Captain Toni Bailey: A Journey Across the Waves

Welcome aboard! I’m Captain Toni Bailey, a passionate yacht captain holding a Master 100GRT license and a lifelong love for the sea. My journey into the maritime world is as colorful and adventurous as the sunsets I chase across the horizon. Each wave tells a story, and I’m here to help you write yours.

A Creative Beginning

Before I embraced the waves, I was the proud owner of a wedding photography business in the vibrant city of San Francisco. Capturing love stories through my lens was not just a job; it was an art form that allowed me to connect with people from all walks of life. I had the privilege of traveling to breathtaking locations—Spain, England, Jamaica, Mexico, and Italy—where I honed my skills and deepened my appreciation for diverse cultures and stunning landscapes.

Every wedding was a unique canvas, and I poured my heart into each frame, capturing the essence of love, joy, and celebration. The laughter, the tears, the fleeting moments of happiness—all of it became a part of my artistic journey. This experience taught me the importance of detail, patience, and the beauty of fleeting moments. It also instilled in me a profound understanding of how to create memorable experiences, a skill that now translates seamlessly into my work as a yacht captain.

Lifelong Sailor and Adventurer

My journey as a sailor began at a young age, with countless hours spent on the water, learning the ropes and developing a deep-seated love for the ocean. The call of the sea was irresistible, and I found myself drawn to the gentle sway of boats and the salty breeze that filled the air. This lifelong passion blossomed when I decided to live full-time on a sailboat, embarking on an incredible adventure that took me from the sun-kissed shores of California to the enchanting islands of Hawaii and along the picturesque coast of Baja Mexico to the mesmerizing Sea of Cortez.

A significant milestone in my sailing career was my first-time crossing of the Pacific during the 2018 Pacific Cup, a thrilling race from San Francisco to Hanalei Bay, Hawaii. As part of a spirited team of seven, this experience was not just about competition; it was a transformative journey that tested my skills, resilience, and love for the ocean. The camaraderie among fellow sailors, the laughter shared over meals, and the breathtaking beauty of the Pacific made it an unforgettable adventure that solidified my commitment to the maritime life.

One of the most exhilarating experiences was delivering a Santa Cruz 70 race sailboat from Honolulu to Los Angeles. The thrill of harnessing the wind and feeling the boat slice through the waves was exhilarating, and the stunning scenery along the way made this delivery a highlight of my sailing career.

In 2020, when the Transpac race was canceled, my crew of five and I decided to embrace the unexpected and cruise to Hawaii instead. This leisurely sail allowed us to slow down as we approached the islands, accommodating the 14-day quarantine requirement by taking 16 days for the crossing. It was during this journey that I fell in love with cruising, discovering the joys of taking my time on the water and appreciating the beauty of the ocean at a relaxed pace. Each day was filled with laughter, shared stories, and moments of quiet reflection as we sailed under the vast expanse of the sky.

Transitioning to Yacht Delivery

While I still cherish my photography roots, my heart now sails in the world of yacht delivery. This transition was a natural evolution of my lifelong love for the sea, allowing me to blend my artistic sensibilities with my nautical expertise. As a delivery captain, I take pride in navigating various vessels with skill and care, ensuring that every journey is not just safe but also a delightful experience tailored to the unique needs of my clients.

I understand that each yacht delivery is a significant milestone for my clients, whether they are purchasing their dream boat or relocating to a new destination. I approach each delivery with the same creativity and attention to detail that I applied to my photography, ensuring that every aspect of the journey is meticulously planned and executed. From route planning to weather considerations, I am dedicated to providing a seamless and enjoyable experience.

Commitment to Client Satisfaction

What sets me apart is my genuine commitment to client satisfaction. I believe that every journey should be as unique as the individuals embarking on it. My approachable demeanor and professionalism create a welcoming atmosphere where you can feel at ease. I take the time to understand your preferences and desires, ensuring that your maritime adventure exceeds your expectations.

Communication is key in my approach. I keep my clients informed every step of the way, sharing updates and insights to make the journey as enjoyable as the destination. Whether you’re a seasoned sailor or new to the world of yachting, I’m here to guide you with patience and expertise.

