Captain Sean
Captain Sean discovered a love for the ocean at an early age while sailing with his father, setting the course for a lifelong connection to the sea. After a brief time away from the water, he returned to sailing in the San Francisco Bay, where he quickly immersed himself in both racing and charter work.
Since 2018, he has worked with USA76, a former America’s Cup IACC yacht, gaining invaluable experience aboard one of the sport’s most iconic vessels. His maritime background also includes commercial fishing in Alaska, sport fish guiding, and time aboard large private yachts. He later served as both Maintenance Director and Captain for a pair of Santa Cruz 70s in Monterey Bay, where he spent two years overseeing operations and delivering unforgettable sailing experiences.
Now based in the Caribbean, Captain Sean brings his expertise, enthusiasm, and easygoing nature to every charter. He holds a 100 Ton Near Coastal Master License with STCW, Sail, and Assistance Towing endorsements, and places the highest priority on safety, service, and guest enjoyment. His philosophy as a captain is simple: create a fun, relaxed atmosphere where everyone can laugh, connect, and fully embrace the beauty and adventure of island life.
Chef Jessa
Born in Colorado and raised in Texas, Chef Jessa has always held a deep appreciation for both food and nature. Though she grew up in the city, her family’s annual trips to the beach and mountains sparked a lifelong love for travel and the great outdoors. After earning her degree in Psychology from Texas State University, Jessa spent several years working in Human Resources—until a bold decision changed the course of her life. She left the corporate world behind to pursue a more adventurous, ocean-based lifestyle, and in 2017, she launched her career as a professional yacht chef in Croatia.
Since then, Jessa’s culinary journey has taken her around the world, allowing her to live and work in remarkable destinations across Europe, Asia, Africa, Australia, and the Caribbean. One of her greatest joys while traveling is experiencing diverse cultures and cuisines, and she thoughtfully incorporates those global influences into her menus—blending bold flavors with fresh, wholesome ingredients.
After first sailing in the Virgin Islands in late 2018, Jessa instantly fell in love with the Caribbean and knew she had found her new home. Over the past seven years, she has been based in the US and British Virgin Islands, working aboard private charters and delighting guests from all over the world with her creative and flavorful dishes.
Jessa holds a Level 2 Certification in Culinary Arts, a 50-Ton United States Coast Guard Captain’s License, and a 200-Hour Yoga Teacher Training Certificate. Her diverse skill set reflects her passion for personal growth and holistic living—both of which shine through in her approach to hospitality.
When she’s not in the galley, Jessa enjoys hiking, snorkeling, scuba diving, reading, practicing yoga, and most of all, curating delicious meals for her loved ones and guests. She is especially passionate about cooking with local seafood, believing there’s something truly special about serving dishes sourced from the very waters you’re sailing through.
On board NENNE, Chef Jessa is committed to creating a vibrant culinary experience tailored to your preferences. She has extensive experience accommodating dietary restrictions and food allergies and will work closely with your group to design the perfect menu for your week. With Jessa in the galley, every meal is crafted with care, creativity, and the spirit of sharing.
Chief Stewardess Angelina Ready (7-10px)
Born and raised on Long Island, New York, Angelina brings a bright, adventurous spirit and a well-rounded skill set to every charter. After earning her degree from the University of Tampa, she embarked on a sailing trip in 2019 that changed the course of her life—sparking a love for the sea that led her to shift careers from bartending to yachting.
Since then, Angelina has embraced a dynamic path in the industry, working in roles ranging from stewardess to chef to captain. She earned her Yachtmaster Offshore certification and continues to expand her seamanship with each passing season. Her passion for guest service, paired with her knowledge of the vessel and love of the ocean, makes her an invaluable part of the NENNE crew during full-capacity charters.
Onboard, Angelina loves connecting with guests, mixing creative cocktails, leading celebrations, and jumping in for a snorkel at any opportunity. Off the water, she enjoys hiking, Pilates, beach days, and discovering new destinations. Friendly, attentive, and always ready to lend a hand, she brings energy and ease to the guest experience—ensuring that every detail feels effortless and every moment is memorable.
