Our Story

spinnaker sailingStephen Estelle catamaran guruAfter much encouragement from friends, clients and colleagues, we took the plunge and created this website. We hope to tell our story as a way to not only entertain, but also to encourage and educate all the sailing dreamers and planners out there. We have owned many yachts (monohulls and catamarans), many in ownership programs, during our sailing career and have sailed 70,000+ miles in different parts of the world. Our story starts in 1992 in Cape Town, South Africa. With the same feeling of ‘wanderlust’ and a dream of traveling around the world, there was only one thing for us to do…make the dream a reality!

Stephen launched our 45ftstephen and estelle cockcroft cooking shrimp aboard their sailboat in nose be madagascar Bruce Roberts design sloop called ‘Royal Salute’ after two years of building her in a friend’s back garden. We left Cape Town harbor soon after and set sail for the east coast of Africa. We explored, discovered, forged friendships, learned about life, sailing, people, cultures and most of all we learned new things about ourselves. This adventure would never have been possible had we not set a deadline and made the decision to cast off the lines.

Our dream became our life! We now are based in the USA (and proud American citizens!), but travel regularly, so much so that the first words out of our family’s mouths usually are “where are you now?” We are living proof that one can successfully meld a career with the cruising lifestyle and that one should never be hampered by the constraints of every day aboard royal salute sailboat in madagascar

Our partnership is born of the same passion for the sea and all its creatures, exotic cultures, and the exploration of faraway lands. We seldom follow the ‘pack’. We are considered slightly unorthodox and sometimes eccentric by the people who know us and we refuse to live by a set schedule. Our incessant quest for freedom and independence is evident throughout the pages of Catamaran Guru™ and possibly stems from our aversion to restrictions on our personal freedoms.

In the process of exploring the world on our boat we, previously considered to be two “Plonkers”, became the “Gurus”, not without a lot of struggle and a steep learning curve on the high seas! Our experiences are documented throughout these pages and we hope that you will enjoy and ultimately learn from our experiences and mistakes. To learn more about us, read our sailing experiences bios here.

Catamaran Guru™, the catamaran experts…?

We definitely do not profess to be the only and ultimate authority in all things catamaran or sailing, since stephen and estelle cockcroft eating dinner aboard their sailboat royal salutethere are at least five correct ways to do things on a yacht. However we have accumulated an enormous amount of information, knowledge, and experience in the last 30+ years while sailing the high seas, teaching sailing, and working in the yachting industry. We mostly learned by trial and error. In those days (the early 90s) when we first set off, there was no internet, bloggers, or forums to get information from. Heck, we were lucky to find a working telephone anywhere! We often had to coax information out of the local “old salts” by trading our precious rum supplies for information about best anchorages, sailing routes, and navigational hazards in the Indian Ocean and Red Sea! So, we have compiled a bunch of that information on a whole variety of sailing and catamaran issues here in the pages of Catamaran Guru™. We hope that you will learn much from our experiences and “wisdom”.

Live-Aboard Cruisers

Many of you who are in the planning and dreaming stages of cruising on a yacht will benefit from our experience as live aboard cruisers. We have not only worked in the industry, but have been and still are long-term live-aboard cruisers ourselves. We have personally taken the HUGE and difficult step of cutting all ties with the land and going off into the “wide blue yonder” on our yacht. We went through the same stages of self-doubt (as many of you will or have done) while extricating ourselves from good and very lucrative careers and our lives in suburbia. We had all the trappings of a good life, the nice house, the fancy cars, and life in the fast lane. Making the leap was not easy but we were determined that we did not simply want to exist. We wanted to live our lives and be free to do so how we pleased! Our experiences, stories, and anecdotes have been assembled in the pages of Catamaran Guru™ for all sailors to use and learn from. Sailing author, Annie Van De Wiele, once said: “The art of the sailor is to leave nothing to chance.”

Sailing Experience

our first boat royal salute

We built our 45-ft Bruce Roberts sloop in our friend’s back yard over a period of two years. Royal Salute was launched in 1992 in Cape Town Harbour from where we cast off to sail around the world.

After living aboard 3 decades (and counting), we sailed over 70,000 miles and visited more than 46 countries, protectorates, and territories. We sailed to foreign lands in Africa, Red Sea, Mediterranean, Caribbean, and North and South America where we landed in strange countries with even stranger cultures, languages, and customs.

