeping on land. Our trip started with six people, but three dropped out along the way. Each time we went ashore, we had to take the dinghy in—a reminder that rest and access to land are never taken for granted.
• Gender and strength balance. On a sailing trip, muscle power really matters. At times, it helps to have a good balance of men’s and women’s strength to manage the demands of the boat.

Q. What practical things did you learn on that trip?

🌿 Things I wish I knew before:

• Bring mosquito repellent (summer = bites).
• Take seasickness precautions 20 minutes before departure.
• Rope-tying should become second nature.
• Stock up on coffee and breakfast essentials.
• Essential oils help if you’re sensitive to smells.
• Boat toilets & showers are luxuries—plan carefully. (And swimming near boats… let’s just say the water isn’t just water 😅).
• Sail for 3–4 hours, then chill—otherwise you’ll feel trapped.
• Bring extra water, batteries, and grounded rituals like journaling or meditation.

Would I recommend it for beginners? If seasickness isn’t an issue, yes. Otherwise, start with a shorter trip first. I’d love to make it a tradition with my kids someday.

Q. What has the dinghy course taught you so far?

1. Loosen up. If you’re stiff, the boat tips. Stay soft, stay aware.
2. Let go when the wind picks up. Hold too tightly, and you capsize. Release control.
3. Balance matters. Distribute your weight, and you’ll stay afloat—and dry.
4. Presence over force. Sailing is about rhythm, not domination. You don’t command the boat—you learn to listen.
5. You don’t have to do it alone. Kind classmates flipped my boat upright when I was too tired to do it myself.
6. Call on spirit. I prayed, I begged the gods, and yes—I tried to channel Moana (though the wetsuit ruined the aesthetic 😅).
7. Build muscles. You should be strong enough to pull yourself out of the water and hop on a boat on your own.

My arms and knees are bruised. But I finished. And I feel stronger.

Q. What do you take away from all of this?

That resilience is learned through rhythm, not force. The ocean doesn’t reward resistance—it rewards listening.

Every time I sail, I remember: soften, balance, breathe.
The way of water is also the way of life.

Next, I cannot wait to explore the ocean world that makes up two-thirds of Earth!

Q. Last question—have you overcome a lifelong fear through sailing?

Yes. I faced the fear of drowning that had stayed with me since Hawai’i. And I learned that courage doesn’t mean you never fall into the water. It means you climb back into the boat—again and again.

Question for the Obsidian Odyssey community

Have you ever done something to overcome your lifelong fear? What was it, and how did it change you?

🌊 Comparative Snapshot: Learning to Sail Around the World

Many of my European friends grew up sailing and skiing—it’s almost second nature to them. That made me curious: what is it like to learn sailing in different parts of the world? Here’s a quick snapshot:

*Approximate entry-level course costs; varies by school.

💃 Major Sailing Races in Europe

I recently watched an interview with a lady who completed the Clipper Round the World Race over 330 days in 2024. Her story was inspiring (she quit her 10-year finance job and went on an adventure before it was too late) and inspired me to put this race list together. Not that I mean I would ever attempt to participate...

✨ Europe offers everything—from glamorous Mediterranean regattas to hardcore Atlantic challenges. If you’re a beginner, Cowes Week, Barcolana, or even a Clipper Race leg are the most accessible entry points.

🏆Major Types of Sailing Races & Where to Start

1. Dinghy Racing (Beginner-Friendly)

• What it is: Small boats (one- or two-person) like Lasers, Optimists, or 420s.
• Where to start: Local yacht clubs and community sailing programs. Many people first race in dinghies before moving to keelboats.
• Why it matters: Builds core skills—wind reading, tactics, agility.

2. Club Regattas (Local Step Up)

• What it is: Friendly competitions at yacht clubs, often weekend events.
• Where to start: Join a sailing club’s “crew list” to race on members’ keelboats.
• Examples: Frostbite racing (winter series), Wednesday night beer can races (casual summer series).

3. Offshore & Coastal Racing

• What it is: Longer-distance racing, often overnight. Demands navigation, endurance, teamwork.
• Where to start: Volunteer as crew in regional races.
• Examples: Fastnet Race (UK), Sydney to Hobart (Australia), Newport-Bermuda (US).

4. Olympic Classes

• What it is: High-performance dinghies and boards (e.g., 49er, Nacra 17, ILCA/Laser, windsurfing, kite foiling).
• Where to start: Regional clubs with Olympic training programs.
• Why it matters: Pathway for serious athletes.

5. Global & Elite Races (Aspirational)

• America’s Cup: The oldest and most prestigious sailing race in the world (professional, cutting-edge technology).
• Volvo Ocean Race (now The Ocean Race): Round-the-world crewed race—grueling, legendary.
• Vendée Globe: Solo, nonstop, around-the-world race—ultimate test of resilience.

✨ If you’re new, start small: try dinghy racing or join a club regatta. From there, the ocean is wide open—whether you want casual weekend racing or dreams of the America’s Cup.

⛵Practical Resources for Getting Started with Sailing

1. Entry-Level Courses

• RYA (Royal Yachting Association) Courses – If you’re in the UK/Europe, start with RYA Level 1 Dinghy Sailing (great for learning wind, balance, and boat basics) or RYA Competent Crew if you want a bigger-boat experience.
• ASA (American Sailing Association) Courses – In North America, ASA 101: Basic Keelboat Sailing is a strong entry point.
• Many community sailing clubs offer affordable intro courses—search for “community sailing center” in your area.

2. Sailing Clubs & Communities

• Join a local yacht or sailing club. Many offer “crew pools,” where beginners can sign up to crew on members’ boats.
• Platforms like CrewSeekers, FindACrew, or local Facebook sailing groups connect you with skippers looking for extra hands.
• Don’t be intimidated—most sailors are happy to welcome beginners who are eager to learn.

3. Gear Essentials

• Life jacket (PFD): Always, always wear one.
• Non-slip shoes: Sailing decks get wet and slippery.
• Sunscreen & sunglasses: Reflection from water can be harsh.
• Gloves: Optional, but helpful for handling ropes.
• Dry bag: To keep phone/journal/essentials safe from spray.

4. Health & Safety

• Seasickness prevention: Take medication before departure (ginger chews, wristbands, or even chocolate, as I learned in Ibiza, can help).
• Hydration: Drink more water than you think you need.
• Stretching & balance: Sailing uses core and leg muscles—yoga and light workouts help.

5. Sailing Apps & Tools

• Windy or PredictWind for weather and wind forecasts.
• Navionics for navigation and charts.
• Tide apps (varies by region) to understand currents and timing.

6. Books & Inspiration

• Sailing Made Easy (ASA) – beginner-friendly manual.
• The Dinghy Bible – clear and visual guide to small-boat sailing.
• Memoirs like Maiden Voyage by Tania Aebi (who sailed solo around the world at 18!) for inspiration.

Fun watch:

7. Mindset Tips (from my own bruises + breakthroughs)

• Stay soft, not rigid—boats tip if you fight them.
• Ask questions, no matter how simple.
• Pack light, stay adaptable.
• Treat sailing as rhythm, not control—nature is your true teacher.

Remember: you don’t need to be an expert or have a yacht to begin. Start small—one course, one day sail, one moment listening to the wind. That’s how the journey begins.