Captain Dan Alonso
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 has also competed in the prestigious Newport Bermuda Solo Race, a true test of seamanship, endurance, and self-reliance. His extensive experience gives him the calm confidence, technical skill, and steady leadership needed to create safe and enjoyable charters.

Dan is also an accomplished scuba diver, rock climber, and skier who is always seeking new ways to connect with nature. That adventurous spirit shapes his approach onboard, where he enjoys creating experiences that celebrate both the beauty of the sea and the thrill of discovery.

Guests appreciate Dan’s easygoing personality, warm sense of humor, and thoughtful hospitality. A natural teacher, he enjoys sharing his knowledge with anyone interested in learning the ropes, offering hands-on guidance in a relaxed and encouraging way.

Whether anchoring in a quiet cove or catching the perfect breeze, Captain Dan works to make each journey safe, smooth, and unforgettable.

Captain Bill Tobin
Captain Bill brings decades of maritime experience, adventure, and hospitality to every voyage. His life on the water began aboard offshore sportfishing boats, where he developed a deep connection to the sea. By his early twenties, he had earned his ASA certifications, opening 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 during an ambitious sailing sabbatical. Together, they logged more than 20,000 nautical miles, traveling from Rhode Island through Belize, Mexico, and the Caribbean before crossing the Atlantic to the Azores and Mediterranean. Their journey continued to Crete, Ireland, Scotland, and Morocco before they crossed the ocean once again.

Before returning full-time to yachting, Bill built a professional career in the medical field and ran his own business. Earlier experience in fine hotels and restaurants also shaped his approach to service, hospitality, and guest care.

Now returned to his true passion, Bill enjoys sailing, entertaining, and helping guests experience new places from the water. His calm demeanor, broad knowledge, and warm hospitality create an atmosphere that feels safe, enriching, and relaxed.

Whether leading a week of island-hopping or settling in for a quiet sunset sail, Captain Bill takes pride in making every voyage comfortable, engaging, and memorable.

Chef Joan Bennett
Chef Joan brings a thoughtful blend of culinary skill, creativity, and hospitality to every charter. Her career began in the service industry as a professional bartender and waitress in several high-end restaurants, where she developed a deep appreciation for fine cuisine, attentive service, and creating memorable guest experiences.

Her love of the sea eventually inspired her to combine her culinary talents with life onboard. Joan has worked as a yacht chef throughout the Caribbean, Adriatic, and Mediterranean, preparing menus aboard vessels including KISMET, CADENCE, and other luxury sailing yachts. Her cooking highlights fresh, seasonal ingredients and the vibrant flavors of the destinations she explores.

Beyond the galley, Joan is also a talented professional photographer. She enjoys capturing candid moments of laughter, connection, and adventure, giving guests beautiful visual memories to take home from their time on the water.

Known for her warm presence and thoughtful approach, Joan creates an atmosphere where guests feel welcomed and at ease. Through beautifully prepared meals, attentive service, and personal touches, she helps ensure each charter remains memorable long after the sails come down.

Chef Randi Brawley
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 worked alongside her mother in the galley, learning how to transform simple provisions into hearty and satisfying meals at sea.

Her professional career began in the gourmet food industry, where she rose through the ranks at Hay Day, Inc., serving as Store Manager, Vice President, and Director of Cooking Schools for an $18 million specialty food market. She later helped launch Tavern on Main and Riverhouse Tavern in Westport, Connecticut, and continued supporting aspiring culinary professionals as a Career Counselor at the Center for Culinary Arts.

In recent years, Randi has combined her culinary expertise with her maritime roots. From 2022 through 2024, she served as Chef and First Mate with Joyride Charters, preparing meals for eight to ten guests aboard 50-foot catamarans in the British Virgin Islands and Greek Islands. Her responsibilities included provisioning, budgeting, menu planning, meal preparation, and assisting as deckhand to help ensure a smooth and enjoyable charter.

With decades of experience in food, hospitality, and life on the water, Randi brings creativity, professionalism, and a warm presence to every voyage. Whether preparing a fresh Mediterranean lunch or helping hoist the sails, her goal is to make guests feel comfortable, welcomed, and thoroughly cared for wherever the journey leads.