Barter trade, sign languagethe cockcrofts island christmans in the bahamas in 2018 and “gifts” to the town elders got us priceless items like a gallon of rum, a fresh chicken, and fruit! Sometimes familiar cultures and customs were a welcome respite from all the unknowns we experienced. After almost three years of sailing to and visiting foreign non-English speaking countries, we were delighted to land on the Rock of Gibraltar where the friendly Irish pubs are a haven of camaraderie for sailors, served up with a steak and kidney pie and lukewarm glasses of Guinness. Mmmm…Heaven! The Caribbean and the Bahamas were our home for a while and we finally “settled” in the US where we ply our trade as yachting and catamaran experts! Our next big adventure is awaiting us!

How We Fund Our Travels

We sold everything we albert the ape and stephen cockcroft sailing aboard royal salute a sailboatowned before we set off from South Africa which provided enough money in the bank to survive for a 2-year planned sabbatical. Within the first season of being away, our national currency collapsed and our savings were suddenly not worth much. It did not stop us, we were “living large” on only $400 a month in the third world! As we moved along, we worked in different countries (if possible) when the boredom of beautiful beaches and palm trees set in…or the cruising kitty got low. We “integrated” easily with the local population, learned the language and worked as delivery crew, bar tenders, day laborers, divers, etc. We bought and sold merchandise like baskets and trinkets, offered our own yacht for charter and ourselves as crew. We did sail training onboard Royal Salute where we made lifelong friends from around the world. When the ocean called again, we simply stocked up and moved on, just to do it again and again somewhere else in the world. Finances never put a damper on things and 20-something years later, we are still drifting around like gypsies.

We got back into business for a while in the Caribbean with a charter management company and manufacturing of catamarans in South Africa. Currently we are free to travel again as we are able to do our “jobs” selling boats and consulting with catamaran manufacturing companies from anywhere in the world. However, we have made Miami / Fort Lauderdale our base.

Charter Yacht Management Experience

In 1996, we decided that it estelle cockcroft christening her catamaran zuri in fort lauderdale in 2005was time to do some productive work and bought into a charter company in Sint Maarten where we lived for about 4 years. We had 70 boats under yacht charter management up and down the Caribbean island chain. It was a wild ride, but so much fun. We were selling dreams and we tried to make our charter guests’ sailing trips a precious and unforgettable experience. While doing this, we gained valuable experience from the owners of the charter yachts. We learned about their concerns, the pros and cons of chartering such a valuable asset, and what the financial benefits the yacht owner gains. This put us in a unique position where we experienced all aspects of charter ownership. After all, we also chartered our own boat and it mattered to us personally. The ultimate goal was and still is, how to reduce the cost of ownership for our buyers. We specialize in using tax advantages legitimately available to you through the “Yacht As A Business” program to acquire a cruising yacht for retirement at a huge discount.

Manufacturing Experience

our Island Spirit 37 catamaranWe built our first monohull in our backyard and learned a lot about the construction and manufacturing of yachts in the process. We loved our monohull, but we were curious about the catamaran concept and first sailed a catamaran in 1993 in the Indian Ocean, a Shuttleworth design. We were intrigued, but like most people at the time, did not trust that the catamaran was safe. After chartering them in the Caribbean for several years, we were sold on the comfort, stability, performance and safety vs. monohulls. We acquired a share in the Island Spirit catamaran manufacturing facility in Cape Town in 2000 and had one built for ourselves.

The Island Spirit brand was introduced into the US market and was a huge success. We sold more than 30 in the US and more than 50 worldwide including our own Island Spirit which we sailed 7000 miles from Cape Town to Miami. We were involved in the design of the exterior and interior features as well as the sail plan of the Island Spirit 401. Some of these unique features are now used as standard features by most of the popular brands like the galley design, anchoring system and Jack-and-Jill bathrooms. Subsequently we had Zuri, our Prout 45, built in Thailand and have consulted with several catamaran manufacturers.

We have partnered with some of the most prestigious names in the sailing industry, McConaghy Yachts and Dubois Naval Architects, Ker Yacht Design and Engineering, and Schionning Designs. We are developing a new range of “next generation” fast luxury sailing catamarans that will rival and exceed anything currently in the luxury sailing yacht market in quality, performance and safety.

