Charles Trimmier

<p><em>The sea has stories. This one is yours.</em></p>
<p>The Caribbean is not a place you visit just once. It is a region you return to again and again, and still feel you have only just begun. You could spend a lifetime exploring these waters and never see it all. That is part of what makes it so compelling. Every journey reveals something new. Each anchorage holds its own rhythm, its own reward.</p>
<p>I help travelers move through this abundance with intention. With deep experience in yacht charter, brokerage, and fleet operations, I bring practical knowledge shaped by real time at sea. But it is not only my résumé that matters. What sets my work apart is the mindset behind it.</p>
<p>When I was a teenager, I was alone on a Hobie 18 on a screaming reach toward Fairhope Pier when a jibe ripped the traveler loose. The mainsail slammed against the shrouds with no rigging left to depower it. I had no steerage, no radio, no engine, and no easy way out. Only instinct and problem-solving kept the boat from striking the pier at full speed. That day I learned what real seamanship demands: calm under pressure, clear risk assessment, and the ability to create a solution when none is obvious. That experience shaped every adventure that followed, and it continues to shape how I design travel for others.</p>
<p>This is not about seeking drama. It is about preparation. When you are far from shore, whether under sail or under water, you cannot rely on signal bars or second chances. You rely on what you know, who you trust, and how well the journey was planned from the start.</p>
<p>That is what I bring to every charter I plan.</p>
<p>Whether you're new to chartering or have sailed these waters before, I help you design an experience that reflects your style and opens the door to something rare. I listen closely, ask the right questions, and draw from a deep understanding of both vessels and destinations. If needed, I will guide you through every step, from selecting the right crew to shaping an itinerary that balances comfort with discovery.</p>
<p><strong>Sample Itineraries</strong></p>
<ul>
<li><strong>Easygoing Island-Hopper:</strong> A relaxed introduction to Caribbean sailing. Enjoy short passages, protected anchorages, and time to explore beach bars, quiet snorkel sites, and welcoming coastal towns.</li>
</ul>
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<ul>
<li><strong>The Gunkholer:</strong> Designed for travelers who value privacy, simplicity, and surprise. This route favors small harbors, hidden coves, and slow days shaped by the sea.</li>
</ul>
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<ul>
<li><strong>Diving and Sailing Combo:</strong> A rare pairing that invites freedom and immersion. One lets you chase the horizon. The other drops you into a world few ever see. Together, they create the kind of experience most only imagine.</li>
</ul>
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<ul>
<li><strong>Cultural Coastlines:</strong> A thoughtful mix of sailing and shore time. Explore local markets, traditional cuisine, regional music, and the stories of people who live with the sea.</li>
</ul>
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<ul>
<li><strong>Celebration Charter:</strong> For honeymoons, anniversaries, or milestone birthdays. These itineraries are planned with care and tailored for unforgettable moments, from private sunset sails to chef-prepared dinners onboard.</li>
</ul>
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<p>There is no checklist for the Caribbean. Even with a lifetime of travel, you would never see it all. That is exactly why every charter should be personal. It is not about covering ground. It is about finding the right rhythm, choosing the right anchorages, and shaping a journey that reflects what matters most to you.</p>
<p>I am here to help you plan that kind of experience with clarity, care, and a steady hand.</p>
<p><strong>Let’s begin the conversation.</strong></p>
<p>I offer private consultations to understand what you're looking for and to shape a travel experience that fits your pace, your style, and your sense of discovery. Whether you’re ready to plan or simply want to explore the possibilities, I invite you to reach out.</p>
<p>I limit the number of clients I work with at one time to ensure each trip receives my full attention. Every itinerary is shaped individually, with a focus on discretion, quality, and trust.</p>
<p><strong>About Your Advisor</strong></p>
<p>I didn’t grow up at a yacht club. I learned to sail on beach cats before I was ten, taught myself to read the wind by watching the water, and earned my first SCUBA certification as a teenager. Over time, I paired diving and sailing into a way of life that has taken me deep into the Caribbean and even deeper into the art of intentional travel.</p>
<p>My role is to help you find what most travelers miss. I bring technical insight, regional knowledge, and a personal approach to designing journeys that are equal parts capable, beautiful, and unforgettable.</p>
<p><strong>Frequently Asked Questions</strong></p>
<p><strong>Do you personally guide the trip? </strong></p>
<p>I am not your captain or dive guide, but I serve as your behind-the-scenes strategist. I help you select the right crew, vessel, and approach, then make sure the experience reflects your expectations and goals.</p>
<p><strong>Is this only for experienced sailors or divers? </strong></p>
<p>Not at all. I work with everyone from seasoned adventurers to first-time guests. What matters is your interest in something deeper than a brochure tour.</p>