Stephen & Estelle’s Profiles

Stephen cockcroft yacht broker and boat as a business expert


Stephen Cockcroft is an accomplished offshore catamaran sailor with 5 decades of sailing and racing in trans-ocean voyages and working in the industry. In addition to representing yacht buyers and sellers as co-founder of Catamaran Guru, he has also served as co-owner of the popular Island Spirit Catamaran factory and co-owner of the third-largest charter company in North America/Caribbean.  |  804-815-5054

Stephen’s involvement in the sailboat and sailing industries are diverse and broad-reaching. As owner of the very successful and popular Island Spirit Catamarans factory, co-owner of the third largest charter company in the Caribbean and North America, and longtime yacht and charter broker, he has gained insight into the inner workings of how to build and buy a yacht as well as how to operate the boat as a business. He has brokered many brands including the Flagship catamaran ranges for Bali, Lagoon, Fountaine Pajot, Nautitech, Xquisite, and Sunreef in the USA and has been involved in product development and customization of
large catamarans for buyers. Stephen is a licensed and bonded yacht and ship broker in the State of Florida and operates his own US-based brokerage house.

Sailing Experience

Stephen racing sailboats

He is an accomplished offshore catamaran sailor having completed multiple trans-ocean voyages including the delivery of his own Island Spirit from Cape Town, South African, to Miami, a voyage of 7,000 NM. He has participated in offshore races on catamarans and most recently he won the Bahamas leg of the Caribbean 1500 on a Prout 50 (pictured right). Stephen is an Instructor Examiner for the American Sailing Association (ASA) having taught hundreds of people to sail catamarans and monohulls in hands-on, live-aboard courses in the Caribbean and the Bahamas.

Stephen and his wife, Estelle, have cruised 70,000+ NM aboard their ocean-going yachts and have visited more than 45 countries. They are sought-after experts on catamarans, yacht ownership solutions, yacht management, liveaboard cruising lifestyle, and understanding the needs and specifications for a successful cruising yacht. Through their thousands of posts on diverse sailing topics on this website and their direct consulting and brokerage relationships, they are a valued resource for all sailors and often become friends with the customers and students that they have worked with.

Catamaran Expertise & Yacht Ownership Programs

Stephen Cockcroft catamaran brokerStephen has represented hundreds of catamaran buyers in transactions as an independent consultant. Stephen Cockcroft has in recent years consulted with several clients helping them buy flagship catamarans like the first Xquisite X5 sold in the US and other large catamarans such as  Lagoon SEVENTY7, Lagoon 620, Fountaine Pajot 59Fountaine Pajot Alegria 67, and others into crewed charter all over the world.

With his vast and diverse experience in the international marine business, Stephen possesses a spectrum of technical, financial, taxation, contractual and sailing lifestyle insights. You want him in your corner representing your interests when buying or selling a yacht. Stephen helps you learn to set up your boat as a business to benefit from business tax deductions, understand the different charter management models, figure out which model helps you achieve your goals, identify ways to offset the cost of yacht ownership, and, most importantly, figure out your exit strategy.



Estelle Cockcroft is an expert in large catamaran sailing, living aboard, and buying and selling yachts. She has traveled 70,000+ NM of remote waterways to explore 45 countries. As Catamaran Guru Co-Founder, Co-Owner, and President, she brokers dozens of catamaran transactions each year and manages its $40M+ annual revenue. Estelle shares her passion for sailing on the Catamaran Guru website and as a qualified Royal Yachting Association captain and American Sailing Association instructor. | 954-249-9764

Adventurous and spirited, Estelle Cockcroft set sail in 1992 from her native South Africa to the United States with her husband, Stephen, and absolutely no sailing experience. Her previous work as a fashion designer for the houses of Hang Ten and Gossard did not prepare her for “living aboard”. But her bravery, tenacity, and willingness to learn served Estelle well. She mastered the ropes quickly and, in the 30+ years since, Estelle has become one of the foremost experts on catamaran sailing and onboard living. In fact, with 70,000+ NM of remote waterways and stops in 45 incredible countries under her belt, she has now lived aboard longer than she ever lived on land.
Estelle puts her considerable sailing experience and business acumen to good use as Co-Founder, Co-Owner, and President of Catamaran Guru. A qualified Yacht Broker and large catamaran specialist, she works with Stephen and Catamaran Guru sales team to support clients through the process of boat building, buying, testing, and selling as well as helping yacht buyers to create yacht businesses to offset the costs of ownership. 

As a former newbie, Estelle now serves as advisor and mentor for novice sailors entering the yachting world. She shares her thoughts on everything from onboard living and galley cooking to sustainable travel and cultural preservation on the Catamaran Guru website and is also a qualified Royal Yachting Association captain and American Sailing Association instructor, imparting the skills new sailors need to hit the high seas with confidence. And, of course, she lives to travel, always on the lookout for her next adventure or perhaps a return trip to her favorite destination: Lebanon and the uncharted territories of the Indian Ocean and the Red Sea.

The couple has also enjoyed exploring the US when they lived aboard a “land yacht” once while in between boats. Their custom Harley Davidson motorcycle has transported them to some of the most spectacular places in the USA. 

Throughout the catamaran community pages on this website, you will find information about her boating experiences and knowledge. Estelle is passionate about cultural preservation and sustainable travel as she feels they are crucial movements to ensure enjoyment of global adventures for generations to come. Always looking out for her next challenge, she relishes testing her nerves and muscles. The freedom and independence of the sailing lifestyle suits her personality as a free spirit. She has no “home” in the traditional sense, because according to her ‘…life is a journey and the journey is her home…”