Seaschool Founders

To meet the needs of sailors and sailing-wannabes that want to learn beyond the ASA courses, in 2022, we established Catamaran Guru Sailing Academy. We offer ASA courses, RYA sailing courses (rare in the US!), and specialty offerings such as liveaboard lifestyle sailings and performance catamaran courses, all on our own late model yachts.

Yacht Ownership  Consultants

Over time, we realized that we could help others achieve their dreams of yacht ownership and the sailing lifestyle. Along the journey, we developed Dream Yacht Charter’s North American programs to sell luxury yachts  placed into their charter fleet as well as programs for owners to operate their boat as a business and benefit from substantial tax advantages that were, and still are, available through the various US government small business stimulus programs.

Today, Catamaran Guru™ is independent of any specific yacht management company or programs. We have developed a variety of boat ownership scenarios with several yacht charter companies and, frequently, help boat owners actively manage their own boats to generate substantial tax advantages to offset the cost of yacht ownership through private ownership.

We independently assess what is right for your situation after speaking at length with you, usually over many conversations.

This offers our yacht buying clients the opportunity to utilize a yacht ownership program that fits their plans and needs with management agreements that meet all the requirements and tests to remain in compliance with the IRS rules.  


Our ramblings, reviews, and reasonable advice are offered as a resource for sailing and catamaran enthusiasts navigating the sometimes “stormy” waters of buying, selling, and cruising a yacht. We are in a unique position to have experienced and understand yacht ownership from every angle. We chartered our own crewed yacht, managed a charter fleet, built our own yachts, we live aboard, have cruised thousands of miles and did our share of racing. Our advice is sound, borne from personal experience. We are passionate about sailing and about exploring the planet and we want everyone to experience life like this!


Historic And Momentous Occasions During Our Travels

We have visited dozens of countries, territories, and dependencies during our sailing voyages around the world. We have crossed several oceans, crisscrossed the Mediterranean Sea, Red Sea, and Caribbean Sea, and have visited more than 30 states in the USA by land.

During our travels, we watched history being made, atrocities being committed, and encountered the people caught in these events, good and bad, in several countries while sailing around Africa, the Middle East, and elsewhere in the world.

Highlights Around The Continent Of Africa

The South African general election of 27 April 1994, where Nelson Mandela became the newly democratically elected President was one such momentous occasion, as was Ethiopia’s recognizing Eritrea’s sovereignty on May 3, 1993. Another was when we were waylaid for a time when the Yemenis started their civil war in 1994, resulting in bombings and piracy around the Red Sea while we were making our way up to Egypt.

In 100 days, beginning in April 1994, the Hutu tribe rampaged through Rwanda and slaughtered an estimated 800,000 Tutsi and their moderate Hutu sympathizers. Everyone in central East Africa was on high alert during this period and the sense of fear and helplessness was palpable. This was perhaps one moment in history that most people would rather not remember but should, so it never happens again! Sadly, Sudan is feeling the effects of “ethnic cleansing” today.

The Red Sea And Middle East

Red Sea DivingThe Red Sea with its notoriously bad weather, sand storms, oil rigs, pirates, and the Suez Canal was a milestone achievement journey for us. Here’s more about our brush with piracy in the Red Sea and information about the piracy map. We were apprehensive about doing the trip but even with all the negatives, this part of our trip was the highlight of a lifetime. Once through the Red Sea, we visited Cypress and went on to Israel and Lebanon. Our Royal Salute was only the second cruising yacht to visit Jounieh, Lebanon after the end of the 16-year civil war. The country looked like a set in a Steven Spielberg movie…the jewel of the Middle East was a complete wreck! After the initial hostile reception by the military when we arrived in the country (visitors to Lebanon was unheard of and we were at first treated as potential troublemakers), we were delighted with the warm welcome by the people in this country and it was hard to eventually leave when we set sail for Turkey.

Interesting Encounters And Personalities

Pemba & Zanzibar, East Africa: We had some very interesting encounters on our journey. We were able to do some spectacular diving on the reefs off of the isolated island of Pemba, once the spice capital of the world, in the Indian Ocean. Now it’s an isolated place, only reachable by boat. White faces were an oddity and visitors of any kind were almost non-existent. The local people were fascinated by the the very sight of ‘farangs’ (white people) frolicking in the shallow waters off their pristine beach. We felt privileged to be there.