A Lifelong Passion

Sailing is more than just a profession for me; it’s a way of life. I thrive on the thrill of navigating diverse maritime conditions and sharing my love for the ocean with others. Whether we’re gliding through calm waters or tackling more challenging seas, my focus remains on delivering an exceptional experience that you’ll cherish forever.

I believe that the ocean has a unique way of bringing people together, fostering connections, and creating lasting memories. I’m passionate about sharing this experience with my clients, whether it’s teaching sailing techniques, sharing stories of my adventures, or simply enjoying the beauty of nature together.

Home is Where the Heart Is

Home is where the heart is, and for me, that means embracing the beauty of the Oregon coast, the vibrant life in Key West, and the dynamic energy of San Francisco. Each of these places holds a special significance in my life, offering unique experiences and opportunities for adventure.

The Oregon coast is a breathtaking expanse of rugged cliffs, sandy beaches, and lush forests. Here, I find solace in the natural beauty that surrounds me while fulfilling my commitment to family. The coastal towns, with their charming atmospheres and tight-knit communities, provide a welcoming environment where I can connect with loved ones. Whether I’m whale watching, exploring scenic drives, or attending local festivals, there’s always something to do and see. The slower pace of life on the coast allows me to recharge and appreciate the simple joys, like enjoying a marionberry pie or taking long walks along the shore.

In contrast, Key West offers a tropical paradise where the sun shines bright and the ocean invites year-round aquatic adventures. The warm waters and friendly, laid-back demeanor of the locals create an atmosphere that feels like a perpetual vacation. I love wandering through the vibrant streets, savoring fresh seafood, and participating in community events that celebrate the island's rich culture. The sound of live music fills the air, and the stunning sunsets are a daily reminder of the beauty that surrounds me.

Balancing my time between these two beautiful locations enriches my life in countless ways. The Oregon coast provides a tranquil retreat and a chance to care for my family, while Key West offers vibrant energy and adventure. I cherish the opportunity to experience the best of both worlds, allowing me to connect with nature and community in different ways.

Additionally, I spend part of my time in San Francisco, where I enjoy the city's dynamic culture and culinary delights. Each visit to San Francisco is filled with new experiences and cherished moments. The bustling streets and iconic landmarks create a lively backdrop for exploration. I enjoy visiting local markets, dining at diverse restaurants, and soaking in the vibrant arts scene. I especially love spending time in North Beach. Known as the city’s "Little Italy," North Beach is rich in history and culture, characterized by its charming streets, Italian restaurants, and lively atmosphere. I enjoy starting my day with a freshly brewed cappuccino at one of the local cafes, soaking in the ambiance as I watch the world go by. North Beach boasts a vibrant nightlife scene, where the streets come alive in the evenings with music, laughter, and the clinking of glasses as people gather in bars and restaurants. Whether it’s enjoying live jazz at a local club or savoring a slice of award-winning pizza at Tony’s Pizza Napoletana, there’s always something exciting happening in this neighborhood.

Setting Sail into the Horizon

As I navigate life across these three remarkable locations, I appreciate the balance it brings to my busy sailing career. The tranquility of the Oregon coast, the vibrant energy of Key West, and the urban excitement of San Francisco create perfect backdrops for both relaxation and adventure.

Sailing is not just about the destination; it’s about the journey. Each voyage is an opportunity to embrace the elements, feel the wind in my hair, and connect with the vastness of the ocean. I find joy in teaching others the art of sailing, sharing the thrill of hoisting the sails, and the satisfaction of navigating the waters. Whether it’s a leisurely day sail or an exhilarating race, every moment spent on the water is a reminder of the freedom and beauty that sailing offers.

Whether I’m sailing under the stars in Key West, enjoying a quiet moment on the rugged shores of Oregon, or exploring the bustling streets of San Francisco, I am constantly reminded of the beauty and joy that life has to offer.

Join me as we embark on unforgettable journeys across the water. With my unique blend of artistic background, extensive sailing experience, and unwavering dedication to client service, I’m here to create magical moments on the open sea. Let’s set sail together and make memories that will last a lifetime.