KISMET

Dan Alonso

Captain

Captain Dan has been at the helm since childhood, charting his first coastal passages at the age of eight. Each summer, he captained his father’s boat from Rhode Island to Maine and back—planting the seeds of a lifelong passion for sailing, exploration, and adventure.

Since those early days, Dan has logged more than 50,000 nautical miles, including numerous offshore and solo passages. He’s competed in the prestigious Newport Bermuda Solo Race, a true test of seamanship and endurance. With a calm confidence earned through experience, he brings both technical skill and steady leadership to every charter.

Dan is also an accomplished scuba diver, rock climber, and skier, always chasing new ways to connect with nature. His love of the outdoors informs his approach on board—creating memorable charters that go beyond sailing to celebrate the beauty of the sea and the thrill of discovery.

Guests are drawn to Dan’s easygoing personality, warm sense of humor, and thoughtful hospitality. He’s a natural teacher who enjoys sharing his knowledge with anyone curious to learn the ropes—offering hands-on guidance in a relaxed, encouraging way.

Whether anchoring in a quiet cove or catching the perfect breeze, Captain Dan ensures each journey is safe, smooth, and unforgettable. Joan brings the perfect blend of skill, creativity, and hospitality to every charter experience. With a strong foundation in the service industry, she began her career as a professional bartender and waitress in several high-end restaurants, where she developed a deep appreciation for fine cuisine, exceptional service, and creating unforgettable guest experiences.

Her love of the sea eventually led her to combine her culinary talents with life aboard, working as a yacht chef in destinations across the Caribbean, Adriatic, and Mediterranean. From Kismet to Cadence and other luxury sailing yachts, Joan has crafted menus that highlight fresh, seasonal ingredients and celebrate the vibrant flavors of the regions she explores.

Joan Bennett

Chef / First Mate

Beyond the galley, Joan is also a talented professional photographer. She takes great joy in capturing candid moments of laughter, connection, and adventure—providing guests with lasting memories through stunning images.

Known for her warm presence and thoughtful approach, Joan creates an atmosphere where guests feel instantly welcomed and at ease. Whether through her beautifully prepared meals, attentive service, or personal touches, she ensures each charter is an experience to savor long after the sails are down.

Randi Brawley

Chef / First Mate

Chef Randi's love for food and sailing began along the shores of Connecticut and Rhode Island, where she spent childhood summers aboard her family’s 32-foot Vanguard. While her brothers handled the lines with their father, Randi was in the galley with her mother—learning how to turn simple provisions into hearty, satisfying meals at sea. Those early days ignited a lifelong passion for hospitality, adventure, and great food.

Her professional journey started in the gourmet food industry, where she quickly rose through the ranks at Hay Day, Inc., serving as Store Manager, Vice President, and Director of Cooking Schools for an $18M specialty food market. She later brought her culinary vision to life as part of the founding teams at Tavern on Main and Riverhouse Tavern in Westport, CT, and continued mentoring aspiring chefs as a Career Counselor at the Center for Culinary Arts.

In recent years, Randi has blended her culinary expertise with her maritime roots. From 2022–2024, she served as chef and first mate with Joyride Charters, preparing meals for 8–10 guests aboard 50-foot catamarans in the British Virgin Islands and the Greek Islands. In addition to provisioning, budgeting, and delivering memorable meals, she also assisted as deckhand—ensuring a smooth, safe, and enjoyable experience for every guest.

With decades of experience in food, service, and life on the water, Randi brings creativity, professionalism, and a warm, welcoming presence to every charter. Whether she’s crafting a fresh Mediterranean lunch or helping to hoist the sails, her goal is simple: to make guests feel at home and well cared for—wherever the voyage may lead.

Bill Tobin

Captain

Captain Bill brings decades of experience, adventure, and hospitality to every voyage. His journey on the water began early, working on offshore sportfishing boats where he developed a deep love for the sea. By his early 20s, he had earned his ASA certifications, which opened the door to independently chartering sailboats and exploring the world under sail.

Alongside his wife, Bill spent five years living aboard a Hallberg Rassy 43 on an ambitious sailing sabbatical. Together, they logged over 20,000 nautical miles, journeying from Rhode Island down through Belize, Mexico, and the Caribbean, then crossing the Atlantic to the Azores and Mediterranean. Their exploration continued east to Crete, north to Ireland and Scotland, south to Morocco, and eventually back across the ocean again—a journey that deepened Bill’s love of both sailing and cultural discovery.

Before returning full-time to the yachting world, Bill had a professional background in the medical field, paired with early career experience in fine hotels and restaurants—which shaped his approach to service, hospitality, and guest care. Now retired from running his own business, he’s returned to his true passion: sailing, entertaining, and creating unforgettable moments at sea.

Whether you’re joining him for a week of island-hopping or simply enjoying a sunset sail, Captain Bill’s calm demeanor, deep knowledge, and warm hospitality ensure a safe, enriching, and memorable charter.