Red Sea & Marine Research: Diving on Jacques Cousteau’s underwater house in the Red Sea on the Shaab Brumi atoll, together with the crew of a marine research ship was a once in a lifetime experience. Check out the video at right of the remaining structure. Famous shark researcher, Eugenie Clark or ‘Shark Lady’ as she is known, in her mail chain was onboard and showed us some spectacular underwater sights, including some too-close encounters with sharks.

Catamaran Gurus Monkey named albert was part of the crew in turkeyTurkey & Our Monkey, Albert: One occasion very close to our hearts was of course when Albert Einstein, a Blue Vervet monkey became a part of Royal Salute’s crew in Turkey. We rescued him from a local bar from a tiny cage. He was aggressive and acted out but Stephen taught him how to be behave in a troop. He settled in nicely, with daily grooming and the occasional swim overboard when he behaved badly. There are many stories related to Albert’s antics and all our friends have pictures, stories and fond memories of our time together. Here are a few bits about Albert the monkey living aboard with us. Sadly, Albert had to stay in Turkey because where we were heading (the island of Malta), primates were not welcome. We left him with a good friend on an orange farm and were gifted a beautiful Turkish carpet in return.

Cuba: We were invited to sail to Cuba by Charles Romero, the former secretary of Che Guevara, where we were given a unique view of life on Cuba and the Cuban Revolution. It was a very special visit that few people will ever get to experience. With Stephen’s background in the South African military, the Cubans felt comfortable in our company and we were introduced to some of the communist revolutionaries. Cuba is at once romantic, beautiful, nostalgic and scary. The Communist ways are all too prevalent. Even though the locals were beyond hospitable and friendly, the feeling of paranoia is everywhere.

Sultan Of Malaysian State of Selangor: The island of Santorini brought a special surprise, not only because it is a spectacular volcanic island but because we were moored next to the Royal Yacht Jugra. We had the chance to meet the Sultan’s son, Idris Shah, who in late 1990s became the sultan. This was a chance encounter, but we struck a fast friendship and met up again across the Atlantic in Sint Maarten for his 50th birthday celebration. It was at this party where we first met the legendary Bob and Jodi from Latitudes & Attitudes fame (now Cruising Outpost) aboard their yacht “Lost Soul”. They have been part of our sailing journey ever since.

RV-ing & Exploring The USA: We purchased an RV and visited 30+ US states. We started in Hollywood, Florida, from the Topeekeegee Yugnee Park and drove west. We spent time in Texas, California, Arizona, Colorado, Utah, Maryland and Virginia among others. While we visited some of the most spectacular places like Lake Powell in Arizona, Moab in Utah, the Grand Canyon, Pike’s Peak (14,000 ft) in Colorado among others, we traveled through the country to connect with our yacht buyers and visit boat shows on both coasts. What a great and adventurous way to do a “job”!

So, as you can tell from just a few highlights from our travels, we have had and are still having an adventure that sometimes boggles the mind. We have the pleasure of sharing the ocean with all of God’s creatures, we are thankful for the privilege and we hope to keep traveling, discovering and learning.

The rhythm of the ever-changing ocean has left a delicate but indelible impression on our lives and we wish all sailors to experience the same pleasure, passion and freedom that only sailing the oceans can evoke. Join Us!


Join Our Community!

Get the latest on catamaran news, sailing events, buying and selling tips, community happenings, webinars & seminars, and much more!

4 thoughts on “Our Story”

  1. You did a 2017 article about anchorages in the BVI – have you done an update as they recover from Huricanes and COVID ??

  2. Hi Steve and Estelle from SA. 30 years on, since leaving SA all I can say is WOW you guys really followed the dream you shared with me before you left. O how I remember your first sailing experience in Royal Salute you know what I am referring to, its because you persevered despite everyone’s scepticism, today we eat humble pie as you enjoy the fruit of your first step into the unknown. I am so happy for you guys. Good to read about your successes and thinking back I would be more surprised if you didn’t have a success story. (Next project how about a book on ALL your adventures)
    Regards Rob

    1. Estelle Cockcroft

      Hi Rob! What a wonderful surprise to hear from you and thank you for the kind words! We have had some ups and downs like everyone but sure are enjoying every minute of it. It is hard not to have fun considering that the ocean is our backyard, our office, our playground, our life! Our very best to you and your family in SA!

Leave a Comment

Your email address will not be published. Required fields are marked *

On Key

Recent Posts