Meet Your Captains

With over 37,500 nautical miles at sea and six ocean crossings, Captain Willy Alcock brings a wealth of practical blue-water sailing experience to every voyage. As an RYA Yachtmaster Offshore (Commercially Endorsed) skipper, Willy has spent years navigating offshore passages between South Africa, the Caribbean, and the United States aboard modern sailing catamarans and cruising yachts.

Willy’s passion lies in blue-water cruising, where careful preparation, sound seamanship, and good decision-making combine to create safe and enjoyable passages. His experience includes passage planning for offshore voyages of several thousand nautical miles, navigating through changing weather systems, managing overnight watches, and ensuring vessel and crew readiness for extended time at sea.

A successful offshore passage begins long before the lines are cast off. Willy takes pride in detailed voyage preparation, including weather routing, navigation planning, provisioning, safety management, fuel and water planning, and sail selection to suit expected conditions. His calm and methodical approach allows guests and crew to relax and enjoy the adventure, knowing that every aspect of the voyage has been carefully considered.

Having completed multiple transatlantic and long-distance deliveries, Willy understands the importance of balancing safety, comfort, and performance. Whether sailing overnight under a canopy of stars, making landfall after days at sea, or enjoying a peaceful coastal cruise, he enjoys sharing his knowledge and passion for sailing with those onboard.

Before pursuing a full-time career at sea, Willy successfully owned and managed a retail and wholesale business for fifteen years. This background developed strong leadership, organisational, and customer-service skills that now serve him well in the charter industry. Guests quickly appreciate his approachable nature, attention to detail, and ability to create a relaxed and enjoyable atmosphere onboard.

Based in the beautiful coastal town of Knysna, South Africa, Willy continues to combine his love of sailing, adventure, and hospitality while helping guests experience the freedom and excitement of life under sail.

“The best part of any voyage is watching confidence grow—whether it’s a crew member standing their first night watch, trimming sails for the first time, or seeing the excitement of making landfall after a successful passage.”

Holding a 100-ton Masters license, Joe has been sailing monohulls and Catamarans for 30 plus years and a ASA instructor for the past 15, teaching 101, 103, 104, 105, 106, 114.

On a cold winter day in Chicago, a matinee viewing of “Captain Ron” became a catalyst for a major change in his life direction. Being disenchanted with the music industry and its lifestyle he packed up his truck and headed to Florida and began working in boat yards, learning from “old salts” while acquiring sea time and gaining experience. Upon earning his Captain license he began working as a tugboat operator until suffering a broken back due to a crane mishap.

While recovering he began reading sailing books and vowed to return to the sea on a sailboat. After years of rehab he traded in his walker for a 32 foot Bayfield cutter and took ASA 101, 103, 104, then departed on a five year sabbatical single-handed through the Bahamas and Caribbean.

He has worked as a delivery captain from Annapolis Maryland to Florida Keys, Bahamas and beyond with more than 50 Gulf Stream crossings

As an ASA instructor, his hands on teaching approach is laid back, stress free and entertaining. He has been the lead instructor in Abaco Bahamas for the past 10 years helping future adventurers achieve their sailing dreams. He has organized flotillas and regattas and was named an ASA Outstanding instructor 4 times.

Chris is a licensed coast guard captain with 100 ton master with sailing and commercial towing endorsements. He has been an ASA instructor since 2007 and is certified to teach ASA 101, 103, 104, 105, 114, 118, and 119. Chris is a life-long sailor with experience sailing dinghies, beach catamarans, racers, cruisers, and cruising catamarans. He also has captained fishing charters and operates commercial marine assistance vessels.

Captain Britt holds a USCG 100 Ton Master license with sailing and towing endorsements and is also an American Sailing Association level 101, 103, 104, and 114 certified instructor. He has spent most of his free time pursuing the “magic” of sailing in many different types of racing dinghies, windsurfing, and kiteboarding. In 2017 he stepped away from his photography career, sold his camera stores, and moved aboard the Green Eyed Lady, a Seawind Catamaran, to “live the dream”! Britt has sailed and instructed the east coast from Portland to Key West, Bahamas, and the entire Caribbean. He is also an American Sailing Outstanding instructor (the top 1% percent of all active status ASA Instructors as determined by surveys that are submitted by their students) Britt is available as a sailing instructor, captain, and delivery captain.

Captain Amy holds a USCG Master’s 25 GT license with sailing endorsement and enjoys sailing on the Chesapeake Bay, her home waters. She is an ASA Instructor for ASA 101, 103, 104, 105, 114 and 118 and has certified 175 students in the past five years. She also is a qualified offshore skipper for the Naval Academy Command and Seamanship Training Squadron. Beyond her volunteer activities, and when not on her own Wauquiez 40, she loves coaching new sailors, and especially sharing the tips and tricks of a catamaran.

Bill is an A.S.A. “Advanced Coastal Cruising, Docking, and Catamaran” instructor, a 25 Ton Master USCG Captain, and a lifelong sailor who taught kids American Red Cross sailing on AMF Sunfish at summer camp. He has about 20k sea miles doing transits in Europe, Caribbean, and all-around N. America. He also spent the past six seasons as lead instructor for A.S.A. 101/103 for about forty students per season. Two of those seasons he was recognized by the previous school for outstanding contributions to the program. Bill has owned two sailboats and now serves as Boson on a club racing boat. His professional work background is Industrial & Systems Engineering; therefore, trained in safe work methods and all the mechanics applicable to sailing.

Growing up on the waters of the Chesapeake Bay as well as living in the Bahamas and Caribbean, Capt. Dave brings a broad range of experience from dive boats to traditional sailing ships. In 1992 Dave spent time in New Orleans as crew and had some bit parts in the movie “Interview with a Vampire”

Captain Dave holds a USCG 100 Ton Master license with sailing and towing endorsements and is also a American Sailing Association level 101, 103, 104, and 114 certified instructor. In addition, Capt. Dave is an active musician (Clarinet/Sax), photographer, and ski instructor! He has been known to bring his sax a charters to entertain the guests! He looks forward to showing you a good time on the water!

Captain “Ohana Dave” Eber brings a unique blend of technical expertise, leadership, and lifelong passion for the water to every charter experience. After careers as a Biomedical Engineer at Johns Hopkins Hospital and a senior executive with leading medical technology companies including Lumenis, Topcon, Alcon, and Thermo Fisher Scientific, he retired early to pursue life on the water full-time.

A lifelong mariner, Captain Dave began his aquatic journey as an Ocean City Beach Patrol lifeguard and Red Cross Water Safety Instructor. An avid scuba diver since 1984, he is also a certified PADI Dive Instructor who has explored and taught diving, most recently in Key West, FL. Today, he holds a US Coast Guard Master Captain’s License with a Sailing Endorsement and ASA certifications in Keelboat Sailing, Basic Coastal Cruising, and Bareboat Cruising.

Hi, I’m Brandon Harris. I grew up on the Chesapeake Bay, where my love for the water began at an early age. Boating has been a part of my life for as long as I can remember, and I’ve been sailing for more than 30 years. Over the years, I’ve gained extensive experience navigating a wide variety of vessels and waterways, developing a deep respect for the sea and the skills needed to travel it safely. Beyond sailing, I’m also a certified scuba diver and instructor, as well as a sailing instructor. I enjoy sharing my knowledge and helping others build confidence on and under the water. Whether teaching new sailors, introducing divers to the underwater world, or exploring new destinations myself, I find great satisfaction in helping people connect with the ocean. Whether I’m offshore, cruising coastal waters, diving a reef, or exploring a quiet anchorage, I enjoy every opportunity to be on and around the water. My lifelong passion for boating, diving, and teaching, combined with decades of hands-on experience, has shaped who I am and continues to drive everything I do.

Captain Yearwood is a licensed United States Coast Guard captain with extensive experience operating sail and power vessels of all sizes including harbor tugs and large ships. He holds a 1,600 ton Master’s license and a second mate unlimited tonnage license. Having grown up on power boats and competitively raced on small and medium size sailboats, including historic Chesapeake log canoes, he is an expert boat handler with exceptional seamanship skills. Captain Yearwood has sailed across the Pacific and Atlantic Oceans, Gulf of Mexico, Caribbean, China Sea, Mediterranean Sea, and North Sea, and the East Coast of the U.S. including the Chesapeake Bay. As a charter boat captain, he enjoys meeting new people and providing clients with a fantastic experience on the water. With a passion for sharing knowledge, he lectures on maritime topics, provides private hands-on vessel operation instruction and delivery services, and is member of the United States Coast Guard Auxiliary instructing boater education courses including the Maryland state course.